VANGUARD/WINDSOR FUNDS INC
485BPOS, 2000-01-28
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                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549


                                   FORM N-1A

     REGISTRATION STATEMENT (NO. 2-14336) UNDER THE SECURITIES ACT OF 1933


                           PRE-EFFECTIVE AMENDMENT NO.
                        POST-EFFECTIVE AMENDMENT NO. 94

                                      AND


        REGISTRATION STATEMENT UNDER THE INVESTMENT COMPANY ACT OF 1940


                                AMENDMENT NO. 97




                             VANGUARD WINDSOR FUNDS
        (EXACT NAME OF REGISTRANT AS SPECIFIED IN DECLARATION OF TRUST)

                     P.O. BOX 2600, VALLEY FORGE, PA 19482
                    (ADDRESS OF PRINCIPAL EXECUTIVE OFFICE)

                  REGISTRANT'S TELEPHONE NUMBER (610) 669-1000

                           R. GREGORY BARTON, ESQUIRE
                                  P.O. BOX 876
                             VALLEY FORGE, PA 19482


               IT IS PROPOSED THAT THIS FILING BECOME EFFECTIVE:
          ON FEBRUARY 18, 2000, PURSUANT TO PARAGRAPH (B) OF RULE 485.


                 APPROXIMATE DATE OF PROPOSED PUBLIC OFFERING:
  AS SOON AS PRACTICABLE AFTER THIS REGISTRATION STATEMENT BECOMES EFFECTIVE.


WE HAVE  ELECTED  TO  REGISTER  AN  INDEFINITE  NUMBER OF  SECURITIES  UNDER THE
SECURITIES ACT OF 1933 PURSUANT TO RULE 24F-2 OF THE  INVESTMENT  COMPANY ACT OF
1940.  REGISTRANT  FILED ITS RULE 24F-2 NOTICE FOR ITS FISCAL YEAR ENDED OCTOBER
31, 1999 WITH THE COMMISSION ON JANUARY 27, 2000.



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                             VANGUARD WINDSOR FUNDS

                             CROSS REFERENCE SHEET

<TABLE>
<CAPTION>
<S>        <C>                                         <C>
FORM N-1A
ITEM NUMBER
- -----------------------------------------------------------------------------------------------------
FORM N-1A
ITEM NUMBER                                            LOCATION IN PROSPECTUS
- -----------------------------------------------------------------------------------------------------
Item 1.    Front and Back Cover Pages .................Front and Back Cover Pages

Item 2.    Risk/Return: Investments, Risk, and
           Performance ................................Fund Profile

Item 3.    Risk/Return Summary: Fee Table .............Fee Table


Item 4.    Investment Objectives, Principal Investment
           Strategies, and Related Risks ..............A Word About Risk; Who Should Invest;
                                                       Primary Investment Strategies

Item 5.    Management's Discussion of Fund
           Performance ................................Herein incorporated by reference to
                                                       Registrant's Annual Report to Shareholders
                                                       dated October 31, 1999 filed with the
                                                       Securities & Exchange Commission's EDGAR
                                                       system December 16, 1999.

Item 6.    Management, Organization, and Capital
           Structure ..................................The Portfolios and Vanguard; Investment
                                                       Advisers

Item 7.    Shareholder Information ....................Share Price; Dividends, Capital Gains, and
                                                       Taxes; Investing with Vanguard

Item 8.    Distribution Arrangements ..................Not Applicable

Item 9.    Financial Highlights Information ...........Financial Highlights

FORM N-1A                                              LOCATION IN STATEMENT OF ADDITIONAL
ITEM NUMBER                                            INFORMATION
- -----------------------------------------------------------------------------------------------------
Item 10.   Cover Page and Table of Contents ...........Cover Page; Table of Contents


Item 11.   Fund History ...............................Description of the Fund

Item 12.   Description of the Fund and its Investments
           and Risks ..................................Investment Policies; Description of the Trust;
                                                       Fundamental Investment Limitations

Item 13.   Management of the Fund .....................Management of the Fund

Item 14.   Control Persons and Principal Holders of
           Securities .................................Management of the Fund

Item 15.   Investment Advisory and Other Services .....Investment Advisory Services

Item 16.   Brokerage Allocation and Other Practices ...Portfolio Transactions

Item 17.   Capital Stock and Other Securities .........Description of the Fund

Item 18.   Purchase, Redemption, and Pricing of Shares.Purchase of Shares; Redemption of Shares;
                                                       Share Price

Item 19.   Taxation of the Fund .......................Description of the Fund


Item 20.   Underwriters ...............................Not Applicable

Item 21.   Calculation of Performance Data ............Yield and Total Return

Item 22.   Financial Statements .......................Financial Statements

</TABLE>

<PAGE>


VANGUARD(R)
WINDSOR (TM) FUND

Prospectus
February 18, 2000


This prospectus contains
financial data for the
Fund through the
fiscal year ended
October 31, 1999.


[A MEMBER OF
THE VANGUARD GROUP LOGO]

<PAGE>

VANGUARD WINDSOR FUND
Prospectus

February 18, 2000

A Growth and Income Stock Mutual Fund
- --------------------------------------------------------------------------------
CONTENTS
- --------------------------------------------------------------------------------
 1 FUND PROFILE                           12 SHARE PRICE

 3 ADDITIONAL INFORMATION                 12 FINANCIAL HIGHLIGHTS

 3 A WORD ABOUT RISK                      14 INVESTING WITH VANGUARD

 3 WHO SHOULD INVEST                         14 SERVICES AND ACCOUNT FEATURES
                                             15 TYPES OF ACCOUNTS
 4 PRIMARY INVESTMENT STRATEGIES             16 BUYING SHARES
                                             18 REDEEMING SHARES
 8 THE FUND AND VANGUARD                     21 TRANSFERRING REGISTRATION
                                             22 FUND AND ACCOUNT UPDATES
 9 INVESTMENT ADVISERS

10 DIVIDENDS, CAPITAL GAINS, AND TAXES    GLOSSARY (inside back cover)
- --------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
WHY READING THIS PROSPECTUS IS IMPORTANT
This  prospectus  explains  the  objective,  risks,  and  strategies of Vanguard
Windsor  Fund.  To  highlight  terms  and  concepts  important  to  mutual  fund
investors,  we have  provided  "Plain  Talk (R)"  explanations  along  the way.
Reading the  prospectus  will help  you to decide  whether the Fund is the right
investment for you. We suggest that you keep it for future reference.
- --------------------------------------------------------------------------------

NEITHER  THE  SECURITIES  AND  EXCHANGE  COMMISSION  NOR  ANY  STATE  SECURITIES
COMMISSION HAS APPROVED OR  DISAPPROVED  OF THESE  SECURITIES OR PASSED UPON THE
ACCURACY OR ADEQUACY OF THIS PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A
CRIMINAL OFFENSE.

<PAGE>

                                                                               1

FUND PROFILE

The following profile summarizes key features of Vanguard Windsor Fund.

INVESTMENT OBJECTIVE

The Fund seeks to provide long-term growth of capital. As a secondary objective,
the Fund seeks to provide some dividend income.

INVESTMENT STRATEGIES
The Fund invests primarily in large- and medium-size  companies whose stocks are
considered  by the Fund's  adviser  to be  undervalued.  Undervalued  stocks are
generally  those that are out of favor with  investors and currently  trading at
prices that, the adviser feels,  are below what the stocks are worth in relation
to   their   earnings.    These   stocks    typically--but    not   always--have
lower-than-average  price/earnings (P/E) ratios and higher-than-average dividend
yields.

PRIMARY RISKS
THE FUND'S TOTAL RETURN,  LIKE STOCK PRICES  GENERALLY,  WILL FLUCTUATE WITHIN A
WIDE RANGE, SO AN INVESTOR COULD LOSE MONEY OVER SHORT OR EVEN LONG PERIODS. The
Fund is also subject to:
- -    Investment  style risk,  which is the chance that  returns  from large- and
     mid-capitalization  value stocks will trail  returns from the overall stock
     market.
- -    Manager risk,  which is the chance that poor security  selection will cause
     the Fund to underperform other funds with similar investment objectives.

PERFORMANCE/RISK INFORMATION

The bar chart and table below  provide an indication of the risk of investing in
the Fund. The bar chart shows the Fund's  performance in each calendar year over
a ten-year  period.  The table shows how the Fund's average annual total returns
for one,  five,  and ten  calendar  years  compare  with those of a  broad-based
securities  market index. Keep in mind that the Fund's past performance does not
indicate how it will perform in the future.

            ----------------------------------------------------
                              ANNUAL TOTAL RETURNS
                              1990         -15.50%
                              1991          28.55%
                              1992          16.50%
                              1993          19.37%
                              1994          -0.15%
                              1995          30.15%
                              1996          26.36%
                              1997          21.97%
                              1998           0.81%
                              1999          11.57%
            ----------------------------------------------------

     During the period shown in the bar chart, the highest return for a calendar
quarter was 18.25%  (quarter  ended March 31, 1991) and the lowest  return for a
quarter was -20.34% (quarter ended September 30, 1990).


<PAGE>

2


      --------------------------------------------------------------------
        AVERAGE ANNUAL TOTAL RETURNS FOR YEARS ENDED DECEMBER 31, 1999
      --------------------------------------------------------------------
                                        1 YEAR      5 YEARS      10 YEARS
      --------------------------------------------------------------------
      Vanguard Windsor Fund             11.57%       17.67%       13.03%
      Standard & Poor's 500 Index       21.04        28.56        18.21
      --------------------------------------------------------------------

FEES AND EXPENSES
The following table describes the fees and expenses you would pay if you buy and
hold shares of the Fund. The expenses shown under Annual Fund Operating Expenses
are based upon those incurred in the fiscal year ended October 31, 1999.

      SHAREHOLDER FEES (fees paid directly from your investment)
      Sales Charge (Load) Imposed on Purchases:              None
      Sales Charge (Load) Imposed on Reinvested Dividends:   None
      Redemption Fee:                                        None
      Exchange Fee:                                          None

      ANNUAL FUND OPERATING EXPENSES (expenses deducted from the
      Fund's assets)
      Management Expenses:                                  0.26%
      12b-1 Distribution Fee:                                None
      Other Expenses:                                       0.02%
       TOTAL ANNUAL FUND OPERATING EXPENSES:                0.28%


     The following example is intended to help you compare the cost of investing
in the Fund with the cost of investing in other mutual funds. It illustrates the
hypothetical  expenses  that you would incur over various  periods if you invest
$10,000 in the Fund.  This example assumes that the Fund provides a return of 5%
a year, and that operating  expenses  remain the same. The results apply whether
or not you redeem your investment at the end of each period.

            ----------------------------------------------------
               1 YEAR      3 YEARS     5 YEARS      10 YEARS
            ----------------------------------------------------
                 $29         $90        $157          $356
            ----------------------------------------------------

     THIS  EXAMPLE  SHOULD NOT BE  CONSIDERED  TO REPRESENT  ACTUAL  EXPENSES OR
PERFORMANCE  FROM THE PAST OR FOR THE  FUTURE.  ACTUAL  FUTURE  EXPENSES  MAY BE
HIGHER OR LOWER THAN THOSE SHOWN.

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                  FUND EXPENSES

All mutual funds have operating  expenses.  These  expenses,  which are deducted
from a fund's gross  income,  are expressed as a percentage of the net assets of
the fund.  Vanguard  Windsor Fund's expense ratio in fiscal year 1999 was 0.28%,
or $2.80 per $1,000 of average net assets.  The average  multi-cap  value mutual
fund had  expenses in 1999 of 1.38%,  or $13.80 per $1,000 of average net assets
(derived  from data  provided as of  December  31,  1999 by Lipper  Inc.,  which
reports on the mutual fund industry).  Management  expenses,  which comprise one
part of operating  expenses,  include investment  advisory fees as well as other
costs of managing a fund--such as account  maintenance,  reporting,  accounting,
legal, and other administrative expenses.

- --------------------------------------------------------------------------------

<PAGE>

                                                                               3

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                                PLAIN TALK ABOUT
                             THE COSTS OF INVESTING

Costs are an important  consideration in choosing a mutual fund.  That's because
you, as a shareholder,  pay the costs of operating a fund,  plus any transaction
costs  associated with the fund's buying and selling of securities.  These costs
can erode a substantial  portion of the gross income or capital  appreciation  a
fund achieves. Even seemingly small differences in expenses can, over time, have
a dramatic effect on a fund's performance.
- --------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
ADDITIONAL INFORMATION

DIVIDENDS AND CAPITAL GAINS               SUITABLE FOR IRAS
Dividends are distributed semiannually    Yes
in June and December; capital gains, if
any, are distributed in December          MINIMUM INITIAL INVESTMENT
                                          $3,000; $1,000 for IRAs and custodial
INVESTMENT ADVISERS                       accounts for minors
- - Wellington Management Company, LLP,
  Boston, Mass., since inception          NEWSPAPER ABBREVIATION
- - Sanford C. Bernstein & Co., Inc., New   Wndsr
  York, N.Y., since June 1, 1999
- - The Vanguard Group, Valley Forge, Pa.   VANGUARD FUND NUMBER
                                          022
INCEPTION DATE
October 23, 1958                          CUSIP NUMBER
                                          922018106
NET ASSETS AS OF OCTOBER 31, 1999
$16.8 billion                             TICKER SYMBOL
                                          VWNDX

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================================================================================
A WORD ABOUT RISK

This  prospectus  describes  risks you would  face as an  investor  in  Vanguard
Windsor  Fund.  It is  important  to keep  in mind  one of the  main  axioms  of
investing: The higher the risk of losing money, the higher the potential reward.
The  reverse,  also,  is  generally  true:  The lower  the  risk,  the lower the
potential  reward.  As you consider an investment in Vanguard  Windsor Fund, you
should also take into account your personal tolerance for the daily fluctuations
of the stock market.

     Look for this [FLAG] symbol  throughout the prospectus.  It is used to mark
detailed  information  about  each  type of risk that you  would  confront  as a
shareholder of the Fund.
================================================================================

WHO SHOULD INVEST

The Fund may be a suitable investment for you if:
- -    You are seeking a value-oriented investment that seeks to provide long-term
     growth as well as some dividend income.
- -    You wish to add a  value-oriented  growth  and  income  stock  fund to your
     existing  holdings,  which could include other stock investments as well as
     bond, money market, and tax-exempt investments.
- -    You are seeking  growth of capital and income over the long term--at  least
     five years.

<PAGE>

4

     THE VANGUARD FUNDS DO NOT PERMIT MARKET-TIMING.  DO NOT INVEST IN THIS FUND
IF YOU ARE A MARKET-TIMER.

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                                PLAIN TALK ABOUT
                             COSTS AND MARKET-TIMING

Some   investors  try  to  profit  from   market-timing--switching   money  into
investments  when they  expect  prices to rise,  and taking  money out when they
expect  the  market  to fall.  As money is  shifted  in and out,  a fund  incurs
expenses  for buying and selling  securities.  These costs are borne by all fund
shareholders,  including the long-term  investors who do not generate the costs.
Therefore,  the Fund  discourages  short-term  trading by,  among other  things,
limiting the number of exchanges it permits.
- --------------------------------------------------------------------------------

     The Fund has adopted the following  policies,  among others,  to discourage
short-term trading:
- -    The Fund  reserves  the right to  reject  any  purchase  request--including
     exchanges from other  Vanguard  funds--that it regards as disruptive to the
     efficient  management  of the Fund.  A purchase  request  could be rejected
     because  of the  timing  of the  investment  or  because  of a  history  of
     excessive trading by the investor.
- -    There is a limit on the  number of times you can  exchange  into and out of
     the Fund (see "Redeeming Shares" in the INVESTING WITH VANGUARD section).
- -    The Fund reserves the right to stop offering shares at any time.

PRIMARY INVESTMENT STRATEGIES

This section explains the strategies that the investment advisers use in pursuit
of the  Fund's  objectives  of  long-term  growth of capital  and some  dividend
income.  It also  explains  how the  advisers  implement  these  strategies.  In
addition,   this  section  discusses  several  important   risks--market   risk,
investment  style risk,  and manager  risk--faced  by investors in the Fund. The
Fund's Board of Trustees  oversees the management of the Fund and may change the
investment strategies in the interest of shareholders.

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                    LARGE-CAP, MID-CAP, AND SMALL-CAP STOCKS

Stocks  of  publicly  traded   companies--and   mutual  funds  that  hold  these
stocks--can be classified by the  companies'  market value,  or  capitalization.
Market  capitalization  changes over time, and there is no "official" definition
of the boundaries of large-,  mid-,  and small-cap  stocks.  Vanguard  generally
defines  large-capitalization  (large-cap)  funds as  those  holding  stocks  of
companies  whose  outstanding  shares have a market value exceeding $12 billion;
mid-cap funds as those holding  stocks of companies  with a market value between
$1 billion and $12  billion;  and  small-cap  funds as those  typically  holding
stocks  of  companies  with a market  value of less  than $1  billion.  Vanguard
periodically reassesses these classifications.

- --------------------------------------------------------------------------------

<PAGE>

                                                                               5

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                          VALUE FUNDS AND GROWTH FUNDS

Value  investing  and growth  investing  are two styles  employed  by stock fund
managers.  Value funds  generally  emphasize  stocks of companies from which the
market does not expect strong growth.  The prices of value stocks  typically are
below-average  in  comparison  to such factors as earnings  and book value,  and
these  stocks  typically  have  above-average   dividend  yields.  Growth  funds
generally focus on companies believed to have above-average potential for growth
in revenue and earnings.  Reflecting the market's high expectations for superior
growth, such stocks typically have low dividend yields and above-average  prices
in relation to such measures as revenue,  earnings,  and book values.  Value and
growth stocks have, in the past, produced similar long-term returns, though each
category has periods when it outperforms the other. In general,  value funds are
appropriate  for investors  who want some dividend  income and the potential for
capital gains but are less tolerant of share-price  fluctuations.  Growth funds,
by contrast,  appeal to investors who will accept more  volatility in hopes of a
greater increase in share price.  Growth funds also may appeal to investors with
taxable  accounts  who want a higher  proportion  of  returns to come as capital
gains (which may be taxed at lower rates than dividend income).

- --------------------------------------------------------------------------------

MARKET EXPOSURE
The Fund is a value  fund.  Its  primary  strategy  is to invest  in large-  and
mid-capitalization  common  stocks that have  favorable  prospects for growth of
earnings and dividend income, but whose prices do not reflect this potential for
positive returns. The Fund may also invest in securities that are convertible to
common stocks.

[FLAG] THE FUND IS SUBJECT TO MARKET RISK,  WHICH IS THE POSSIBILITY  THAT STOCK
     PRICES OVERALL WILL DECLINE OVER SHORT OR EVEN LONG PERIODS.  STOCK MARKETS
     TEND TO MOVE IN  CYCLES,  WITH  PERIODS  OF RISING  PRICES  AND  PERIODS OF
     FALLING PRICES.

     To illustrate the volatility of stock prices, the following table shows the
best,  worst,  and average total returns for the U.S.  stock market over various
periods as measured by the Standard & Poor's 500 Index,  a widely used barometer
of market  activity.  (Total returns  consist of dividend  income plus change in
market  price.)  Note that the returns  shown do not include the costs of buying
and selling  stocks or other  expenses  that a real-world  investment  portfolio
would  incur.  Note,  also,  that the gap between best and worst tends to narrow
over the long term.

      --------------------------------------------------------------------
                      U.S. STOCK MARKET RETURNS (1926-1999)
                            1 YEAR    5 YEARS    10 YEARS    20 YEARS
      --------------------------------------------------------------------
      Best                   54.2%     28.6%       19.9%       17.9%
      Worst                 -43.1     -12.4        -0.9         3.1
      Average                13.2      11.0        11.1        11.1
      --------------------------------------------------------------------

     The table  covers all of the 1-, 5-,  10-,  and 20-year  periods  from 1926
through 1999. You can see, for example,  that while the average return on stocks
for all of the 5-year periods was 11.0%,  returns for individual  5-year periods
ranged from a -12.4% average (from 1928


<PAGE>

6


through 1932) to 28.6% (from 1995 through 1999).  These average  returns reflect
past  performance on common stocks;  you should not regard them as an indication
of  future  returns  from  either  the  stock  market as a whole or this Fund in
particular.


[FLAG] THE FUND IS SUBJECT TO INVESTMENT  STYLE RISK,  WHICH IS THE  POSSIBILITY
     THAT  RETURNS  FROM LARGE- AND  MID-CAPITALIZATION  VALUE STOCKS WILL TRAIL
     RETURNS FROM OTHER ASSET CLASSES OR THE OVERALL  STOCK MARKET.  AS A GROUP,
     VALUE  STOCKS  TEND TO GO THROUGH  CYCLES OF DOING  BETTER--OR  WORSE--THAN
     COMMON STOCKS IN GENERAL.  THESE  PERIODS HAVE, IN THE PAST,  LASTED FOR AS
     LONG AS SEVERAL YEARS.

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                              FUND DIVERSIFICATION

In general, the more diversified a fund's stock holdings,  the less likely it is
that a specific  stock's poor  performance  will hurt the fund. One measure of a
fund's  diversification  is the percentage of its assets  represented by its ten
largest  holdings.  The  average  U.S.  equity  mutual fund has about 30% of its
assets invested in its ten largest holdings,  while some less-diversified mutual
funds  have more than 50% of their  assets  invested  in the  stocks of just ten
companies.
- --------------------------------------------------------------------------------

SECURITY SELECTION
Vanguard  Windsor Fund  employs two primary  investment  advisers,  each of whom
independently  chooses and  maintains a portfolio of common stocks for the Fund.
Each adviser is responsible for a specific percentage of the Fund's assets.

     These investment  advisers employ active  investment  methods,  which means
that securities are bought and sold according to the advisers' evaluations about
companies  and their  financial  prospects,  and about the stock  market and the
economy in general.  Each adviser  will sell a security  when it is no longer as
attractive as alternative investments.
     While each adviser uses a different process to select securities,  both are
committed to investing in large- and mid-cap stocks that, in their opinion,  are
undervalued.  Undervalued  stocks are generally those that are out of favor with
investors and currently  trading at prices that,  the adviser  feels,  are below
what  the  stocks  are  worth  in  relation  to  their  earnings.  These  stocks
typically--but not always--have  lower-than-average  price/earnings (P/E) ratios
and higher-than-average dividend yields.
     Wellington  Management Company,  LLP (Wellington  Management) managed about
75% of the Fund's  assets as of October  31,  1999.  A stock's  value is the key
element in Wellington  Management's  selection  process.  Wellington  Management
considers several  fundamental  factors,  including the stock's projected growth
rate, earnings  potential,  dividend yield, and P/E ratio. To be a candidate for
purchase,  a stock must have strong prospects for capital  appreciation,  but be
trading at a price/earnings (P/E) ratio that is lower than what is expected of a
stock with such potential.
     Sanford C.  Bernstein & Co., Inc.  (Bernstein),  which managed about 24% of
the Fund's assets as of October 31, 1999, also uses traditional methods of stock
selection--research  and analysis--to  identify undervalued stocks. In addition,
Bernstein employs quantitative valuation tools to identify attractive stocks and
the most opportune time to purchase them.
     The Vanguard Group (Vanguard) typically will manage any Fund assets held in
cash reserves and may invest in stock index  futures.  This strategy is intended
to keep the Fund more fully  invested in common stocks while  retaining  cash on
hand to meet liquidity


<PAGE>

                                                                               7


needs. See "Other Investment  Policies and Risks" for more details on the Fund's
policy on futures.

     The Fund is generally managed without regard to tax ramifications.

[FLAG] THE FUND IS SUBJECT TO MANAGER RISK,  WHICH IS THE  POSSIBILITY  THAT THE
     ADVISERS MAY DO A POOR JOB OF SELECTING STOCKS.

TURNOVER RATE

Although the Fund  generally  seeks to invest for the long term,  it retains the
right to sell  securities  regardless of how long the securities have been held.
The Fund's average  turnover rate for the past five years has been about 46%. (A
turnover  rate of 100% would occur,  for example,  if the Fund sold and replaced
securities valued at 100% of its net assets within a one-year period.)


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                  TURNOVER RATE

Before  investing in a mutual fund,  you should review its turnover  rate.  This
gives an  indication  of how  transaction  costs could affect the fund's  future
returns.  In general,  the greater the volume of buying and selling by the fund,
the greater the impact that brokerage  commissions and other  transaction  costs
will have on its return. Also, funds with high turnover rates may be more likely
to generate  capital gains that must be  distributed to  shareholders  as income
subject to taxes.  As of October 31,  1999,  the average  turnover  rate for all
domestic stock funds was approximately 87%, according to Morningstar, Inc.

- --------------------------------------------------------------------------------

OTHER INVESTMENT POLICIES AND RISKS
Besides investing in undervalued  common stocks, the Fund may make certain other
kinds of investments to achieve its objective.
     Although  the  Fund  typically  does not make  significant  investments  in
securities of companies  based outside the United States,  it reserves the right
to invest up to 20% of its assets in foreign securities. These securities may be
traded in U.S. or foreign  markets.  To the extent that it owns foreign  stocks,
the Fund is subject to (1) country risk, which is the possibility that political
events (such as a war),  financial  problems  (such as government  default),  or
natural  disasters (such as an earthquake)  will weaken a country's  economy and
cause investments in that country to lose money; and (2) currency risk, which is
the possibility  that Americans  investing  abroad could lose money because of a
rise in the value of the U.S. dollar versus foreign currencies.
     The Fund may invest in money market instruments,  fixed-income  securities,
convertible securities, and other equity securities such as preferred stock. The
Fund may invest up to 15% of its assets in  restricted  securities  with limited
marketability or other illiquid securities.

     The Fund may also  invest,  to a limited  extent,  in futures  and  options
contracts,  which  are  traditional  types of  derivatives.  Losses  (or  gains)
involving  futures can  sometimes be  substantial--in  part because a relatively
small  price  movement  in a futures  contract  may result in an  immediate  and
substantial  loss (or gain)  for a fund.  This  Fund  will not use  futures  for
speculative  purposes  or as  leveraged  investments  that  magnify the gains or
losses of an investment.  The Fund's obligation under futures contracts will not
exceed 20% of its total assets.


<PAGE>

8

     The reasons for which the Fund will invest in futures and options are:
- -    To keep cash on hand to meet  shareholder  redemptions or other needs while
     simulating full investment in stocks.
- -    To reduce the Fund's  transaction costs or add value when these instruments
     are favorably priced.

     The Fund may temporarily  depart from its normal  investment  policies--for
instance,   by  investing   substantially  in  cash  reserves--in   response  to
extraordinary market, economic, political, or other conditions. In doing so, the
Fund may succeed in avoiding losses but otherwise fail to achieve its investment
objective.


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                   DERIVATIVES

A derivative is a financial contract whose value is based on (or "derived" from)
a  traditional  security  (such  as a stock  or a  bond),  an  asset  (such as a
commodity like gold), or a market index (such as the S&P 500 Index). Futures and
options are derivatives  that have been trading on regulated  exchanges for more
than two decades.  These  "traditional"  derivatives are standardized  contracts
that can easily be bought and sold,  and whose market values are  determined and
published  daily. It is these  characteristics  that  differentiate  futures and
options from the relatively new types of derivatives. If used for speculation or
as leveraged investments, derivatives can carry considerable risks.
- --------------------------------------------------------------------------------

THE FUND AND VANGUARD

The Fund is a member of The Vanguard  Group, a family of more than 35 investment
companies  with more than 100 funds holding assets worth more than $530 billion.
All of the  Vanguard  funds  share  in the  expenses  associated  with  business
operations, such as personnel, office space, equipment, and advertising.

     Vanguard  also  provides   marketing   services  to  the  funds.   Although
shareholders do not pay sales commissions or 12b-1  distribution fees, each fund
pays its allocated share of The Vanguard Group's marketing costs.

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                      VANGUARD'S UNIQUE CORPORATE STRUCTURE

The Vanguard Group is truly a MUTUAL mutual fund company. It is owned jointly by
the funds it oversees and thus  indirectly by the  shareholders  in those funds.
Most other mutual funds are operated by for-profit management companies that may
be owned by one person,  by a group of individuals,  or by investors who own the
management  company's stock. By contrast,  Vanguard  provides its services on an
"at-cost"  basis,  and the funds' expense  ratios  reflect only these costs.  No
separate  management  company reaps profits or absorbs losses from operating the
funds.
- --------------------------------------------------------------------------------

<PAGE>

                                                                               9

INVESTMENT ADVISERS

The Fund employs two primary investment  advisers for the bulk of its assets and
uses Vanguard's Core Management Group to manage its cash reserves.  Each adviser
manages the Fund  subject to the  control of the  Trustees  and  officers of the
Fund.

WELLINGTON MANAGEMENT COMPANY, LLP
     Wellington  Management  Company,  LLP  (Wellington  Management),  75  State
Street,  Boston, MA 02109, served as the Fund's sole investment adviser from the
Fund's inception in 1958 until June of 1999.
     Wellington  Management's  advisory fee is paid  quarterly,  and is based on
certain annual  percentage rates applied to the Fund's average  month-end assets
for each quarter. In addition, Wellington Management's advisory fee is increased
or decreased,  based on the cumulative investment  performance of its portion of
the Fund over a trailing  36-month period as compared with the cumulative  total
return of the Standard and Poor's 500 Index over the same period.

SANFORD C. BERNSTEIN & CO., INC.
     Sanford C. Bernstein & Co., Inc.  (Bernstein),  767 Fifth Avenue, New York,
NY  10153,  was  added  as an  investment  adviser  to the Fund in June of 1999.
Bernstein's  advisory  fee is paid  quarterly,  and is based on  certain  annual
percentage  rates  applied  to the  Fund's  average  month-end  assets  for each
quarter. In addition,  Bernstein's advisory fee is increased or decreased, based
on the  cumulative  investment  performance  of its  portion  of the Fund over a
trailing  36-month  period as compared with the  cumulative  total return of the
Russell 1000 Value Index over the same period.

THE VANGUARD GROUP
     The Vanguard  Group  (Vanguard),  P.O. Box 2600,  Valley  Forge,  PA 19482,
founded in 1974,  is a wholly  owned  subsidiary  of the Vanguard  funds.  As of
October 31, 1999, Vanguard served as adviser for about $345.6 billion in assets.
The Fund receives advisory services from Vanguard on an at-cost basis.

     For the  fiscal  year ended  October  31,  1999,  the  aggregate  amount of
investment  advisory fees paid by the Fund  represented an effective annual rate
of 0.12% of the Fund's  average  net assets  before a decrease of 0.08% based on
performance.
     The Fund has authorized the advisers to choose brokers or dealers to handle
the purchase and sale of securities  for the Fund, and to get the best available
price and most  favorable  execution  from  these  brokers  with  respect to all
transactions.
     In the  interest  of  obtaining  better  execution  of a  transaction,  the
advisers  may choose  brokers who charge  higher  commissions.  If more than one
broker can obtain the best  available  price and most  favorable  execution of a
transaction,  then the  advisers  are  authorized  to  choose a broker  who,  in
addition to executing the  transaction,  will provide  research  services to the
advisers or the Fund. Also, the Fund may direct the advisers to use a particular
broker for certain  transactions in exchange for commission  rebates or research
services provided to the Fund.
     The Board of Trustees may, without prior approval from shareholders, change
the terms of an advisory agreement or hire a new investment adviser--either as a
replacement for an existing adviser or as an additional adviser. Any significant
change in the Fund's advisory  arrangements will be communicated to shareholders
in writing. In addition, as the Fund's


<PAGE>

10


sponsor and overall manager,  The Vanguard Group may provide investment advisory
services to the Fund, on an at-cost basis, at any time.


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                               THE FUND'S ADVISERS

Wellington  Management  Company,  LLP  (Wellington  Management) is an investment
advisory  firm founded in 1928.  As of October 31, 1999,  Wellington  Management
managed more than $224 billion in assets. The manager responsible for overseeing
Wellington Management's portion of the Fund is:

CHARLES T. FREEMAN,  Senior Vice President and Partner of Wellington Management;
has worked in investment management since 1967; with Wellington Management since
1969; B.S., M.B.A.,  University of Pennsylvania.  Mr. Freeman was appointed Fund
Manager in January  1996,  following  the  retirement  of John B. Neff,  who had
managed the Fund since 1964.  Mr.  Freeman had been Assistant Fund Manager since
1974.

Sanford C.  Bernstein & Co., Inc.  (Bernstein)  is an  investment  advisory firm
founded in 1967. As of October 31, 1999,  Bernstein  managed about $85.6 billion
in assets.  Two managers are responsible for overseeing  Bernstein's  portion of
the Fund.  MARILYN G. FEDAK,  Chief Investment  Officer and Chairman of the U.S.
Equity Investment Policy Group at Bernstein since 1993; has worked in investment
management  since 1972; has managed  portfolio  investments  since 1976;  joined
Bernstein in 1984; B.A., Smith College;  M.B.A., Harvard Business School. STEVEN
PISARKIEWICZ,  with Bernstein since 1989;  Senior Portfolio  Manager since 1997;
B.S., University of Missouri; M.B.A., University of California at Berkeley.

The manager  responsible for Vanguard's portion of the Fund is GEORGE U. SAUTER,
Managing  Director of Vanguard and head of Vanguard's Core Management Group; has
worked  in  investment   management  since  1985;  primary   responsibility  for
Vanguard's stock indexing policy and strategy since joining the company in 1987;
A.B., Dartmouth College; M.B.A., University of Chicago.

- --------------------------------------------------------------------------------



DIVIDENDS, CAPITAL GAINS, AND TAXES

FUND DISTRIBUTIONS
The Fund  distributes to shareholders  virtually all of its net income (interest
and dividends,  less  expenses),  as well as any capital gains realized from the
sale of its holdings.  Income  dividends  generally are  distributed in June and
December;  capital  gains  distributions  generally  occur in December.  You can
receive  distributions  of income dividends or capital gains in cash, or you can
have them automatically reinvested in more shares of the Fund.

BASIC TAX POINTS
Vanguard will send you a statement  each year showing the tax status of all your
distributions.  In addition,  taxable investors should be aware of the following
basic tax points:
- -    Distributions  are taxable to you whether or not you reinvest these amounts
     in additional Fund shares.
- -    Distributions   declared  in  December--if  paid  to  you  by  the  end  of
     January--are taxable as if received in December.


<PAGE>

                                                                              11


- -    Any dividends and short-term  capital gains that you receive are taxable to
     you as ordinary income for federal income tax purposes.
- -    Any  distributions  of net  long-term  capital  gains are taxable to you as
     long-term capital gains for federal income tax purposes, no matter how long
     you've owned shares in the Fund.
- -    Capital gains  distributions  may vary  considerably from year to year as a
     result of the Fund's normal investment activities and cash flows.
- -    A sale or exchange of Fund shares is a taxable  event.  This means that you
     may have a capital gain to report as income, or a capital loss to report as
     a deduction, when you complete your federal income tax return.
- -    State and local  income  taxes may apply to any  dividend or capital  gains
     distributions  that you  receive,  as well as your gains or losses from any
     sale or exchange of Fund shares.

GENERAL INFORMATION
BACKUP  WITHHOLDING.   By  law,  Vanguard  must  withhold  31%  of  any  taxable
distributions  or  redemptions  from your  account if you do not provide us with
your  correct  taxpayer  identification  number and certify  that it is correct.
Similarly,  Vanguard  must withhold from your account if the IRS instructs us to
do so.
FOREIGN  INVESTORS.  The Vanguard funds  generally do not offer their shares for
sale outside of the United States.  Foreign  investors should be aware that U.S.
withholding and estate taxes may apply to any investments in Vanguard funds.
INVALID  ADDRESSES.  If a dividend or capital gains distribution check mailed to
your address of record is returned as undeliverable, Vanguard will automatically
reinvest  all future  distributions  until you  provide us with a valid  mailing
address.
TAX CONSEQUENCES.  This prospectus provides general tax information only. If you
are investing through a tax-deferred retirement account, such as an IRA, special
tax rules apply. Please consult your tax adviser for detailed  information about
a fund's tax consequences for you.


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                               "BUYING A DIVIDEND"

Unless you are investing through a tax-deferred  retirement  account (such as an
IRA),  it is not to your  advantage  to buy shares of a fund  shortly  before it
makes a  distribution,  because  doing so can cost you money in  taxes.  This is
known as "buying a dividend."  For example:  on December 15, you invest  $5,000,
buying 250 shares for $20 each. If the fund pays a distribution  of $1 per share
on December 16, its share price would drop to $19 (not counting  market change).
You still have only $5,000 (250 shares x $19 = $4,750 in share  value,  plus 250
shares x $1 = $250 in  distributions),  but you owe tax on the $250 distribution
you  received--even  if you  reinvest  it in more  shares.  To avoid  "buying  a
dividend," check a fund's distribution schedule before you invest.
- --------------------------------------------------------------------------------

<PAGE>

12

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                  DISTRIBUTIONS

As a  shareholder,  you are  entitled  to your share of the fund's  income  from
interest and dividends, and gains from the sale of investments. You receive such
earnings as either an income  dividend or a capital gains  distribution.  Income
dividends come from both the dividends that the fund earns from its holdings and
the  interest it receives  from its money market and bond  investments.  Capital
gains are realized  whenever the fund sells securities for higher prices than it
paid for them. These capital gains are either short-term or long-term, depending
on whether the fund held the  securities  for one year or less, or more than one
year.

- --------------------------------------------------------------------------------

SHARE PRICE

The Fund's share price,  called its net asset value,  or NAV, is calculated each
business day after the close of regular  trading on the New York Stock  Exchange
(the NAV is not  calculated  on  holidays  or other  days when the  Exchange  is
closed).  Net asset  value per share is computed by adding up the total value of
the Fund's  investments  and other assets,  subtracting  any of its  liabilities
(debts), and then dividing by the number of Fund shares outstanding:


                      TOTAL ASSETS - LIABILITIES
NET ASSET VALUE =  -------------------------------
                     NUMBER OF SHARES OUTSTANDING

     Knowing the daily net asset value is useful to you as a shareholder because
it indicates the current value of your investment. The Fund's NAV, multiplied by
the  number of  shares  you own,  gives you the  dollar  amount  you would  have
received had you sold all of your shares back to the Fund that day.
     A NOTE ON PRICING:  The Fund's  investments  will be priced at their market
value when market  quotations are readily  available.  When these quotations are
not  readily  available,  investments  will  be  priced  at  their  fair  value,
calculated according to procedures adopted by the Fund's Board of Trustees.
     The Fund's  share price can be found  daily in the mutual fund  listings of
most major newspapers under the heading "Vanguard  Funds." Different  newspapers
use different abbreviations of the Fund's name, but the most common is WNDSR.

FINANCIAL HIGHLIGHTS

The following financial  highlights table is intended to help you understand the
Fund's financial  performance for the past five years,  and certain  information
reflects  financial  results for a single Fund share.  The total  returns in the
table represent the rate that an investor would have earned or lost each year on
an investment  in the Fund  (assuming  reinvestment  of all dividend and capital
gains  distributions).  This  information  has been derived  from the  financial
statements audited by PricewaterhouseCoopers LLP, independent accountants, whose
report--along  with the Fund's financial  statements--is  included in the Fund's
most recent annual report to  shareholders.  You may have the annual report sent
to you without charge by contacting Vanguard.


<PAGE>

                                                                              13

<TABLE>

- ----------------------------------------------------------------------------------------------
                                               VANGUARD WINDSOR FUND
                                               YEAR ENDED OCTOBER 31,
                        ----------------------------------------------------------------------
                           1999          1998          1997          1996          1995
- ----------------------------------------------------------------------------------------------
<S>                     <C>           <C>           <C>           <C>           <C>
NET ASSET VALUE,
 BEGINNING OF YEAR       $16.34        $19.55        $16.99        $15.55        $14.55
- ----------------------------------------------------------------------------------------------
INVESTMENT OPERATIONS
 Net Investment Income      .27           .23           .36           .43           .44
 Net Realized and
  Unrealized Gain
  (Loss) on Investments    1.77          (.32)         3.94          2.85          1.86
                        ----------------------------------------------------------------------
   Total from Investment
    Operations             2.04          (.09)         4.30          3.28          2.30
                        ----------------------------------------------------------------------
DISTRIBUTIONS
 Dividends from Net
  Investment Income        (.24)         (.24)         (.41)         (.46)         (.44)
 Distributions from
  Realized Capital Gains  (1.23)        (2.88)        (1.33)        (1.38)         (.86)
                        ----------------------------------------------------------------------
   Total Distributions    (1.47)        (3.12)        (1.74)        (1.84)        (1.30)
- ----------------------------------------------------------------------------------------------
NET ASSET VALUE, END
 OF YEAR                 $16.91        $16.34        $19.55        $16.99        $15.55
==============================================================================================

TOTAL RETURN             13.74%        -0.78%        27.04%        23.16%        17.80%
==============================================================================================

RATIOS/SUPPLEMENTAL DATA
 Net Assets, End of
  Year (Millions)       $16,824       $18,355       $20,678       $15,841       $13,008
 Ratio of Total
  Expenses to Average
  Net Assets              0.28%         0.27%         0.27%         0.31%         0.45%
 Ratio of Net
  Investment Income to
  Average Net Assets      1.56%         1.31%         1.89%         2.75%         3.01%
 Turnover Rate              56%           48%           61%           34%           32%
==============================================================================================

</TABLE>

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                   HOW TO READ THE FINANCIAL HIGHLIGHTS TABLE

The Fund began  fiscal 1999 with a net asset value  (price) of $16.34 per share.
During  the  year,  the Fund  earned  $0.27  per share  from  investment  income
(interest  and  dividends)  and  $1.77  per  share  from  investments  that  had
appreciated  in value or that were sold for higher prices than the Fund paid for
them.
Shareholders  received $1.47 per share in the form of dividend and capital gains
distributions.  A portion of each year's  distributions  may come from the prior
year's income or capital gains.
The  earnings  ($2.04  per  share)  minus the  distributions  ($1.47  per share)
resulted in a share price of $16.91 at the end of the year. This was an increase
of $0.57 per share (from  $16.34 at the  beginning  of the year to $16.91 at the
end of the year).  For a shareholder  who  reinvested the  distributions  in the
purchase of more shares, the total return from the Fund was 13.74% for the year.
As of October 31, 1999, the Fund had $16.8 billion in net assets.  For the year,
its expense ratio was 0.28% ($2.80 per $1,000 of net assets); and net investment
income  amounted  to 1.56%  of its  average  net  assets.  It sold and  replaced
securities valued at 56% of its net assets.

- --------------------------------------------------------------------------------




"Standard & Poor's (R),"  "S&P(R),"  "S&P 500(R),"  "Standard & Poor's 500," and
"500" are trademarks of The McGraw-Hill Companies, Inc. Frank Russell Company is
the owner of the trademarks and copyrights relating to the Russell Indexes.


<PAGE>

14

- --------------------------------------------------------------------------------
INVESTING WITH VANGUARD
Are you looking for the most  convenient  way to open or add money to a Vanguard
account?  Obtain instant access to fund information?  Establish an account for a
minor child or for your retirement savings?
     Vanguard  can help.  Our goal is to make it easy and pleasant for you to do
business with us.
     The following  sections of the prospectus briefly explain the many services
we offer.  Booklets providing detailed information are available on the services
marked with a [BOOKLET]. Please call us to request copies.
- --------------------------------------------------------------------------------

SERVICES AND ACCOUNT FEATURES
Vanguard  offers many services that make it convenient to buy, sell, or exchange
shares, or to obtain fund or account information.
- --------------------------------------------------------------------------------
TELEPHONE REDEMPTIONS (SALES AND EXCHANGES)
Automatically set up for this Fund unless you notify us otherwise.
- --------------------------------------------------------------------------------
VANGUARD (R) DIRECT DEPOSIT SERVICE [BOOKLET]
Automatic  method  for  depositing  your  paycheck  or U.S.  government  payment
(including Social Security and government pension checks) into your account.
- --------------------------------------------------------------------------------
VANGUARD(R) AUTOMATIC EXCHANGE SERVICE [BOOKLET]
Automatic  method for  moving a fixed  amount of money  from one  Vanguard  fund
account to another.
- --------------------------------------------------------------------------------
VANGUARD FUND EXPRESS(R) [BOOKLET]
Electronic  method for buying or selling shares.  You can transfer money between
your  Vanguard  fund account and an account at your bank,  savings and loan,  or
credit union on a systematic schedule or whenever you wish.
- --------------------------------------------------------------------------------
VANGUARD DIVIDEND EXPRESS (TM) [BOOKLET]
Electronic method for transferring  dividend and/or capital gains  distributions
directly  from your  Vanguard  fund account to your bank,  savings and loan,  or
credit union account.
- --------------------------------------------------------------------------------
VANGUARD TELE-ACCOUNT(R) 1-800-662-6273 (ON-BOARD) [BOOKLET]

Toll-free  24-hour access to Vanguard fund and account  information--as  well as
some  transactions--by  using any touch-tone phone.  Tele-Account provides total
return,  share price, price change, and yield quotations for all Vanguard funds;
gives your account balances and history (e.g., last transaction, latest dividend
distribution);  and  allows  you to sell or  exchange  shares  to and from  most
Vanguard funds.

- --------------------------------------------------------------------------------
ACCESS VANGUARD(TM) www.vanguard.com [COMPUTER]

You can use your  personal  computer to perform  certain  transactions  for most
Vanguard  funds by accessing our website.  To establish  this service,  you must
register  through our website.  We will then mail you an account access password
that  allows  you  to  process  the  following   financial  and   administrative
transactions online:

- -    Open a new account.*
- -    Buy, sell, or exchange shares of most funds.
- -    Change your name/address.

<PAGE>

                                                                              15


- -    Add/change fund options (including dividend options, Vanguard Fund Express,
     bank instructions,  checkwriting, and Vanguard Automatic Exchange Service).
     (Some  restrictions may apply.) Please call our Client Services  Department
     for assistance.


*Only current Vanguard shareholders can open a new account online, by exchanging
 shares from other existing Vanguard accounts.
- --------------------------------------------------------------------------------
INVESTOR INFORMATION DEPARTMENT: 1-800-662-7447 (SHIP) TEXT TELEPHONE:
1-800-952-3335
Call  Vanguard for  information  on our funds,  fund  services,  and  retirement
accounts, and to request literature.
- --------------------------------------------------------------------------------

CLIENT SERVICES DEPARTMENT: 1-800-662-2739 (CREW) TEXT TELEPHONE: 1-800-749-7273

Call Vanguard for information on your account, account transactions, and account
statements.
- --------------------------------------------------------------------------------
SERVICES  FOR  CLIENTS  OF  VANGUARD'S  INSTITUTIONAL  DIVISION:  1-888-809-8102
Vanguard's  Institutional  Division offers a variety of specialized services for
large  institutional   investors,   including  the  ability  to  effect  account
transactions through private electronic networks and third-party recordkeepers.
- --------------------------------------------------------------------------------

TYPES OF ACCOUNTS

Individuals and institutions can establish a variety of accounts with Vanguard.
- --------------------------------------------------------------------------------
FOR ONE OR MORE PEOPLE
Open an account in the name of one (individual) or more (joint tenants) people.
- --------------------------------------------------------------------------------
FOR HOLDING PERSONAL TRUST ASSETS [BOOKLET]
Invest assets held in an existing personal trust.
- --------------------------------------------------------------------------------
FOR INDIVIDUAL RETIREMENT ACCOUNTS [BOOKLET]
Open a  traditional  IRA account or a Roth IRA  account.  Eligibility  and other
requirements  are  established  by federal law and  Vanguard  custodial  account
agreements. For more information, please call 1-800-662-7447 (SHIP).
- --------------------------------------------------------------------------------
FOR AN ORGANIZATION [BOOKLET]
Open an account as a corporation,  partnership,  endowment, foundation, or other
entity.
- --------------------------------------------------------------------------------
FOR THIRD-PARTY TRUSTEE RETIREMENT INVESTMENTS
Open an account as a retirement trust or plan based on an existing  corporate or
institutional  plan.  These  accounts  are  established  by the  trustee  of the
existing plan.
- --------------------------------------------------------------------------------
VANGUARD PROTOTYPE PLANS
Open a  variety  of  retirement  accounts  using  Vanguard  prototype  plans for
individuals,  sole proprietorships,  and small businesses. For more information,
please call 1-800-662-2003.
- --------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
A NOTE ON INVESTING WITH VANGUARD THROUGH OTHER FIRMS
You may purchase or sell Fund shares through a financial  intermediary such as a
bank,  broker,  or investment  adviser.  If you invest with Vanguard  through an
intermediary,  please read that firm's program  materials  carefully to learn of
any  special  rules  that may apply.  For  example,  special  terms may apply to
additional service features, fees, or other policies.  Consult your intermediary
to determine when your order will be priced.
- --------------------------------------------------------------------------------
<PAGE>

16

BUYING SHARES

You buy your shares at the Fund's next-determined net asset value after Vanguard
receives your request.  As long as your request is received  before the close of
trading on the New York Stock Exchange,  generally 4 p.m. Eastern time, you will
buy your shares at that day's net asset value.
- --------------------------------------------------------------------------------
MINIMUM INVESTMENT TO . . .
open a new account
$3,000 (regular account); $1,000 (traditional IRAs and Roth IRAs).

add to an existing account
$100 by mail or exchange; $1,000 by wire.
- --------------------------------------------------------------------------------
A NOTE ON LOW BALANCES

The Fund  reserves  the  right to close any  nonretirement  fund  account  whose
balance falls below the minimum initial  investment.  The Fund will deduct a $10
annual fee in June if your  nonretirement  account balance at that time is below
$2,500.  The low balance fee is waived for investors who have aggregate Vanguard
account assets of $50,000 or more.

- --------------------------------------------------------------------------------
BY MAIL TO . . . [ENVELOPE]
open a new account

Complete and sign the account registration form and enclose your check.

add to an existing account
Mail your check with an  Invest-By-Mail  form  detached  from your  confirmation
statement to the address listed on the form. Please do not alter  Invest-By-Mail
forms, since they are fund- and account-specific.

Make your check payable to: The Vanguard Group-22
All  purchases  must be made in U.S.  dollars,  and checks must be drawn on U.S.
banks.

First-class mail to:           Express or Registered mail to:
The Vanguard Group             The Vanguard Group
P.O. Box 1110                  455 Devon Park Drive
Valley Forge, PA 19482-1110    Wayne, PA 19087-1815

For clients of Vanguard's Institutional Division . . .

First-class mail to:           Express or Registered mail to:
The Vanguard Group             The Vanguard Group
P.O. Box 2900                  455 Devon Park Drive
Valley Forge, PA 19482-2900    Wayne, PA 19087-1815
- --------------------------------------------------------------------------------
IMPORTANT  NOTE:  To prevent  check fraud,  Vanguard will not accept checks made
payable to third parties.
- --------------------------------------------------------------------------------
BY TELEPHONE TO . . . [TELEPHONE]
open a new account

Call Vanguard  Tele-Account*  24 hours a day--or Client Services during business
hours--to exchange from another Vanguard fund account with the same registration
(name, address,  taxpayer  identification  number, and account type). (Note that
some restrictions apply to index fund accounts.)


<PAGE>

                                                                              17

add to an existing account

Call Vanguard  Tele-Account*  24 hours a day--or Client Services during business
hours--to exchange from another Vanguard fund account with the same registration
(name, address,  taxpayer  identification  number, and account type). (Note that
some restrictions  apply to index fund accounts.) Use Vanguard Fund Express (see
"Services and Account Features") to transfer assets from your bank account. Call
Client Services before your first use to verify that this option is available.

Vanguard Tele-Account          Client Services
1-800-662-6273                 1-800-662-2739

*You must obtain a Personal  Identification Number through Tele-Account at least
 seven days before you request your first exchange.
- --------------------------------------------------------------------------------

IMPORTANT  NOTE:  Once  you  have  initiated  a  telephone   transaction  and  a
confirmation  number has been assigned,  the transaction  cannot be revoked.  We
reserve the right to refuse any purchase request.

- --------------------------------------------------------------------------------
BY WIRE TO OPEN A NEW ACCOUNT OR ADD TO AN EXISTING ACCOUNT [WIRE]

Call Client  Services to arrange your wire  transaction.  Wire  transactions  to
retirement  accounts are only  available for asset  transfers and rollovers from
other financial institutions.  Individual IRA contributions will not be accepted
by wire.

Wire to:
FRB ABA 021001088
HSBC Bank USA

For credit to:
Account: 000112046
Vanguard Incoming Wire Account

In favor of:
Vanguard Windsor Fund-22
[Account number, or temporary number for a new account]

[Registered account owner(s)]

[Registered address]
- --------------------------------------------------------------------------------

You can redeem (that is, sell or exchange) shares purchased by check or Vanguard
Fund  Express  at any time.  However,  while  your  redemption  request  will be
processed  at the  next-determined  net asset value after it is  received,  your
redemption  proceeds  will not be available  until  payment for your purchase is
collected, which may take up to ten calendar days.

- --------------------------------------------------------------------------------

A NOTE ON LARGE  PURCHASES
It is important that you call Vanguard  before you invest a large dollar amount.
It is our responsibility to consider the interests of all Fund shareholders, and
so we  reserve  the right to refuse any  purchase  that may  disrupt  the Fund's
operation or performance.

- --------------------------------------------------------------------------------

<PAGE>

18

REDEEMING SHARES

This section describes how you can redeem--that is, sell or exchange--the Fund's
shares.

When Selling Shares:
- -    Vanguard sends the redemption proceeds to you or a designated third party.*
- -    You can sell all or part of your Fund shares at any time.

*May require a signature guarantee; see footnote on page 21.

When Exchanging Shares:
- -    The redemption proceeds are used to purchase shares of a different Vanguard
     fund.
- -    You must meet the receiving fund's minimum investment requirements.
- -    Vanguard reserves the right to revise or terminate the exchange  privilege,
     limit the amount of an exchange, or reject an exchange at any time, without
     notice.
- -    In  order  to  exchange  into  an  account  with a  different  registration
     (including a different name, address, or taxpayer  identification  number),
     you must include the guaranteed signatures of all current account owners on
     your written instructions.

In both  cases,  your  transaction  will be based on the Fund's  next-determined
share price, subject to any special rules discussed in this prospectus.
- --------------------------------------------------------------------------------
NOTE:  Once a redemption  is initiated  and a  confirmation  number  given,  the
transaction CANNOT be canceled.

- --------------------------------------------------------------------------------

HOW TO REQUEST A REDEMPTION

You can request a  redemption  from your Fund  account in any one of three ways:
online, by telephone, or by mail.

     The Vanguard funds whose shares you cannot  exchange online or by telephone
are VANGUARD U.S.  STOCK INDEX FUNDS,  VANGUARD  BALANCED  INDEX FUND,  VANGUARD
INTERNATIONAL  STOCK INDEX FUNDS,  VANGUARD REIT INDEX FUND, and VANGUARD GROWTH
AND INCOME FUND. These funds do, however,  permit online and telephone exchanges
within  IRAs and other  retirement  accounts.  If you sell shares of these funds
online, you will receive a redemption check at your address of record.
- --------------------------------------------------------------------------------
ONLINE REQUESTS [COMPUTER]
ACCESS VANGUARD at www.vanguard.com
You can use your personal  computer to sell or exchange  shares of most Vanguard
funds by accessing our website.  To establish  this  service,  you must register
through our website.  We will then mail you an account access password that will
enable  you to sell  or  exchange  shares  online  (as  well  as  perform  other
transactions).

- --------------------------------------------------------------------------------
TELEPHONE REQUESTS [TELEPHONE]
All Account Types Except Retirement:
Call Vanguard  Tele-Account  24 hours a day--or Client  Services during business
hours-- to sell or exchange  shares.  You can exchange  shares from this Fund to
open an account in another Vanguard fund or to add to an existing  Vanguard fund
account with an identical registration.

Retirement Accounts:
You can  exchange--but  not  sell--shares  by  calling  Tele-Account  or  Client
Services.

<PAGE>

                                                                              19

Vanguard Tele-Account          Client Services
1-800-662-6273                 1-800-662-2739
- --------------------------------------------------------------------------------
SPECIAL  INFORMATION:  We will automatically  establish the telephone redemption
option for your  account,  unless you instruct us  otherwise  in writing.  While
telephone  redemption is easy and convenient,  this account  feature  involves a
risk of loss from  unauthorized or fraudulent  transactions.  Vanguard will take
reasonable  precautions  to protect your  account from fraud.  You should do the
same by keeping your account information  private and immediately  reviewing any
account  statements  that  we  send  to  you.  Make  sure  to  contact  Vanguard
immediately about any transaction you believe to be unauthorized.
- --------------------------------------------------------------------------------
We reserve the right to refuse a telephone redemption if the caller is unable to
provide:
- -    The ten-digit account number.
- -    The name and address exactly as registered on the account.
- -    The primary Social Security or employer identification number as registered
     on the account.

- -    The  Personal   Identification   Number,   if  applicable   (for  instance,
     Tele-Account).

     Please note that Vanguard will not be  responsible  for any account  losses
due to telephone  fraud, so long as we have taken reasonable steps to verify the
caller's identity.  If you wish to remove the telephone  redemption feature from
your account, please notify us in writing.
- --------------------------------------------------------------------------------
A NOTE ON  UNUSUAL  CIRCUMSTANCES
Vanguard  reserves the right to revise or  terminate  the  telephone  redemption
privilege at any time,  without notice.  In addition,  Vanguard can stop selling
shares or postpone  payment at times when the New York Stock  Exchange is closed
or under any emergency  circumstances  as determined by the U.S.  Securities and
Exchange Commission.  If you experience difficulty making a telephone redemption
during  periods  of  drastic  economic  or market  change,  you can send us your
request  by  regular or express  mail.  Follow  the  instructions  on selling or
exchanging shares by mail in this section.
- --------------------------------------------------------------------------------
MAIL REQUESTS [ENVELOPE]
All Account Types Except Retirement:
Send a letter of instruction signed by all registered  account holders.  Include
the fund name and  account  number and (if you are  selling) a dollar  amount or
number  of shares  OR (if you are  exchanging)  the name of the fund you want to
exchange  into and a dollar  amount or number of  shares.  To  exchange  into an
account  with a different  registration  (including a different  name,  address,
taxpayer identification number, or account type), you must provide Vanguard with
written  instructions  that  include the  guaranteed  signatures  of all current
owners of the fund from which you wish to redeem.

Vanguard Retirement Accounts:
For information on how to request distributions from:
- -    Traditional IRAs and Roth IRAs--call Client Services.
- -    SEP-IRAs, SIMPLE IRAs, 403(b)(7) custodial accounts, and Profit-Sharing and
     Money Purchase Pension (Keogh) Plans--call  Individual  Retirement Plans at
     1-800-662-2003.

Depending on your account  registration  type,  additional  documentation may be
required.

<PAGE>

20


First-class mail to:           Express or Registered mail to:
The Vanguard Group             The Vanguard Group
P.O. Box 1110                  455 Devon Park Drive
Valley Forge, PA 19482-1110    Wayne, PA 19087-1815

For clients of Vanguard's Institutional Division . . .

First-class mail to:           Express or Registered mail to:
The Vanguard Group             The Vanguard Group
P.O. Box 2900                  455 Devon Park Drive
Valley Forge, PA 19482-2900    Wayne, PA 19087-1815
- --------------------------------------------------------------------------------
A NOTE ON LARGE REDEMPTIONS

It is important that you call Vanguard  before you redeem a large dollar amount.
It is our responsibility to consider the interests of all fund shareholders, and
so we reserve the right to delay  delivery of your  redemption  proceeds--up  to
seven days--if the amount may disrupt the Fund's operation or performance.
     If you redeem more than  $250,000  worth of Fund  shares  within any 90-day
period,  the  Fund  reserves  the  right  to pay  part or all of the  redemption
proceeds above $250,000  in-kind,  i.e., in securities,  rather than in cash. If
payment is made in-kind,  you may incur  brokerage  commissions  if you elect to
sell the securities for cash.
- --------------------------------------------------------------------------------

OPTIONS FOR REDEMPTION PROCEEDS
You may receive your redemption  proceeds in one of three ways: check,  exchange
to another Vanguard fund, or Fund Express redemption.

- --------------------------------------------------------------------------------
CHECK REDEMPTIONS
Normally,  Vanguard  will  mail  your  check  within  two  business  days  of  a
redemption.
- --------------------------------------------------------------------------------
EXCHANGE REDEMPTIONS
As described  above, an exchange  involves using the proceeds of your redemption
to purchase shares of another Vanguard fund.
- --------------------------------------------------------------------------------

FUND EXPRESS REDEMPTIONS
Vanguard  will  electronically  transfer  funds to your  pre-linked  checking or
savings account.

- --------------------------------------------------------------------------------
FOR OUR MUTUAL PROTECTION
For your best interests and ours, Vanguard applies these additional requirements
to redemptions:

REQUEST IN "GOOD ORDER"
All redemption requests must be received by Vanguard in "good order." This means
that your request must include:
- -    The Fund name and account number.
- -    The amount of the transaction (in dollars or shares).
- -    Signatures  of all owners  exactly as  registered  on the account (for mail
     requests).
- -    Signature  guarantees (if required).*
- -    Any supporting legal documentation that may be required.
- -    Any outstanding certificates representing shares to be redeemed.

<PAGE>

                                                                              21


*For instance,  a signature guarantee must be provided by all registered account
 shareholders  when redemption  proceeds are to be sent to a different person or
 address. A signature guarantee can be obtained from most commercial and savings
 banks,  credit  unions,  trust  companies, or  member firms  of  a  U.S.  stock
 exchange.

TRANSACTIONS ARE PROCESSED AT THE NEXT-DETERMINED SHARE PRICE AFTER VANGUARD HAS
RECEIVED ALL REQUIRED INFORMATION.
- --------------------------------------------------------------------------------
LIMITS ON ACCOUNT ACTIVITY
Because  excessive account  transactions can disrupt  management of the Fund and
increase the Fund's costs for all shareholders, Vanguard limits account activity
as follows:
- -    You may make no more than TWO  SUBSTANTIVE  "ROUND TRIPS"  THROUGH THE FUND
     during any 12-month period.
- -    Your round trips through the Fund must be at least 30 days apart.
- -    The Fund may refuse a share purchase at any time, for any reason.
- -    Vanguard may revoke an investor's telephone exchange privilege at any time,
     for any reason.

A "round trip" is a redemption  from the Fund  followed by a purchase  back into
the  Fund.  Also,  a  "round  trip"  covers  transactions  accomplished  by  any
combination  of methods,  including  transactions  conducted by check,  wire, or
exchange to/from another Vanguard fund. "Substantive" means a dollar amount that
Vanguard  determines,  in  its  sole  discretion,  could  adversely  affect  the
management of the Fund.

- --------------------------------------------------------------------------------
RETURN YOUR SHARE CERTIFICATES
Any portion of your account represented by share certificates cannot be redeemed
until you return the  certificates  to Vanguard.  Certificates  must be returned
(unsigned),  along with a letter  requesting  the sale or  exchange  you wish to
process, via certified mail to:

The Vanguard Group
455 Devon Park Drive
Wayne, PA 19087-1815
- --------------------------------------------------------------------------------

ALL TRADES ARE FINAL
Vanguard  will not cancel any  transaction  request  (including  any purchase or
redemption)  that we believe to be authentic once the request has been initiated
and a confirmation number assigned.
- --------------------------------------------------------------------------------
UNCASHED CHECKS
Please cash your distribution or redemption  checks promptly.  Vanguard will not
pay interest on uncashed checks.

- --------------------------------------------------------------------------------

TRANSFERRING REGISTRATION

You can  transfer  the  registration  of your Fund  shares to  another  owner by
completing a transfer form and sending it to Vanguard.

First-class mail to:           Express or Registered mail to:
The Vanguard Group             The Vanguard Group
P.O. Box 1110                  455 Devon Park Drive
Valley Forge, PA 19482-1110    Wayne, PA 19087-1815

<PAGE>

22

For clients of Vanguard's Institutional Division . . .

First-class mail to:           Express or Registered mail to:
The Vanguard Group             The Vanguard Group
P.O. Box 2900                  455 Devon Park Drive
Valley Forge, PA 19482-2900    Wayne, PA 19087-1815
- --------------------------------------------------------------------------------

FUND AND ACCOUNT UPDATES

STATEMENTS AND REPORTS
We will send you account and tax  statements to help you keep track of your Fund
account  throughout  the year as well as when you are preparing  your income tax
returns.

     In addition,  you will  receive  financial  reports  about the Fund twice a
year.  These   comprehensive   reports  include  an  assessment  of  the  Fund's
performance  (and a comparison  to its industry  benchmark),  an overview of the
financial  markets,  a  report  from  the  advisers,  and the  Fund's  financial
statements which include a listing of the Fund's holdings.
     To keep  the  Fund's  costs  as low as  possible  (so  that  you and  other
shareholders can keep more of the Fund's investment earnings), Vanguard attempts
to  eliminate  duplicate  mailings  to the same  address.  When two or more Fund
shareholders  have the same last name and address,  we send just one Fund report
to that address--instead of mailing separate reports to each shareholder. If you
want us to send  separate  reports,  notify our Client  Services  Department  at
1-800-662-2739.

- --------------------------------------------------------------------------------
CONFIRMATION STATEMENT
Sent each time you buy,  sell, or exchange  shares;  confirms the trade date and
the amount of your transaction.
- --------------------------------------------------------------------------------
PORTFOLIO SUMMARY [BOOKLET]
Mailed  quarterly for most  accounts;  shows the market value of your account at
the close of the statement period, as well as distributions,  purchases,  sales,
and exchanges for the current calendar year.
- --------------------------------------------------------------------------------
FUND FINANCIAL REPORTS
Mailed in December and June for this Fund.
- --------------------------------------------------------------------------------
TAX STATEMENTS
Generally  mailed in January;  report previous year's dividend and capital gains
distributions,  proceeds from the sale of shares, and distributions from IRAs or
other retirement accounts.
- --------------------------------------------------------------------------------
AVERAGE COST REVIEW STATEMENT [BOOKLET]

Issued quarterly for most taxable accounts (accompanies your Portfolio Summary);
shows the average  cost of shares that you redeemed  during the  calendar  year,
using only the average cost single category method.

- --------------------------------------------------------------------------------

<PAGE>

                     (THIS PAGE INTENTIONALLY LEFT BLANK.)

<PAGE>

                     (THIS PAGE INTENTIONALLY LEFT BLANK.)

<PAGE>

GLOSSARY OF INVESTMENT TERMS

CAPITAL GAINS DISTRIBUTION
Payment to mutual fund  shareholders  of gains  realized on securities  that the
fund has sold at a profit, minus any realized losses.

CASH RESERVES
Cash deposits,  short-term bank deposits,  and money market  instruments,  which
include U.S.  Treasury bills,  bank  certificates  of deposit (CDs),  repurchase
agreements, commercial paper, and banker's acceptances.

COMMON STOCK
A security  representing  ownership  rights in a  corporation.  A stockholder is
entitled  to share in the  company's  profits,  some of which may be paid out as
dividends.



DIVIDEND INCOME
Payment to  shareholders  of income from  interest or  dividends  generated by a
fund's investments.

EXPENSE RATIO
The  percentage  of a fund's  average net assets used to pay its  expenses.  The
expense ratio  includes  management  fees,  administrative  fees,  and any 12b-1
distribution fees.

FUND DIVERSIFICATION
Holding a variety of securities so that a fund's return is not badly hurt by the
poor performance of a single security, industry, or country.

GROWTH STOCK FUND
A mutual fund that emphasizes stocks of companies believed to have above-average
prospects for growth.  Reflecting market  expectations for superior growth,  the
prices of  growth  stocks  often are  relatively  high in  comparison  with such
factors as revenue, earnings, book value, and dividends.

INVESTMENT ADVISER
An  organization  that  makes  the  day-to-day   decisions  regarding  a  fund's
investments.

MUTUAL FUND
An  investment  company  that pools the money of many people and invests it in a
variety of securities in an effort to achieve a specific objective over time.

NET ASSET VALUE (NAV)
The market value of a mutual fund's total assets, minus liabilities,  divided by
the  number of shares  outstanding.  The value of a single  share is called  its
share value or share price.

PRICE/EARNINGS (P/E) RATIO
The current share price of a stock,  divided by its per-share earnings (profits)
from the past year. A stock selling for $20, with earnings of $2 per share,  has
a price/earnings ratio of 10.

PRINCIPAL
The amount of money you put into an investment.

SECURITIES
Stocks, bonds, and other investment vehicles.

TOTAL RETURN
A percentage change,  over a specified time period, in a mutual fund's net asset
value,  with the ending net asset value adjusted to account for the reinvestment
of all distributions of dividends and capital gains.

VALUE STOCK FUND
A mutual fund that  emphasizes  stocks of companies  whose growth  prospects are
generally   regarded  as  subpar  by  the  market.   Reflecting   these   market
expectations,  the  prices  of  value  stocks  typically  are  below-average  in
comparison with such factors as revenue, earnings, book value, and dividends.

VOLATILITY
The  fluctuations  in value of a mutual  fund or other  security.  The greater a
fund's volatility, the wider the fluctuations between its high and low prices.

YIELD
Income  (interest  or  dividends)  earned  by  an  investment,  expressed  as  a
percentage of the investment's price.

<PAGE>

                                                  [THE VANGUARD GROUP(R) LOGO]

                                                     Post Office Box 2600
                                                     Valley Forge, PA 19482-2600


FOR MORE INFORMATION
If you'd like more information about
Vanguard Windsor Fund, the
following documents are available
free upon request:

ANNUAL/SEMIANNUAL REPORT TO
SHAREHOLDERS
Additional information about the
Fund's investments is available in
the Fund's annual and semiannual
reports to shareholders. In these
reports, you will find a discussion
of the market conditions and
investment strategies that
significantly affected the Fund's
performance during the most recent
fiscal year.

STATEMENT OF ADDITIONAL
INFORMATION (SAI)
The SAI provides more detailed
information about the Fund.

The current annual and semiannual
reports and the SAI are
incorporated by reference into
(and are thus legally a part of)
this prospectus.

To receive a free copy of the latest
annual or semiannual report or the
SAI, or to request additional
information about the Fund or other
Vanguard funds, please contact us
as follows:

THE VANGUARD GROUP
INVESTOR INFORMATION
DEPARTMENT
P.O. BOX 2600
VALLEY FORGE, PA 19482-2600

TELEPHONE:
1-800-662-7447 (SHIP)

TEXT TELEPHONE:
1-800-952-3335

WORLD WIDE WEB:
WWW.VANGUARD.COM

If you are a current Fund shareholder
and would like information about
your account, account transactions,
and/or account statements,
please call:

CLIENT SERVICES DEPARTMENT
TELEPHONE:
1-800-662-2739 (CREW)

TEXT TELEPHONE:
1-800-749-7273

INFORMATION PROVIDED BY THE
SECURITIES AND EXCHANGE
COMMISSION (SEC)
You can review and copy
information about the Fund
(including the SAI) at the SEC's
Public Reference Room in
Washington, DC. To find out more
about this public service, call the
SEC at 1-800-SEC-0330. Reports and
other information about the Fund are
also available on the SEC's website
(www.sec.gov), or you can receive
copies of this information, for a fee,
by writing the Public Reference
Section, Securities and Exchange
Commission, Washington, DC
20549-6009.

Fund's Investment Company Act
file number: 811-834


(C) 2000 The Vanguard Group, Inc.
All rights reserved.
Vanguard Marketing Corporation,
Distributor.

P022N-02/18/2000

<PAGE>


VANGUARD(R)
WINDSOR(TM) FUND

Participant Prospectus
February 18, 2000


This prospectus contains
financial data for the
Fund through the
fiscal year ended
October 31, 1999.


[A MEMBER OF
THE VANGUARD GROUP LOGO]

<PAGE>

VANGUARD WINDSOR FUND
Participant Prospectus

February 18, 2000

A Growth and Income Stock Mutual Fund
- --------------------------------------------------------------------------------
CONTENTS
- --------------------------------------------------------------------------------
 1 FUND PROFILE                           10 DIVIDENDS, CAPITAL GAINS, AND TAXES

 3 ADDITIONAL INFORMATION                 11 SHARE PRICE

 3 A WORD ABOUT RISK                      11 FINANCIAL HIGHLIGHTS

 3 WHO SHOULD INVEST                      13 INVESTING WITH VANGUARD

 4 PRIMARY INVESTMENT STRATEGIES          14 ACCESSING FUND INFORMATION BY
                                             COMPUTER
 8 THE FUND AND VANGUARD
                                          GLOSSARY (inside back cover)
 9 INVESTMENT ADVISERS
- --------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
WHY READING THIS PROSPECTUS IS IMPORTANT
This  prospectus  explains  the  objective,  risks,  and  strategies of Vanguard
Windsor  Fund.  To  highlight  terms  and  concepts  important  to  mutual  fund
investors,  we have  provided  "Plain  Talk(R)"  explanations  along  the way.
Reading the  prospectus  will help  you to decide  whether the Fund is the right
investment for you. We suggest that you keep it for future reference.
- --------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
IMPORTANT NOTE
This prospectus is intended for participants in employer-sponsored retirement or
savings plans. Another version--for  investors who would like to open a personal
investment account--can be obtained by calling Vanguard at 1-800-662-7447.
- --------------------------------------------------------------------------------

NEITHER  THE  SECURITIES  AND  EXCHANGE  COMMISSION  NOR  ANY  STATE  SECURITIES
COMMISSION HAS APPROVED OR  DISAPPROVED  OF THESE  SECURITIES OR PASSED UPON THE
ACCURACY OR ADEQUACY OF THIS PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A
CRIMINAL OFFENSE.

<PAGE>

                                                                               1

FUND PROFILE

The following profile summarizes key features of Vanguard Windsor Fund.

INVESTMENT OBJECTIVE

The Fund seeks to provide long-term growth of capital. As a secondary objective,
the Fund seeks to provide some dividend income.

INVESTMENT STRATEGIES
The Fund invests primarily in large- and medium-size  companies whose stocks are
considered  by the Fund's  adviser  to be  undervalued.  Undervalued  stocks are
generally  those that are out of favor with  investors and currently  trading at
prices that, the adviser feels,  are below what the stocks are worth in relation
to   their   earnings.    These   stocks    typically--but    not   always--have
lower-than-average  price/earnings (P/E) ratios and higher-than-average dividend
yields.

PRIMARY RISKS
THE FUND'S TOTAL RETURN,  LIKE STOCK PRICES  GENERALLY,  WILL FLUCTUATE WITHIN A
WIDE RANGE, SO AN INVESTOR COULD LOSE MONEY OVER SHORT OR EVEN LONG PERIODS. The
Fund is also subject to:
- -    Investment  style risk,  which is the chance that  returns  from large- and
     mid-capitalization  value stocks will trail  returns from the overall stock
     market.
- -    Manager risk,  which is the chance that poor security  selection will cause
     the Fund to underperform other funds with similar investment objectives.

PERFORMANCE/RISK INFORMATION

The bar chart and table below  provide an indication of the risk of investing in
the Fund. The bar chart shows the Fund's  performance in each calendar year over
a ten-year  period.  The table shows how the Fund's average annual total returns
for one,  five,  and ten  calendar  years  compare  with those of a  broad-based
securities  market index. Keep in mind that the Fund's past performance does not
indicate how it will perform in the future.

            ----------------------------------------------------
                              ANNUAL TOTAL RETURNS
                              1990         -15.50%
                              1991          28.55%
                              1992          16.50%
                              1993          19.37%
                              1994          -0.15%
                              1995          30.15%
                              1996          26.36%
                              1997          21.97%
                              1998           0.81%
                              1999          11.57%
            ----------------------------------------------------

     During the period shown in the bar chart, the highest return for a calendar
quarter was 18.25%  (quarter  ended March 31, 1991) and the lowest  return for a
quarter was -20.34% (quarter ended September 30, 1990).


<PAGE>

2


      --------------------------------------------------------------------
        AVERAGE ANNUAL TOTAL RETURNS FOR YEARS ENDED DECEMBER 31, 1999
      --------------------------------------------------------------------
                                        1 YEAR      5 YEARS      10 YEARS
      --------------------------------------------------------------------
      Vanguard Windsor Fund             11.57%       17.67%       13.03%
      Standard & Poor's 500 Index       21.04        28.56        18.21
      --------------------------------------------------------------------

FEES AND EXPENSES
The following table describes the fees and expenses you would pay if you buy and
hold shares of the Fund. The expenses shown under Annual Fund Operating Expenses
are based upon those incurred in the fiscal year ended October 31, 1999.

      SHAREHOLDER FEES (fees paid directly from your investment)
      Sales Charge (Load) Imposed on Purchases:              None
      Sales Charge (Load) Imposed on Reinvested Dividends:   None
      Redemption Fee:                                        None
      Exchange Fee:                                          None

      ANNUAL FUND OPERATING EXPENSES (expenses deducted from the
      Fund's assets)
      Management Expenses:                                  0.26%
      12b-1 Distribution Fee:                                None
      Other Expenses:                                       0.02%
       TOTAL ANNUAL FUND OPERATING EXPENSES:                0.28%


     The following example is intended to help you compare the cost of investing
in the Fund with the cost of investing in other mutual funds. It illustrates the
hypothetical  expenses  that you would incur over various  periods if you invest
$10,000 in the Fund.  This example assumes that the Fund provides a return of 5%
a year, and that operating  expenses  remain the same. The results apply whether
or not you redeem your investment at the end of each period.

            ----------------------------------------------------
               1 YEAR      3 YEARS     5 YEARS      10 YEARS
            ----------------------------------------------------
                 $29         $90        $157          $356
            ----------------------------------------------------

     THIS  EXAMPLE  SHOULD NOT BE  CONSIDERED  TO REPRESENT  ACTUAL  EXPENSES OR
PERFORMANCE  FROM THE PAST OR FOR THE  FUTURE.  ACTUAL  FUTURE  EXPENSES  MAY BE
HIGHER OR LOWER THAN THOSE SHOWN.

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                  FUND EXPENSES

All mutual funds have operating  expenses.  These  expenses,  which are deducted
from a fund's gross  income,  are expressed as a percentage of the net assets of
the fund.  Vanguard  Windsor Fund's expense ratio in fiscal year 1999 was 0.28%,
or $2.80 per $1,000 of average net assets.  The average  multi-cap  value mutual
fund had  expenses in 1999 of 1.38%,  or $13.80 per $1,000 of average net assets
(derived  from data  provided as of  December  31,  1999 by Lipper  Inc.,  which
reports on the mutual fund industry).  Management  expenses,  which comprise one
part of operating  expenses,  include investment  advisory fees as well as other
costs of managing a fund--such as account  maintenance,  reporting,  accounting,
legal, and other administrative expenses.

- --------------------------------------------------------------------------------

<PAGE>

                                                                               3

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                             THE COSTS OF INVESTING

Costs are an important  consideration in choosing a mutual fund.  That's because
you, as a shareholder,  pay the costs of operating a fund,  plus any transaction
costs  associated with the fund's buying and selling of securities.  These costs
can erode a substantial  portion of the gross income or capital  appreciation  a
fund achieves. Even seemingly small differences in expenses can, over time, have
a dramatic effect on a fund's performance.
- --------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
ADDITIONAL INFORMATION

DIVIDENDS AND CAPITAL GAINS               NET ASSETS AS OF OCTOBER 31, 1999
Dividends are distributed semiannually    $16.8 billion
in June and December; capital gains, if
any, are distributed in December          NEWSPAPER ABBREVIATION
                                          Wndsr
INVESTMENT ADVISERS
- - Wellington Management Company, LLP,     VANGUARD FUND NUMBER
  Boston, Mass., since inception          022
- - Sanford C. Bernstein & Co., Inc., New
  York, N.Y., since June 1, 1999          CUSIP NUMBER
- - The Vanguard Group, Valley Forge, Pa.   922018106

INCEPTION DATE                            TICKER SYMBOL
October 23, 1958                          VWNDX

- --------------------------------------------------------------------------------

================================================================================
A WORD ABOUT RISK

This  prospectus  describes  risks you would  face as an  investor  in  Vanguard
Windsor  Fund.  It is  important  to keep  in mind  one of the  main  axioms  of
investing: The higher the risk of losing money, the higher the potential reward.
The  reverse,  also,  is  generally  true:  The lower  the  risk,  the lower the
potential  reward.  As you consider an investment in Vanguard  Windsor Fund, you
should also take into account your personal tolerance for the daily fluctuations
of the stock market.

     Look for this [FLAG] symbol  throughout the prospectus.  It is used to mark
detailed  information  about  each  type of risk that you  would  confront  as a
shareholder of the Fund.
================================================================================

WHO SHOULD INVEST

The Fund may be a suitable investment for you if:
- -    You are seeking a value-oriented investment that seeks to provide long-term
     growth as well as some dividend income.
- -    You wish to add a  value-oriented  growth  and  income  stock  fund to your
     existing  holdings,  which could include other stock investments as well as
     bond, money market, and tax-exempt investments.
- -    You are seeking  growth of capital and income over the long term--at  least
     five years.

     THE VANGUARD FUNDS DO NOT PERMIT MARKET-TIMING.  DO NOT INVEST IN THIS FUND
IF YOU ARE A MARKET-TIMER.

<PAGE>

4

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                             COSTS AND MARKET-TIMING

Some   investors  try  to  profit  from   market-timing--switching   money  into
investments  when they  expect  prices to rise,  and taking  money out when they
expect  the  market  to fall.  As money is  shifted  in and out,  a fund  incurs
expenses  for buying and selling  securities.  These costs are borne by all fund
shareholders,  including the long-term  investors who do not generate the costs.
Therefore,  the Fund  discourages  short-term  trading by,  among other  things,
limiting the number of exchanges it permits.
- --------------------------------------------------------------------------------

     The Fund has adopted the following  policies,  among others,  to discourage
short-term trading:
- -    The Fund  reserves  the right to  reject  any  purchase  request--including
     exchanges from other  Vanguard  funds--that it regards as disruptive to the
     efficient  management  of the Fund.  A purchase  request  could be rejected
     because  of the  timing  of the  investment  or  because  of a  history  of
     excessive trading by the investor.
- -    There is a limit on the  number of times you can  exchange  into and out of
     the Fund (see "Redeeming Shares" in the INVESTING WITH VANGUARD section).
- -    The Fund reserves the right to stop offering shares at any time.

PRIMARY INVESTMENT STRATEGIES

This section explains the strategies that the investment advisers use in pursuit
of the  Fund's  objectives  of  long-term  growth of capital  and some  dividend
income.  It also  explains  how the  advisers  implement  these  strategies.  In
addition,   this  section  discusses  several  important   risks--market   risk,
investment  style risk,  and manager  risk--faced  by investors in the Fund. The
Fund's Board of Trustees  oversees the management of the Fund and may change the
investment strategies in the interest of shareholders.

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                    LARGE-CAP, MID-CAP, AND SMALL-CAP STOCKS

Stocks  of  publicly  traded   companies--and   mutual  funds  that  hold  these
stocks--can be classified by the  companies'  market value,  or  capitalization.
Market  capitalization  changes over time, and there is no "official" definition
of the boundaries of large-,  mid-,  and small-cap  stocks.  Vanguard  generally
defines  large-capitalization  (large-cap)  funds as  those  holding  stocks  of
companies  whose  outstanding  shares have a market value exceeding $12 billion;
mid-cap funds as those holding  stocks of companies  with a market value between
$1 billion and $12  billion;  and  small-cap  funds as those  typically  holding
stocks  of  companies  with a market  value of less  than $1  billion.  Vanguard
periodically reassesses these classifications.

- --------------------------------------------------------------------------------

<PAGE>

                                                                               5

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                          VALUE FUNDS AND GROWTH FUNDS

Value  investing  and growth  investing  are two styles  employed  by stock fund
managers.  Value funds  generally  emphasize  stocks of companies from which the
market does not expect strong growth.  The prices of value stocks  typically are
below-average  in  comparison  to such factors as earnings  and book value,  and
these  stocks  typically  have  above-average   dividend  yields.  Growth  funds
generally focus on companies believed to have above-average potential for growth
in revenue and earnings.  Reflecting the market's high expectations for superior
growth, such stocks typically have low dividend yields and above-average  prices
in relation to such measures as revenue,  earnings,  and book values.  Value and
growth stocks have, in the past, produced similar long-term returns, though each
category has periods when it outperforms the other. In general,  value funds are
appropriate  for investors  who want some dividend  income and the potential for
capital gains but are less tolerant of share-price  fluctuations.  Growth funds,
by contrast,  appeal to investors who will accept more  volatility in hopes of a
greater increase in share price.  Growth funds also may appeal to investors with
taxable  accounts  who want a higher  proportion  of  returns to come as capital
gains (which may be taxed at lower rates than dividend income).

- --------------------------------------------------------------------------------

MARKET EXPOSURE
The Fund is a value  fund.  Its  primary  strategy  is to invest  in large-  and
mid-capitalization  common  stocks that have  favorable  prospects for growth of
earnings and dividend income, but whose prices do not reflect this potential for
positive returns. The Fund may also invest in securities that are convertible to
common stocks.

[FLAG] THE FUND IS SUBJECT TO MARKET RISK,  WHICH IS THE POSSIBILITY  THAT STOCK
     PRICES OVERALL WILL DECLINE OVER SHORT OR EVEN LONG PERIODS.  STOCK MARKETS
     TEND TO MOVE IN  CYCLES,  WITH  PERIODS  OF RISING  PRICES  AND  PERIODS OF
     FALLING PRICES.

     To illustrate the volatility of stock prices, the following table shows the
best,  worst,  and average total returns for the U.S.  stock market over various
periods as measured by the Standard & Poor's 500 Index,  a widely used barometer
of market  activity.  (Total returns  consist of dividend  income plus change in
market  price.)  Note that the returns  shown do not include the costs of buying
and selling  stocks or other  expenses  that a real-world  investment  portfolio
would  incur.  Note,  also,  that the gap between best and worst tends to narrow
over the long term.

      --------------------------------------------------------------------
                      U.S. STOCK MARKET RETURNS (1926-1999)
                            1 YEAR    5 YEARS    10 YEARS    20 YEARS
      --------------------------------------------------------------------
      Best                   54.2%     28.6%       19.9%       17.9%
      Worst                 -43.1     -12.4        -0.9         3.1
      Average                13.2      11.0        11.1        11.1
      --------------------------------------------------------------------

     The table  covers all of the 1-, 5-,  10-,  and 20-year  periods  from 1926
through 1999. You can see, for example,  that while the average return on stocks
for all of the 5-year periods was 11.0%,  returns for individual  5-year periods
ranged from a -12.4% average (from 1928


<PAGE>

6


through 1932) to 28.6% (from 1995 through 1999).  These average  returns reflect
past  performance on common stocks;  you should not regard them as an indication
of  future  returns  from  either  the  stock  market as a whole or this Fund in
particular.


[FLAG] THE FUND IS SUBJECT TO INVESTMENT  STYLE RISK,  WHICH IS THE  POSSIBILITY
     THAT  RETURNS  FROM LARGE- AND  MID-CAPITALIZATION  VALUE STOCKS WILL TRAIL
     RETURNS FROM OTHER ASSET CLASSES OR THE OVERALL  STOCK MARKET.  AS A GROUP,
     VALUE  STOCKS  TEND TO GO THROUGH  CYCLES OF DOING  BETTER--OR  WORSE--THAN
     COMMON STOCKS IN GENERAL.  THESE  PERIODS HAVE, IN THE PAST,  LASTED FOR AS
     LONG AS SEVERAL YEARS.

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                              FUND DIVERSIFICATION

In general, the more diversified a fund's stock holdings,  the less likely it is
that a specific  stock's poor  performance  will hurt the fund. One measure of a
fund's  diversification  is the percentage of its assets  represented by its ten
largest  holdings.  The  average  U.S.  equity  mutual fund has about 30% of its
assets invested in its ten largest holdings,  while some less-diversified mutual
funds  have more than 50% of their  assets  invested  in the  stocks of just ten
companies.
- --------------------------------------------------------------------------------

SECURITY SELECTION
Vanguard  Windsor Fund  employs two primary  investment  advisers,  each of whom
independently  chooses and  maintains a portfolio of common stocks for the Fund.
Each adviser is responsible for a specific percentage of the Fund's assets.

     These investment  advisers employ active  investment  methods,  which means
that securities are bought and sold according to the advisers' evaluations about
companies  and their  financial  prospects,  and about the stock  market and the
economy in general.  Each adviser  will sell a security  when it is no longer as
attractive as alternative investments.
     While each adviser uses a different process to select securities,  both are
committed to investing in large- and mid-cap stocks that, in their opinion,  are
undervalued.  Undervalued  stocks are generally those that are out of favor with
investors and currently  trading at prices that,  the adviser  feels,  are below
what  the  stocks  are  worth  in  relation  to  their  earnings.  These  stocks
typically--but not always--have  lower-than-average  price/earnings (P/E) ratios
and higher-than-average dividend yields.
     Wellington  Management Company,  LLP (Wellington  Management) managed about
75% of the Fund's  assets as of October  31,  1999.  A stock's  value is the key
element in Wellington  Management's  selection  process.  Wellington  Management
considers several  fundamental  factors,  including the stock's projected growth
rate, earnings  potential,  dividend yield, and P/E ratio. To be a candidate for
purchase,  a stock must have strong prospects for capital  appreciation,  but be
trading at a price/earnings (P/E) ratio that is lower than what is expected of a
stock with such potential.
     Sanford C.  Bernstein & Co., Inc.  (Bernstein),  which managed about 24% of
the Fund's assets as of October 31, 1999, also uses traditional methods of stock
selection--research  and analysis--to  identify undervalued stocks. In addition,
Bernstein employs quantitative valuation tools to identify attractive stocks and
the most opportune time to purchase them.
     The Vanguard Group (Vanguard) typically will manage any Fund assets held in
cash reserves and may invest in stock index  futures.  This strategy is intended
to keep the Fund more fully  invested in common stocks while  retaining  cash on
hand to meet liquidity


<PAGE>

                                                                               7


needs. See "Other Investment  Policies and Risks" for more details on the Fund's
policy on futures.

     The Fund is generally managed without regard to tax ramifications.

[FLAG] THE FUND IS SUBJECT TO MANAGER RISK,  WHICH IS THE  POSSIBILITY  THAT THE
     ADVISERS MAY DO A POOR JOB OF SELECTING STOCKS.

TURNOVER RATE

Although the Fund  generally  seeks to invest for the long term,  it retains the
right to sell  securities  regardless of how long the securities have been held.
The Fund's average  turnover rate for the past five years has been about 46%. (A
turnover  rate of 100% would occur,  for example,  if the Fund sold and replaced
securities valued at 100% of its net assets within a one-year period.)


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                  TURNOVER RATE

Before  investing in a mutual fund,  you should review its turnover  rate.  This
gives an  indication  of how  transaction  costs could affect the fund's  future
returns.  In general,  the greater the volume of buying and selling by the fund,
the greater the impact that brokerage  commissions and other  transaction  costs
will have on its return. Also, funds with high turnover rates may be more likely
to generate  capital gains that must be  distributed to  shareholders  as income
subject to taxes.  As of October 31,  1999,  the average  turnover  rate for all
domestic stock funds was approximately 87%, according to Morningstar, Inc.

- --------------------------------------------------------------------------------

OTHER INVESTMENT POLICIES AND RISKS
Besides investing in undervalued  common stocks, the Fund may make certain other
kinds of investments to achieve its objective.
     Although  the  Fund  typically  does not make  significant  investments  in
securities of companies  based outside the United States,  it reserves the right
to invest up to 20% of its assets in foreign securities. These securities may be
traded in U.S. or foreign  markets.  To the extent that it owns foreign  stocks,
the Fund is subject to (1) country risk, which is the possibility that political
events (such as a war),  financial  problems  (such as government  default),  or
natural  disasters (such as an earthquake)  will weaken a country's  economy and
cause investments in that country to lose money; and (2) currency risk, which is
the possibility  that Americans  investing  abroad could lose money because of a
rise in the value of the U.S. dollar versus foreign currencies.
     The Fund may invest in money market instruments,  fixed-income  securities,
convertible securities, and other equity securities such as preferred stock. The
Fund may invest up to 15% of its assets in  restricted  securities  with limited
marketability or other illiquid securities.

     The Fund may also  invest,  to a limited  extent,  in futures  and  options
contracts,  which  are  traditional  types of  derivatives.  Losses  (or  gains)
involving  futures can  sometimes be  substantial--in  part because a relatively
small  price  movement  in a futures  contract  may result in an  immediate  and
substantial  loss (or gain)  for a fund.  This  Fund  will not use  futures  for
speculative  purposes  or as  leveraged  investments  that  magnify the gains or
losses of an investment.  The Fund's obligation under futures contracts will not
exceed 20% of its total assets.


<PAGE>

8

     The reasons for which the Fund will invest in futures and options are:
- -    To keep cash on hand to meet  shareholder  redemptions or other needs while
     simulating full investment in stocks.
- -    To reduce the Fund's  transaction costs or add value when these instruments
     are favorably priced.

     The Fund may temporarily  depart from its normal  investment  policies--for
instance,   by  investing   substantially  in  cash  reserves--in   response  to
extraordinary market, economic, political, or other conditions. In doing so, the
Fund may succeed in avoiding losses but otherwise fail to achieve its investment
objective.


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                   DERIVATIVES

A derivative is a financial contract whose value is based on (or "derived" from)
a  traditional  security  (such  as a stock  or a  bond),  an  asset  (such as a
commodity like gold), or a market index (such as the S&P 500 Index). Futures and
options are derivatives  that have been trading on regulated  exchanges for more
than two decades.  These  "traditional"  derivatives are standardized  contracts
that can easily be bought and sold,  and whose market values are  determined and
published  daily. It is these  characteristics  that  differentiate  futures and
options from the relatively new types of derivatives. If used for speculation or
as leveraged investments, derivatives can carry considerable risks.
- --------------------------------------------------------------------------------

THE FUND AND VANGUARD

The Fund is a member of The Vanguard  Group, a family of more than 35 investment
companies  with more than 100 funds holding assets worth more than $530 billion.
All of the  Vanguard  funds  share  in the  expenses  associated  with  business
operations, such as personnel, office space, equipment, and advertising.

     Vanguard  also  provides   marketing   services  to  the  funds.   Although
shareholders do not pay sales commissions or 12b-1  distribution fees, each fund
pays its allocated share of The Vanguard Group's marketing costs.

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                      VANGUARD'S UNIQUE CORPORATE STRUCTURE

The Vanguard Group is truly a MUTUAL mutual fund company. It is owned jointly by
the funds it oversees and thus  indirectly by the  shareholders  in those funds.
Most other mutual funds are operated by for-profit management companies that may
be owned by one person,  by a group of individuals,  or by investors who own the
management  company's stock. By contrast,  Vanguard  provides its services on an
"at-cost"  basis,  and the funds' expense  ratios  reflect only these costs.  No
separate  management  company reaps profits or absorbs losses from operating the
funds.
- --------------------------------------------------------------------------------

<PAGE>

                                                                               9

INVESTMENT ADVISERS

The Fund employs two primary investment  advisers for the bulk of its assets and
uses Vanguard's Core Management Group to manage its cash reserves.  Each adviser
manages the Fund  subject to the  control of the  Trustees  and  officers of the
Fund.

WELLINGTON MANAGEMENT COMPANY, LLP
     Wellington  Management  Company,  LLP  (Wellington  Management),  75  State
Street,  Boston, MA 02109, served as the Fund's sole investment adviser from the
Fund's inception in 1958 until June of 1999.
     Wellington  Management's  advisory fee is paid  quarterly,  and is based on
certain annual  percentage rates applied to the Fund's average  month-end assets
for each quarter. In addition, Wellington Management's advisory fee is increased
or decreased,  based on the cumulative investment  performance of its portion of
the Fund over a trailing  36-month period as compared with the cumulative  total
return of the Standard and Poor's 500 Index over the same period.

SANFORD C. BERNSTEIN & CO., INC.
     Sanford C. Bernstein & Co., Inc.  (Bernstein),  767 Fifth Avenue, New York,
NY 10153,  was added as an investment  adviser to the Fund in June of 1999. Like
Wellington Management,  Bernstein's advisory fee is paid quarterly, and is based
on certain  annual  percentage  rates  applied to the Fund's  average  month-end
assets for each quarter. In addition,  Bernstein's  advisory fee is increased or
decreased,  based on the cumulative investment performance of its portion of the
Fund over a trailing  36-month  period as  compared  with the  cumulative  total
return of the Russell 1000 Value Index over the same period.

THE VANGUARD GROUP
     The Vanguard  Group  (Vanguard),  P.O. Box 2600,  Valley  Forge,  PA 19482,
founded in 1974,  is a wholly  owned  subsidiary  of the Vanguard  funds.  As of
October 31, 1999, Vanguard served as adviser for about $345.6 billion in assets.
The Fund receives advisory services from Vanguard on an at-cost basis.

     For the  fiscal  year ended  October  31,  1999,  the  aggregate  amount of
investment  advisory fees paid by the Fund  represented an effective annual rate
of 0.12% of the Fund's  average  net assets  before a decrease of 0.08% based on
performance.
     The Fund has authorized the advisers to choose brokers or dealers to handle
the purchase and sale of securities  for the Fund, and to get the best available
price and most  favorable  execution  from  these  brokers  with  respect to all
transactions.
     In the  interest  of  obtaining  better  execution  of a  transaction,  the
advisers  may choose  brokers who charge  higher  commissions.  If more than one
broker can obtain the best  available  price and most  favorable  execution of a
transaction,  then the  advisers  are  authorized  to  choose a broker  who,  in
addition to executing the  transaction,  will provide  research  services to the
advisers or the Fund. Also, the Fund may direct the advisers to use a particular
broker for certain  transactions in exchange for commission  rebates or research
services provided to the Fund.
     The Board of Trustees may, without prior approval from shareholders, change
the terms of an advisory agreement or hire a new investment adviser--either as a
replacement for an existing adviser or as an additional adviser. Any significant
change in the Fund's advisory  arrangements will be communicated to shareholders
in writing. In addition, as the Fund's


<PAGE>

10


sponsor and overall manager,  The Vanguard Group may provide investment advisory
services to the Fund, on an at-cost basis, at any time.


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                               THE FUND'S ADVISERS

Wellington  Management  Company,  LLP  (Wellington  Management) is an investment
advisory  firm founded in 1928.  As of October 31, 1999,  Wellington  Management
managed more than $224 billion in assets. The manager responsible for overseeing
Wellington Management's portion of the Fund is:

CHARLES T. FREEMAN,  Senior Vice President and Partner of Wellington Management;
has worked in investment management since 1967; with Wellington Management since
1969; B.S., M.B.A.,  University of Pennsylvania.  Mr. Freeman was appointed Fund
Manager in January  1996,  following  the  retirement  of John B. Neff,  who had
managed the Fund since 1964.  Mr.  Freeman had been Assistant Fund Manager since
1974.

Sanford C.  Bernstein & Co., Inc.  (Bernstein)  is an  investment  advisory firm
founded in 1967. As of October 31, 1999,  Bernstein  managed about $85.6 billion
in assets.  Two managers are responsible for overseeing  Bernstein's  portion of
the Fund.  MARILYN G. FEDAK,  Chief Investment  Officer and Chairman of the U.S.
Equity Investment Policy Group at Bernstein since 1993; has worked in investment
management  since 1972; has managed  portfolio  investments  since 1976;  joined
Bernstein in 1984; B.A., Smith College;  M.B.A., Harvard Business School. STEVEN
PISARKIEWICZ,  with Bernstein since 1989;  Senior Portfolio  Manager since 1997;
B.S., University of Missouri; M.B.A., University of California at Berkeley.

The manager  responsible for Vanguard's portion of the Fund is GEORGE U. SAUTER,
Managing  Director of Vanguard and head of Vanguard's Core Management Group; has
worked  in  investment   management  since  1985;  primary   responsibility  for
Vanguard's stock indexing policy and strategy since joining the company in 1987;
A.B., Dartmouth College; M.B.A., University of Chicago.

- --------------------------------------------------------------------------------



DIVIDENDS, CAPITAL GAINS, AND TAXES

The Fund  distributes to shareholders  virtually all of its net income (interest
and dividends,  less  expenses),  as well as any capital gains realized from the
sale of its holdings.  Income  dividends  generally are  distributed in June and
December; capital gains distributions generally occur in December.
     Your  dividend  and  capital  gains  distributions  will be  reinvested  in
additional  Fund  shares  and  accumulate  on a  tax-deferred  basis  if you are
investing through an employer-sponsored retirement or savings plan. You will not
owe taxes on these  distributions until you begin withdrawals from the plan. You
should consult your plan administrator, your plan's Summary Plan Description, or
your tax adviser about the tax consequences of plan withdrawals.


<PAGE>

                                                                              11

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                  DISTRIBUTIONS

As a  shareholder,  you are  entitled  to your share of the fund's  income  from
interest and dividends, and gains from the sale of investments. You receive such
earnings as either an income  dividend or a capital gains  distribution.  Income
dividends come from both the dividends that the fund earns from its holdings and
the  interest it receives  from its money market and bond  investments.  Capital
gains are realized  whenever the fund sells securities for higher prices than it
paid for them. These capital gains are either short-term or long-term, depending
on whether the fund held the  securities  for one year or less, or more than one
year.

- --------------------------------------------------------------------------------

SHARE PRICE

The Fund's share price,  called its net asset value,  or NAV, is calculated each
business day after the close of regular  trading on the New York Stock  Exchange
(the NAV is not  calculated  on  holidays  or other  days when the  Exchange  is
closed).  Net asset  value per share is computed by adding up the total value of
the Fund's  investments  and other assets,  subtracting  any of its  liabilities
(debts), and then dividing by the number of Fund shares outstanding:


                      TOTAL ASSETS - LIABILITIES
NET ASSET VALUE =  -------------------------------
                     NUMBER OF SHARES OUTSTANDING

     Knowing the daily net asset value is useful to you as a shareholder because
it indicates the current value of your investment. The Fund's NAV, multiplied by
the  number of  shares  you own,  gives you the  dollar  amount  you would  have
received had you sold all of your shares back to the Fund that day.
     A NOTE ON PRICING:  The Fund's  investments  will be priced at their market
value when market  quotations are readily  available.  When these quotations are
not  readily  available,  investments  will  be  priced  at  their  fair  value,
calculated according to procedures adopted by the Fund's Board of Trustees.
     The Fund's  share price can be found  daily in the mutual fund  listings of
most major newspapers under the heading "Vanguard  Funds." Different  newspapers
use different abbreviations of the Fund's name, but the most common is WNDSR.

FINANCIAL HIGHLIGHTS

The following financial  highlights table is intended to help you understand the
Fund's financial  performance for the past five years,  and certain  information
reflects  financial  results for a single Fund share.  The total  returns in the
table represent the rate that an investor would have earned or lost each year on
an investment  in the Fund  (assuming  reinvestment  of all dividend and capital
gains  distributions).  This  information  has been derived  from the  financial
statements audited by PricewaterhouseCoopers LLP, independent accountants, whose
report--along  with the Fund's financial  statements--is  included in the Fund's
most recent annual report to  shareholders.  You may have the annual report sent
to you without charge by contacting Vanguard.


<PAGE>

12
FINANCIAL HIGHLIGHTS (CONTINUED)

<TABLE>

- ----------------------------------------------------------------------------------------------
                                               VANGUARD WINDSOR FUND
                                               YEAR ENDED OCTOBER 31,
                        ----------------------------------------------------------------------
                           1999          1998          1997          1996          1995
- ----------------------------------------------------------------------------------------------
<S>                     <C>           <C>           <C>           <C>           <C>
NET ASSET VALUE,
 BEGINNING OF YEAR       $16.34        $19.55        $16.99        $15.55        $14.55
- ----------------------------------------------------------------------------------------------
INVESTMENT OPERATIONS
 Net Investment Income      .27           .23           .36           .43           .44
 Net Realized and
  Unrealized Gain
  (Loss) on Investments    1.77          (.32)         3.94          2.85          1.86
                        ----------------------------------------------------------------------
   Total from Investment
    Operations             2.04          (.09)         4.30          3.28          2.30
                        ----------------------------------------------------------------------
DISTRIBUTIONS
 Dividends from Net
  Investment Income        (.24)         (.24)         (.41)         (.46)         (.44)
 Distributions from
  Realized Capital Gains  (1.23)        (2.88)        (1.33)        (1.38)         (.86)
                        ----------------------------------------------------------------------
   Total Distributions    (1.47)        (3.12)        (1.74)        (1.84)        (1.30)
- ----------------------------------------------------------------------------------------------
NET ASSET VALUE, END
 OF YEAR                 $16.91        $16.34        $19.55        $16.99        $15.55
==============================================================================================

TOTAL RETURN             13.74%        -0.78%        27.04%        23.16%        17.80%
==============================================================================================

RATIOS/SUPPLEMENTAL DATA
 Net Assets, End of
  Year (Millions)       $16,824       $18,355       $20,678       $15,841       $13,008
 Ratio of Total
  Expenses to Average
  Net Assets              0.28%         0.27%         0.27%         0.31%         0.45%
 Ratio of Net
  Investment Income to
  Average Net Assets      1.56%         1.31%         1.89%         2.75%         3.01%
 Turnover Rate              56%           48%           61%           34%           32%
==============================================================================================

</TABLE>

- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                   HOW TO READ THE FINANCIAL HIGHLIGHTS TABLE

The Fund began  fiscal 1999 with a net asset value  (price) of $16.34 per share.
During  the  year,  the Fund  earned  $0.27  per share  from  investment  income
(interest  and  dividends)  and  $1.77  per  share  from  investments  that  had
appreciated  in value or that were sold for higher prices than the Fund paid for
them.
Shareholders  received $1.47 per share in the form of dividend and capital gains
distributions.  A portion of each year's  distributions  may come from the prior
year's income or capital gains.
The  earnings  ($2.04  per  share)  minus the  distributions  ($1.47  per share)
resulted in a share price of $16.91 at the end of the year. This was an increase
of $0.57 per share (from  $16.34 at the  beginning  of the year to $16.91 at the
end of the year).  For a shareholder  who  reinvested the  distributions  in the
purchase of more shares, the total return from the Fund was 13.74% for the year.
As of October 31, 1999, the Fund had $16.8 billion in net assets.  For the year,
its expense ratio was 0.28% ($2.80 per $1,000 of net assets); and net investment
income  amounted  to 1.56%  of its  average  net  assets.  It sold and  replaced
securities valued at 56% of its net assets.

- --------------------------------------------------------------------------------




"Standard & Poor's(R),"  "S&P(R),"  "S&P  500(R),"  "Standard & Poor's 500," and
"500" are trademarks of The McGraw-Hill Companies, Inc. Frank Russell Company is
the owner of the trademarks and copyrights relating to the Russell Indexes.


<PAGE>

                                                                              13

INVESTING WITH VANGUARD

The Fund is an investment  option in your  retirement or savings plan. Your plan
administrator  or your  employee  benefits  office can provide you with detailed
information  on how to  participate in your plan and how to elect the Fund as an
investment option.

- -    If you have any questions about the Fund or Vanguard, including those about
     the Fund's investment objective,  strategies,  or risks, contact Vanguard's
     Participant Services Center, toll-free, at 1-800-523-1188.

- -    If you have questions about your account,  contact your plan  administrator
     or the organization that provides recordkeeping services for your plan.

INVESTMENT OPTIONS AND ALLOCATIONS
Your  plan's  specific  provisions  may  allow  you to  change  your  investment
selections,  the amount of your  contributions,  or how your  contributions  are
allocated  among the  investment  choices  available  to you.  Contact your plan
administrator or employee benefits office for more details.

TRANSACTIONS
Contributions,  exchanges,  or redemptions of the Fund's shares are processed as
soon as they have been received by Vanguard in good order. Good order means that
your request includes complete  information on your contribution,  exchange,  or
redemption, and that Vanguard has received the appropriate assets.

     In all cases,  your transaction  will be based on a Fund's  next-determined
net asset value after  Vanguard  receives  your  request (or, in the case of new
contributions,  the  next-determined net asset value after Vanguard receives the
order from your plan administrator).  As long as this request is received before
the close of trading on the New York Stock  Exchange,  generally 4 p.m.  Eastern
time, you will receive that day's net asset value.


EXCHANGES
The exchange  privilege (your ability to redeem shares from one fund to purchase
shares of another  fund) may be available to you through your plan.  Although we
make every  effort to maintain  the exchange  privilege,  Vanguard  reserves the
right to revise or terminate this privilege,  limit the amount of an exchange or
reject any exchange,  at any time, without notice.  Because excessive  exchanges
can potentially  disrupt the management of the Fund and increase its transaction
costs,  Vanguard  limits  participant  exchange  activity  to no more  than FOUR
SUBSTANTIVE  "ROUND TRIPS"  THROUGH THE FUND (at least 90 days apart) during any
12-month  period.  A "round  trip" is a redemption  from the Fund  followed by a
purchase back into the Fund.  "Substantive"  means a dollar amount that Vanguard
determines, in its sole discretion, could adversely affect the management of the
Fund.
     Before  making an exchange to or from another fund  available in your plan,
consider the following:
- -    Certain investment options,  particularly funds made up of company stock or
     investment contracts, may be subject to unique restrictions.
- -    Make sure to read that fund's  prospectus.  Contact  Participant  Services,
     toll-free, at 1-800-523-1188 for a copy.
- -    Vanguard can accept exchanges only as permitted by your plan.  Contact your
     plan  administrator for details on the exchange policies that apply to your
     plan.

<PAGE>

14

ACCESSING FUND INFORMATION BY COMPUTER

- --------------------------------------------------------------------------------
VANGUARD ON THE WORLD WIDE WEB www.vanguard.com
Use your personal computer to visit Vanguard's education-oriented website, which
provides  timely news and  information  about  Vanguard  funds and services;  an
online  "university"  that  offers  a  variety  of  mutual  fund  classes;   and
easy-to-use,  interactive  tools to help you  create  your  own  investment  and
retirement strategies.
- --------------------------------------------------------------------------------

<PAGE>

                     (THIS PAGE INTENTIONALLY LEFT BLANK.)

<PAGE>

                     (THIS PAGE INTENTIONALLY LEFT BLANK.)

<PAGE>

GLOSSARY OF INVESTMENT TERMS

CAPITAL GAINS DISTRIBUTION
Payment to mutual fund  shareholders  of gains  realized on securities  that the
fund has sold at a profit, minus any realized losses.

CASH RESERVES
Cash deposits,  short-term bank deposits,  and money market  instruments,  which
include U.S.  Treasury bills,  bank  certificates  of deposit (CDs),  repurchase
agreements, commercial paper, and banker's acceptances.

COMMON STOCK
A security  representing  ownership  rights in a  corporation.  A stockholder is
entitled  to share in the  company's  profits,  some of which may be paid out as
dividends.



DIVIDEND INCOME
Payment to  shareholders  of income from  interest or  dividends  generated by a
fund's investments.

EXPENSE RATIO
The  percentage  of a fund's  average net assets used to pay its  expenses.  The
expense ratio  includes  management  fees,  administrative  fees,  and any 12b-1
distribution fees.

FUND DIVERSIFICATION
Holding a variety of securities so that a fund's return is not badly hurt by the
poor performance of a single security, industry, or country.

GROWTH STOCK FUND
A mutual fund that emphasizes stocks of companies believed to have above-average
prospects for growth.  Reflecting market  expectations for superior growth,  the
prices of  growth  stocks  often are  relatively  high in  comparison  with such
factors as revenue, earnings, book value, and dividends.

INVESTMENT ADVISER
An  organization  that  makes  the  day-to-day   decisions  regarding  a  fund's
investments.

MUTUAL FUND
An  investment  company  that pools the money of many people and invests it in a
variety of securities in an effort to achieve a specific objective over time.

NET ASSET VALUE (NAV)
The market value of a mutual fund's total assets, minus liabilities,  divided by
the  number of shares  outstanding.  The value of a single  share is called  its
share value or share price.

PRICE/EARNINGS (P/E) RATIO
The current share price of a stock,  divided by its per-share earnings (profits)
from the past year. A stock selling for $20, with earnings of $2 per share,  has
a price/earnings ratio of 10.

PRINCIPAL
The amount of money you put into an investment.

SECURITIES
Stocks, bonds, and other investment vehicles.

TOTAL RETURN
A percentage change,  over a specified time period, in a mutual fund's net asset
value,  with the ending net asset value adjusted to account for the reinvestment
of all distributions of dividends and capital gains.

VALUE STOCK FUND
A mutual fund that  emphasizes  stocks of companies  whose growth  prospects are
generally   regarded  as  subpar  by  the  market.   Reflecting   these   market
expectations,  the  prices  of  value  stocks  typically  are  below-average  in
comparison with such factors as revenue, earnings, book value, and dividends.

VOLATILITY
The  fluctuations  in value of a mutual  fund or other  security.  The greater a
fund's volatility, the wider the fluctuations between its high and low prices.

YIELD
Income  (interest  or  dividends)  earned  by  an  investment,  expressed  as  a
percentage of the investment's price.

<PAGE>

                                                    [THE VANGUARD GROUP(R) LOGO]

                                                     Institutional Division
                                                     Post Office Box 2900
                                                     Valley Forge, PA 19482-2900

FOR MORE INFORMATION
If you'd like more information about
Vanguard Windsor Fund, the
following documents are available
free upon request:

ANNUAL/SEMIANNUAL REPORT TO
SHAREHOLDERS
Additional information about the
Fund's investments is available in
the Fund's annual and semiannual
reports to shareholders. In these
reports, you will find a discussion
of the market conditions and
investment strategies that
significantly affected the Fund's
performance during the most recent
fiscal year.

STATEMENT OF ADDITIONAL
INFORMATION (SAI)
The SAI provides more detailed
information about the Fund.

The current annual and semiannual
reports and the SAI are
incorporated by reference into
(and are thus legally a part of)
this prospectus.

To receive a free copy of the latest
annual or semiannual report or the
SAI, or to request additional
information about the Fund or other
Vanguard funds, please contact us
as follows:

THE VANGUARD GROUP
PARTICIPANT SERVICES CENTER
P.O. BOX 2900
VALLEY FORGE, PA 19482-2900

TELEPHONE:
1-800-523-1188

TEXT TELEPHONE:
1-800-523-8004

WORLD WIDE WEB:
WWW.VANGUARD.COM

INFORMATION PROVIDED BY THE
SECURITIES AND EXCHANGE
COMMISSION (SEC)

You can review and copy
information about the Fund
(including the SAI) at the SEC's
Public Reference Room in
Washington, DC. To find out more
about this public service, call the
SEC at 1-800-SEC-0330. Reports and
other information about the Fund are
also available on the SEC's website
(www.sec.gov), or you can receive
copies of this information, for a fee,
by writing the Public Reference
Section, Securities and Exchange
Commission, Washington, DC
20549-6009.

Fund's Investment Company Act
file number: 811-834


(C) 2000 The Vanguard Group, Inc.
All rights reserved.
Vanguard Marketing Corporation,
Distributor.

I022N-02/18/2000


<PAGE>

VANGUARD(R)
WINDSOR II(TM) FUND


Prospectus
February 18, 2000

This  prospectus  contains
financial  data for the
Fund through the
fiscal year ended
October 31, 1999.


[A MEMBER OF THE VANGUARD GROUP LOGO]
<PAGE>


VANGUARD WINDSOR II FUND
Prospectus
February 18, 2000


A Growth and Income Stock Mutual Fund


- --------------------------------------------------------------------------------
CONTENTS
1  FUND PROFILE                         12  SHARE PRICE
3  ADDITIONAL INFORMATION               12  FINANCIAL HIGHLIGHTS
3  A WORD ABOUT RISK                    14  INVESTING WITH VANGUARD
3  WHO SHOULD INVEST                         14  SERVICES AND ACCOUNT FEATURES
4  PRIMARY INVESTMENT STRATEGIES             15  TYPES OF ACCOUNTS
8  THE FUND AND VANGUARD                     16  BUYING SHARES
9  INVESTMENT ADVISER                        18  REDEEMING SHARES
10 DIVIDENDS, CAPITAL GAINS, AND TAXES       21  TRANSFERRING REGISTRATION
                                             22  FUND AND ACCOUNT UPDATES
                                        GLOSSARY (inside back cover)
- --------------------------------------------------------------------------------


- --------------------------------------------------------------------------------
WHY READING THIS PROSPECTUS IS IMPORTANT
This  prospectus  explains the  objective,  risks,  and  strategies  of Vanguard
Windsor II Fund.  To  highlight  terms and  concepts  important  to mutual  fund
investors, we have provided "Plain Talk (R)" explanations along the way. Reading
the prospectus will help you to decide whether the Fund is the right  investment
for you. We suggest that you keep it for future reference.
- -------------------------------------------------------------------------------





















NEITHER  THE  SECURITIES  AND  EXCHANGE  COMMISSION  NOR  ANY  STATE  SECURITIES
COMMISSION HAS APPROVED OR  DISAPPROVED  OF THESE  SECURITIES OR PASSED UPON THE
ACCURACY OR ADEQUACY OF THIS PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A
CRIMINAL OFFENSE.
<PAGE>


                                                                               1

FUND PROFILE
The following profile summarizes key features of Vanguard Windsor II Fund.


INVESTMENT OBJECTIVE
The Fund seeks to provide long-term growth of capital. As a secondary objective,
the Fund seeks to provide some dividend income.


INVESTMENT STRATEGIES
The Fund invests  primarily in large and medium-size  companies whose stocks are
considered  by the Fund's  advisers to be  undervalued.  Undervalued  stocks are
generally  those that are out of favor with  investors and currently  trading at
prices that, the adviser feels,  are below what the stocks are worth in relation
to   their   earnings.    These   stocks    typically--but    not   always--have
lower-than-average  price/earnings (P/E) ratios and higher-than-average dividend
yields.

PRIMARY RISKS
THE FUND'S TOTAL RETURN,  LIKE STOCK PRICES  GENERALLY,  WILL FLUCTUATE WITHIN A
WIDE RANGE, SO AN INVESTOR COULD LOSE MONEY OVER SHORT OR EVEN LONG PERIODS. The
Fund is also subject to:

- -    Investment  style risk,  which is the chance that  returns  from large- and
     mid-capitalization  value stocks will trail  returns from the overall stock
     market.
- -    Manager risk,  which is the chance that poor security  selection will cause
     the Fund to underperform other funds with similar investment objectives.



PERFORMANCE/RISK INFORMATION
The bar chart and table below  provide an indication of the risk of investing in
the Fund. The bar chart shows the Fund's  performance in each calendar year over
a ten-year  period.  The table shows how the Fund's average annual total returns
for one,  five,  and ten  calendar  years  compare  with those of a  broad-based
securities  market index. Keep in mind that the Fund's past performance does not
indicate how the Fund will perform in the future.

              ----------------------------------------------------
                              ANNUAL TOTAL RETURNS
              ----------------------------------------------------
                          1990                -9.98%
                          1991                28.70%
                          1992                11.99%
                          1993                13.60%
                          1994                -1.16%
                          1995                38.83%
                          1996                24.18%
                          1997                32.37%
                          1998                16.36%
                          1999                -5.81%
              ----------------------------------------------------

     During the period shown in the bar chart, the highest return for a calendar
quarter was 17.90%  (quarter  ended March 31, 1991) and the lowest  return for a
quarter was -15.05% (quarter ended September 30, 1990).

<PAGE>

2




      --------------------------------------------------------------------
           AVERAGE ANNUAL TOTAL RETURNS FOR YEARS ENDED DECEMBER 31, 1999
                                   1 YEAR         5 YEARS        10 YEARS
      --------------------------------------------------------------------
      Vanguard Windsor II Fund      -5.81%          20.13%         13.80%
      Standard & Poor's 500 Index   21.04           28.56          18.21
      --------------------------------------------------------------------

FEES AND EXPENSES
The following table describes the fees and expenses you would pay if you buy and
hold shares of the Fund. The expenses shown under Annual Fund Operating Expenses
are based upon those incurred in the fiscal year ended October 31, 1999.

      SHAREHOLDER FEES (fees paid directly from your investment)
      Sales Charge (Load) Imposed on Purchases:              None
      Sales Charge (Load) Imposed on Reinvested Dividends:   None
      Redemption Fee:                                        None
      Exchange Fee:                                          None


      ANNUAL FUND OPERATING EXPENSES (expenses deducted from the
      Fund's assets)
      Management Expenses:                                   0.35%
      12b-1 Distribution Fee:                                None
      Other Expenses:                                        0.02%
       TOTAL ANNUAL FUND OPERATING EXPENSES:                 0.37%



     The following example is intended to help you compare the cost of investing
in the Fund with the cost of investing in other mutual funds. It illustrates the
hypothetical  expenses  that you would incur over various  periods if you invest
$10,000 in the Fund.  This example assumes that the Fund provides a return of 5%
a year, and that operating  expenses  remain the same. The results apply whether
or not you redeem your investment at the end of each period.




              -------------------------------------------------
                1 YEAR      3 YEARS    5 YEARS      10 YEARS
              -------------------------------------------------
                  $38         $119       $208         $468
              -------------------------------------------------


     THIS  EXAMPLE  SHOULD NOT BE  CONSIDERED  TO REPRESENT  ACTUAL  EXPENSES OR
PERFORMANCE  FROM THE PAST OR FOR THE  FUTURE.  ACTUAL  FUTURE  EXPENSES  MAY BE
HIGHER OR LOWER THAN THOSE SHOWN.


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                  FUND EXPENSES
All mutual funds have operating  expenses.  These  expenses,  which are deducted
from a fund's gross  income,  are expressed as a percentage of the net assets of
the fund.  Vanguard  Windsor  II Fund's  expense  ratio in fiscal  year 1999 was
0.37%,  or $3.70 per $1,000 of average net assets.  The average  large-cap value
mutual fund had  expenses in 1999 of 1.26%,  or $12.60 per $1,000 of average net
assets (derived from data provided as of December 31, 1999 by Lipper Inc., which
reports on the mutual fund industry).  Management  expenses,  which comprise one
part of operating  expenses,  include investment  advisory fees as well as other
costs of managing a fund--such as account  maintenance,  reporting,  accounting,
legal, and other administrative expenses.
- --------------------------------------------------------------------------------


<PAGE>

                                                                               3


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                             THE COSTS OF INVESTING
 Costs are an important  consideration in choosing a mutual fund. That's because
 you, as a shareholder,  pay the costs of operating a fund, plus any transaction
 costs associated with the fund's buying and selling of securities.  These costs
 can erode a substantial  portion of the gross income or capital  appreciation a
 fund  achieves.  Even seemingly  small  differences in expenses can, over time,
 have a dramatic effect on a fund's performance.
- --------------------------------------------------------------------------------



- --------------------------------------------------------------------------------
ADDITIONAL INFORMATION
DIVIDENDS AND CAPITAL GAINS       NET ASSETS AS OF OCTOBER 31, 1999
Dividends are distributed         $30.5 billion
semiannually in June and
December; capital gains, if any,  SUITABLE FOR IRAS
are distributed in December       Yes

INVESTMENT ADVISERS               MINIMUM INITIAL INVESTMENT
Vanguard Windsor II Fund          $3,000; $1,000 for IRAs and custodial accounts
uses four advisers:               for minors
- -Barrow, Hanley, Mewhinney
 & Strauss, Inc., Dallas,         NEWSPAPER ABBREVIATION
 Tex., since 1985                 WndsrII
- -Equinox Capital Management LLC,
 New York, N.Y., since 1991       VANGUARD FUND NUMBER
- -Tukman Capital Management, Inc., 073
 Larkspur, Calif. since 1991
 Mass., since 2000                CUSIP NUMBER
- -The Vanguard Group, Valley       922018205
 Forge, Pa., since 1991
                                  TICKER SYMBOL
INCEPTION DATE                    VWNFX
June 24, 1985
- --------------------------------------------------------------------------------


================================================================================
A WORD ABOUT RISK

This  prospectus  describes  risks you would  face as an  investor  in  Vanguard
Windsor  II Fund.  It is  important  to keep in mind one of the main  axioms  of
investing: The higher the risk of losing money, the higher the potential reward.
The  reverse,  also,  is  generally  true:  The lower  the  risk,  the lower the
potential reward. As you consider an investment in Vanguard Windsor II Fund, you
should also take into account your personal tolerance for the daily fluctuations
of the stock market.
     Look for this [FLAG] symbol  throughout the prospectus.  It is used to mark
detailed  information  about  each  type of risk that you  would  confront  as a
shareholder of the Fund.
================================================================================



WHO SHOULD INVEST

The Fund may be a suitable investment for you if:
- -    You wish to add a  value-oriented  growth  and  income  stock  fund to your
     existing  holdings,  which could include other stock investments as well as
     bond, money market, and tax-exempt investments.
- -    You are  seeking  growth  of  capital  over the long  term--at  least  five
     years--as well as some dividend income.
<PAGE>


4

     THE VANGUARD FUNDS DO NOT PERMIT MARKET-TIMING.  DO NOT INVEST IN THIS FUND
IF YOU ARE A MARKET-TIMER.


- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                            COSTS AND MARKET-TIMING
Some   investors  try  to  profit  from   market-timing--switching   money  into
investments  when they  expect  prices to rise,  and taking  money out when they
expect  the  market  to fall.  As money is  shifted  in and out,  a fund  incurs
expenses  for buying and selling  securities.  These costs are borne by all fund
shareholders,  including the long-term  investors who do not generate the costs.
Therefore,  the Fund  discourages  short-term  trading by,  among other  things,
limiting the number of exchanges it permits.
- --------------------------------------------------------------------------------


     The Fund has adopted the following  policies,  among others,  to discourage
short-term trading:


- -    The Fund  reserves  the right to  reject  any  purchase  request--including
     exchanges from other  Vanguard  funds--that it regards as disruptive to the
     efficient  management  of the Fund.  A purchase  request  could be rejected
     because  of the  timing  of the  investment  or  because  of a  history  of
     excessive trading by the investor.


- -    There is a limit to the  number of times you can  exchange  into and out of
     the Fund (see "Redeeming Shares" in the INVESTING WITH VANGUARD section).
- -    The Fund reserves the right to stop offering shares at any time.



PRIMARY INVESTMENT STRATEGIES
This section explains the strategies that the investment advisers use in pursuit
of the  Fund's  objectives  of  long-term  growth of capital  and some  dividend
income.  It also  explains  how the  advisers  implement  these  strategies.  In
addition,   this  section  discusses  several  important   risks--market   risk,
investment  style risk,  and manager  risk--faced  by investors in the Fund. The
Fund's Board of Trustees  oversees the management of the Fund and may change the
investment strategies in the interest of shareholders.





- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                   LARGE-CAP, MID-CAP, AND SMALL-CAP STOCKS
Stocks  of  publicly  traded   companies--and   mutual  funds  that  hold  these
stocks--can be classified by the  companies'  market value,  or  capitalization.
Market  capitalization  changes over time, and there is no "official" definition
of the boundaries of large-,  mid-,  and small-cap  stocks.  Vanguard  generally
defines  large-capitalization  (large-cap)  funds as  those  holding  stocks  of
companies  whose  outstanding  shares have a market value exceeding $12 billion;
mid-cap funds as those holding  stocks of companies  with a market value between
$1 billion and $12  billion;  and  small-cap  funds as those  typically  holding
stocks  of  companies  with a market  value of less  than $1  billion.  Vanguard
periodically reassesses these classifications.
- --------------------------------------------------------------------------------




<PAGE>


                                                                               5


- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                         VALUE FUNDS AND GROWTH FUNDS
Value  investing  and growth  investing  are two styles  employed  by stock fund
managers.  Value funds  generally  emphasize  stocks of companies from which the
market does not expect strong growth.  The prices of value stocks  typically are
below-average  in  comparison  to such factors as earnings  and book value,  and
these  stocks  typically  have  above-average   dividend  yields.  Growth  funds
generally focus on companies believed to have above-average potential for growth
in revenue and earnings.  Reflecting the market's high expectations for superior
growth, such stocks typically have low dividend yields and above-average  prices
in relation to such measures as revenue,  earnings,  and book values.  Value and
growth stocks have, in the past, produced similar long-term returns, though each
category has periods when it outperforms the other. In general,  value funds are
appropriate  for investors  who want some dividend  income and the potential for
capital gains but are less tolerant of share-price  fluctuations.  Growth funds,
by contrast,  appeal to investors who will accept more  volatility in hopes of a
greater increase in share price.  Growth funds also may appeal to investors with
taxable  accounts  who want a higher  proportion  of  returns to come as capital
gains (which may be taxed at lower rates than dividend income).
- --------------------------------------------------------------------------------


MARKET EXPOSURE
The Fund is a value fund. It employs four  investment  advisers to carry out its
primary  strategy  of  investing  in a broadly  diversified  group of large- and
mid-capitalization  companies  that  have  favorable  prospects  for  growth  of
earnings and dividend income but whose prices do not reflect these prospects.

[FLAG] THE FUND IS SUBJECT TO MARKET RISK,  WHICH IS THE POSSIBILITY  THAT STOCK
     PRICES OVERALL WILL DECLINE OVER SHORT OR EVEN LONG PERIODS.  STOCK MARKETS
     TEND TO MOVE IN  CYCLES,  WITH  PERIODS  OF RISING  PRICES  AND  PERIODS OF
     FALLING PRICES.

     To illustrate the volatility of stock prices, the following table shows the
best,  worst,  and average total returns for the U.S.  stock market over various
periods as measured by the Standard & Poor's 500 Index,  a widely used barometer
of market  activity.  (Total returns  consist of dividend  income plus change in
market  price.)  Note that the returns  shown do not include the costs of buying
and selling  stocks or other  expenses  that a real-world  investment  portfolio
would  incur.  Note,  also,  that the gap between best and worst tends to narrow
over the long term.



               ----------------------------------------------------
                      U.S. STOCK MARKET RETURNS (1926-1999)
                           1 YEAR    5 YEARS   10 YEARS  20 YEARS
               ----------------------------------------------------
               Best         54.2%     28.6%      19.9%     17.9%
               Worst       -43.1     -12.4       -0.9       3.1
               Average      13.2      11.0       11.1      11.1
               ----------------------------------------------------


     The table  covers all of the 1-, 5-,  10-,  and 20-year  periods  from 1926
through 1999. You can see, for example,  that while the average return on stocks
for all of the 5-year periods was 11.0%,  returns for individual  5-year periods
ranged from a -12.4% average (from 1928

<PAGE>


6


through 1932) to 28.6% (from 1995 through 1999).  These average  returns reflect
past  performance on common stocks;  you should not regard them as an indication
of  future  returns  from  either  the  stock  market as a whole or this Fund in
particular.


[FLAG] THE FUND IS SUBJECT TO INVESTMENT  STYLE RISK,  WHICH IS THE  POSSIBILITY
     THAT  RETURNS  FROM LARGE- AND  MID-CAPITALIZATION  VALUE STOCKS WILL TRAIL
     RETURNS FROM OTHER ASSET CLASSES OR THE OVERALL  STOCK MARKET.  AS A GROUP,
     VALUE  STOCKS  TEND TO GO THROUGH  CYCLES OF DOING  BETTER--OR  WORSE--THAN
     COMMON STOCKS IN GENERAL.  THESE  PERIODS HAVE, IN THE PAST,  LASTED FOR AS
     LONG AS SEVERAL YEARS.


SECURITY SELECTION
Vanguard  Windsor  II  Fund  employs  four  investment  advisers,  each  of whom
independently  chooses and  maintains a portfolio of common stocks for the Fund.
Each adviser is responsible for a specific percentage of the Fund's assets.
     These investment  advisers employ active  investment  methods,  which means
that securities are bought and sold according to the advisers' evaluations about
companies  and their  financial  prospects,  and about the stock  market and the
economy in general.  Each adviser  will sell a security  when it is no longer as
attractive as an alternative investment.
     While each adviser uses a different process to select securities,  all four
are committed to investing in large- and mid-cap  stocks that, in their opinion,
are  undervalued.  Undervalued  stocks are generally those that are out of favor
with  investors and currently  trading at prices that,  the adviser  feels,  are
below what the stocks are worth in  relation  to their  earnings.  These  stocks
typically--but not always--have  lower-than-average  price/earnings (P/E) ratios
and higher-than-average dividend yields.
     Barrow,  Hanley,  Mewhinney & Strauss, Inc. (Barrow Hanley),  which managed
about 64% of the Fund's assets as of October 31, 1999, uses traditional  methods
of stock selection--research and analysis--to identify undervalued securities. A
security  will be sold  when,  in  Barrow  Hanley's  opinion,  its  share  price
accurately  reflects  the  security's  overall  worth.  At that  point,  another
undervalued  security  will be  chosen.  No more  than  15% of  Barrow  Hanley's
portfolio is devoted to a single industry.
     Tukman Capital  Management,  Inc. (Tukman),  which managed about 12% of the
Fund's assets as of October 31, 1999, also uses traditional  research methods to
select undervalued securities. Tukman typically buys stocks of financially sound
companies in growing business sectors and holds them for three to five years, on
average.
     Equinox  Capital  Management LLC (Equinox),  which managed about 14% of the
Fund's  assets as of October 31,  1999,  uses its own  fundamental  research and
proprietary software to identify  undervalued  securities with attractive growth
and dividend prospects.  Like Barrow Hanley, it avoids large concentrations in a
single industry.
     The Vanguard Group (Vanguard),  which managed about 6% of the Fund's assets
as of October 31, 1999, selects stocks from a "universe" of about 550 companies.
Vanguard,   using  quantitative  models,  evaluates  the  stocks  using  several
fundamental factors, such as a stock's price in relation to its projected growth
rate. The stocks  selected are expected,  as a group,  to outperform the Russell
1000 Value Index, a benchmark of large- and mid-cap value stocks.
     Vanguard  is  responsible  for the  balance  of the  Fund's  assets as cash
reserves  (about 4% as of October  31,  1999).  Vanguard  invests in stock index
features so that the cash reserve  portion of the Fund's  portfolio  may achieve
performance  similar to that of common stocks. This strategy is intended to keep
the Fund more fully invested in common stocks while

<PAGE>

                                                                               7


retaining cash on hand to meet liquidity needs. See "Other  Investment  Policies
and Risks" for more details on the Fund's policy on futures.
     The Fund is generally managed without regard to tax ramifications.


[FLAG] THE FUND IS SUBJECT TO MANAGER RISK,  WHICH IS THE  POSSIBILITY  THAT THE
     ADVISERS MAY DO A POOR JOB OF SELECTING STOCKS.


TURNOVER RATE
Although the Fund  generally  seeks to invest for the long term,  it retains the
right to sell  securities  regardless of how long the securities have been held.
The Fund's average  turnover rate for the past five years has been about 30%. (A
turnover  rate of 100% would occur,  for example,  if the Fund sold and replaced
securities valued at 100% of its net assets within a one-year period.)

- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                                 TURNOVER RATE
Before  investing in a mutual fund,  you should review its turnover  rate.  This
gives an  indication  of how  transaction  costs could affect the fund's  future
returns.  In general,  the greater the volume of buying and selling by the fund,
the greater the impact that brokerage  commissions and other  transaction  costs
will have on its return. Also, funds with high turnover rates may be more likely
to generate  capital gains that must be  distributed to  shareholders  as income
subject to taxes.  As of October 31,  1999,  the average  turnover  rate for all
domestic stock funds was approximately 87%, according to Morningstar, Inc.
- --------------------------------------------------------------------------------

OTHER INVESTMENT POLICIES AND RISKS
Besides investing in common stocks of value companies, the Fund may make certain
other kinds of investments to achieve its objective.
     Although  the  Fund  typically  does not make  significant  investments  in
securities of companies  based outside the United States,  it reserves the right
to invest up to 20% of its assets in foreign securities. These securities may be
traded in U.S. or foreign  markets.  To the extent that it owns foreign  stocks,
the Fund is subject to (1) country risk, which is the possibility that political
events (such as a war),  financial  problems  (such as government  default),  or
natural  disasters (such as an earthquake)  will weaken a country's  economy and
cause investments in that country to lose money; and (2) currency risk, which is
the possibility  that Americans  investing  abroad could lose money because of a
rise in the value of the U.S. dollar versus foreign currencies.
     The Fund may invest in money market instruments,  fixed-income  securities,
convertible securities, and other equity securities such as preferred stock. The
Fund may invest up to 15% of its assets in  restricted  securities  with limited
marketability or other illiquid securities.
     The Fund may also  invest,  to a limited  extent,  in futures  and  options
contracts,  which  are  traditional  types of  derivatives.  Losses  (or  gains)
involving  futures can  sometimes be  substantial--in  part because a relatively
small  price  movement  in a futures  contract  may result in an  immediate  and
substantial  loss (or gain)  for a fund.  This  Fund  will not use  futures  for
speculative  purposes  or as  leveraged  investments  that  magnify the gains or
losses of an investment.  The Fund's obligation under futures contracts will not
exceed 20% of its total assets.


<PAGE>


8

The reasons for which the Fund will invest in futures and options are:

- -    To keep cash on hand to meet  shareholder  redemptions or other needs while
     simulating full investment in stocks.
- -    To reduce the Fund's  transaction costs or add value when these instruments
     are favorably priced.

     The Fund may temporarily  depart from its normal  investment  policies--for
instance,   by  investing   substantially  in  cash  reserves--in   response  to
extraordinary market, economic, political, or other conditions. In doing so, the
Fund may succeed in avoiding losses but otherwise fail to achieve its investment
objective.


- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                                  DERIVATIVES
A derivative is a financial contract whose value is based on (or "derived" from)
a  traditional  security  (such  as a stock  or a  bond),  an  asset  (such as a
commodity like gold), or a market index (such as the S&P 500 Index). Futures and
options are derivatives  that have been trading on regulated  exchanges for more
than two decades.  These  "traditional"  derivatives are standardized  contracts
that can easily be bought and sold,  and whose market values are  determined and
published  daily. It is these  characteristics  that  differentiate  futures and
options from the relatively new types of derivatives. If used for speculation or
as leveraged investments, derivatives can carry considerable risks.
- --------------------------------------------------------------------------------



THE FUND AND VANGUARD


The Fund is a member of The Vanguard  Group, a family of more than 35 investment
companies  with more than 100 funds holding assets worth more than $530 billion.
All of the  Vanguard  funds  share  in the  expenses  associated  with  business
operations, such as personnel, office space, equipment, and advertising.

     Vanguard  also  provides   marketing   services  to  the  funds.   Although
shareholders do not pay sales commissions or 12b-1  distribution fees, each fund
pays its allocated share of The Vanguard Group's marketing costs.



- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                     VANGUARD'S UNIQUE CORPORATE STRUCTURE
The Vanguard Group is truly a MUTUAL mutual fund company. It is owned jointly by
the funds it oversees and thus  indirectly by the  shareholders  in those funds.
Most other mutual funds are operated by for-profit management companies that may
be owned by one person,  by a group of individuals,  or by investors who own the
management  company's stock. By contrast,  Vanguard  provides its services on an
"at-cost"  basis,  and the funds' expense  ratios  reflect only these costs.  No
separate  management  company reaps profits or absorbs losses from operating the
funds.
- --------------------------------------------------------------------------------




<PAGE>
                                                                               9

INVESTMENT ADVISERS

The Fund employs four investment advisers.  Each manages a portion of the Fund's
assets subject to the control of the Trustees and officers of the Fund.


BARROW, HANLEY, MEWHINNEY, & STRAUSS, INC.
     Barrow,  Hanley,  Mewhinney,  & Strauss,  Inc.(Barrow Hanley), One McKinney
Plaza,  3232 McKinney  Avenue,  15th Floor,  Dallas,  TX 75204, is an investment
advisory  firm  founded  in  1979.  Barrow  Hanley  is  owned  by  United  Asset
Management,  1 International  Place,  Boston, MA 02110.  Barrow Hanley currently
manages more than $35 billion in stock and bond portfolios.
     Barrow  Hanley's  advisory fee is paid  quarterly,  and is based on certain
annual  percentage rates applied to the Fund's average month-end assets for each
quarter. In addition,  Barrow Hanley's advisory fee may be adjusted based on the
cumulative  investment  performance  of its portion of the Fund as compared with
the  cumulative  return  of the  Standard  & Poor's  500/BARRA  Value  Index,  a
benchmark  of stocks from the S&P 500 Index with lower than  average  price/book
ratios.  Under the fee schedule,  Barrow  Hanley's basic fee may be increased or
decreased by as much as 25%.

EQUINOX CAPITAL MANAGEMENT LLC
     Equinox Capital Management LLC (Equinox),  590 Madison Avenue,  41st Floor,
New York, NY 10022, is an investment advisory firm founded in 1989. It currently
manages more than $13 billion in assets.
     Equinox's  advisory fee is paid  quarterly,  and is based on certain annual
percentage  rates  applied  to the  Fund's  average  month-end  assets  for each
quarter.  In  addition,  Equinox's  advisory  fee may be  adjusted  based on the
cumulative investment performance of its portion of the Fund as compared to that
of the Russell 1000 Value Index. Under the fee schedule, Equinox's basic fee may
be increased or decreased by as much as 50%.

TUKMAN CAPITAL MANAGEMENT, INC.
     Tukman  Capital  Management,   Inc.(Tukman),  60  East  Sir  Francis  Drake
Boulevard,  Larkspur,  CA 94939, is an investment advisory firm founded in 1980.
It currently manages more than $3.7 billion in assets.
     Tukman's  advisory fee is paid  quarterly,  and is based on certain  annual
percentage  rates  applied  to the  Fund's  average  month-end  assets  for each
quarter.  In  addition,  Tukman's  advisory  fee may be  adjusted  based  on the
cumulative investment performance of its portion of the Fund as compared to that
of the  S&P 500  Index.  Under  the  fee  schedule,  Tukman's  basic  fee may be
increased or decreased by as much as 50%.

THE VANGUARD GROUP
     The Vanguard  Group  (Vanguard),  P.O. Box 2600,  Valley  Forge,  PA 19482,
founded in 1974,  is a wholly  owned  subsidiary  of the Vanguard  funds.  As of
October 31, 1999, Vanguard served as adviser for about $345.6 billion in assets.
The Fund receives advisory services from Vanguard on an at-cost basis.

     For the  fiscal  year ended  October  31,  1999,  the  aggregate  amount of
investment  advisory fees paid by the Fund  represented an effective annual rate
of 0.12% of the Fund's  average  net assets  before a decrease of 0.01% based on
performance.
     The Fund has authorized the advisers to choose brokers or dealers to handle
the purchase and sale of securities  for the Fund, and to get the best available
price and most  favorable  execution  from  these  brokers  with  respect to all
transactions.
     In the  interest  of  obtaining  better  execution  of a  transaction,  the
advisers  may choose  brokers who charge  higher  commissions.  If more than one
broker can obtain the best  available  price and most  favorable  execution of a
transaction,  then the  advisers  are  authorized  to  choose a broker  who,  in
addition to executing the transaction, will provide research ser-



<PAGE>
10


vices to the advisers or the Fund. Also, the Fund may direct the advisers to use
a particular broker for certain  transactions in exchange for commission rebates
or research services provided to the Fund.
     The Board of Trustees may, without prior approval from shareholders, change
the terms of an advisory agreement or hire a new investment adviser--either as a
replacement for an existing adviser or as an additional adviser. Any significant
change in the Fund's advisory  arrangements will be communicated to shareholders
in writing. In addition, as the Fund's sponsor and overall manager, The Vanguard
Group may provide investment advisory services to the Fund, on an at-cost basis,
at any time.



- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                              THE FUND'S ADVISERS
The manager  responsible for Barrow Hanley's portion of Vanguard Windsor II Fund
since  1985 is  JAMES P.  BARROW,  Partner  of  Barrow  Hanley;  has  worked  in
investment management since 1963; with Barrow Hanley since 1979; B.S. University
of South Carolina.

The manager  responsible for Equinox's  portion of the Fund since 1991 is RONALD
J. ULRICH, President, Director, and founder of Equinox; has worked in investment
management since 1973; B.S. Lehigh University; M.B.A., New York University.

The managers  responsible  for Tukman's  portion of the Fund are MELVIN  TUKMAN,
President,  Director, and founder of Tukman; has worked in investment management
since 1971; A.B., Hunter College; M.B.A., Harvard Business School; and DANIEL L.
GROSSMAN,  Vice  President  and  Portfolio  Manager  of  Tukman;  has  worked in
investment management since 1978; M.B.A., Stanford University.

The manager  responsible for Vanguard's portion of the Fund is GEORGE U. SAUTER,
Managing  Director of Vanguard and head of Vanguard's Core Management Group; has
worked  in  investment   management  since  1985;  primary   responsibility  for
Vanguard's stock indexing policy and strategy since joining the company in 1987;
A.B., Dartmouth College; M.B.A., University of Chicago.
- --------------------------------------------------------------------------------





DIVIDENDS, CAPITAL GAINS, AND TAXES


FUND DISTRIBUTIONS
The Fund  distributes to shareholders  virtually all of its net income (interest
and dividends,  less  expenses),  as well as any capital gains realized from the
sale of its holdings.  Income  dividends  generally are  distributed in June and
December;  capital  gains  distributions  generally  occur in December.  You can
receive  distributions  of income dividends or capital gains in cash, or you can
have them automatically reinvested in more shares of the Fund.

BASIC TAX POINTS

Vanguard will send you a statement each year showing the tax status of all your
distributions. In addition, taxable investors should be aware of the following
basic tax points:

- - Distributions are taxable to you whether or not you reinvest these amounts in
 additional Fund shares.
- - Distributions declared in December--if paid to you by the end of January--are
 taxable as if received in December.


<PAGE>


                                                                              11


- -    Any dividends and short-term  capital gains that you receive are taxable to
     you as ordinary income for federal income tax purposes.
- -    Any  distributions  of net  long-term  capital  gains are taxable to you as
     long-term capital gains for federal income tax purposes, no matter how long
     you've owned shares in the Fund.
- -    Capital gains  distributions  may vary  considerably from year to year as a
     result of the Fund's normal investment activities and cash flows.
- -    A sale or exchange of Fund shares is a taxable  event.  This means that you
     may have a capital gain to report as income, or a capital loss to report as
     a deduction, when you complete your federal income tax return.
- -    State and local  income  taxes may apply to any  dividend or capital  gains
     distributions  that you  receive,  as well as your gains or losses from any
     sale or exchange of Fund shares.

GENERAL INFORMATION
BACKUP  WITHHOLDING.   By  law,  Vanguard  must  withhold  31%  of  any  taxable
distributions  or  redemptions  from your  account if you do not provide us with
your  correct  taxpayer  identification  number and certify  that it is correct.
Similarly,  Vanguard  must withhold from your account if the IRS instructs us to
do so.
FOREIGN  INVESTORS.  The Vanguard funds  generally do not offer their shares for
sale outside of the United States.  Foreign  investors should be aware that U.S.
withholding and estate taxes may apply to any investments in Vanguard funds.
INVALID  ADDRESSES.  If a dividend or capital gains distribution check mailed to
your address of record is returned as undeliverable, Vanguard will automatically
reinvest  all future  distributions  until you  provide us with a valid  mailing
address.
TAX CONSEQUENCES.  This prospectus provides general tax information only. If you
are investing through a tax-deferred retirement account, such as an IRA, special
tax rules apply. Please consult your tax adviser for detailed  information about
a fund's tax consequences for you.


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                               "BUYING A DIVIDEND"
Unless you are investing through a tax-deferred  retirement  account (such as an
IRA),  it is not to your  advantage  to buy shares of a fund  shortly  before it
makes a  distribution,  because  doing so can cost you money in  taxes.  This is
known as "buying a dividend."  For example:  on December 15, you invest  $5,000,
buying 250 shares for $20 each. If the fund pays a distribution  of $1 per share
on December 16, its share price would drop to $19 (not counting  market change).
You still have only $5,000 (250 shares x $19 = $4,750 in share  value,  plus 250
shares x $1 = $250 in  distributions),  but you owe tax on the $250 distribution
you  received--even  if you  reinvest  it in more  shares.  To avoid  "buying  a
dividend," check a fund's distribution schedule before you invest.
- --------------------------------------------------------------------------------





<PAGE>

12


- --------------------------------------------------------------------------------
                                PLAIN TALK ABOUT
                                 DISTRIBUTIONS
As a  shareholder,  you are  entitled  to your share of the fund's  income  from
interest and dividends, and gains from the sale of investments. You receive such
earnings as either an income  dividend or a capital gains  distribution.  Income
dividends come from both the dividends that the fund earns from its holdings and
the  interest it receives  from its money market and bond  investments.  Capital
gains are realized  whenever the fund sells securities for higher prices than it
paid for them. These capital gains are either short-term or long-term, depending
on whether the fund held the  securities  for one year or less, or more than one
year.
- --------------------------------------------------------------------------------


SHARE PRICE
The Fund's share price,  called its net asset value,  or NAV, is calculated each
business day after the close of regular  trading on the New York Stock  Exchange
(the NAV is not  calculated  on  holidays  or other  days when the  Exchange  is
closed).  Net asset  value per share is computed by adding up the total value of
the Fund's  investments  and other assets,  subtracting  any of its  liabilities
(debts), and then dividing by the number of Fund shares outstanding:


           NET ASSET VALUE = TOTAL ASSETS - LIABILITIES
                         -------------------------------
                          NUMBER OF SHARES OUTSTANDING

     Knowing the daily net asset value is useful to you as a shareholder because
it indicates the current value of your investment. The Fund's NAV, multiplied by
the  number of  shares  you own,  gives you the  dollar  amount  you would  have
received had you sold all of your shares back to the Fund that day.
     A NOTE ON PRICING:  The Fund's  investments  will be priced at their market
value when market  quotations are readily  available.  When these quotations are
not  readily  available,  investments  will  be  priced  at  their  fair  value,
calculated according to procedures adopted by the Fund's Board of Trustees.
     The Fund's  share price can be found  daily in the mutual fund  listings of
most major newspapers under the heading "Vanguard  Funds." Different  newspapers
use different abbreviations of the Fund's name, but the most common is WNDSRII.



FINANCIAL HIGHLIGHTS
The following financial  highlights table is intended to help you understand the
Fund's financial  performance for the past five years,  and certain  information
reflects  financial  results for a single Fund share.  The total  returns in the
table represent the rate that an investor would have earned or lost each year on
an investment  in the Fund  (assuming  reinvestment  of all dividend and capital
gains  distributions).  This  information  has been derived  from the  financial
statements audited by PricewaterhouseCoopers LLP, independent accountants, whose
report--along  with the Fund's financial  statements--is  included in the Fund's
most recent


<PAGE>


                                                                              13


annual  report  to  shareholders.  You may have the  annual  report  sent to you
without charge by contacting Vanguard.



<TABLE>
<CAPTION>
- ------------------------------------------------------------------------------------------------------
                                                       VANGUARD WINDSOR II FUND
                                                         YEAR ENDED OCTOBER 31,
                                      ----------------------------------------------------------------
                                         1999           1998          1997          1996         1995
- ------------------------------------------------------------------------------------------------------
<S>                                     <C>            <C>           <C>           <C>          <C>
NET ASSET VALUE,BEGINNING OF YEAR      $31.07         $29.36        $24.04        $20.06        $17.33
- ------------------------------------------------------------------------------------------------------
INVESTMENT OPERATIONS
 Net Investment Income                    .64            .65           .64           .62           .58
 Net Realized and Unrealized Gain (Loss)
   on Investments                         .73           3.91          6.47          4.63          3.17
                                      ----------------------------------------------------------------
   Total from Investment Operations      1.37           4.56          7.11          5.25          3.75
                                      ----------------------------------------------------------------
DISTRIBUTIONS
 Dividends from Net Investment Income    (.74)          (.66)         (.63)         (.58)         (.55)
 Distributions from Realized Capital
   Gains                                (2.67)         (2.19)        (1.16)         (.69)         (.47)
                                      ----------------------------------------------------------------
   Total Distributions                  (3.41)         (2.85)        (1.79)        (1.27)        (1.02)
- ------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF YEAR           $29.03         $31.07        $29.36        $24.04        $20.06
======================================================================================================
TOTAL RETURN                             4.57%         16.51%        31.27%        27.17%        23.08%
======================================================================================================
RATIOS/SUPPLEMENTAL DATA
 Net Assets, End of Year (Millions)   $30,541        $29,639       $22,568       $14,758       $10,272
 Ratio of Total Expenses to Average
   Net Assets                            0.37%          0.41%         0.37%         0.39%         0.40%
 Ratio of Net Investment Income to
   Average Net Assets                    2.08%          2.16%         2.49%         2.92%         3.27%
 Turnover Rate                             26%            31%           30%           32%           30%
======================================================================================================
</TABLE>




- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                  HOW TO READ THE FINANCIAL HIGHLIGHTS TABLE

The Fund began  fiscal 1999 with a net asset value  (price) of $31.07 per share.
During  the  year,  the Fund  earned  $0.64  per share  from  investment  income
(interest  and  dividends)  and  $0.73  per  share  from  investments  that  had
appreciated  in value or that were sold for higher prices than the Fund paid for
them.

Shareholders  received $3.41 per share in the form of dividend and capital gains
distributions.  A portion of each year's  distributions  may come from the prior
year's income or capital gains.

The  earnings  ($1.37  per  share)  minus the  distributions  ($3.41  per share)
resulted in a share price of $29.03 at the end of the year.  This was a decrease
of $2.04 per share (from  $31.07 at the  beginning  of the year to $29.03 at the
end of the year).  For a shareholder  who  reinvested the  distributions  in the
purchase of more shares, the total return from the Fund was 4.57% for the year.

As of October 31, 1999, the Fund had $30.5 billion in net assets.  For the year,
its expense ratio was 0.37% ($3.70 per $1,000 of net assets); and net investment
income  amounted  to 2.08%  of its  average  net  assets.  It sold and  replaced
securities valued at 26% of its net assets.
- --------------------------------------------------------------------------------









"Standard & Poor's (R),"  "S&P(R),"  "S&P 500(R),"  "Standard & Poor's 500," and
"500" are trademarks of The McGraw-Hill Companies, Inc. Frank Russell Company is
the owner of the trademarks and copyrights relating to the Russell Indexes.


<PAGE>



14

 -------------------------------------------------------------------------------
INVESTING WITH VANGUARD

Are you looking for the most  convenient  way to open or add money to a Vanguard
account?  Obtain instant access to fund information?  Establish an account for a
minor child or for your  retirement  savings?
     Vanguard  can help.  Our goal is to make it easy and pleasant for you to do
business with us.
     The following  sections of the prospectus briefly explain the many services
we offer.  Booklets providing detailed information are available on the services
marked with a [BOOKLET]. Please call us to request copies.
- --------------------------------------------------------------------------------

SERVICES AND ACCOUNT FEATURES

Vanguard  offers many services that make it convenient to buy, sell, or exchange
shares, or to obtain fund or account information.
- --------------------------------------------------------------------------------
TELEPHONE REDEMPTIONS (SALES AND EXCHANGES)
Automatically set up for this Fund unless you notify us otherwise.
- --------------------------------------------------------------------------------
VANGUARD (R) DIRECT DEPOSIT SERVICE [BOOKLET]
Automatic  method  for  depositing  your  paycheck  or U.S.  government  payment
(including Social Security and government pension checks) into your account.
- --------------------------------------------------------------------------------
VANGUARD (R) AUTOMATIC EXCHANGE SERVICE [BOOKLET]
Automatic  method for  moving a fixed  amount of money  from one  Vanguard  fund
account to another.
- --------------------------------------------------------------------------------
VANGUARD FUND EXPRESS (R) [BOOKLET]
Electronic  method for buying or selling shares.  You can transfer money between
your  Vanguard  fund account and an account at your bank,  savings and loan,  or
credit union on a systematic schedule or whenever you wish.
- --------------------------------------------------------------------------------
VANGUARD DIVIDEND EXPRESS (TM) [BOOKLET]
Electronic method for transferring  dividend and/or capital gains  distributions
directly  from your  Vanguard  fund account to your bank,  savings and loan,  or
credit union account.
- --------------------------------------------------------------------------------

VANGUARD TELE-ACCOUNT(R) 1-800-662-6273 (ON-BOARD)[BOOKLET]
Toll-free  24-hour access to Vanguard fund and account  information--as  well as
some  transactions--by  using any touch-tone phone.  Tele-Account provides total
return,  share price, price change, and yield quotations for all Vanguard funds;
gives your account balances and history (e.g., last transaction, latest dividend
distribution);  and  allows  you to sell or  exchange  shares  to and from  most
Vanguard funds.
- --------------------------------------------------------------------------------
ACCESS VANGUARD(TM) www.vanguard.com [COMPUTER]
You can use your  personal  computer to perform  certain  transactions  for most
Vanguard  funds by accessing our website.  To establish  this service,  you must
register  through our website.  We will then mail you an account access password
that  allows  you  to  process  the  following   financial  and   administrative
transactions online:
- -    Open a new account.*
- -    Buy, sell, or exchange shares of most funds.
- -    Change your name/address.

<PAGE>


                                                                              15


- -    Add/change fund options (including dividend options, Vanguard Fund Express,
     bank instructions,  checkwriting, and Vanguard Automatic Exchange Service).
     (Some  restrictions may apply.) Please call our Client Services  Department
     for assistance.


*Only current Vanguard shareholders can open a new account online, by exchanging
shares from other existing Vanguard accounts.
- --------------------------------------------------------------------------------
INVESTOR INFORMATION DEPARTMENT: 1-800-662-7447 (SHIP) TEXT TELEPHONE:
1-800-952-3335
Call  Vanguard for  information  on our funds,  fund  services,  and  retirement
accounts, and to request literature.
- --------------------------------------------------------------------------------

CLIENT SERVICES DEPARTMENT: 1-800-662-2739 (CREW) TEXT TELEPHONE: 1-800-749-7273
Call Vanguard for information on your account, account transactions, and account
statements.

- --------------------------------------------------------------------------------

SERVICES  FOR  CLIENTS  OF  VANGUARD'S  INSTITUTIONAL  DIVISION:  1-888-809-8102
Vanguard's  Institutional  Division offers a variety of specialized services for
large  institutional   investors,   including  the  ability  to  effect  account
transactions through private electronic networks and third-party recordkeepers.
- --------------------------------------------------------------------------------



TYPES OF ACCOUNTS

Individuals and institutions can establish a variety of accounts with Vanguard.
- --------------------------------------------------------------------------------
FOR ONE OR MORE PEOPLE
Open an account in the name of one (individual) or more (joint tenants) people.
- --------------------------------------------------------------------------------
FOR HOLDING PERSONAL TRUST ASSETS [BOOKLET]
Invest assets held in an existing personal trust.
- --------------------------------------------------------------------------------
FOR INDIVIDUAL RETIREMENT ACCOUNTS [BOOKLET]
Open a  traditional  IRA account or a Roth IRA  account.  Eligibility  and other
requirements  are  established  by federal law and  Vanguard  custodial  account
agreements. For more information, please call 1-800-662-7447 (SHIP).
- --------------------------------------------------------------------------------
FOR AN ORGANIZATION [BOOKLET]
Open an account as a corporation,  partnership,  endowment, foundation, or other
entity.
- --------------------------------------------------------------------------------
FOR THIRD-PARTY TRUSTEE RETIREMENT INVESTMENTS
Open an account as a retirement trust or plan based on an existing  corporate or
institutional  plan.  These  accounts  are  established  by the  trustee  of the
existing plan.
- --------------------------------------------------------------------------------
VANGUARD PROTOTYPE PLANS
Open a  variety  of  retirement  accounts  using  Vanguard  prototype  plans for
individuals,  sole proprietorships,  and small businesses. For more information,
please call 1-800-662-2003.
- --------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
A NOTE ON INVESTING WITH VANGUARD THROUGH OTHER FIRMS
You may purchase or sell Fund shares through a financial  intermediary such as a
bank,  broker,  or investment  adviser.  If you invest with Vanguard  through an
intermediary,  please read that firm's program  materials  carefully to learn of
any  special  rules  that may apply.  For  example,  special  terms may apply to
additional service features, fees, or other policies.  Consult your intermediary
to determine when your order will be priced.
- --------------------------------------------------------------------------------
<PAGE>


16

BUYING SHARES

You buy your shares at the Fund's next-determined net asset value after Vanguard
receives your request.  As long as your request is received  before the close of
trading on the New York Stock Exchange,  generally 4 p.m. Eastern time, you will
buy your shares at that day's net asset value.
- --------------------------------------------------------------------------------
MINIMUM INVESTMENT TO . . .
open a new account
$3,000 (regular account); $1,000 (traditional IRAs and Roth IRAs).

add to an existing account
$100 by mail or exchange; $1,000 by wire.
- --------------------------------------------------------------------------------

A NOTE ON LOW BALANCES
The Fund  reserves  the  right to close any  nonretirement  fund  account  whose
balance falls below the minimum initial  investment.  The Fund will deduct a $10
annual fee in June if your  nonretirement  account balance at that time is below
$2,500.  The low balance fee is waived for investors who have aggregate Vanguard
account assets of $50,000 or more.
- --------------------------------------------------------------------------------
BY MAIL TO . . .[ENVELOPE]
open a new account
Complete and sign the account registration form and enclose your check.

add to an existing account
Mail your check with an  Invest-By-Mail  form  detached  from your  confirmation
statement to the address listed on the form. Please do not alter  Invest-By-Mail
forms, since they are fund- and account-specific.

Make your check payable to: The Vanguard Group-73
All  purchases  must be made in U.S.  dollars,  and checks must be drawn on U.S.
banks.

First-class mail to:          Express or Registered mail to:
The Vanguard Group            The Vanguard Group
P.O. Box 1110                 455 Devon Park Drive
Valley Forge, PA 19482-1110   Wayne, PA 19087-1815

For clients of Vanguard's Institutional Division . . .


First-class mail to:          Express or Registered mail to:
The Vanguard Group            The Vanguard Group
P.O. Box 2900                 455 Devon Park Drive
Valley Forge, PA 19482-2900   Wayne, PA 19087-1815
- --------------------------------------------------------------------------------
IMPORTANT  NOTE:  To prevent  check fraud,  Vanguard will not accept checks made
payable to third parties.
- --------------------------------------------------------------------------------
BY TELEPHONE TO . . .[TELEPHONE]
open a new account
Call Vanguard  Tele-Account*  24 hours a day--or Client Services during business
hours--to exchange from another Vanguard fund account with the same registration
(name, address,  taxpayer  identification  number, and account type). (Note that
some restrictions apply to index fund accounts.)

<PAGE>



                                                                              17


add to an existing account
Call Vanguard  Tele-Account*  24 hours a day--or Client Services during business
hours--to exchange from another Vanguard fund account with the same registration
(name, address,  taxpayer  identification  number, and account type). (Note that
some restrictions  apply to index fund accounts.) Use Vanguard Fund Express (see
"Services and Account Features") to transfer assets from your bank account. Call
Client Services before your first use to verify that this option is available.


Vanguard Tele-Account     Client Services
1-800-662-6273            1-800-662-2739

*You must obtain a Personal  Identification Number through Tele-Account at least
seven days before you request your first exchange.
- --------------------------------------------------------------------------------

IMPORTANT  NOTE:  Once  you  have  initiated  a  telephone   transaction  and  a
confirmation  number has been assigned,  the transaction  cannot be revoked.  We
reserve the right to refuse any purchase request.
- --------------------------------------------------------------------------------
BY WIRE TO OPEN A NEW ACCOUNT OR ADD TO AN EXISTING ACCOUNT [WIRE]
Call Client  Services to arrange your wire  transaction.  Wire  transactions  to
retirement  accounts are only  available for asset  transfers and rollovers from
other financial institutions.  Individual IRA contributions will not be accepted
by wire.


Wire to:
FRB ABA 021001088
HSBC Bank USA

For credit to:
Account: 000112046
Vanguard Incoming Wire Account


In favor of:
Vanguard Windsor II Fund-73
[Account number, or temporary number for a new account]
[Registered account owner(s)]
[Registered address]
- --------------------------------------------------------------------------------
You can redeem (that is, sell or exchange) shares purchased by check or Vanguard
Fund  Express  at any time.  However,  while  your  redemption  request  will be
processed  at the  next-determined  net asset value after it is  received,  your
redemption  proceeds  will not be available  until  payment for your purchase is
collected, which may take up to ten calendar days.
- --------------------------------------------------------------------------------
A NOTE ON LARGE  PURCHASES
It is important that you call Vanguard  before you invest a large dollar amount.
It is our responsibility to consider the interests of all Fund shareholders, and
so we  reserve  the right to refuse any  purchase  that may  disrupt  the Fund's
operation or performance.
- --------------------------------------------------------------------------------

<PAGE>



18

REDEEMING SHARES

This section describes how you can redeem--that is, sell or exchange--the Fund's
shares.

When Selling Shares:
- -    Vanguard sends the redemption proceeds to you or a designated third party.*
- -    You can sell all or part of your Fund shares at any time.


*May require a signature guarantee; see footnote on page 21.


When Exchanging Shares:
- -    The redemption proceeds are used to purchase shares of a different Vanguard
     fund.
- -    You must meet the receiving fund's minimum investment requirements.
- -    Vanguard reserves the right to revise or terminate the exchange  privilege,
     limit the amount of an exchange, or reject an exchange at any time, without
     notice.


- -    In  order  to  exchange  into  an  account  with a  different  registration
     (including a different name, address, or taxpayer  identification  number),
     you must include the guaranteed signatures of all current account owners on
     your written instructions.

In both  cases,  your  transaction  will be based on the Fund's  next-determined
share price, subject to any special rules discussed in this prospectus.
- --------------------------------------------------------------------------------
NOTE:  Once a redemption  is initiated  and a  confirmation  number  given,  the
transaction CANNOT be canceled.
- --------------------------------------------------------------------------------

HOW TO REQUEST A REDEMPTION
You can request a  redemption  from your Fund  account in any one of three ways:
online, by telephone, or by mail.
     The Vanguard funds whose shares you cannot  exchange online or by telephone
are VANGUARD U.S.  STOCK INDEX FUNDS,  VANGUARD  BALANCED  INDEX FUND,  VANGUARD
INTERNATIONAL  STOCK INDEX FUNDS,  VANGUARD REIT INDEX FUND, and VANGUARD GROWTH
AND INCOME FUND. These funds do, however,  permit online and telephone exchanges
within  IRAs and other  retirement  accounts.  If you sell shares of these funds
online, you will receive a redemption check at your address of record.
- --------------------------------------------------------------------------------
ONLINE REQUESTS [COMPUTER]
ACCESS VANGUARD at www.vanguard.com
You can use your personal  computer to sell or exchange  shares of most Vanguard
funds by accessing our website.  To establish  this  service,  you must register
through our website.  We will then mail you an account access password that will
enable  you to sell  or  exchange  shares  online  (as  well  as  perform  other
transactions).
- --------------------------------------------------------------------------------
TELEPHONE REQUESTS [TELEPHONE]
All Account Types Except Retirement:
Call Vanguard  Tele-Account  24 hours a day--or Client  Services during business
hours--to  sell or exchange  shares.  You can exchange  shares from this Fund to
open an account in another Vanguard fund or to add to an existing  Vanguard fund
account with an identical registration.

Retirement Accounts:
You can  exchange--but  not  sell--shares  by  calling  Tele-Account  or  Client
Services.
<PAGE>


                                                                              19

Vanguard Tele-Account     Client Services
1-800-662-6273            1-800-662-2739
- --------------------------------------------------------------------------------
SPECIAL  INFORMATION:  We will automatically  establish the telephone redemption
option for your  account,  unless you instruct us  otherwise  in writing.  While
telephone  redemption is easy and convenient,  this account  feature  involves a
risk of loss from  unauthorized or fraudulent  transactions.  Vanguard will take
reasonable  precautions  to protect your  account from fraud.  You should do the
same by keeping your account information  private and immediately  reviewing any
account  statements  that  we  send  to  you.  Make  sure  to  contact  Vanguard
immediately about any transaction you believe to be unauthorized.
- --------------------------------------------------------------------------------
We reserve the right to refuse a telephone redemption if the caller is unable to
provide:
- -    The ten-digit account number.
- -    The name and address exactly as registered on the account.
- -    The primary Social Security or employer identification number as registered
     on the account.

- -    The  Personal   Identification   Number,   if  applicable   (for  instance,
     Tele-Account).

     Please note that Vanguard will not be  responsible  for any account  losses
due to telephone  fraud, so long as we have taken reasonable steps to verify the
caller's identity.  If you wish to remove the telephone  redemption feature from
your account, please notify us in writing.
- --------------------------------------------------------------------------------
A NOTE ON  UNUSUAL  CIRCUMSTANCES
Vanguard  reserves the right to revise or  terminate  the  telephone  redemption
privilege at any time,  without notice.  In addition,  Vanguard can stop selling
shares or postpone  payment at times when the New York Stock  Exchange is closed
or under any emergency  circumstances  as determined by the U.S.  Securities and
Exchange Commission.  If you experience difficulty making a telephone redemption
during  periods  of  drastic  economic  or market  change,  you can send us your
request  by  regular or express  mail.  Follow  the  instructions  on selling or
exchanging shares by mail in this section.
- --------------------------------------------------------------------------------
MAIL REQUESTS [ENVELOPE]
All Account Types Except Retirement:
Send a letter of instruction signed by all registered  account holders.  Include
the fund name and  account  number and (if you are  selling) a dollar  amount or
number  of shares  OR (if you are  exchanging)  the name of the fund you want to
exchange  into and a dollar  amount or number of  shares.  To  exchange  into an
account  with a different  registration  (including a different  name,  address,
taxpayer identification number, or account type), you must provide Vanguard with
written  instructions  that  include the  guaranteed  signatures  of all current
owners of the fund from which you wish to redeem.

Vanguard Retirement Accounts:
For information on how to request distributions from:
- -    Traditional IRAs and Roth IRAs--call Client Services.
- -    SEP-IRAs, SIMPLE IRAs, 403(b)(7) custodial accounts, and Profit-Sharing and
     Money Purchase Pension (Keogh) Plans--call  Individual  Retirement Plans at
     1-800-662-2003.

Depending on your account  registration  type,  additional  documentation may be
required.

<PAGE>


20


First-class mail to:          Express or Registered mail to:
The Vanguard Group            The Vanguard Group
P.O. Box 1110                 455 Devon Park Drive
Valley Forge, PA 19482-1110   Wayne, PA 19087-1815


For clients of Vanguard's Institutional Division . . .

First-class mail to:          Express or Registered mail to:
The Vanguard Group            The Vanguard Group
P.O. Box 2900                 455 Devon Park Drive
Valley Forge, PA 19482-2900   Wayne, PA 19087-1815
- --------------------------------------------------------------------------------

A NOTE ON LARGE REDEMPTIONS
It is important that you call Vanguard  before you redeem a large dollar amount.
It is our responsibility to consider the interests of all fund shareholders, and
so we reserve the right to delay  delivery of your  redemption  proceeds--up  to
seven days--if the amount may disrupt the Fund's operation or performance.
     If you redeem more than  $250,000  worth of Fund  shares  within any 90-day
period,  the  Fund  reserves  the  right  to pay  part or all of the  redemption
proceeds above $250,000  in-kind,  i.e., in securities,  rather than in cash. If
payment is made in-kind,  you may incur  brokerage  commissions  if you elect to
sell the securities for cash.
- --------------------------------------------------------------------------------

OPTIONS FOR REDEMPTION PROCEEDS
You may receive your redemption  proceeds in one of three ways: check,  exchange
to another Vanguard fund, or Fund Express redemption.

- --------------------------------------------------------------------------------
CHECK REDEMPTIONS
Normally,  Vanguard  will  mail  your  check  within  two  business  days  of  a
redemption.
- --------------------------------------------------------------------------------
EXCHANGE REDEMPTIONS
As described  above, an exchange  involves using the proceeds of your redemption
to purchase shares of another Vanguard fund.
- --------------------------------------------------------------------------------

FUND EXPRESS REDEMPTIONS
Vanguard  will  electronically  transfer  funds to your  pre-linked  checking or
savings account.

- --------------------------------------------------------------------------------


FOR OUR MUTUAL PROTECTION
For your best interests and ours, Vanguard applies these additional requirements
to redemptions:

REQUEST IN "GOOD ORDER"
All redemption requests must be received by Vanguard in "good order." This means
that your request must include:
- -    The Fund name and account number.
- -    The amount of the transaction (in dollars or shares).
- -    Signatures  of all owners  exactly as  registered  on the account (for mail
     requests).
- -    Signature  guarantees (if required).*
- -    Any supporting legal documentation that may be required.
- -    Any outstanding certificates representing shares to be redeemed.
<PAGE>


                                                                              21


*For instance,  a signature guarantee must be provided by all registered account
shareholders  when redemption  proceeds are to be sent to a different  person or
address. A signature  guarantee can be obtained from most commercial and savings
banks, credit unions, trust companies, or member firms of a U.S. stock exchange.


TRANSACTIONS ARE PROCESSED AT THE NEXT-DETERMINED SHARE PRICE AFTER VANGUARD HAS
RECEIVED ALL REQUIRED INFORMATION.
- --------------------------------------------------------------------------------
LIMITS ON ACCOUNT ACTIVITY
Because  excessive account  transactions can disrupt  management of the Fund and
increase the Fund's costs for all shareholders, Vanguard limits account activity
as follows:

- -    You may make no more than TWO  SUBSTANTIVE  "ROUND TRIPS"  THROUGH THE FUND
     during any 12-month period.
- -    Your round trips through the Fund must be at least 30 days apart.
- -    The Fund may refuse a share purchase at any time, for any reason.
- -    Vanguard may revoke an investor's telephone exchange privilege at any time,
     for any reason.

A "round trip" is a redemption  from the Fund  followed by a purchase  back into
the  Fund.  Also,  a  "round  trip"  covers  transactions  accomplished  by  any
combination  of methods,  including  transactions  conducted by check,  wire, or
exchange to/from another Vanguard fund. "Substantive" means a dollar amount that
Vanguard  determines,  in  its  sole  discretion,  could  adversely  affect  the
management of the Fund.

- --------------------------------------------------------------------------------
RETURN YOUR SHARE CERTIFICATES
Any portion of your account represented by share certificates cannot be redeemed
until you return the  certificates  to Vanguard.  Certificates  must be returned
(unsigned),  along with a letter  requesting  the sale or  exchange  you wish to
process, via certified mail to:

The Vanguard Group
455 Devon Park Drive
Wayne, PA 19087-1815
- --------------------------------------------------------------------------------

ALL TRADES ARE FINAL
Vanguard  will not cancel any  transaction  request  (including  any purchase or
redemption)  that we believe to be authentic once the request has been initiated
and a confirmation number assigned.
- --------------------------------------------------------------------------------
UNCASHED CHECKS
Please cash your distribution or redemption  checks promptly.  Vanguard will not
pay interest on uncashed checks.
- --------------------------------------------------------------------------------


TRANSFERRING REGISTRATION

You can  transfer  the  registration  of your Fund  shares to  another  owner by
completing a transfer form and sending it to Vanguard.

First-class mail to:          Express or Registered mail to:
The Vanguard Group            The Vanguard Group
P.O. Box 1110                 455 Devon Park Drive
Valley Forge, PA 19482-1110   Wayne, PA 19087-1815
<PAGE>


22

For clients of Vanguard's Institutional Division . . .

First-class mail to:          Express or Registered mail to:
The Vanguard Group            The Vanguard Group
P.O. Box 2900                 455 Devon Park Drive
Valley Forge, PA 19482-2900   Wayne, PA 19087-1815
- --------------------------------------------------------------------------------

FUND AND ACCOUNT UPDATES
STATEMENTS AND REPORTS
We will send you account and tax  statements to help you keep track of your Fund
account  throughout  the year as well as when you are preparing  your income tax
returns.
     In addition,  you will  receive  financial  reports  about the Fund twice a
year.  These   comprehensive   reports  include  an  assessment  of  the  Fund's
performance  (and a comparison  to its industry  benchmark),  an overview of the
financial  markets,  a  report  from  the  advisers,  and the  Fund's  financial
statements which include a listing of the Fund's holdings.
     To keep  the  Fund's  costs  as low as  possible  (so  that  you and  other
shareholders can keep more of the Fund's investment earnings), Vanguard attempts
to  eliminate  duplicate  mailings  to the same  address.  When two or more Fund
shareholders  have the same last name and address,  we send just one Fund report
to that address--instead of mailing separate reports to each shareholder. If you
want us to send  separate  reports,  notify our Client  Services  Department  at
1-800-662-2739.
- --------------------------------------------------------------------------------

CONFIRMATION STATEMENT
Sent each time you buy,  sell, or exchange  shares;  confirms the trade date and
the amount of your transaction.
- --------------------------------------------------------------------------------
PORTFOLIO SUMMARY [BOOKLET]
Mailed  quarterly for most  accounts;  shows the market value of your account at
the close of the statement period, as well as distributions,  purchases,  sales,
and exchanges for the current calendar year.
- --------------------------------------------------------------------------------
FUND FINANCIAL REPORTS
Mailed in December and June for this Fund.
- --------------------------------------------------------------------------------
TAX STATEMENTS
Generally  mailed in January;  report previous year's dividend and capital gains
distributions,  proceeds from the sale of shares, and distributions from IRAs or
other retirement accounts.
- --------------------------------------------------------------------------------

AVERAGE COST REVIEW STATEMENT [BOOKLET]
Issued quarterly for most taxable accounts (accompanies your Portfolio Summary);
shows the average  cost of shares that you redeemed  during the  calendar  year,
using only the average cost single category method.

- --------------------------------------------------------------------------------









<PAGE>

























                     (THIS PAGE INTENTIONALLY LEFT BLANK.)
























<PAGE>

















                     (THIS PAGE INTENTIONALLY LEFT BLANK.)














<PAGE>


GLOSSARY OF INVESTMENT TERMS


CAPITAL GAINS DISTRIBUTION
Payment to mutual fund  shareholders  of gains  realized on securities  that the
fund has sold at a profit, minus any realized losses.

CASH RESERVES
Cash deposits,  short-term  bank deposits,  and money market  instruments  which
include U.S.  Treasury bills,  bank  certificates  of deposit (CDs),  repurchase
agreements, commercial paper, and banker's acceptances.

COMMON STOCK
A security  representing  ownership  rights in a  corporation.  A stockholder is
entitled  to share in the  company's  profits,  some of which may be paid out as
dividends.


DIVIDEND INCOME
Payment to  shareholders  of income from  interest or  dividends  generated by a
fund's investments.


EXPENSE RATIO
The  percentage  of a fund's  average net assets used to pay its  expenses.  The
expense ratio  includes  management  fees,  administrative  fees,  and any 12b-1
distribution fees.

FUND DIVERSIFICATION
Holding a variety of securities so that a fund's return is not badly hurt by the
poor performance of a single security, industry, or country.


GROWTH STOCK FUND
A mutual fund that emphasizes stocks of companies believed to have above-average
prospects for growth.  Reflecting market  expectations for superior growth,  the
prices of  growth  stocks  often are  relatively  high in  comparison  with such
factors as revenue, earnings, book value, and dividends.


INVESTMENT ADVISER
An  organization  that  makes  the  day-to-day   decisions  regarding  a  fund's
investments.

MUTUAL FUND
An  investment  company  that pools the money of many people and invests it in a
variety of securities in an effort to achieve a specific objective over time.

NET ASSET VALUE (NAV)
The market value of a mutual fund's total assets, minus liabilities,  divided by
the  number of shares  outstanding.  The value of a single  share is called  its
share value or share price.

PRICE/EARNINGS (P/E) RATIO
The current share price of a stock,  divided by its per-share earnings (profits)
from the past year. A stock selling for $20, with earnings of $2 per share,  has
a price/earnings ratio of 10.


PRINCIPAL
The amount of money you put into an investment.

SECURITIES
Stocks, bonds, and other investment vehicles.


TOTAL RETURN
A percentage change,  over a specified time period, in a mutual fund's net asset
value,  with the ending net asset value adjusted to account for the reinvestment
of all distributions of dividends and capital gains.

VALUE STOCK FUND
A mutual fund that  emphasizes  stocks of companies  whose growth  prospects are
generally   regarded  as  subpar  by  the  market.   Reflecting   these   market
expectations,  the  prices  of  value  stocks  typically  are  below-average  in
comparison with such factors as revenue, earnings, book value, and dividends.

VOLATILITY
The  fluctuations  in value of a mutual  fund or other  security.  The greater a
fund's volatility, the wider the fluctuations between its high and low prices.

YIELD
Income  (interest  or  dividends)  earned  by  an  investment,  expressed  as  a
percentage of the investment's price.
<PAGE>

[SHIP LOGO]
Post Office Box 2600
Valley Forge, PA 19482-2600

FOR MORE INFORMATION
If you'd  like  more  information about
Vanguard  Windsor II Fund,  the
following documents are available
free upon request:

ANNUAL/SEMIANNUAL REPORT
TO SHAREHOLDERS
Additional  information about the
Fund's  investments is available in
the Fund's annual and semiannual
reports to shareholders. In these
reports, you will find a discussion of
the market conditions and
investment strategies that
significantly affected the Fund's
performance during the most recent
fiscal year.

STATEMENT  OF  ADDITIONAL
INFORMATION  (SAI)
The SAI  provides  more  detailed
information about the Fund.

The  current  annual and  semiannual
reports  and the SAI are
incorporated  by reference  into (and
are thus legally a part of) this
prospectus.

To receive a free copy of the latest
annual or  semiannual  report or the
SAI, or to request additional
information about the Fund or other
Vanguard funds, please contact us
as follows:

THE VANGUARD GROUP
INVESTOR INFORMATION
DEPARTMENT
P.O. BOX 2600
VALLEY FORGE, PA 19482-2600

TELEPHONE:
1-800-662-7447 (SHIP)

TEXT TELEPHONE:
1-800-952-3335

WORLD WIDE WEB:
WWW.VANGUARD.COM



If you are a current  Fund  shareholder
and would like  information  about
your account, account transactions,
and/or account statements, please
call:

CLIENT SERVICES DEPARTMENT
TELEPHONE:
1-800-662-2739 (CREW)


TEXT TELEPHONE:
1-800-749-7273


INFORMATION  PROVIDED BY THE
SECURITIES AND EXCHANGE
COMMISSION  (SEC)
You can review  and copy
information  about the Fund
(including  the SAI) at the SEC's
Public Reference Room in
Washington, DC. To find out more
about this public service,  call the
SEC at  1-800-SEC-0330.  Reports and
other information about the Fund are
also available on the SEC's website
(www.sec.gov), or you can receive
copies of this  information,  for a fee,
by writing the Public Reference
Section, Securities and Exchange
Commission, Washington, DC
20549-6009.


Fund's Investment Company Act
file number: 811-834




(C) 2000 The Vanguard Group, Inc.
All rights reserved.
Vanguard Marketing
Corporation,
Distributor.

P073N-02/18/2000


<PAGE>

VANGUARD(R)
WINDSOR II (TM) FUND


Participant Prospectus
February 18, 2000

This prospectus contains
financial data for the
Fund through the
fiscal year ended
October 31, 1999.


[A MEMBER OF THE VANGUARD GROUP LOGO]

<PAGE>


VANGUARD WINDSOR II FUND
Participant Prospectus
February 18, 2000


A Growth and Income Stock Mutual Fund


- --------------------------------------------------------------------------------
CONTENTS
1  FUND PROFILE                         10 DIVIDENDS, CAPITAL GAINS, AND TAXES
3  ADDITIONAL INFORMATION               11 SHARE PRICE
3  A WORD ABOUT RISK                    11 FINANCIAL HIGHLIGHTS
3  WHO SHOULD INVEST                    13 INVESTING WITH VANGUARD
4  PRIMARY INVESTMENT STRATEGIES        14 ACCESSING FUND INFORMATION BY
8  THE FUND AND VANGUARD                   COMPUTER
8  INVESTMENT ADVISER                   GLOSSARY (inside back cover)
- --------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
WHY READING THIS PROSPECTUS IS IMPORTANT
This  prospectus  explains the  objective,  risks,  and  strategies  of Vanguard
Windsor II Fund.  To  highlight  terms and  concepts  important  to mutual  fund
investors, we have provided "Plain Talk (R)" explanations along the way. Reading
the prospectus will help you to decide whether the Fund is the right  investment
for you. We suggest that you keep it for future reference.
- -------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
IMPORTANT NOTE
This prospectus is intended for participants in employer-sponsored retirement or
savings plans. Another version--for  investors who would like to open a personal
investment account--can be obtained by calling Vanguard at 1-800-662-7447.
- -------------------------------------------------------------------------------

















NEITHER  THE  SECURITIES  AND  EXCHANGE  COMMISSION  NOR  ANY  STATE  SECURITIES
COMMISSION HAS APPROVED OR  DISAPPROVED  OF THESE  SECURITIES OR PASSED UPON THE
ACCURACY OR ADEQUACY OF THIS PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A
CRIMINAL OFFENSE.
<PAGE>


                                                                               1

FUND PROFILE
The following profile summarizes key features of Vanguard Windsor II Fund.


INVESTMENT OBJECTIVE
The Fund seeks to provide long-term growth of capital. As a secondary objective,
the Fund seeks to provide some dividend income.


INVESTMENT STRATEGIES
The Fund invests  primarily in large and medium-size  companies whose stocks are
considered  by the Fund's  advisers to be  undervalued.  Undervalued  stocks are
generally  those that are out of favor with  investors and currently  trading at
prices that, the adviser feels,  are below what the stocks are worth in relation
to   their   earnings.    These   stocks    typically--but    not   always--have
lower-than-average  price/earnings (P/E) ratios and higher-than-average dividend
yields.

PRIMARY RISKS
THE FUND'S TOTAL RETURN,  LIKE STOCK PRICES  GENERALLY,  WILL FLUCTUATE WITHIN A
WIDE RANGE, SO AN INVESTOR COULD LOSE MONEY OVER SHORT OR EVEN LONG PERIODS. The
Fund is also subject to:
- -    Investment  style risk,  which is the chance that  returns  from large- and
     mid-capitalization  value stocks will trail  returns from the overall stock
     market.
- -    Manager risk,  which is the chance that poor security  selection will cause
     the Fund to underperform other funds with similar investment objectives.


PERFORMANCE/RISK INFORMATION
The bar chart and table below  provide an indication of the risk of investing in
the Fund. The bar chart shows the Fund's  performance in each calendar year over
a ten-year  period.  The table shows how the Fund's average annual total returns
for one,  five,  and ten  calendar  years  compare  with those of a  broad-based
securities  market index. Keep in mind that the Fund's past performance does not
indicate how the Fund will perform in the future.

              ----------------------------------------------------
                              ANNUAL TOTAL RETURNS
              ----------------------------------------------------
                          1990                -9.98%
                          1991                28.70%
                          1992                11.99%
                          1993                13.60%
                          1994                -1.16%
                          1995                38.83%
                          1996                24.18%
                          1997                32.37%
                          1998                16.36%
                          1999                -5.81%
              ----------------------------------------------------

     During the period shown in the bar chart, the highest return for a calendar
quarter was 17.90%  (quarter  ended March 31, 1991) and the lowest  return for a
quarter was -15.05% (quarter ended September 30, 1990).


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2



      --------------------------------------------------------------------
           AVERAGE ANNUAL TOTAL RETURNS FOR YEARS ENDED DECEMBER 31, 1999
                                   1 YEAR         5 YEARS        10 YEARS
      --------------------------------------------------------------------
      Vanguard Windsor II Fund      -5.81%          20.13%         13.80%
      Standard & Poor's 500 Index   21.04           28.56          18.21
      --------------------------------------------------------------------

FEES AND EXPENSES
The following table describes the fees and expenses you would pay if you buy and
hold shares of the Fund. The expenses shown under Annual Fund Operating Expenses
are based upon those incurred in the fiscal year ended October 31, 1999.

      SHAREHOLDER FEES (fees paid directly from your investment)
      Sales Charge (Load) Imposed on Purchases:              None
      Sales Charge (Load) Imposed on Reinvested Dividends:   None
      Redemption Fee:                                        None
      Exchange Fee:                                          None


      ANNUAL FUND OPERATING EXPENSES (expenses deducted from the
      Fund's assets)
      Management Expenses:                                   0.35%
      12b-1 Distribution Fee:                                None
      Other Expenses:                                        0.02%
       TOTAL ANNUAL FUND OPERATING EXPENSES:                 0.37%



     The following example is intended to help you compare the cost of investing
in the Fund with the cost of investing in other mutual funds. It illustrates the
hypothetical  expenses  that you would incur over various  periods if you invest
$10,000 in the Fund.  This example assumes that the Fund provides a return of 5%
a year, and that operating  expenses  remain the same. The results apply whether
or not you redeem your investment at the end of each period.


              -------------------------------------------------
                1 YEAR      3 YEARS    5 YEARS      10 YEARS
              -------------------------------------------------
                  $38         $119       $208         $468
              -------------------------------------------------


     THIS  EXAMPLE  SHOULD NOT BE  CONSIDERED  TO REPRESENT  ACTUAL  EXPENSES OR
PERFORMANCE  FROM THE PAST OR FOR THE  FUTURE.  ACTUAL  FUTURE  EXPENSES  MAY BE
HIGHER OR LOWER THAN THOSE SHOWN.



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                               PLAIN TALK ABOUT
                                 FUND EXPENSES
All mutual funds have operating  expenses.  These  expenses,  which are deducted
from a fund's gross  income,  are expressed as a percentage of the net assets of
the fund.  Vanguard  Windsor  II Fund's  expense  ratio in fiscal  year 1999 was
0.37%,  or $3.70 per $1,000 of average net assets.  The average  large-cap value
mutual fund had  expenses in 1999 of 1.26%,  or $12.60 per $1,000 of average net
assets (derived from data provided as of December 31, 1999 by Lipper Inc., which
reports on the mutual fund industry).  Management  expenses,  which comprise one
part of operating  expenses,  include investment  advisory fees as well as other
costs of managing a fund--such as account  maintenance,  reporting,  accounting,
legal, and other administrative expenses.
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<PAGE>


                                                                               3

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                               PLAIN TALK ABOUT
                            THE COSTS OF INVESTING
Costs are an important  consideration in choosing a mutual fund.  That's because
you, as a shareholder,  pay the costs of operating a fund,  plus any transaction
costs  associated with the fund's buying and selling of securities.  These costs
can erode a substantial  portion of the gross income or capital  appreciation  a
fund achieves. Even seemingly small differences in expenses can, over time, have
a dramatic effect on a fund's performance.
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- --------------------------------------------------------------------------------
ADDITIONAL INFORMATION            INCEPTION DATE
DIVIDENDS AND CAPITAL GAINS       June 24, 1985
Dividends are distributed
semiannually in June and          NET ASSETS AS OF OCTOBER 31, 1999
December; capital gains, if any,  $30.5 billion
are distributed in December

INVESTMENT ADVISERS               NEWSPAPER ABBREVIATION
Vanguard Windsor II Fund          WndsrII
uses four advisers:
- -Barrow, Hanley, Mewhinney        VANGUARD FUND NUMBER
 & Strauss, Inc., Dallas,         073
 Tex., since 1985
- -Equinox Capital Management LLC,  CUSIP NUMBER
 New York, N.Y., since 1991       922018205
- -Tukman Capital Management, Inc.,
 Larkspur, Calif. since 1991      TICKER SYMBOL
 Mass., since 2000                VWNFX
- -The Vanguard Group, Valley
 Forge, Pa., since 1991
- --------------------------------------------------------------------------------



================================================================================
A WORD ABOUT RISK

This  prospectus  describes  risks you would  face as an  investor  in  Vanguard
Windsor  II Fund.  It is  important  to keep in mind one of the main  axioms  of
investing: The higher the risk of losing money, the higher the potential reward.
The  reverse,  also,  is  generally  true:  The lower  the  risk,  the lower the
potential reward. As you consider an investment in Vanguard Windsor II Fund, you
should also take into account your personal tolerance for the daily fluctuations
of the stock market.
     Look for this [FLAG] symbol  throughout the prospectus.  It is used to mark
detailed  information  about  each  type of risk that you  would  confront  as a
shareholder of the Fund.
================================================================================



WHO SHOULD INVEST

The Fund may be a suitable investment for you if:
- -    You wish to add a  value-oriented  growth  and  income  stock  fund to your
     existing  holdings,  which could include other stock investments as well as
     bond, money market, and tax-exempt investments.
- -    You are  seeking  growth  of  capital  over the long  term--at  least  five
     years--as well as some dividend income.
<PAGE>


4

     THE VANGUARD FUNDS DO NOT PERMIT MARKET-TIMING.  DO NOT INVEST IN THIS FUND
IF YOU ARE A MARKET-TIMER.


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                               PLAIN TALK ABOUT
                            COSTS AND MARKET-TIMING
Some   investors  try  to  profit  from   market-timing--switching   money  into
investments  when they  expect  prices to rise,  and taking  money out when they
expect  the  market  to fall.  As money is  shifted  in and out,  a fund  incurs
expenses  for buying and selling  securities.  These costs are borne by all fund
shareholders,  including the long-term  investors who do not generate the costs.
Therefore,  the Fund  discourages  short-term  trading by,  among other  things,
limiting the number of exchanges it permits.
- --------------------------------------------------------------------------------

     The Fund has adopted the following  policies,  among others,  to discourage
short-term trading:

- -    The Fund  reserves  the right to  reject  any  purchase  request--including
     exchanges from other  Vanguard  funds--that it regards as disruptive to the
     efficient  management  of the Fund.  A purchase  request  could be rejected
     because  of the  timing  of the  investment  or  because  of a  history  of
     excessive trading by the investor.

- -    There is a limit to the  number of times you can  exchange  into and out of
     the Fund (see "Exchanges" in the INVESTING WITH VANGUARD section).
- -    The Fund reserves the right to stop offering shares at any time.


PRIMARY INVESTMENT STRATEGIES


This section explains the strategies that the investment advisers use in pursuit
of the  Fund's  objectives  of  long-term  growth of capital  and some  dividend
income.  It also  explains  how the  advisers  implement  these  strategies.  In
addition,   this  section  discusses  several  important   risks--market   risk,
investment  style risk,  and manager  risk--faced  by investors in the Fund. The
Fund's Board of Trustees  oversees the management of the Fund and may change the
investment strategies in the interest of shareholders.

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                                PLAIN TALK ABOUT
                   LARGE-CAP, MID-CAP, AND SMALL-CAP STOCKS
Stocks  of  publicly  traded   companies--and   mutual  funds  that  hold  these
stocks--can be classified by the  companies'  market value,  or  capitalization.
Market  capitalization  changes over time, and there is no "official" definition
of the boundaries of large-,  mid-,  and small-cap  stocks.  Vanguard  generally
defines  large-capitalization  (large-cap)  funds as  those  holding  stocks  of
companies  whose  outstanding  shares have a market value exceeding $12 billion;
mid-cap funds as those holding  stocks of companies  with a market value between
$1 billion and $12  billion;  and  small-cap  funds as those  typically  holding
stocks  of  companies  with a market  value of less  than $1  billion.  Vanguard
periodically reassesses these classifications.
- --------------------------------------------------------------------------------




<PAGE>


                                                                               5


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                               PLAIN TALK ABOUT
                         VALUE FUNDS AND GROWTH FUNDS
Value  investing  and growth  investing  are two styles  employed  by stock fund
managers.  Value funds  generally  emphasize  stocks of companies from which the
market does not expect strong growth.  The prices of value stocks  typically are
below-average  in  comparison  to such factors as earnings  and book value,  and
these  stocks  typically  have  above-average   dividend  yields.  Growth  funds
generally focus on companies believed to have above-average potential for growth
in revenue and earnings.  Reflecting the market's high expectations for superior
growth, such stocks typically have low dividend yields and above-average  prices
in relation to such measures as revenue,  earnings,  and book values.  Value and
growth stocks have, in the past, produced similar long-term returns, though each
category has periods when it outperforms the other. In general,  value funds are
appropriate  for investors  who want some dividend  income and the potential for
capital gains but are less tolerant of share-price  fluctuations.  Growth funds,
by contrast,  appeal to investors who will accept more  volatility in hopes of a
greater increase in share price.  Growth funds also may appeal to investors with
taxable  accounts  who want a higher  proportion  of  returns to come as capital
gains (which may be taxed at lower rates than dividend income).
- --------------------------------------------------------------------------------



MARKET EXPOSURE
The Fund is a value fund. It employs four  investment  advisers to carry out its
primary  strategy  of  investing  in a broadly  diversified  group of large- and
mid-capitalization  companies  that  have  favorable  prospects  for  growth  of
earnings and dividend income but whose prices do not reflect these prospects.

[FLAG] THE FUND IS SUBJECT TO MARKET RISK,  WHICH IS THE POSSIBILITY  THAT STOCK
     PRICES OVERALL WILL DECLINE OVER SHORT OR EVEN LONG PERIODS.  STOCK MARKETS
     TEND TO MOVE IN  CYCLES,  WITH  PERIODS  OF RISING  PRICES  AND  PERIODS OF
     FALLING PRICES.


     To illustrate the volatility of stock prices, the following table shows the
best,  worst,  and average total returns for the U.S.  stock market over various
periods as measured by the Standard & Poor's 500 Index,  a widely used barometer
of market  activity.  (Total returns  consist of dividend  income plus change in
market  price.)  Note that the returns  shown do not include the costs of buying
and selling  stocks or other  expenses  that a real-world  investment  portfolio
would  incur.  Note,  also,  that the gap between best and worst tends to narrow
over the long term.

               ----------------------------------------------------
                      U.S. STOCK MARKET RETURNS (1926-1999)
                           1 YEAR    5 YEARS   10 YEARS  20 YEARS
               ----------------------------------------------------
               Best         54.2%     28.6%      19.9%     17.9%
               Worst       -43.1     -12.4       -0.9       3.1
               Average      13.2      11.0       11.1      11.1
               ----------------------------------------------------

     The table  covers all of the 1-, 5-,  10-,  and 20-year  periods  from 1926
through 1999. You can see, for example,  that while the average return on stocks
for all of the 5-year periods was 11.0%,  returns for individual  5-year periods
ranged from a -12.4% average (from 1928

<PAGE>


6


through 1932) to 28.6% (from 1995 through 1999).  These average  returns reflect
past  performance on common stocks;  you should not regard them as an indication
of  future  returns  from  either  the  stock  market as a whole or this Fund in
particular.


[FLAG] THE FUND IS SUBJECT TO INVESTMENT  STYLE RISK,  WHICH IS THE  POSSIBILITY
     THAT  RETURNS  FROM LARGE- AND  MID-CAPITALIZATION  VALUE STOCKS WILL TRAIL
     RETURNS FROM OTHER ASSET CLASSES OR THE OVERALL  STOCK MARKET.  AS A GROUP,
     VALUE  STOCKS  TEND TO GO THROUGH  CYCLES OF DOING  BETTER--OR  WORSE--THAN
     COMMON STOCKS IN GENERAL.  THESE  PERIODS HAVE, IN THE PAST,  LASTED FOR AS
     LONG AS SEVERAL YEARS.



SECURITY SELECTION
Vanguard  Windsor  II  Fund  employs  four  investment  advisers,  each  of whom
independently  chooses and  maintains a portfolio of common stocks for the Fund.
Each adviser is responsible for a specific percentage of the Fund's assets.
     These investment  advisers employ active  investment  methods,  which means
that securities are bought and sold according to the advisers' evaluations about
companies  and their  financial  prospects,  and about the stock  market and the
economy in general.  Each adviser  will sell a security  when it is no longer as
attractive as an alternative investment.
     While each adviser uses a different process to select securities,  all four
are committed to investing in large- and mid-cap  stocks that, in their opinion,
are  undervalued.  Undervalued  stocks are generally those that are out of favor
with  investors and currently  trading at prices that,  the adviser  feels,  are
below what the stocks are worth in  relation  to their  earnings.  These  stocks
typically--but not always--have  lower-than-average  price/earnings (P/E) ratios
and higher-than-average dividend yields.
     Barrow,  Hanley,  Mewhinney & Strauss, Inc. (Barrow Hanley),  which managed
about 64% of the Fund's assets as of October 31, 1999, uses traditional  methods
of stock selection--research and analysis--to identify undervalued securities. A
security  will be sold  when,  in  Barrow  Hanley's  opinion,  its  share  price
accurately  reflects  the  security's  overall  worth.  At that  point,  another
undervalued  security  will be  chosen.  No more  than  15% of  Barrow  Hanley's
portfolio is devoted to a single industry.
     Tukman Capital  Management,  Inc. (Tukman),  which managed about 12% of the
Fund's assets as of October 31, 1999, also uses traditional  research methods to
select undervalued securities. Tukman typically buys stocks of financially sound
companies in growing business sectors and holds them for three to five years, on
average.
     Equinox  Capital  Management LLC (Equinox),  which managed about 14% of the
Fund's  assets as of October 31,  1999,  uses its own  fundamental  research and
proprietary software to identify  undervalued  securities with attractive growth
and dividend prospects.  Like Barrow Hanley, it avoids large concentrations in a
single industry.
     The Vanguard Group (Vanguard),  which managed about 6% of the Fund's assets
as of October 31, 1999, selects stocks from a "universe" of about 550 companies.
Vanguard,   using  quantitative  models,  evaluates  the  stocks  using  several
fundamental factors, such as a stock's price in relation to its projected growth
rate. The stocks  selected are expected,  as a group,  to outperform the Russell
1000 Value Index, a benchmark of large- and mid-cap value stocks.
     Vanguard  is  responsible  for the  balance  of the  Fund's  assets as cash
reserves  (about 4% as of October  31,  1999).  Vanguard  invests in stock index
features so that the cash reserve  portion of the Fund's  portfolio  may achieve
performance  similar to that of common stocks. This strategy is intended to keep
the Fund more fully invested in common stocks while

<PAGE>

                                                                               7


retaining cash on hand to meet liquidity needs. See "Other  Investment  Policies
and Risks" for more details on the Fund's policy on futures.

     The Fund is generally managed without regard to tax ramifications.

[FLAG] THE FUND IS SUBJECT TO MANAGER RISK,  WHICH IS THE  POSSIBILITY  THAT THE
     ADVISERS MAY DO A POOR JOB OF SELECTING STOCKS.


TURNOVER RATE
Although the Fund  generally  seeks to invest for the long term,  it retains the
right to sell  securities  regardless of how long the securities have been held.
The Fund's average  turnover rate for the past five years has been about 30%. (A
turnover  rate of 100% would occur,  for example,  if the Fund sold and replaced
securities valued at 100% of its net assets within a one-year period.)


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                               PLAIN TALK ABOUT
                                 TURNOVER RATE
Before  investing in a mutual fund,  you should review its turnover  rate.  This
gives an  indication  of how  transaction  costs could affect the fund's  future
returns.  In general,  the greater the volume of buying and selling by the fund,
the greater the impact that brokerage  commissions and other  transaction  costs
will have on its return. Also, funds with high turnover rates may be more likely
to generate  capital gains that must be  distributed to  shareholders  as income
subject to taxes.  As of October 31,  1999,  the average  turnover  rate for all
domestic stock funds was approximately 87%, according to Morningstar, Inc.
- --------------------------------------------------------------------------------



OTHER INVESTMENT POLICIES AND RISKS
Besides investing in common stocks of value companies, the Fund may make certain
other kinds of investments to achieve its objective.



     Although  the  Fund  typically  does not make  significant  investments  in
securities of companies  based outside the United States,  it reserves the right
to invest up to 20% of its assets in foreign securities. These securities may be
traded in U.S. or foreign  markets.  To the extent that it owns foreign  stocks,
the Fund is subject to (1) country risk, which is the possibility that political
events (such as a war),  financial  problems  (such as government  default),  or
natural  disasters (such as an earthquake)  will weaken a country's  economy and
cause investments in that country to lose money; and (2) currency risk, which is
the possibility  that Americans  investing  abroad could lose money because of a
rise in the value of the U.S. dollar versus foreign currencies.
     The Fund may invest in money market instruments,  fixed-income  securities,
convertible securities, and other equity securities such as preferred stock. The
Fund may invest up to 15% of its assets in  restricted  securities  with limited
marketability or other illiquid securities.

     The Fund may also  invest,  to a limited  extent,  in futures  and  options
contracts,  which  are  traditional  types of  derivatives.  Losses  (or  gains)
involving  futures can  sometimes be  substantial--in  part because a relatively
small  price  movement  in a futures  contract  may result in an  immediate  and
substantial  loss (or gain)  for a fund.  This  Fund  will not use  futures  for
speculative  purposes  or as  leveraged  investments  that  magnify the gains or
losses of an investment.  The Fund's obligation under futures contracts will not
exceed 20% of its total assets.


<PAGE>


8


     The reasons for which the Fund will invest in futures and options are:
- -    To keep cash on hand to meet  shareholder  redemptions or other needs while
     simulating full investment in stocks.
- -    To reduce the Fund's  transaction costs or add value when these instruments
     are favorably priced.

     The Fund may temporarily  depart from its normal  investment  policies--for
instance,   by  investing   substantially  in  cash  reserves--in   response  to
extraordinary market, economic, political, or other conditions. In doing so, the
Fund may succeed in avoiding losses but otherwise fail to achieve its investment
objective.


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                               PLAIN TALK ABOUT
                                  DERIVATIVES
A derivative is a financial contract whose value is based on (or "derived" from)
a  traditional  security  (such  as a stock  or a  bond),  an  asset  (such as a
commodity like gold), or a market index (such as the S&P 500 Index). Futures and
options are derivatives  that have been trading on regulated  exchanges for more
than two decades.  These  "traditional"  derivatives are standardized  contracts
that can easily be bought and sold,  and whose market values are  determined and
published  daily. It is these  characteristics  that  differentiate  futures and
options from the relatively new types of derivatives. If used for speculation or
as leveraged investments, derivatives can carry considerable risks.
- --------------------------------------------------------------------------------

THE FUND AND VANGUARD


The Fund is a member of The Vanguard  Group, a family of more than 35 investment
companies  with more than 100 funds holding assets worth more than $530 billion.
All of the  Vanguard  funds  share  in the  expenses  associated  with  business
operations, such as personnel, office space, equipment, and advertising.

     Vanguard  also  provides   marketing   services  to  the  funds.   Although
shareholders do not pay sales commissions or 12b-1  distribution fees, each fund
pays its allocated share of The Vanguard Group's marketing costs.



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                               PLAIN TALK ABOUT
                     VANGUARD'S UNIQUE CORPORATE STRUCTURE
The Vanguard Group is truly a MUTUAL mutual fund company. It is owned jointly by
the funds it oversees and thus  indirectly by the  shareholders  in those funds.
Most other mutual funds are operated by for-profit management companies that may
be owned by one person,  by a group of individuals,  or by investors who own the
management  company's stock. By contrast,  Vanguard  provides its services on an
"at-cost"  basis,  and the funds' expense  ratios  reflect only these costs.  No
separate  management  company reaps profits or absorbs losses from operating the
funds.
- --------------------------------------------------------------------------------

INVESTMENT ADVISERS

The Fund employs four investment advisers.  Each manages a portion of the Fund's
assets subject to the control of the Trustees and officers of the Fund.
<PAGE>


                                                                               9


BARROW, HANLEY, MEWHINNEY, & STRAUSS, INC.
     Barrow,  Hanley,  Mewhinney,  & Strauss,  Inc.(Barrow Hanley), One McKinney
Plaza,  3232 McKinney  Avenue,  15th Floor,  Dallas,  TX 75204, is an investment
advisory  firm  founded  in  1979.  Barrow  Hanley  is  owned  by  United  Asset
Management,  1 International  Place,  Boston, MA 02110.  Barrow Hanley currently
manages more than $35 billion in stock and bond portfolios.
     Barrow  Hanley's  advisory fee is paid  quarterly,  and is based on certain
annual  percentage rates applied to the Fund's average month-end assets for each
quarter. In addition,  Barrow Hanley's advisory fee may be adjusted based on the
cumulative  investment  performance  of its portion of the Fund as compared with
the  cumulative  return  of the  Standard  & Poor's  500/BARRA  Value  Index,  a
benchmark  of stocks from the S&P 500 Index with lower than  average  price/book
ratios.  Under the fee schedule,  Barrow  Hanley's basic fee may be increased or
decreased by as much as 25%.

EQUINOX CAPITAL MANAGEMENT LLC
     Equinox Capital Management LLC (Equinox),  590 Madison Avenue,  41st Floor,
New York, NY 10022, is an investment advisory firm founded in 1989. It currently
manages more than $13 billion in assets.
     Equinox's  advisory fee is paid  quarterly,  and is based on certain annual
percentage  rates  applied  to the  Fund's  average  month-end  assets  for each
quarter.  In  addition,  Equinox's  advisory  fee may be  adjusted  based on the
cumulative investment performance of its portion of the Fund as compared to that
of the Russell 1000 Value Index. Under the fee schedule, Equinox's basic fee may
be increased or decreased by as much as 50%.

TUKMAN CAPITAL MANAGEMENT, INC.
     Tukman  Capital  Management,   Inc.(Tukman),  60  East  Sir  Francis  Drake
Boulevard,  Larkspur,  CA 94939, is an investment advisory firm founded in 1980.
It currently manages more than $3.7 billion in assets.
     Tukman's  advisory fee is paid  quarterly,  and is based on certain  annual
percentage  rates  applied  to the  Fund's  average  month-end  assets  for each
quarter.  In  addition,  Tukman's  advisory  fee may be  adjusted  based  on the
cumulative investment performance of its portion of the Fund as compared to that
of the  S&P 500  Index.  Under  the  fee  schedule,  Tukman's  basic  fee may be
increased or decreased by as much as 50%.

THE VANGUARD GROUP
     The Vanguard  Group  (Vanguard),  P.O. Box 2600,  Valley  Forge,  PA 19482,
founded in 1974,  is a wholly  owned  subsidiary  of the Vanguard  funds.  As of
October 31, 1999, Vanguard served as adviser for about $345.6 billion in assets.
The Fund receives advisory services from Vanguard on an at-cost basis.

     For the  fiscal  year ended  October  31,  1999,  the  aggregate  amount of
investment  advisory fees paid by the Fund  represented an effective annual rate
of 0.12% of the Fund's  average  net assets  before a decrease of 0.01% based on
performance.
     The Fund has authorized the advisers to choose brokers or dealers to handle
the purchase and sale of securities  for the Fund, and to get the best available
price and most  favorable  execution  from  these  brokers  with  respect to all
transactions.
     In the  interest  of  obtaining  better  execution  of a  transaction,  the
advisers  may choose  brokers who charge  higher  commissions.  If more than one
broker can obtain the best  available  price and most  favorable  execution of a
transaction,  then the  advisers  are  authorized  to  choose a broker  who,  in
addition to executing the transaction, will provide research ser-

<PAGE>

10


vices to the advisers or the Fund. Also, the Fund may direct the advisers to use
a particular broker for certain  transactions in exchange for commission rebates
or research services provided to the Fund.
     The Board of Trustees may, without prior approval from shareholders, change
the terms of an advisory agreement or hire a new investment adviser--either as a
replacement for an existing adviser or as an additional adviser. Any significant
change in the Fund's advisory  arrangements will be communicated to shareholders
in writing. In addition, as the Fund's sponsor and overall manager, The Vanguard
Group may provide investment advisory services to the Fund, on an at-cost basis,
at any time.


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                               PLAIN TALK ABOUT
                              THE FUND'S ADVISERS
The manager  responsible for Barrow Hanley's portion of Vanguard Windsor II Fund
since  1985 is  JAMES P.  BARROW,  Partner  of  Barrow  Hanley;  has  worked  in
investment management since 1963; with Barrow Hanley since 1979; B.S. University
of South Carolina.

The manager  responsible for Equinox's  portion of the Fund since 1991 is RONALD
J. ULRICH, President, Director, and founder of Equinox; has worked in investment
management since 1973; B.S. Lehigh University; M.B.A., New York University.

The managers  responsible  for Tukman's  portion of the Fund are MELVIN  TUKMAN,
President,  Director, and founder of Tukman; has worked in investment management
since 1971; A.B., Hunter College; M.B.A., Harvard Business School; and DANIEL L.
GROSSMAN,  Vice  President  and  Portfolio  Manager  of  Tukman;  has  worked in
investment management since 1978; M.B.A., Stanford University.

The manager  responsible for Vanguard's portion of the Fund is GEORGE U. SAUTER,
Managing  Director of Vanguard and head of Vanguard's Core Management Group; has
worked  in  investment   management  since  1985;  primary   responsibility  for
Vanguard's stock indexing policy and strategy since joining the company in 1987;
A.B., Dartmouth College; M.B.A., University of Chicago.
- --------------------------------------------------------------------------------


DIVIDENDS, CAPITAL GAINS, AND TAXES


The Fund  distributes to shareholders  virtually all of its net income (interest
and dividends,  less  expenses),  as well as any capital gains realized from the
sale of its holdings.  Income  dividends  generally are  distributed in June and
December; capital gains distributions generally occur in December.
     Your  dividend  and  capital  gains  distributions  will be  reinvested  in
additional  Fund  shares  and  accumulate  on a  tax-deferred  basis  if you are
investing through an employer-sponsored retirement or savings plan. You will not
owe taxes on these  distributions until you begin withdrawals from the plan. You
should consult your plan administrator, your plan's Summary Plan Description, or
your tax adviser about the tax consequences of plan withdrawals.

<PAGE>

                                                                              11



- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                                 DISTRIBUTIONS
As a  shareholder,  you are  entitled  to your share of the fund's  income  from
interest and dividends, and gains from the sale of investments. You receive such
earnings as either an income  dividend or a capital gains  distribution.  Income
dividends come from both the dividends that the fund earns from its holdings and
the  interest it receives  from its money market and bond  investments.  Capital
gains are realized  whenever the fund sells securities for higher prices than it
paid for them. These capital gains are either short-term or long-term, depending
on whether the fund held the  securities  for one year or less, or more than one
year.
- --------------------------------------------------------------------------------



SHARE PRICE


The Fund's share price,  called its net asset value,  or NAV, is calculated each
business day after the close of regular  trading on the New York Stock  Exchange
(the NAV is not  calculated  on  holidays  or other  days when the  Exchange  is
closed).  Net asset  value per share is computed by adding up the total value of
the Fund's  investments  and other assets,  subtracting  any of its  liabilities
(debts), and then dividing by the number of Fund shares outstanding:


          NET ASSET VALUE = TOTAL ASSETS - LIABILITIES
                         -------------------------------
                          NUMBER OF SHARES OUTSTANDING

     Knowing the daily net asset value is useful to you as a shareholder because
it indicates the current value of your investment. The Fund's NAV, multiplied by
the  number of  shares  you own,  gives you the  dollar  amount  you would  have
received had you sold all of your shares back to the Fund that day.
     A NOTE ON PRICING:  The Fund's  investments  will be priced at their market
value when market  quotations are readily  available.  When these quotations are
not  readily  available,  investments  will  be  priced  at  their  fair  value,
calculated according to procedures adopted by the Fund's Board of Trustees.
     The Fund's  share price can be found  daily in the mutual fund  listings of
most major newspapers under the heading "Vanguard  Funds." Different  newspapers
use different abbreviations of the Fund's name, but the most common is WNDSRII.



FINANCIAL HIGHLIGHTS
The following financial  highlights table is intended to help you understand the
Fund's financial  performance for the past five years,  and certain  information
reflects  financial  results for a single Fund share.  The total  returns in the
table represent the rate that an investor would have earned or lost each year on
an investment  in the Fund  (assuming  reinvestment  of all dividend and capital
gains  distributions).  This  information  has been derived  from the  financial
statements audited by PricewaterhouseCoopers LLP, independent accountants, whose
report--along  with the Fund's financial  statements--is  included in the Fund's
most recent annual report to  shareholders.  You may have the annual report sent
to you without charge by contacting Vanguard.



<PAGE>


12

FINANCIAL HIGHLIGHTS (CONTINUED)


<TABLE>
<CAPTION>
- ------------------------------------------------------------------------------------------------------
                                                       VANGUARD WINDSOR II FUND
                                                         YEAR ENDED OCTOBER 31,
                                      ----------------------------------------------------------------
                                         1999           1998          1997          1996         1995
- ------------------------------------------------------------------------------------------------------
<S>                                     <C>            <C>           <C>           <C>          <C>
NET ASSET VALUE,BEGINNING OF YEAR      $31.07         $29.36        $24.04        $20.06        $17.33
- ------------------------------------------------------------------------------------------------------
INVESTMENT OPERATIONS
 Net Investment Income                    .64            .65           .64           .62           .58
 Net Realized and Unrealized Gain (Loss)
   on Investments                         .73           3.91          6.47          4.63          3.17
                                      ----------------------------------------------------------------
   Total from Investment Operations      1.37           4.56          7.11          5.25          3.75
                                      ----------------------------------------------------------------
DISTRIBUTIONS
 Dividends from Net Investment Income    (.74)          (.66)         (.63)         (.58)         (.55)
 Distributions from Realized Capital
   Gains                                (2.67)         (2.19)        (1.16)         (.69)         (.47)
                                      ----------------------------------------------------------------
   Total Distributions                  (3.41)         (2.85)        (1.79)        (1.27)        (1.02)
- ------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF YEAR           $29.03         $31.07        $29.36        $24.04        $20.06
======================================================================================================
TOTAL RETURN                             4.57%         16.51%        31.27%        27.17%        23.08%
======================================================================================================
RATIOS/SUPPLEMENTAL DATA
 Net Assets, End of Year (Millions)   $30,541        $29,639       $22,568       $14,758       $10,272
 Ratio of Total Expenses to Average
   Net Assets                            0.37%          0.41%         0.37%         0.39%         0.40%
 Ratio of Net Investment Income to
   Average Net Assets                    2.08%          2.16%         2.49%         2.92%         3.27%
 Turnover Rate                             26%            31%           30%           32%           30%
======================================================================================================
</TABLE>




- --------------------------------------------------------------------------------
                               PLAIN TALK ABOUT
                  HOW TO READ THE FINANCIAL HIGHLIGHTS TABLE
The Fund began  fiscal 1999 with a net asset value  (price) of $31.07 per share.
During  the  year,  the Fund  earned  $0.64  per share  from  investment  income
(interest  and  dividends)  and  $0.73  per  share  from  investments  that  had
appreciated  in value or that were sold for higher prices than the Fund paid for
them.

Shareholders  received $3.41 per share in the form of dividend and capital gains
distributions.  A portion of each year's  distributions  may come from the prior
year's income or capital gains.

The  earnings  ($1.37  per  share)  minus the  distributions  ($3.41  per share)
resulted in a share price of $29.03 at the end of the year.  This was a decrease
of $2.04 per share (from  $31.07 at the  beginning  of the year to $29.03 at the
end of the year).  For a shareholder  who  reinvested the  distributions  in the
purchase of more shares, the total return from the Fund was 4.57% for the year.

As of October 31, 1999, the Fund had $30.5 billion in net assets.  For the year,
its expense ratio was 0.37% ($3.70 per $1,000 of net assets); and net investment
income  amounted  to 2.08%  of its  average  net  assets.  It sold and  replaced
securities valued at 26% of its net assets.
- --------------------------------------------------------------------------------











"Standard & Poor's (R),"  "S&P(R),"  "S&P 500(R),"  "Standard & Poor's 500," and
"500" are trademarks of The McGraw-Hill Companies, Inc. Frank Russell Company is
the owner of the trademarks and copyrights relating to the Russell Indexes.

<PAGE>


                                                                              13

INVESTING WITH VANGUARD

The Fund is an investment  option in your  retirement or savings plan. Your plan
administrator  or your  employee  benefits  office can provide you with detailed
information  on how to  participate in your plan and how to elect the Fund as an
investment option.

- -    If you have any questions about the Fund or Vanguard, including those about
     the Fund's investment objective,  strategies,  or risks, contact Vanguard's
     Participant Services Center, toll-free, at 1-800-523-1188.

- -    If you have questions about your account,  contact your plan  administrator
     or the organization that provides recordkeeping services for your plan.

INVESTMENT OPTIONS AND ALLOCATIONS

Your  plan's  specific  provisions  may  allow  you to  change  your  investment
selections,  the amount of your  contributions,  or how your  contributions  are
allocated  among the  investment  choices  available  to you.  Contact your plan
administrator or employee benefits office for more details.


TRANSACTIONS

Contributions,  exchanges,  or redemptions of the Fund's shares are processed as
soon as they have been received by Vanguard in good order. Good order means that
your request includes complete  information on your contribution,  exchange,  or
redemption, and that Vanguard has received the appropriate assets.

     In all cases,  your transaction  will be based on a Fund's  next-determined
net asset value after  Vanguard  receives  your  request (or, in the case of new
contributions,  the  next-determined net asset value after Vanguard receives the
order from your plan administrator).  As long as this request is received before
the close of trading on the New York Stock  Exchange,  generally 4 p.m.  Eastern
time, you will receive that day's net asset value.


EXCHANGES

The exchange  privilege (your ability to redeem shares from one fund to purchase
shares of another  fund) may be available to you through your plan.  Although we
make every  effort to maintain  the exchange  privilege,  Vanguard  reserves the
right to revise or terminate this privilege,  limit the amount of an exchange or
reject any exchange,  at any time, without notice.  Because excessive  exchanges
can potentially  disrupt the management of the Fund and increase its transaction
costs,  Vanguard  limits  participant  exchange  activity  to no more  than FOUR
SUBSTANTIVE  "ROUND TRIPS"  THROUGH THE FUND (at least 90 days apart) during any
12-month  period.  A "round  trip" is a redemption  from the Fund  followed by a
purchase back into the Fund.  "Substantive"  means a dollar amount that Vanguard
determines, in its sole discretion, could adversely affect the management of the
Fund.
     Before  making an exchange to or from another fund  available in your plan,
consider the following:
- -    Certain investment options,  particularly funds made up of company stock or
     investment contracts, may be subject to unique restrictions.
- -    Make sure to read that fund's  prospectus.  Contact  Participant  Services,
     toll-free, at 1-800-523-1188 for a copy.
- -    Vanguard can accept exchanges only as permitted by your plan.  Contact your
     plan  administrator for details on the exchange policies that apply to your
     plan.
<PAGE>


14

ACCESSING FUND INFORMATION BY COMPUTER
- --------------------------------------------------------------------------------
VANGUARD ON THE WORLD WIDE WEB www.vanguard.com
Use your personal computer to visit Vanguard's education-oriented website, which
provides  timely news and  information  about  Vanguard  funds and services;  an
online  "university"  that  offers  a  variety  of  mutual  fund  classes;   and
easy-to-use,  interactive  tools to help you  create  your  own  investment  and
retirement strategies.
- --------------------------------------------------------------------------------










































<PAGE>

























                     (THIS PAGE INTENTIONALLY LEFT BLANK.)
























<PAGE>

























                     (THIS PAGE INTENTIONALLY LEFT BLANK.)

<PAGE>

GLOSSARY OF INVESTMENT TERMS


CAPITAL GAINS DISTRIBUTION
Payment to mutual fund  shareholders  of gains  realized on securities  that the
fund has sold at a profit, minus any realized losses.

CASH RESERVES
Cash deposits,  short-term  bank deposits,  and money market  instruments  which
include U.S.  Treasury bills,  bank  certificates  of deposit (CDs),  repurchase
agreements, commercial paper, and banker's acceptances.

COMMON STOCK
A security  representing  ownership  rights in a  corporation.  A stockholder is
entitled  to share in the  company's  profits,  some of which may be paid out as
dividends.


DIVIDEND INCOME
Payment to  shareholders  of income from  interest or  dividends  generated by a
fund's investments.


EXPENSE RATIO
The  percentage  of a fund's  average net assets used to pay its  expenses.  The
expense ratio  includes  management  fees,  administrative  fees,  and any 12b-1
distribution fees.

FUND DIVERSIFICATION
Holding a variety of securities so that a fund's return is not badly hurt by the
poor performance of a single security, industry, or country.


GROWTH STOCK FUND
A mutual fund that emphasizes stocks of companies believed to have above-average
prospects for growth.  Reflecting market  expectations for superior growth,  the
prices of  growth  stocks  often are  relatively  high in  comparison  with such
factors as revenue, earnings, book value, and dividends.


INVESTMENT ADVISER
An  organization  that  makes  the  day-to-day   decisions  regarding  a  fund's
investments.

MUTUAL FUND
An  investment  company  that pools the money of many people and invests it in a
variety of securities in an effort to achieve a specific objective over time.

NET ASSET VALUE (NAV)
The market value of a mutual fund's total assets, minus liabilities,  divided by
the  number of shares  outstanding.  The value of a single  share is called  its
share value or share price.

PRICE/EARNINGS (P/E) RATIO
The current share price of a stock,  divided by its per-share earnings (profits)
from the past year. A stock selling for $20, with earnings of $2 per share,  has
a price/earnings ratio of 10.


PRINCIPAL
The amount of money you put into an investment.

SECURITIES
Stocks, bonds, and other investment vehicles.


TOTAL RETURN
A percentage change,  over a specified time period, in a mutual fund's net asset
value,  with the ending net asset value adjusted to account for the reinvestment
of all distributions of dividends and capital gains.

VALUE STOCK FUND
A mutual fund that  emphasizes  stocks of companies  whose growth  prospects are
generally   regarded  as  subpar  by  the  market.   Reflecting   these   market
expectations,  the  prices  of  value  stocks  typically  are  below-average  in
comparison with such factors as revenue, earnings, book value, and dividends.

VOLATILITY
The  fluctuations  in value of a mutual  fund or other  security.  The greater a
fund's volatility, the wider the fluctuations between its high and low prices.

YIELD
Income  (interest  or  dividends)  earned  by  an  investment,  expressed  as  a
percentage of the investment's price.
<PAGE>


[SHIP LOGO]
Institutional Division
Post Office Box 2900
Valley Forge, PA 19482-2900

FOR MORE INFORMATION
If you'd  like  more  information about
Vanguard  Windsor II Fund,  the
following documents are available
free upon request:

ANNUAL/SEMIANNUAL REPORT
TO SHAREHOLDERS
Additional  information about the
Fund's  investments is available in
the Fund's annual and semiannual
reports to shareholders. In these
reports, you will find a discussion of
the market conditions and
investment strategies that
significantly affected the Fund's
performance during the most recent
fiscal year.

STATEMENT  OF  ADDITIONAL
INFORMATION  (SAI)
The SAI  provides  more  detailed
information about the Fund.

The  current  annual and  semiannual
reports  and the SAI are
incorporated  by reference  into (and
are thus legally a part of) this
prospectus.

To receive a free copy of the latest
annual or  semiannual  report or the
SAI, or to request additional
information about the Fund or other
Vanguard funds, please contact us
as follows:

THE VANGUARD GROUP
PARTICIPANT SERVICES CENTER
P.O. BOX 2900
VALLEY FORGE, PA 19482-2900

TELEPHONE:
1-800-523-1188

TEXT TELEPHONE:
1-800-523-8004

WORLD WIDE WEB:
WWW.VANGUARD.COM


INFORMATION  PROVIDED BY THE
SECURITIES AND EXCHANGE
COMMISSION  (SEC)

You can review  and copy
information  about the Fund
(including  the SAI) at the SEC's
Public Reference Room in
Washington, DC. To find out more
about this public service,  call the
SEC at  1-800-SEC-0330.  Reports and
other information about the Fund are
also available on the SEC's website
(www.sec.gov), or you can receive
copies of this  information,  for a fee,
by writing the Public Reference
Section, Securities and Exchange
Commission, Washington, DC
20549-6009.

Fund's Investment Company Act
file number: 811-834




(C) 2000 The Vanguard Group, Inc.
All rights reserved.
Vanguard Marketing
Corporation,
Distributor.

IO73N-02/18/2000

<PAGE>


                                     PART B

                            VANGUARD(R) WINDSOR FUNDS
                                  (THE TRUST)

                      STATEMENT OF ADDITIONAL INFORMATION



                               FEBRUARY 18, 2000


This Statement is not a prospectus,  but should be read in conjunction  with the
current  Prospectuses  (dated February 18, 2000) relating to the Windsor Fund or
the Windsor II Fund, as  appropriate.  To obtain  either  Prospectus or the most
recent  Annual  Report to  Shareholders,  which  contains the Trust's  financial
statements as hereby incorporated by reference, please call:



                         INVESTOR INFORMATION DEPARTMENT
                                 1-800-662-7447


                                TABLE OF CONTENTS

                                                                PAGE
                                                                ----
DESCRIPTION OF THE TRUST.........................................B-1
INVESTMENT POLICIES..............................................B-3
SHARE PRICE......................................................B-8
PURCHASE OF SHARES...............................................B-9
REDEMPTION OF SHARES.............................................B-9
YIELD AND TOTAL RETURN...........................................B-10
FUNDAMENTAL INVESTMENT LIMITATIONS...............................B-12

MANAGEMENT OF THE FUNDS ........................................ B-13

INVESTMENT ADVISORY SERVICES.....................................B-16
PORTFOLIO TRANSACTIONS...........................................B-24

COMPARATIVE INDEXES .............................................B-25

FINANCIAL STATEMENTS.............................................B-27

                            DESCRIPTION OF THE TRUST


ORGANIZATION


The Trust was organized as Wellington  Equity Fund, a Delaware  corporation,  in
1958.  It then  merged into a Maryland  corporation  in 1973,  and  subsequently
reorganized  into  a  Pennsylvania  business  trust  in  1985.  The  Trust  then
reorganized as a Maryland corporation later in 1985. It was reorganized again as
a Delaware business trust in May 1998. Prior to its reorganization as a Delaware
business trust, the Trust was known as Vanguard/Windsor Funds, Inc. The Trust is
registered  with the United  States  Securities  and  Exchange  Commission  (the
Commission)  under  the  Investment  Company  Act of 1940  (the  1940 Act) as an
open-end,  diversified management investment company. The Trust currently offers
the following Funds:



                              VANGUARD WINDSOR FUND
                            VANGUARD WINDSOR II FUND
                (INDIVIDUALLY, THE FUND;COLLECTIVELY, THE FUNDS)

     The Trust has the ability to offer  additional  funds or classes of shares.
There is no limit on the number of full and fractional shares that the Trust may
issue for a single fund or class of shares.

                                      B-1
<PAGE>


SERVICE PROVIDERS


     CUSTODIAN.  State  Street  Bank and Trust  Company,  225  Franklin  Street,
Boston,  Massachusetts  02110, serves as the Funds' custodian.  The custodian is
responsible for maintaining the Funds' assets and keeping all necessary accounts
and records of Fund assets.

     INDEPENDENT ACCOUNTANTS.  PricewaterhouseCoopers LLP, 30 South 17th Street,
Philadelphia,  Pennsylvania 19103, serves as the Funds' independent accountants.
The accountants audit financial statements and provide other related services.

     TRANSFER  AND   DIVIDEND-PAYING   AGENT.  The  Funds'  transfer  agent  and
dividend-paying  agent is The Vanguard  Group,  Inc.,  100  Vanguard  Boulevard,
Malvern, Pennsylvania 19355.


CHARACTERISTICS OF THE FUNDS' SHARES

     RESTRICTIONS  ON HOLDING OR DISPOSING OF SHARES.  There are no restrictions
on the right of  shareholders  to retain or dispose of the Funds' shares,  other
than the possible future  termination of the Funds.  The Funds may be terminated
by reorganization into another mutual fund or by liquidation and distribution of
the  assets of the  affected  funds.  Unless  terminated  by  reorganization  or
liquidation, the Funds will continue indefinitely.

     SHAREHOLDER  LIABILITY.  The Funds were organized under Delaware law, which
provides  that  shareholders  of a  business  trust  are  entitled  to the  same
limitations of personal  liability as  shareholders  of a corporation  organized
under Delaware law. Effectively,  this means that a shareholder of the Fund will
not be personally liable for payment of the Fund's debts except by reason of his
or her own conduct or acts. In addition,  a shareholder  could incur a financial
loss on account of a Fund  obligation  only if the Fund itself had no  remaining
assets with which to meet such  obligation.  We believe that the  possibility of
such a situation arising is extremely remote.

     DIVIDEND  RIGHTS.  The  shareholders  of a fund are entitled to receive any
dividends or other distributions declared for such fund. No shares have priority
or  preference  over  any  other  shares  of  the  same  fund  with  respect  to
distributions. Distributions will be made from the assets of a fund, and will be
paid ratably to all  shareholders of the fund (or class) according to the number
of shares of such fund (or class) held by  shareholders  on the record date. The
amount of income  dividends per share may vary between separate share classes of
the same fund based upon  differences  in the way that  expenses  are  allocated
between share classes pursuant to a multiple class plan.


     VOTING  RIGHTS.  Shareholders  are  entitled  to vote on a matter if: (i) a
shareholder  vote is required  under the 1940 Act;  (ii) the matter  concerns an
amendment to the Declaration of Trust that would adversely  affect to a material
degree the rights and preferences of the shares of any class or series; or (iii)
the Trustees determine that it is necessary or desirable to obtain a shareholder
vote.  The 1940 Act requires a  shareholder  vote under  various  circumstances,
including to elect or remove  Trustees upon the written  request of shareholders
representing 10% or more of the Fund's net assets, and to change any fundamental
policy of the Fund. Shareholders of the Fund receive one vote for each dollar of
net  asset  value  owned on the  record  date,  and a  fractional  vote for each
fractional dollar of net asset value owned on the record date. However, only the
shares of the fund affected by a particular  matter are entitled to vote on that
matter.  Voting  rights  are  non-cumulative  and cannot be  modified  without a
majority vote.

     LIQUIDATION  RIGHTS.  In the  event of  liquidation,  shareholders  will be
entitled to receive a pro rata share of the net assets of the applicable Fund.

     PREEMPTIVE RIGHTS. There are no preemptive rights associated with shares of
the Funds.

     CONVERSION RIGHTS. There are no conversion rights associated with shares of
the Funds.

     REDEMPTION  PROVISIONS.  The Funds' redemption  provisions are described in
their  current  prospectuses  and  elsewhere  in this  Statement  of  Additional
Information.

     SINKING FUND PROVISIONS. The Funds have no sinking fund provisions.

     CALLS OR  ASSESSMENT.  The Funds' shares,  when issued,  are fully paid and
non-assessable.


                                      B-2
<PAGE>



TAX STATUS OF THE FUNDS

Each  Fund  intends  to  qualify  as  a  "regulated  investment  company"  under
Subchapter M of the Internal  Revenue Code. This special tax status means that a
Fund will not be liable for federal tax on income and capital gains  distributed
to  shareholders.  In order to preserve its tax status,  a Fund must comply with
certain requirements.  If a Fund fails to meet these requirements in any taxable
year, it will be subject to tax on its taxable  income at corporate  rates,  and
all distributions from earnings and profits,  including any distributions of net
tax-exempt   income  and  net  long-term  capital  gains,  will  be  taxable  to
shareholders  as  ordinary  income.  In  addition,  a Fund could be  required to
recognize  unrealized  gains,  pay  substantial  taxes  and  interest,  and make
substantial  distributions  before  regaining  its  tax  status  as a  regulated
investment company.


                              INVESTMENT POLICIES

The following  policies  supplement the  investment  objectives and policies set
forth in each Fund's Prospectus.

REPURCHASE AGREEMENTS


Each Fund may invest in repurchase agreements with domestic banks, or brokers or
dealers, either for temporary defensive purposes due to market conditions, or to
generate  income from its excess cash  balances.  A  repurchase  agreement is an
agreement  under which the Fund acquires a  fixed-income  security  (generally a
security  issued  by the  U.S.  Government  or an  agency  thereof,  a  banker's
acceptance or a certificate of deposit) from a domestic bank,  broker or dealer,
subject to resale to the seller at an agreed upon price and date  (normally  the
next   business   day).  A  repurchase   agreement  may  be  considered  a  loan
collateralized by securities.  The resale price reflects an agreed upon interest
rate  effective  for the  period  the  instrument  is held by the  series and is
unrelated  to  the  interest  rate  on  the  underlying  instrument.   In  these
transactions,  the securities  acquired by the Fund (including  accrued interest
earned thereon) must have a total value in excess of the value of the repurchase
agreement and are held by a custodian bank until repurchased.  In addition,  the
Board of Trustees will monitor the repurchase  agreement  transactions  for each
Fund  generally and will  establish  guidelines  and standards for review by the
investment adviser of the  creditworthiness  of any bank, broker or dealer party
to a repurchase agreement relating to any of the Funds.

     The use of repurchase  agreements  involves certain risks. For example,  if
the seller of the  securities  under an agreement  defaults on its obligation to
repurchase  the  underlying  securities  at a  time  when  the  value  of  these
securities  has  declined,  the Fund may  incur a loss upon  disposition  of the
securities.  If the seller  becomes  insolvent  and  subject to  liquidation  or
reorganization  under bankruptcy or other laws, a bankruptcy court may determine
that the underlying  securities are collateral for a loan by the Fund not within
the  control  of the  Fund  and  therefore  subject  to sale by the  trustee  in
bankruptcy.  Finally,  it  is  possible  that  the  Fund  may  not  be  able  to
substantiate  its  interest  in the  underlying  securities.  While  the  Funds'
management  acknowledges these risks, it is expected that they can be controlled
through careful monitoring procedures.


LENDING OF SECURITIES


Each  Fund may lend its  portfolio  securities  for  either  short or  long-term
periods to qualified institutional investors (typically brokers,  dealers, banks
or other  financial  institutions)  who need to  borrow  securities  in order to
complete certain  transactions,  such as covering short sales, avoiding failures
to deliver  securities  or  completing  arbitrage  operations.  By  lending  its
portfolio  securities,  each Fund  attempts to increase  its income  through the
receipt of  interest  on the loan.  Any gain or loss in the market  price of the
securities  loaned that might occur during the term of the loan would be for the
account  of the  Fund.  The  terms  and  the  structure  of such  loans  must be
consistent with the 1940 Act, and the Rules and  Regulations or  interpretations
of the Commission thereunder.  These provisions limit the amount of securities a
fund may lend to 33 1/3% of the Fund's  total  assets,  and require that (a) the
borrower  pledge and maintain  with the Fund  collateral  consisting of cash, an
irrevocable  letter of credit or  securities  issued or guaranteed by a domestic
bank or the United


                                      B-3
<PAGE>



States Government having a value at all times not less than 100% of the value of
the  securities  loaned,  (b) the borrower add to such  collateral  whenever the
price of the securities  loaned rises (i.e.,  the borrower "marks to the market"
on a daily basis),  (c) the loan be made subject to  termination  by the Fund at
any time, and (d) the Fund receives  reasonable  interest on the loan (which may
include the Fund investing any cash  collateral in interest  bearing  short-term
investments),  any  distributions  on the loaned  securities and any increase in
their market value. Loan arrangements made will comply with all other applicable
regulatory  requirements,  including  the rules of the New York Stock  Exchange,
which rules require the  borrower,  after  notice,  to redeliver the  securities
within the normal settlement time of three business days. All relevant facts and
circumstances,   including  the  creditworthiness  of  the  broker,   dealer  or
institution,  will be considered in making decisions with respect to the lending
of securities, subject to review by the Board of Trustees.


     At the  present  time,  the Staff of the  Commission  does not object if an
investment  company pays  reasonable  negotiated  fees in connection with loaned
securities,  so long as such  fees  are set  forth  in a  written  contract  and
approved by the investment company's Trustees.  In addition,  voting rights pass
with  the  loaned  securities,  but if a  material  event  occurs  affecting  an
investment on loan, the loan must be called and the securities voted.


VANGUARD INTERFUND LENDING PROGRAM


The Commission has issued an exemptive order permitting the Funds to participate
in Vanguard's interfund lending program.  This program allows the Vanguard funds
to borrow  money from and loan money to each other for  temporary  or  emergency
purposes.  The  program  is  subject to a number of  conditions,  including  the
requirement  that no fund may borrow or lend money through the program unless it
receives a more  favorable  interest rate than is available  from a typical bank
for a comparable transaction. In addition, a fund may participate in the program
only if and to the extent that such  participation is consistent with the fund's
investment  objective and other investment  policies.  The Boards of Trustees of
the Vanguard  funds are  responsible  for ensuring  that the  interfund  lending
program operates in compliance with all conditions of the Commission's exemptive
order.



TEMPORARY INVESTMENTS

The Funds may take temporary  defensive  measures that are inconsistent with the
Funds' normal fundamental or non-fundamental  investment policies and strategies
in response to adverse market,  economic,  political or other  conditions.  Such
measures could include  investments in (a) highly liquid short-term fixed income
securities issued by or on behalf of municipal or corporate issuers, obligations
of the U.S. Government and its agencies, commercial paper, and bank certificates
of  deposit;  (b) shares of other  investment  companies  which have  investment
objectives  consistent  with  those  of  the  Fund;  (c)  repurchase  agreements
involving any such securities; and (d) other money market instruments.  There is
no limit on the extent to which the Funds may take temporary defensive measures.
In  taking  such  measures,  the  Funds  may fail to  achieve  their  investment
objectives.


FOREIGN INVESTMENTS

As indicated in the Prospectuses,  each of the Funds may invest up to 20% of its
assets in securities  of foreign  companies.  Investors  should  recognize  that
investing in foreign companies involves certain special considerations which are
not typically associated with investing in U.S. companies.

     COUNTRY  RISK. As foreign  companies  are not generally  subject to uniform
accounting,  auditing and financial reporting standards and practices comparable
to those applicable to domestic companies,  there may be less publicly available
information  about certain  foreign  companies  than about  domestic  companies.
Securities of some foreign companies are generally less liquid and more volatile
than  securities  of  comparable  domestic  companies.  There is generally  less
government  supervision  and regulation of stock  exchanges,  brokers and listed
companies  than in the  U.S.  In  addition,  with  respect  to  certain  foreign
countries, there is the possibility of

                                      B-4
<PAGE>


expropriation  or confiscatory  taxation,  political or social  instability,  or
diplomatic  developments  which could  affect U.S.  investments  in companies in
those countries.

     Although the Funds will  endeavor to achieve the most  favorable  execution
costs in their portfolio  transactions in foreign securities,  fixed commissions
on many foreign stock exchanges are generally higher than negotiated commissions
on U.S. exchanges.  In addition,  it is expected that the expenses for custodial
arrangements of the Funds' foreign  securities will be somewhat greater than the
expenses for the custodial  arrangement  for handling  U.S.  securities of equal
value.

     Certain foreign  governments  levy  withholding  taxes against dividend and
interest  income.  Although  in some  countries  a  portion  of  these  taxes is
recoverable,  the non-recovered portion of foreign withholding taxes will reduce
the income the Funds receive from their foreign investments.

     CURRENCY  RISK.  Since  the  stocks of  foreign  companies  are  frequently
denominated  in foreign  currencies,  and since the Funds may  temporarily  hold
uninvested  reserves  in bank  deposits  in foreign  currencies,  a Fund will be
affected  favorably or  unfavorably by changes in currency rates and in exchange
control regulations,  and may incur costs in connection with conversions between
various  currencies.  The investment  policies of the Funds permit them to enter
into forward foreign currency exchange  contracts in order to hedge holdings and
commitments  against  changes  in the  level  of  future  currency  rates.  Such
contracts  involve an  obligation  to purchase or sell a specific  currency at a
future date at a price set at the time of the contract.



     FEDERAL TAX  TREATMENT OF NON-U.S.  TRANSACTIONS.  Special rules govern the
Federal income tax treatment of certain  transactions  denominated in terms of a
currency  other than the U.S.  dollar or determined by reference to the value of
one or more  currencies  other than the U.S.  dollar.  The types of transactions
covered by the special rules include the following:  (i) the  acquisition of, or
becoming the obligor under, a bond or other debt instrument  (including,  to the
extent provided in Treasury regulations,  preferred stock); (ii) the accruing of
certain  trade  receivables  and  payables;  and  (iii)  the  entering  into  or
acquisition  of any  forward  contract,  futures  contract,  option  or  similar
financial instrument if such instrument is not marked to market. The disposition
of a currency other than the U.S. dollar by a taxpayer whose functional currency
is the U.S.  dollar is also  treated as a  transaction  subject  to the  special
currency rules. However,  foreign  currency-related  regulated futures contracts
and nonequity options are generally not subject to the special currency rules if
they are or would be  treated as sold for their fair  market  value at  year-end
under the  marking-to-market  rules applicable to other futures contracts unless
an  election  is made  to have  such  currency  rules  apply.  With  respect  to
transactions  covered by the special  rules,  foreign  currency  gain or loss is
calculated separately from any gain or loss on the underlying transaction and is
normally  taxable as ordinary  income or loss.  A taxpayer may elect to treat as
capital  gain or  loss  foreign  currency  gain or  loss  arising  from  certain
identified  forward  contracts,  futures  contracts and options that are capital
assets in the hands of the  taxpayer  and which are not part of a straddle.  The
Treasury Department issued regulations under which certain  transactions subject
to  the  special  currency  rules  that  are  part  of a  "section  988  hedging
transaction" (as defined in the Internal  Revenue Code of 1986, as amended,  and
the Treasury regulations) will be integrated and treated as a single transaction
or otherwise  treated  consistently  for purposes of the Code.  Any gain or loss
attributable to the foreign  currency  component of a transaction  engaged in by
the Fund which is not  subject to the  special  currency  rules (such as foreign
equity  investments  other  than  certain  preferred  stock)  will be treated as
capital  gain or loss and will  not be  segregated  from the gain or loss on the
underlying   transaction.   It  is   anticipated   that  some  of  the  non-U.S.
dollar-denominated investments and foreign currency contracts the Funds may make
or enter into will be subject to the special currency rules described above.


ILLIQUID SECURITIES

Each  Fund  may  invest  up to 15% of its net  assets  in  illiquid  securities.
Illiquid  securities are  securities  that may not be sold or disposed of in the
ordinary  course of business  within seven  business days at  approximately  the
value at which they are being carried on the Fund's books.

                                      B-5
<PAGE>



     Each Fund may invest in restricted, privately placed securities that, under
the  Commission's  rules,  may be sold only to qualified  institutional  buyers.
Because these securities can be resold only to qualified  institutional  buyers,
they may be considered illiquid securities--meaning that they could be difficult
for the Fund to convert to cash if needed.

     If a  substantial  market  develops for a restricted  security  held by the
Fund, it will be treated as a liquid security, in accordance with procedures and
guidelines  approved by the Fund's Board of Trustees.  This  generally  includes
securities  that are  unregistered  that can be sold to qualified  institutional
buyers in accordance  with Rule 144A under the  Securities Act of 1933 (the 1933
Act). While the Fund's investment adviser determines the liquidity of restricted
securities  on  a  daily  basis,   the  Board  oversees  and  retains   ultimate
responsibility  for the  adviser's  decisions.  Several  factors  that the Board
considers in monitoring these decisions include the valuation of a security, the
availability  of  qualified   institutional  buyers,  and  the  availability  of
information about the security's issuer.



FUTURES CONTRACTS


Each Fund may enter  into  stock  futures  contracts,  options,  and  options on
futures  contracts only for the purpose of remaining fully invested and reducing
transaction  costs.  Futures  contracts provide for the future sale by one party
and purchase by another party of a specified amount of a specific  security at a
specified  future time and at a specified  price.  Futures  contracts  which are
standardized as to maturity date and underlying  financial instrument are traded
on national futures exchanges. Futures exchanges and trading are regulated under
the Commodity Exchange Act by the Commodity Futures Trading Commission (CFTC), a
U.S. Government agency. Assets committed to futures contracts will be segregated
to the extent required by law.

     Although  futures  contracts  by their  terms call for actual  delivery  or
acceptance of the underlying securities,  in most cases the contracts are closed
out before the settlement date without the making or taking of delivery. Closing
out an open futures position is done by taking an opposite position  ("buying" a
contract  which has  previously  been  "sold,"  "selling" a contract  previously
"purchased")  in an identical  contract to  terminate  the  position.  Brokerage
commissions are incurred when a futures contract is bought or sold.

     Futures traders are required to make a good faith margin deposit in cash or
government  securities  with a broker or custodian to initiate and maintain open
positions  in  futures  contracts.  A  margin  deposit  is  intended  to  assure
completion of the contract  (delivery or acceptance of the underlying  security)
if it is not terminated  prior to the specified  delivery date.  Minimal initial
margin  requirements are established by the futures exchange and may be changed.
Brokers may establish  deposit  requirements  which are higher than the exchange
minimums.  Futures  contracts are customarily  purchased and sold on margin that
may range upward from less than 5% of the value of the contract being traded.

     After a futures contract  position is opened,  the value of the contract is
marked to market daily. If the futures contract price changes to the extent that
the  margin  on  deposit  does  not  satisfy  margin  requirements,  payment  of
additional  "variation"  margin will be  required.  Conversely,  a change in the
contract  value may reduce the  required  margin,  resulting  in a repayment  of
excess margin to the contract holder.  Variation margin payments are made to and
from the futures  broker for as long as the  contract  remains  open.  Each Fund
expects to earn interest income on its margin deposits.

     Traders in futures contracts may be broadly  classified as either "hedgers"
or   "speculators."   Hedgers  use  the  futures  markets  primarily  to  offset
unfavorable  changes in the value of securities  otherwise  held for  investment
purposes or expected to be acquired by them.  Speculators  are less  inclined to
own the securities  underlying the futures  contracts which they trade,  and use
futures contracts with the expectation of realizing profits from fluctuations in
interest  rates.  Each Fund intends to use futures  contracts only for bona fide
hedging purposes.


     Regulations of the CFTC applicable to the Funds require that all of each of
the Fund's futures transactions constitute bona fide hedging transactions except
to the extent that the aggregate initial


                                      B-6
<PAGE>



margins and premiums  required to  establish  any  non-hedging  positions do not
exceed five percent of the value of the Funds.  Each Fund will only sell futures
contracts  to protect  securities  it owns  against  price  declines or purchase
contracts to protect  against an increase in the price of  securities it intends
to  purchase.  As evidence of this  hedging  interest,  each Fund  expects  that
approximately  75% of its futures contract  purchases will be "completed";  that
is,  equivalent  amounts of related  securities  will have been purchased or are
being purchased by the Fund upon sale of open futures contracts.


     Although  techniques other than the sale and purchase of futures  contracts
could  be  used  to  control  the  exposure  of  the  Fund's  income  to  market
fluctuations,  the use of futures  contracts  may be a more  effective  means of
hedging this exposure.  While each Fund will incur  commission  expenses in both
opening  and  closing  out  futures  positions,   these  costs  are  lower  than
transaction costs incurred in the purchase and sale of portfolio securities.

     RESTRICTIONS ON THE USE OF FUTURES  CONTRACTS AND OPTIONS.  A Fund will not
enter  into  futures  contract  transactions  to the  extent  that,  immediately
thereafter,  the sum of its initial margin deposits on open contracts exceeds 5%
of the market value of the Fund's  total  assets.  In addition,  a Fund will not
enter into futures  contracts to the extent that its outstanding  obligations to
purchase  securities  under these contracts and its investments in options would
exceed 20% of the Fund's total assets.  Assets committed to futures contracts or
options will be held in a segregated account.

     RISK FACTORS IN FUTURES TRANSACTIONS. Positions in futures contracts may be
closed  out only on an  exchange  which  provides  a  secondary  market for such
futures.  However, there can be no assurance that a liquid secondary market will
exist for any particular futures contract at any specific time. Thus, it may not
be  possible  to  close a  futures  position.  In the  event  of  adverse  price
movements,  a Fund would  continue to be required to make daily cash payments to
maintain its required  margin.  In such  situations,  if a Fund has insufficient
cash, it may have to sell portfolio securities to meet daily margin requirements
at a time when it may be  disadvantageous  to do so. In addition,  a Fund may be
required to make delivery of the  instruments  underlying  interest rate futures
contracts it holds.  The inability to close options and futures  positions  also
could have an adverse impact on the ability to effectively  hedge its portfolio.
A Fund  will  minimize  the risk  that it will be  unable to close out a futures
contract by only  entering into futures  contracts  which are traded on national
futures exchanges and for which there appears to be a liquid secondary market.

     The risk of loss in trading  futures  contracts in some  strategies  can be
substantial,  due to the extremely  high degree of leverage  involved in futures
pricing.  As a result,  a relatively  small price movement in a futures contract
may result in immediate and substantial  loss (as well as gain) to the investor.
For  example,  if at the  time of  purchase,  10% of the  value  of the  futures
contract is deposited as margin,  a subsequent  10% decrease in the value of the
futures contract would result in a total loss of the margin deposit,  before any
deduction for the transaction  costs, if the account were then closed out. A 15%
decrease would result in a loss equal to 150% of the original  margin deposit if
the contract were closed out. Thus, a purchase or sale of a futures contract may
result in losses in excess of the  amount  invested  in the  contract.  However,
because  the  futures  strategies  of each Fund are  engaged in only for hedging
purposes, the advisers do not believe that the Funds are subject to the risks of
loss  frequently  associated  with  futures  transactions.   Either  Fund  would
presumably have sustained comparable losses if, instead of the futures contract,
it had invested in the underlying security and sold it after the decline.

     RISK FACTORS IN OPTIONS TRANSACTIONS.  When a Fund invests in an option, it
purchases  the  right to buy (call  options)  or sell  (put  options)  specified
securities,  at a specified  price,  on a  specified  date or within a specified
period  of  time.  In  consideration  of the  right  to buy or  sell  underlying
securities,  the Fund pays a premium, which represents the maximum amount of the
Fund's  potential  loss on the  transaction  if it chooses not to  exercise  the
option or enter into a closing  transaction before the option's  expiration.  Of
course,  securities purchased pursuant to a call option may subsequently decline
in value, to the Fund's detriment.  Similarly, securities sold pursuant to a put
option may subsequently rise in value, with the Fund missing out on these gains.
In both cases,

                                      B-7
<PAGE>


the Fund would have  incurred  transaction  costs to  exercise  the  option,  in
addition to the option premium.

     There  is the risk of loss by a Fund of  margin  deposits  in the  event of
bankruptcy  of a broker  with  whom the Fund has an open  position  in a futures
contract or related  option.  Additionally,  investments  in futures and options
involve the risk that the  investment  adviser will  incorrectly  predict  stock
market and interest rate trends.

     Most futures exchanges limit the amount of fluctuation permitted in futures
contract  prices during a single  trading day. The daily limit  establishes  the
maximum  amount that the price of a futures  contract may vary either up or down
from the previous day's settlement  price at the end of a trading session.  Once
the daily limit has been reached in a particular type of contract, no trades may
be made on that day at a price beyond that limit.  The daily limit  governs only
price  movement  during a particular  trading day and  therefore  does not limit
potential  losses,  because the limit may prevent the liquidation of unfavorable
positions.  Futures contract prices have  occasionally  moved to the daily limit
for  several  consecutive  trading  days  with  little  or no  trading,  thereby
preventing  prompt  liquidation of future  positions and subjecting some futures
traders to substantial losses.


     FEDERAL TAX  TREATMENT  OF FUTURES  CONTRACTS.  Each Fund is  required  for
Federal income tax purposes to recognize as income for each taxable year its net
unrealized  gains and losses on certain  futures  contracts as of the end of the
year as well as those  actually  realized  during the year. In these cases,  any
gain or loss recognized  with respect to a futures  contract is considered to be
60%  long-term  capital  gain or loss and 40%  short-term  capital gain or loss,
without  regard to the  holding  period  of the  contract.  Gains and  losses on
certain other futures contracts  (primarily non-U.S.  futures contracts) are not
recognized  until the  contracts  are closed and are  treated  as  long-term  or
short-term  depending on the holding  period of the  contract.  Sales of futures
contracts  which  are  intended  to  hedge  against  a  change  in the  value of
securities  held by a Fund may affect the holding period of such securities and,
consequently,   the  nature  of  the  gain  or  loss  on  such  securities  upon
disposition.  A Fund may be  required  to defer  the  recognition  of  losses on
futures  contracts to the extent of any unrecognized  gains on related positions
held by the Fund.

     In order for a Fund to continue to qualify for Federal income tax treatment
as a  regulated  investment  company,  at least  90% of its gross  income  for a
taxable year must be derived from qualifying income; i.e., dividends,  interest,
income  derived from loans of  securities,  gains from the sale of securities or
foreign currencies,  or other income derived with respect to the Fund's business
of investing in securities or currencies.  It is  anticipated  that any net gain
recognized  on  futures  contracts  will be  considered  qualifying  income  for
purposes of the 90% requirement.

     A Fund will distribute to shareholders annually any net capital gains which
have been  recognized for Federal  income tax purposes on futures  transactions.
Such distributions will be combined with distributions of capital gains realized
on the Fund's other  investments and shareholders  will be advised on the nature
of the transactions.



                                  SHARE PRICE

Each Fund's  share  price,  or "net asset  value" per share,  is  calculated  by
dividing the total assets of the Fund, less all liabilities, by the total number
of shares outstanding.  The net asset value is determined as of the close of the
New York Stock Exchange  (generally 4:00 p.m. Eastern time) on each day that the
Exchange is open for trading.

     Portfolio  securities  for which market  quotations  are readily  available
(includes those securities listed on national securities  exchanges,  as well as
those quoted on the NASDAQ Stock Market) will be valued at the last quoted sales
price on the day the valuation is made. Such securities  which are not traded on
the  valuation  date are  valued  at the mean of the bid and ask  prices.  Price
information on  exchange-listed  securities is taken from the exchange where the
security is primarily  traded.  Securities  may be valued on the basis of prices
provided by a pricing  service when such prices are believed to reflect the fair
market value of such securities.

                                      B-8
<PAGE>


     Short-term instruments (those acquired with remaining maturities of 60 days
or less) may be valued at cost, plus or minus any amortized discount or premium,
which approximates market value.

     Bonds  and  other  fixed-income  securities  may be  valued on the basis of
prices  provided by a pricing  service  when such prices are believed to reflect
the fair  market  value of such  securities.  The prices  provided  by a pricing
service  may be  determined  without  regard to bid or last sale  prices of each
security,  but take into  account  institutional-size  transactions  in  similar
groups of securities as well as any developments related to specific securities.

     Foreign securities are valued at the last quoted sales price,  according to
the broadest and most representative  market,  available at the time the Fund is
valued.  If events  which  materially  affect the value of a Fund's  investments
occur after the close of the  securities  markets on which such  securities  are
primarily  traded,  those investments may be valued by such methods as the Board
of Trustees deems in good faith to reflect fair value.


     In  determining  the  Fund's  net asset  value per  share,  all  assets and
liabilities  initially  expressed in foreign  currencies  will be converted into
U.S.  dollars using the  officially  quoted daily  exchange rates used by Morgan
Stanley Capital International in calculating their various benchmarking indexes.
This  officially  quoted  exchange rate may be determined  prior to or after the
close of a particular  securities  market. If such quotations are not available,
the rate of exchange will be determined in accordance with policies  established
in good faith by the Board of Trustees.


     Other assets and securities  for which no quotations are readily  available
or which are restricted as to sale (or resale) are valued by such methods as the
Board of Trustees deems in good faith to reflect fair value.

     The  share  price  for  each  Fund can be found  daily in the  mutual  fund
listings of most major newspapers under the heading of Vanguard Funds.


                               PURCHASE OF SHARES

The purchase price of shares of each Fund is the net asset value next determined
after the order is received in Good Order, as defined in the Prospectus. The net
asset value is calculated as of the close of the New York Stock Exchange on each
day the Exchange is open for business.  An order  received prior to the close of
the Exchange will be executed at the price computed on the date of receipt;  and
an order  received after the close of the Exchange will be executed at the price
computed on the next day the Exchange is open.


     Each Fund  reserves  the right in its sole  discretion  (i) to suspend  the
offering of its shares,  (ii) to reject  purchase orders when in the judgment of
management  such  rejection  is in the best  interest of the Fund,  and (iii) to
reduce or waive the minimum  investment for or any other restrictions on initial
and  subsequent  investments  for certain  fiduciary  accounts  such as employee
benefit plans or under  circumstances where certain economies can be achieved in
sales of each Fund's shares.



                              REDEMPTION OF SHARES


     Each Fund may suspend redemption privileges or postpone the date of payment
(i) during any period that the New York Stock Exchange is closed,  or trading on
the Exchange is  restricted as  determined  by the  Commission;  (ii) during any
period when an emergency exists, as defined by the rules of the Commission, as a
result of which it is not  reasonably  practicable  for the Fund to  dispose  of
securities  owned by it, or to  determine  fairly the value of its  assets;  and
(iii) for such other periods as the Commission may permit.

     Each  Fund has made an  election  with  the  Commission  to pay in cash all
redemptions  requested by any shareholder of record limited in amount during any
90-day  period to the lesser of  $250,000 or 1% of the net assets of the Fund at
the beginning of such period.


                                      B-9
<PAGE>



     No charge is made by either Fund for  redemptions.  Shares  redeemed may be
worth more or less than what was paid for them, depending on the market value of
the Fund's portfolio securities.


     SIGNATURE GUARANTEES.  To protect your account, the Funds and Vanguard from
fraud,  signature guarantees are required for certain  redemptions.  A signature
guarantee verifies the authenticity of your signature. Examples of situations in
which signature guarantees are required are: (1) ALL REDEMPTIONS,  REGARDLESS OF
THE AMOUNT INVOLVED,  WHEN THE PROCEEDS ARE TO BE PAID TO SOMEONE OTHER THAN THE
REGISTERED  ACCOUNT  OWNER(S)  AND/OR TO AN ADDRESS  OTHER  THAN THE  ADDRESS OF
RECORD; AND (2) SHARE TRANSFER  REQUESTS.  These requirements are not applicable
to redemptions in Vanguard's  prototype  retirement plans,  except in connection
with: (1)  distributions  made when the proceeds are to be paid to someone other
than the plan  participant;  (2) certain  authorizations  to effect exchanges by
telephone;  and (3) when  proceeds are to be wired.  These  requirements  may be
waived by the Funds in certain instances.

     Signature  guarantees  can be  obtained  from a bank,  broker  or any other
guarantor that Vanguard  deems  acceptable.  NOTARIES  PUBLIC ARE NOT ACCEPTABLE
GUARANTORS.


                             YIELD AND TOTAL RETURN


The yield of Vanguard  Windsor Fund for the thirty-day  period ended October 31,
1999 was 1.56%,  and the yield for Vanguard  Windsor II Fund for the same period
was 2.35%.

     The average  annual total  returns for Vanguard  Windsor Fund for the one-,
five- and ten-year  periods  ending  October 31, 1999 were 13.74%,  15.77%,  and
12.46%,  respectively.  The average annual total returns for the one-, five- and
ten-year  periods for Vanguard Windsor II Fund were 4.57%,  20.15%,  and 14.52%,
respectively.


AVERAGE ANNUAL TOTAL RETURN

Average annual total return is the average annual  compounded rate of return for
the  periods of one year,  five  years,  ten years or the life of the Fund,  all
ended on the last day of a recent month.  Average annual total return quotations
will  reflect  changes  in the price of the Fund's  shares  and assume  that all
dividends and capital gains  distributions  during the  respective  periods were
reinvested in Fund shares.  Average annual total return is calculated by finding
the average annual compounded rates of return of a hypothetical  investment over
such periods  according to the following formula (average annual total return is
then expressed as a percentage):

                               T = (ERV/P)(1/N)-1

  Where:

          T   = average annual total return
          P   = a hypothetical  initial investment of $1,000
          n   = number of years
          ERV = ending  redeemable  value:ERV is the value, at the end
                of the applicable period, of a hypothetical $1,000
                investment made at the beginning of the applicable
                period


AVERAGE ANNUAL AFTER-TAX TOTAL RETURN QUOTATION

We calculate the Fund's  average  annual  after-tax  total return by finding the
average annual  compounded  rate of return over the 1-, 5-, and 10-year  periods
that would equate the initial amount invested to the after-tax value,  according
to the following formulas:


After-tax return:


                                P (1+T)(N) = ATV

                                      B-10
<PAGE>



  Where:



          P   =  a hypothetical initial payment of $1,000
          T   =  average annual after-tax total return
          n   =  number of years
          ATV =  after-tax value at the end of the 1-, 5-, or 10-year
                periods of a hypothetical $1,000 payment made at the
                beginning of the time period, assuming no liquidation
                of the investment at the end of the measurement periods

Instructions.

1.   Assume all distributions by the Fund are  reinvested--less the taxes due on
     such  distributions--at  the price on the  reinvestment  dates  during  the
     period.  Adjustments  may be made for  subsequent  re-characterizations  of
     distributions.

2.   Calculate  the  taxes  due on  distributions  by the Fund by  applying  the
     highest federal  marginal tax rates to each component of the  distributions
     on the reinvestment date (e.g.,  ordinary income,  short-term capital gain,
     long-term  capital gain,  etc.).  For periods after  December 31, 1997, the
     federal marginal tax rates used for the calculations are 39.6% for ordinary
     income and  short-term  capital gains and 20% for long-term  capital gains.
     Note that the  applicable tax rates may vary over the  measurement  period.
     Assume no taxes are due on the portions of any distributions  classified as
     exempt  interest  or  non-taxable  (i.e.,  return of  capital).  Ignore any
     potential tax liabilities other than federal tax liabilities  (e.g.,  state
     and local taxes).

3.   Include all recurring  fees that are charged to all  shareholder  accounts.
     For any  account  fees that vary  with the size of the  account,  assume an
     account size equal to the Fund's mean (or median) account size. Assume that
     no  additional  taxes or tax credits  result from any  redemption of shares
     required to pay such fees.

4.   State the total return quotation to the nearest hundredth of one percent.


CUMULATIVE TOTAL RETURN

Cumulative  total  return is the  cumulative  rate of  return on a  hypothetical
initial  investment of $1,000 for a specified  period.  Cumulative  total return
quotations reflect changes in the price of the Fund's shares and assume that all
dividends and capital gains  distributions  during the period were reinvested in
Fund shares.  Cumulative  total return is calculated  by finding the  cumulative
rates of a return of a hypothetical  investment over such periods,  according to
the  following  formula   (cumulative  total  return  is  then  expressed  as  a
percentage):


                                 C = (ERV/P)-1

  Where:

          C    = cumulative total return
          P    = a hypothetical  initial  investment of $1,000
          ERV  = ending redeemable value: ERV is the value, at the end
                 of the applicable period, of a hypothetical $1,000
                 investment made at the beginning of the applicable
                 period

SEC YIELDS

Yield is the net  annualized  yield based on a  specified  30-day (or one month)
period  assuming  semiannual  compounding  of  income.  Yield is  calculated  by
dividing the net  investment  income per share  earned  during the period by the
maximum offering price per share on the last day of the period, according to the
following formula:

                          YIELD = 2[((A-B)/CD+1)(6)-1]

                                      B-11
<PAGE>


  Where:

          a =  dividends  and  interest  earned  during  the period
          b =  expenses accrued for the period (net of  reimbursements)
          c =  the average daily number of shares outstanding during
               the period that were entitled to receive dividends
          d =  the maximum offering price per share on the last day of
               the period

                       FUNDAMENTAL INVESTMENT LIMITATIONS

Each Fund is subject to the following fundamental investment limitations,  which
cannot be changed in any  material  way without the approval of the holders of a
majority of the affected  Fund's  shares.  For these  purposes,  a "majority" of
shares  means  shares  representing  the lesser of: (i) 67% or more of the votes
cast to approve a change,  so long as shares  representing  more than 50% of the
Fund's net asset value are present or  represented  by proxy;  or (ii) more than
50% of the Fund's net asset value.

     BORROWING. The Fund may not borrow money, except for temporary or emergency
purposes in an amount not exceeding  15% of the Fund's net assets.  The Fund may
borrow  money  through  banks,  reverse  repurchase  agreements,  or  Vanguard's
interfund  lending program only, and must comply with all applicable  regulatory
conditions.  The  Fund  may not make any  additional  investments  whenever  its
outstanding borrowings exceed 5% of net assets.

     COMMODITIES.  The Fund may not invest in  commodities,  except  that it may
invest in stock  futures  contracts,  stock options and options on stock futures
contracts.  No more than 5% of the  Fund's  total  assets may be used as initial
margin deposit for futures  contracts,  and no more than 20% of the Fund's total
assets may be invested in futures contracts or options at any time.

     DIVERSIFICATION. With respect to 75% of its total assets, the Fund may not:
(i)  purchase  more than 10% of the  outstanding  voting  securities  of any one
issuer; or (ii) purchase  securities of any issuer if, as a result, more than 5%
of the Fund's total assets would be invested in that issuer's  securities.  This
limitation  does not apply to obligations of the United States  Government,  its
agencies, or instrumentalities.

     ILLIQUID SECURITIES. The Fund may not acquire any security if, as a result,
more  than  15% of its net  assets  would be  invested  in  securities  that are
illiquid.

     INDUSTRY CONCENTRATION.  The Fund may not invest more than 25% of its total
assets in any one industry.

     INVESTING FOR CONTROL. The Fund may not invest in a company for purposes of
controlling its management.

     INVESTMENT  COMPANIES.  The Fund may not  invest  in any  other  investment
company, except through a merger,  consolidation or acquisition of assets, or to
the extent permitted by Section 12 of the 1940 Act.  Investment  companies whose
shares the Fund acquires pursuant to Section 12 must have investment  objectives
and investment policies consistent with those of the Fund.

     LOANS.  The Fund may not lend  money to any  person  except  by  purchasing
fixed-income  securities  that  are  publicly  distributed;   by  entering  into
repurchase agreements, provided, however, that repurchase agreements maturing in
more  than  seven  days,  together  with  securities  which do not have  readily
available market quotations,  will not exceed 15% of the Fund's total assets; by
lending  its  portfolio  securities,  or through  Vanguard's  interfund  lending
program.

     MARGIN.  The Fund may not purchase  securities on margin or sell securities
short,  except as  permitted  by the  Fund's  investment  policies  relating  to
commodities.

     REAL ESTATE.  The Fund may not invest directly in real estate,  although it
may invest in securities of companies that deal in real estate.
                                      B-12
<PAGE>


     SENIOR  SECURITIES.  The Fund may not issue  senior  securities,  except in
compliance with the 1940 Act.

     The  investment  limitations  set forth  above are  considered  at the time
investment securities are purchased.  If a percentage  restriction is adhered to
at the time the  investment is made, a later  increase in  percentage  resulting
from a change in the market  value of assets will not  constitute a violation of
such restriction.


     None  of  these  limitations  prevents  a Fund  from  participating  in The
Vanguard Group  (Vanguard).  Because each Fund is a member of the Group,  it may
own  securities  issued by Vanguard,  make loans to Vanguard,  and contribute to
Vanguard's costs or other financial  requirement.  See "Management of the Funds"
for more information.


                            MANAGEMENT OF THE FUNDS



OFFICERS AND TRUSTEES


The Officers of the Funds manage its day-to-day  operations and are  responsible
to the Funds' Board of Trustees.  The Trustees set broad  policies for the Funds
and choose its Officers. The following is a list of the Trustees and Officers of
the Funds and a statement of their present  positions and principal  occupations
during the past five years.  As a group,  the Fund's  Trustees  and Officers own
less than 1% of the outstanding shares of each Fund. Each Trustee also serves as
a Director  of The  Vanguard  Group,  Inc.,  and as a Trustee of each of the 103
funds  administered by Vanguard (102 in the case of Mr.  Malkiel,  and 93 in the
case of Mr.  MacLaury).  The mailing address of the Trustees and Officers of the
Funds is Post Office Box 876, Valley Forge, PA 19482.



JOHN J. BRENNAN, (DOB: 7/29/1954) Chairman, Chief Executive Officer & Trustee*
Chairman,  Chief Executive Officer and Director of The Vanguard Group, Inc., and
Trustee of each of the investment companies in The Vanguard Group.


JOANN  HEFFERNAN  HEISEN,  (DOB: 1/25/1950)  Trustee
Vice President, Chief Information Officer, and member of the Executive Committee
of Johnson & Johnson (Pharmaceuticals/Consumer  Products), Director of Johnson &
Johnson*MERCK Consumer Pharmaceuticals Co., The Medical Center at Princeton, and
Women's Research and Education Institute.


BRUCE K. MACLAURY, (DOB: 5/7/1931) Trustee
President  Emeritus  of  The  Brookings  Institution  (Independent  Non-Partisan
Research  Organization);  Director of American  Express Bank, Ltd., The St. Paul
Companies, Inc. (Insurance and Financial Services), and National Steel Corp.


BURTON G. MALKIEL, (DOB: 8/28/1932) Trustee
Chemical Bank Chairman's Professor of Economics, Princeton University;  Director
of Prudential Insurance Co. of America, Banco Bilbao Gestinova, Baker Fentress &
Co.  (Investment  Management),  The Jeffrey Co.  (Holding  Company),  and Select
Sector SPDR Trust (Exchange-Traded Mutual Fund).

ALFRED M. RANKIN, JR., (DOB: 10/8/1941) Trustee
Chairman,  President, Chief Executive Officer, and Director of NACCO Industries,
Inc. (Machinery/ Coal/Appliances);  and Director of The BFGoodrich Co. (Aircraft
Systems/Manufacturing/ Chemicals).

JOHN C. SAWHILL, (DOB: 6/12/1936) Trustee
President  and Chief  Executive  Officer of The Nature  Conservancy  (Non-Profit
Conservation Group);  Director of Pacific Gas and Electric Co., Procter & Gamble
Co., NACCO Industries (Machinery/Coal/ Appliances), and Newfield Exploration Co.
(Energy); formerly, Director and Senior Partner of McKinsey & Co., and President
of New York University.


                                      B-13
<PAGE>


JAMES O. WELCH, JR., (DOB: 5/13/1931) Trustee
Retired Chairman of Nabisco Brands, Inc. (Food Products);  retired Vice Chairman
and  Director  of RJR  Nabisco  (Food and  Tobacco  Products);  Director of TECO
Energy, Inc., and Kmart Corp.


J. LAWRENCE WILSON, (DOB: 3/2/1936) Trustee
Retired Chairman of Rohm & Haas Co. (Chemicals);  Director of Cummins Engine Co.
(Diesel Engine Company),  and The Mead Corp.  (Paper  Products);  and Trustee of
Vanderbilt University.


RAYMOND J. KLAPINSKY, (DOB: 12/7/1938) Secretary*
Managing Director of The Vanguard Group, Inc.;  Secretary of The Vanguard Group,
Inc. and of each of the investment companies in The Vanguard Group.

THOMAS J. HIGGINS, (DOB: 5/21/1957) Treasurer*
Principal  of The Vanguard  Group,  Inc.;  Treasurer  of each of the  investment
companies in The Vanguard Group.

ROBERT D. SNOWDEN, (DOB: 9/4/1961) Controller*
Principal of The Vanguard  Group,  Inc.;  Controller  of each of the  investment
companies in The Vanguard Group.


* Officers of the Fund are "interested persons" as defined in the 1940 Act.



THE VANGUARD GROUP


Each Fund is a member  of The  Vanguard  Group of  Investment  Companies,  which
consists of more than 100 funds.  Through their  jointly-owned  subsidiary,  The
Vanguard Group, Inc.  (Vanguard),  the Funds and the other funds in The Vanguard
Group obtain at cost virtually all of their corporate management, administrative
and distribution  services.  Vanguard also provides investment advisory services
on an at-cost basis to certain of the Vanguard funds.

     Vanguard  employs  a  supporting  staff of  management  and  administrative
personnel  needed  to  provide  the  requisite  services  to the  funds and also
furnishes the funds with necessary office space, furnishings and equipment. Each
fund pays its share of Vanguard's  total expenses which are allocated  among the
funds under methods approved by the Board of Trustees of each fund. In addition,
each fund bears its own direct expenses,  such as legal,  auditing and custodian
fees.

     The funds' Officers are also Officers and employees of Vanguard. No Officer
or employee owns, or is permitted to own, any securities of any external adviser
for the funds.

     Vanguard  adheres to a Code of Ethics  established  pursuant  to Rule 17j-1
under the 1940 Act.  The Code is  designed  to  prevent  unlawful  practices  in
connection  with the purchase or sale of securities by persons  associated  with
Vanguard.  Under  Vanguard's Code of Ethics,  certain  officers and employees of
Vanguard who are  considered  access persons are permitted to engage in personal
securities  transactions.  However,  such transactions are subject to procedures
and  guidelines  similar  to,  and in many cases more  restrictive  than,  those
recommended by a blue ribbon panel of mutual fund industry executives.

     Vanguard was  established and operates under an Amended and Restated Funds'
Service  Agreement which was approved by the  shareholders of each of the funds.
The amounts  which each of the funds has invested in Vanguard are adjusted  from
time to time in order to maintain the  proportionate  relationship  between each
fund's  relative  net assets and its  contribution  to  Vanguard's  capital.  At
October 31, 1999, Vanguard Windsor Fund had contributed capital of $3,551,000 to
Vanguard,  representing  0.02% of the Fund's  net assets and 3.5% of  Vanguard's
capitalization;  at that time,  Vanguard Windsor II Fund had contributed capital
of $6,582,000 to Vanguard,  representing 0.02% of the Fund's net assets and 6.6%
of Vanguard's capitalization.  The Amended and Restated Funds' Service Agreement
provides for the  following  arrangement:  (a) each  Vanguard fund may be called
upon to invest up to 0.40% of its current net assets in Vanguard and


                                      B-14
<PAGE>



(b) there is no other  limitation  on the dollar  amount that each Vanguard fund
may contribute to Vanguard's capitalization.

     MANAGEMENT.  Corporate management and administrative  services include: (1)
executive  staff;  (2) accounting and financial;  (3) legal and regulatory;  (4)
shareholder  account  maintenance;  (5)  monitoring  and  control  of  custodian
relationships;  (6)  shareholder  reporting;  and (7) review and  evaluation  of
advisory and other services provided to the funds by third parties.

     DISTRIBUTION.  Vanguard Marketing Corporation, a wholly-owned subsidiary of
The Vanguard Group, Inc. provides all distribution and marketing  activities for
the funds in the Group. The principal distribution expenses are for advertising,
promotional  materials and marketing personnel.  Distribution  services may also
include  organizing  and offering to the public,  from time to time, one or more
new investment  companies which will become members of The Vanguard  Group.  The
Trustees and Officers of Vanguard  determine the amount to be spent  annually on
distribution  activities,  the manner  and amount to be spent on each fund,  and
whether to organize new investment companies.

     One half of the distribution expenses of a marketing and promotional nature
is allocated among the funds based upon their relative net assets. The remaining
one half of these  expenses is allocated  among the funds based upon each fund's
sales for the preceding 24 months  relative to the total sales of the funds as a
Group,   provided,   however,   that  no  fund's  aggregate  quarterly  rate  of
contribution  for  distribution  expenses of a marketing and promotional  nature
shall  exceed 125% of the average  distribution  expense  rate for The  Vanguard
Group, and no Fund shall incur annual distribution  expenses in excess of .02 of
1% of its average  month-end  net assets.  During the fiscal years ended October
31, 1997, 1998, and 1999, the Funds incurred the following  approximate  amounts
of The Vanguard Group's management (including transfer agency), distribution and
marketing expenses.


FUND                                1997            1998            1999
- ----                                ----            ----            ----
Vanguard Windsor Fund            $37,527,000     $44,738,000    $41,316,000
Vanguard Windsor Fund II         $40,231,000     $68,805,000    $81,702,000


     INVESTMENT ADVISORY SERVICES.  An experienced  investment  management staff
employed  directly  by Vanguard  provides  investment  advisory  services to the
Funds,  and many  other  Vanguard  funds.  These  services  are  provided  on an
internalized,  at-cost basis.  The compensation and other expenses of this staff
are paid by the funds utilizing these services.



TRUSTEE COMPENSATION


The  same  individuals  serve  as  Trustees  of all  Vanguard  funds  (with  two
exceptions,  which are noted below), and each fund pays a proportionate share of
the Trustees'  compensation.  The funds employ their officers on a shared basis,
as well. However,  officers are compensated by The Vanguard Group, Inc., not the
funds.

     INDEPENDENT TRUSTEES. The funds compensate their independent Trustees--that
is, the ones who are not also officers of the fund--in three ways:

 .    The  independent  Trustees  receive an annual fee for their  service to the
     funds, which is subject to reduction based on absences from scheduled Board
     meetings.

 .    The  independent  Trustees are reimbursed for the travel and other expenses
     that they incur in attending Board meetings.
 .    Upon retirement,  the independent  Trustees receive an aggregate annual fee
     of  $1,000  for each year  served  on the  Board,  up to  fifteen  years of
     service.  This annual fee is paid for ten years  following  retirement,  or
     until each Trustee's death.



     "INTERESTED"  TRUSTEE.  Mr. Brennan serves as a Trustee, but is not paid in
this  capacity.  He is,  however,  paid in his role as officer  of The  Vanguard
Group, Inc.


                                      B-15
<PAGE>



     COMPENSATION TABLE. The following table provides  compensation  details for
each of the Trustees.  We list the amounts paid as  compensation  and accrued as
retirement benefits by the fund for each Trustee.  In addition,  the table shows
the total  amount of benefits  that we expect each  Trustee to receive  from all
Vanguard funds upon  retirement,  and the total amount of  compensation  paid to
each Trustee by all Vanguard funds.



                             VANGUARD WINDSOR FUNDS
                               COMPENSATION TABLE

<TABLE>
<CAPTION>
<S>                                              <C>             <C>            <C>                 <C>
                                                              PENSION OR
                                                              RETIREMENT                            TOTAL
                                                               BENEFITS                         COMPENSATION
                                                AGGREGATE      ACCRUED AS       ESTIMATED          FROM ALL
                                              COMPENSATION   PART OF THESE       ANNUAL            VANGUARD
                                               FROM THESE        FUNDS'       BENEFITS UPON    FUNDS PAID TO
 NAMES OF TRUSTEES                               FUNDS(1)      EXPENSES(1)      RETIREMENT       TRUSTEES(2)
- ---------------------------------------------------------------------------------------------------------------
John C. Bogle (3). . . .                          None            None             None              None
John J. Brennan . . .                             None            None             None              None
Barbara Barnes Hauptfuhrer(4). . .                $1,616          $205           $15,000                $0
JoAnn Heffernan Heisen                            $9,696          $534           $15,000           $80,000
Bruce K. MacLaury . .                             $10,048         $905           $12,000           $75,000
Burton G. Malkiel . .                             $9,767          $883           $15,000           $80,000
Alfred M. Rankin, Jr.                             $9,696          $646           $15,000           $80,000
John C. Sawhill . . .                             $9,696          $819           $15,000           $80,000
James O. Welch, Jr. .                             $9,696          $945           $15,000           $80,000
J. Lawrence Wilson. .                             $9,696          $682           $15,000           $80,000
</TABLE>


(1)  The amounts  shown in this column are based on the Funds' fiscal year ended
     October 31, 1999.

(2)  The amounts reported in this column reflect the total  compensation paid to
     each Trustee for his or her service as Trustee of 103  Vanguard  funds (102
     in the case of Mr.  Malkiel;  93 in the case of Mr.  MacLaury) for the 1999
     calendar year.

(3)  Mr. Bogle has retired from the Funds' Board, effective December 31, 1999.

(4)  Mrs. Hauptfuhrer has retired from the Funds' Board,  effective December 31,
     1998.


                          INVESTMENT ADVISORY SERVICES

                             VANGUARD WINDSOR FUND


The Fund employs a multi-manager approach, using two primary investment advisers
for the bulk of its assets and Vanguard's  Core  Management  Group to manage its
cash reserves.


WELLINGTON MANAGEMENT COMPANY, LLP

Wellington Management Company, LLP (Wellington  Management) manages a portion of
the assets of  Vanguard  Windsor  Fund.  Wellington  Management  discharges  its
responsibilities  pursuant to an investment advisory agreement and is subject to
the control of the Officers and Trustees of the Fund. Wellington Management is a
Massachusetts limited liability partnership,  and the following persons serve as
managing  partners  of  Wellington  Management:  Laurie  A.  Gabriel,  Duncan M.
McFarland,   and  John  R.  Ryan.  Wellington  Management  and  its  predecessor
organizations have provided investment advisory services to investment companies
since 1928 and to investment  counseling clients since 1960. Charles T. Freeman,
Senior  Vice  President  and  Partner of  Wellington  Management,  has served as
portfolio manager of the Fund since January, 1996.


                                      B-16
<PAGE>



     Vanguard Windsor Fund pays Wellington  Management a basic fee at the end of
each fiscal  quarter,  calculated  by applying a  quarterly  rate,  based on the
following annual  percentage rates, to Vanguard Windsor Fund's average month-end
net  assets  managed  by  Wellington   Management  (the  Wellington   Management
Portfolio) for the quarter:


NET ASSETS                                 ANNUAL RATE
- ----------                                 -----------
First $17.5 billion                            0.125%
Assets in excess of $17.5 billion of the
Wellington Management Portfolio                0.100%

     The basic fee paid to Wellington  Management  may be increased or decreased
by  applying  an  adjustment  formula  based on  investment  performance  of the
Wellington  Management  Portfolio.  Such  formula  provides  for an  increase or
decrease in the basic fee paid to Wellington Management each quarter,  depending
upon  the  Wellington  Management  Portfolio's  investment  performance  for the
thirty-six  months  preceding the end of the quarter  relative to the investment
record of the  Standard and Poor's 500  Composite  Stock Price Index (the Index)
for the same period.


The Basic Fee, as provided above, shall be increased or decreased by applying an
incentive/penalty  fee  adjustment  based on the  investment  performance of the
Wellington  Management  Portfolio relative to the investment  performance of the
Index.

     The following table sets forth the adjustment  factors to the base advisory
fee payable by the Fund to Wellington  Management under this investment advisory
agreement.



For the first $17.5 billion of assets:


          CUMULATIVE 36-MONTH                    PERFORMANCE FEE
          PERFORMANCE VERSUS THE INDEX           ADJUSTMENT*
          ---------------------------            ------------------
          Less than -12%................         -0.67 x Basic Fee
          Between -12% and -6%..........         -0.33 x Basic Fee
          Between -6% and 6%............          0.00 x Basic Fee
          Between 6% and 12%............         +0.33 x Basic Fee
          More than 12%.................         +0.67 x Basic Fee

For assets over $17.5 billion:


          CUMULATIVE 36-MONTH                    PERFORMANCE FEE
          PERFORMANCE VERSUS THE INDEX           ADJUSTMENT*
          ----------------------------           ------------------
          Less than -12%................         -0.90 x Basic Fee
          Between -12% and -6%..........         -0.45 x Basic Fee
          Between -6% and 6%............          0.00 x Basic Fee
          Between 6% and 12%............         +0.45 x Basic Fee
          More than 12%.................         +0.90 x Basic Fee



* For purposes of this calculation,  the basic fee is calculated by applying the
quarterly  rate  against  average  assets over the  36-month  period;  provided,
however,  that certain  adjustments  to the  Wellington  Management  Portfolio's
average assets may be made as necessary to reflect Windsor Fund's  conversion to
a multi-manager structure on June 1, 1999.

     For purposes of incentive/penalty  adjustments,  the investment performance
of the  Wellington  Management  Portfolio  for  any  period  is  expressed  as a
percentage of "Wellington  Management  Portfolio Unit Value" at the beginning of
the  period.  This  percentage  is equal to the sum of:  (i) the  change  in the
"Wellington  Management  Portfolio Unit Value" during the period; (ii) the value
of Vanguard  Windsor Fund's cash  distributions  from the Wellington  Management
Portfolio's  net  investment  income and  realized  net capital  gains  (whether
long-term or short-term) having an ex-


                                      B-17
<PAGE>



dividend date occurring  within the period;  and (iii) the unit value of capital
gains  taxes paid or accrued  during the  period by  Vanguard  Windsor  Fund for
undistributed  realized  long-term  capital gains  realized from the  Wellington
Management  Portfolio.  The investment record of the S&P Index for any period is
expressed as a percentage of the S&P Index level at the beginning of the period.
This  percentage  is equal to the sum of (i) the  change in the level of the S&P
Index during the period, and (ii) the value,  computed consistently with the S&P
Index, of cash  distributions  having an ex-dividend  date occurring  within the
period made by companies whose securities comprise the S&P Index.

     In addition,  certain  adjustments  to the  investment  performance  of the
Wellington  Management  Portfolio  may be made as necessary  to reflect  Windsor
Fund's conversion to a multi-manager structure on June 1, 1999.

     During the fiscal years ended October 31, 1997,  1998,  and 1999,  Vanguard
Windsor Fund incurred the following advisory fees owed to Wellington Management:


                                              1997          1998         1999
                                              ----          ----         ----
Basic Fee...................           $23,502,000   $24,971,000   $19,713,650
Increase or Decrease for Performance
Adjustment                             (11,821,000)  (15,501,000)  (14,040,175)
                                       ------------  ------------   ------------
Total.......................           $11,681,000    $9,470,000    $5,673,475
                                       ===========    ==========    ==========

SANFORD C. BERNSTEIN & CO., INC.

Sanford C. Bernstein & Co., Inc.  (Bernstein) manages a portion of the assets of
Vanguard Windsor Fund. Bernstein discharges its responsibilities  pursuant to an
investment  advisory agreement and is subject to the control of the Officers and
Trustees of the Fund.

     The Fund pays Bernstein a basic fee at the end of each of the Fund's fiscal
quarters, calculated by applying a quarterly rate, based on the following annual
percentage rates, to the average month-end net assets of the Bernstein Portfolio
for the quarter:


               NET ASSETS                      ANNUAL RATE
               ----------                      -----------
               First $1 billion........            0.15%
               Next $2 billion.........            0.14%
               Next $2 billion.........            0.12%
               Assets in excess of $5 billion      0.10%


     Subject to a transition rule described in the Agreement,  the Basic Fee, as
provided  above,  will be increased or decreased by the amount of a  Performance
Fee Adjustment  (Adjustment).  The Adjustment will be calculated as a percentage
of the Basic Fee and will change proportionately with the investment performance
of the Fund  relative to the  investment  performance  of the Russell 1000 Value
Index (the Index) for the  thirty-six  month period  ending with the  applicable
quarter. The Adjustment applies as follows:


CUMULATIVE 36-MONTH                        PERFORMANCE FEE ADJUSTMENT
PERFORMANCE VERSUS THE INDEX               AS A PERCENTAGE OF BASIC FEE*
- ----------------------------               -----------------------------
Trails by more than 9%......               -50%
Trails by 0 to 9%...........               Linear decrease from 0 to -50%
Exceeds by 0 to 9%..........               Linear increase from 0 to +50%
Exceeds by more than 9%.....               +50%

* For purposes of this calculation,  the Basic Fee is calculated by applying the
quarterly  rate  against the average  assets over the same time period which the
performance is measured.


                                      B-18
<PAGE>


     TRANSITION RULE FOR CALCULATING ADVISER'S COMPENSATION. The Performance Fee
Adjustment  will not be fully operable until June 1, 2002.  Until that time, the
following transition rules will apply:

     (A) JUNE 1, 1999 THROUGH MAY 31, 2000. The Adviser's  compensation  will be
the Basic Fee. No Performance Fee Adjustment will apply during this period.


     (B) JUNE 1,  2000  THROUGH  JUNE 30,  2002.  Beginning  June 1,  2000,  the
Performance Fee Adjustment will take effect on a progressive  basis with regards
to the number of months  elapsed  between July 1, 1999 and the quarter for which
the Adviser's fee is being  computed.  During this period,  the  Performance Fee
Adjustment will be multiplied by a fraction.  The fraction will equal the number
of months elapsed since July 1, 1999 divided by thirty-six.


     (C) ON AND AFTER JULY 1, 2002.  Beginning July 1, 2002, the Performance Fee
Adjustment will be fully operable.

     OTHER  SPECIAL  RULES  RELATING TO ADVISER'S  COMPENSATION.  The  following
special rules will also apply to the Adviser's compensation:

     BERNSTEIN  PORTFOLIO   PERFORMANCE.   The  investment  performance  of  the
Bernstein Portfolio for any period,  expressed as a percentage of the "Bernstein
Portfolio  unit value" at the beginning of such period,  will be the sum of: (i)
the change in the Bernstein  Portfolio  unit value during such period;  (ii) the
unit value of the Fund's cash distributions  from the Bernstein  Portfolio's net
investment  income  and  realized  net  capital  gains  (whether   long-term  or
short-term)  having an ex-dividend date occurring within such period;  and (iii)
the unit value of capital gains taxes paid or accrued  during such period by the
Fund for  undistributed  realized  long-term  capital  gains  realized  from the
Bernstein Portfolio. For this purpose, the unit value of distributions per share
of realized  capital gains, of dividends per share paid from  investment  income
and of capital gains taxes per share  reinvested  in the Bernstein  Portfolio at
the unit value in effect at the close of  business  on the  record  date for the
payment of such  distributions  and dividends and the date on which provision is
made for such taxes, after giving effect to such distributions,  dividends,  and
taxes.

  "BERNSTEIN PORTFOLIO UNIT VALUE." The "Bernstein Portfolio unit value" will be
determined  by dividing  the total net assets of the  Bernstein  Portfolio  by a
given number of units. The number of units in the Bernstein  Portfolio initially
will  equal  to the  total  shares  outstanding  of the  Fund on  June 1,  1999.
Subsequently,  as assets are added to or withdrawn from the Bernstein Portfolio,
the number of units of the  Bernstein  Portfolio  will be adjusted  based on the
unit value of the Bernstein Portfolio on the day such changes are executed.

     INDEX  PERFORMANCE.  The  investment  record of the  Index for any  period,
expressed as a percentage of the Index at the beginning of such period,  will be
the sum of: (i) the change in the level of the Index  during  such  period,  and
(ii) the  value,  computed  consistently  with the  Index of cash  distributions
having an ex-dividend  date occurring within such period made by companies whose
securities  comprise the Index.  For this  purpose,  cash  distributions  on the
securities  which  comprise the Index will be treated as reinvested in the Index
at least as frequently as the end of each calendar quarter following the payment
of the dividend.


     During the fiscal  year ended  October  31,  1999,  Vanguard  Windsor  Fund
incurred the following advisory fees owed to Bernstein:

                                                       1999
                                                       ----
Basic Fee...................                     $2,309,256
Increase or Decrease for Performance
Adjustment..................                              0
Total.......................                     $2,309,256
                                                 ==========




                            VANGUARD WINDSOR II FUND

Vanguard  Windsor  II Fund  employs  a  multi-manager  approach  utilizing  four
investment advisers.

                                      B-19
<PAGE>


BARROW, HANLEY, MEWHINNEY & STRAUSS


Vanguard Windsor II Fund has entered into an investment  advisory agreement with
Barrow, Hanley, Mewhinney & Strauss, Inc. (Barrow Hanley) to manage a portion of
the equity  allocation  of Vanguard  Windsor II Fund  (approximately  64%, as of
October 31, 1999).  Under this  agreement,  Barrow Hanley manages the investment
and reinvestment of the designated assets and continuously  reviews,  supervises
and administers the investment  program of Vanguard Windsor II Fund with respect
to those assets.  Barrow Hanley discharges its  responsibilities  subject to the
control of the Officers and Trustees of the Fund.

     Barrow Hanley is a Nevada corporation  controlled by the following officers
of Barrow Hanley:  James Purdy Barrow,  Principal;  Bryant Miller  Hanley,  Jr.,
President,  Secretary and Treasurer;  Richard Albert Englander,  Principal;  and
Joseph Ray Nixon, Principal.

  Vanguard Windsor II Fund pays Barrow Hanley a basic fee at the end of each
fiscal quarter, calculated by applying a quarterly rate, based on the following
annual percentage rates, to the average month-end net assets of Vanguard Windsor
II Fund managed by Barrow Hanley for the quarter:



          NET ASSETS                          ANNUAL RATE
          ----------                          -----------
          First $200 million......                0.300%
          Next $300 million.......                0.200%
          Next $500 million.......                0.150%
          Over $1 billion.........                0.125%


     The Fund's  payments to Barrow Hanley under the above  schedule are subject
to an incentive/  penalty fee arrangement  which compares the performance of the
Fund's assets  managed by Barrow Hanley with the  performance  of the Standard &
Poor's/BARRA   Value  Index.   This  arrangement   provides  for  the  following
adjustments to Barrow Hanley's basic fee:



CUMULATIVE 36-MONTH                      PERFORMANCE FEE
PERFORMANCE VERSUS THE INDEX             ADJUSTMENT*
- ----------------------------             -----------------
Less than or equal to -9%.....           -0.25 x Basic Fee
Between -9% and -6%...........           -0.15 x Basic Fee
Between -6% and 6%............            0.00 x Basic Fee
Between 6% and 9%.............           +0.15 x Basic Fee
More than 9%..................           +0.25 x Basic Fee


* For purposes of this calculation,  the basic fee is calculated by applying the
quarterly rate against average assets over the 36-month period.

     The BARRA  Value  Index  includes  stocks in the  Standard  and  Poor's 500
Composite  Stock Price Index with lower than  average  ratios of market price to
book value. These types of stocks are often referred to as "value" stocks.



     The  investment  performance  of the portion of Vanguard  Windsor II Fund's
assets managed by Barrow Hanley (the Barrow Hanley  Portfolio) for any period is
expressed as a percentage  of the "Barrow  Hanley  Portfolio  Unit Value" at the
beginning of such period. This percentage is equal to the sum of: (i) the change
in the Barrow  Hanley  Portfolio  Unit Value during such  period;  (ii) the unit
value of the Fund's cash  distributions  from the Barrow Hanley  Portfolio's net
investment  income  and  realized  net  capital  gains  (whether   long-term  or
short-term)  having an ex-dividend date occurring within such period;  and (iii)
the unit value of capital  gains  taxes paid or accrued  during  such  period by
Vanguard  Windsor II Fund for  undistributed  realized  long-term  capital gains
realized from the Barrow Hanley Portfolio.

     The "Barrow Hanley Portfolio Unit Value" will be determined by dividing the
total net assets of the Barrow Hanley  Portfolio by a given number of units.  On
the initial date of the agreement, the


                                      B-20
<PAGE>



number of units in the Barrow  Hanley  Portfolio  was equal to the total  shares
outstanding of Vanguard  Windsor II Fund. After such initial date, as assets are
added to or withdrawn from the Barrow Hanley  Portfolio,  the number of units of
the Barrow  Hanley  Portfolio  will be  adjusted  based on the unit value of the
Barrow Hanley Portfolio on the day such changes are executed.


     The investment  record of the BARRA Value Index is calculated  quarterly by
(i)  multiplying  the total return for the quarter  (change in market price plus
dividends)  of each stock  included in the BARRA Value Index by its weighting in
the BARRA  Value  Index at the  beginning  of the  quarter,  and (ii) adding the
values discussed in (i). For any period, therefore, the investment record of the
BARRA Value Index will be the  compounded  quarterly  returns of the BARRA Value
Index.


     During the fiscal years ended October 31, 1997,  1998,  and 1999,  Vanguard
Windsor II Fund incurred the following advisory fees owed to Barrow Hanley:



                                               1997         1998          1999
                                               ----         ----          ----
Basic Fee...................            $16,925,953  $24,225,773   $27,518,622
Increase or Decrease for Performance
Adjustment                                2,495,021    3,887,915    (1,429,591)
                                          ---------    ---------    -----------
Total.......................            $19,420,974  $28,113,688    $26,089,031
                                        ===========  ===========    ===========



OTHER ADVISERS


On November 1, 1991,  Vanguard Windsor II Fund added Equinox Capital  Management
(Equinox) and Tukman  Capital  Management  (Tukman) to manage the investment and
reinvestment of a portion of its equity allocation  (approximately  14% and 12%,
respectively, as of October 31, 1999). Additionally,  Vanguard's Core Management
Group was  added to  manage a  portion  of  Vanguard  Windsor  II Fund's  equity
allocation  (approximately  6%, as of October  31,  1999).  Equinox,  Tukman and
Vanguard's Core Management  Group  discharge their  respective  responsibilities
subject to the control of the Trustees and Officers of the Fund.



EQUINOX


Equinox is a Delaware  Limited  Liability  Company  controlled  by the following
officers of Equinox: Ronald J. Ulrich, President and Director; and Wendy D. Lee,
Managing Director.


     Under the terms of an investment  advisory  agreement,  Vanguard Windsor II
Fund pays Equinox a basic fee at the end of each fiscal  quarter,  calculated by
applying a quarterly rate,  based on the following annual  percentage  rates, to
the portion of Vanguard  Windsor II Fund's average  month-end net assets managed
by Equinox for the quarter:


               NET ASSETS                      ANNUAL RATE
               ----------                      -----------
               First $400 million.....             .200%
               Next $600 million......             .150%
               Next $1 billion........             .125%
               Assets in excess of $2 billion      .100%

     The basic fee paid to Equinox may be  increased or decreased by applying an
adjustment  formula  based  on the  investment  performance  of the  portion  of
Vanguard  Windsor II Fund's  assets  managed by Equinox (the Equinox  Portfolio)
relative  to the  investment  of the  Russell  1000 Value  Index.  Such  formula
provides  for an  increase  or  decrease  in the basic fee paid to Equinox  each
quarter,  depending upon the Equinox Portfolio's  investment performance for the
thirty-six months preceding the end of the quarter.

                                      B-21
<PAGE>


     The following table sets forth the adjustment  factors to the base advisory
fee payable by the Equinox  Portfolio to Equinox under this investment  advisory
agreement:


CUMULATIVE 36-MONTH                         PERFORMANCE FEE
PERFORMANCE VERSUS THE INDEX                ADJUSTMENT*
- ----------------------------                -----------------
Less than -9%.................              -0.50 x Basic Fee
Between -9% and -4.5%.........              -0.25 x Basic Fee
Between -4.5% and 4.5%........               0.00 x Basic Fee
Between 4.5% and 9%...........              +0.25 x Basic Fee
More than 9%..................              +0.50 x Basic Fee


* For purposes of this calculation,  the basic fee is calculated by applying the
quarterly rate against average assets over the 36-month period.




     The  investment  performance  of the  Equinox  Portfolio  for any period is
expressed as a percentage of the "Equinox Portfolio Unit Value" at the beginning
of such period.  This  percentage  is equal to the sum of: (i) the change in the
Equinox Portfolio Unit Value during such period; (ii) the unit value of Vanguard
Windsor II Fund's cash  distributions  from the Equinox Portfolio net investment
income and realized net capital gains (whether  long-term or short-term)  having
an ex-dividend  date occurring  within such period;  and (iii) the unit value of
capital  gains taxes paid or accrued  during such period by Vanguard  Windsor II
Fund for  undistributed  realized  long-term  capital  gains  realized  from the
Equinox Portfolio.

     The "Equinox Portfolio Unit Value" will be determined by dividing the total
net assets of the Equinox  Portfolio by a given number of units.  On the initial
date of the agreement, the number of units in the Equinox Portfolio was equal to
the total shares  outstanding  of Vanguard  Windsor II Fund.  After such initial
date, as assets are added to or withdrawn from the Equinox Portfolio, the number
of units of the Equinox  Portfolio  will be adjusted  based on the unit value of
the Equinox Portfolio on the day such changes are executed.

     The  investment  record of the Russell 1000 Value Index will be  calculated
quarterly by (i)  multiplying  the total  return for the quarter  (change in the
market price plus  dividends)  of each stock  included in the Russell 1000 Value
Index by its  weighting in the Russell 1000 Value Index at the  beginning of the
quarter, and (ii) adding the values discussed in (i). For any period, therefore,
the  investment  record of the Russell  1000 Value Index will be the  compounded
quarterly returns of the Russell 1000 Value Index.


     During the fiscal years ended October 31, 1997,  1998,  and 1999,  Vanguard
Windsor II Fund incurred the following advisory fees owed to Equinox:



                                                  1997         1998        1999
                                                  ----         ----        ----
Basic Fee...................                $2,791,342   $3,945,052  $4,992,060
Increase or Decrease for Performance
Adjustment                                     408,295      868,234   1,788,014
                                               -------      -------   ---------
Total.......................                $3,199,637   $4,813,286  $6,780,074
                                            ==========   ==========  ==========

     These fees were paid under a previous  fee  schedule  that  provided  for a
higher rate of fees.


TUKMAN

Tukman is a Delaware corporation controlled by the following officers of Tukman:
Melvin  T.  Tukman,  President  and  Director;  and  Daniel  L.  Grossman,  Vice
President.

     Under the terms of an investment advisory agreement, the Fund pays Tukman a
basic fee at the end of each fiscal quarter,  calculated by applying a quarterly
rate, based on the following annual

                                      B-22
<PAGE>


percentage  rates,  to the average  month-end  assets of the portion of Vanguard
Windsor II Fund's assets managed by Tukman:


          NET ASSETS                                 ANNUAL RATE
          ----------                                 -----------
          First $25 million......                       0.400%
          Next $125 million......                       0.350%
          Next $350 million......                       0.250%
          Next $500 million......                       0.200%
          Over $1 billion........                       0.150%



     The Fund's  payments to Tukman  under the above  schedule are subject to an
incentive/penalty  fee  arrangement  which compares the  performance of the Fund
assets  managed  by Tukman  with the  performance  of the  Standard & Poor's 500
Composite  Stock  Price  Index.  This  arrangement  provides  for the  following
adjustments to Tukman's basic fee:



CUMULATIVE 36-MONTH                    PERFORMANCE FEE
PERFORMANCE VERSUS THE INDEX           ADJUSTMENT*
- ----------------------------           -----------------
Less than or equal to -12%....         -0.50 x Basic Fee
Between -12% and -6%..........         -0.25 x Basic Fee
Between -6% and 6%............          0.00 x Basic Fee
Between 6% and 12%............         +0.25 x Basic Fee
More than 12%.................         +0.50 x Basic Fee


* For purposes of this calculation,  the basic fee is calculated by applying the
quarterly rate against average assets over the 36-month period.

     The  investment  performance  of the portion of Vanguard  Windsor II Fund's
assets managed by Tukman (the Tukman Portfolio) for any period is expressed as a
percentage of the "Tukman Portfolio Unit Value" at the beginning of such period.
The  percentage  is equal to the sum of: (i) the change in the Tukman  Portfolio
Unit Value during such period; (ii) the unit value of Vanguard Windsor II Fund's
cash  distributions from the Tukman Portfolio net investment income and realized
net capital gains (whether  long-term or short-term)  having an ex-dividend date
occurring  within such period;  and (iii) the unit value of capital  gains taxes
paid or accrued during such period by Vanguard Windsor II Fund for undistributed
realized long-term capital gains realized from the Tukman Portfolio.

     The "Tukman  Portfolio Unit Value" will be determined by dividing the total
net assets of the Tukman  Portfolio by a given  number of units.  On the initial
date of the agreement,  the number of units in the Tukman Portfolio was equal to
the total shares  outstanding  of Vanguard  Windsor II Fund.  After such initial
date, as assets are added to or withdrawn from the Tukman Portfolio,  the number
of units of the Tukman Portfolio will be adjusted based on the unit value of the
Tukman Portfolio on the day such changes are executed.

     The  investment  record of the S&P 500 will be calculated  quarterly by (i)
multiplying  the total  return  for the  quarter  (change  in market  price plus
dividends) of each stock included in the S&P 500 by its weighting in the S&P 500
at the  beginning of the quarter,  and (ii) adding the values  discussed in (i).
For any  period,  therefore,  the  investment  record of the S&P 500 will be the
compounded quarterly returns of the S&P 500.



     During the fiscal years ended October 31, 1997,  1998,  and 1999,  Vanguard
Windsor II Fund incurred the following advisory fees owed to Tukman:



                                          1997         1998             1999
                                          ----         ----             ----
Basic Fee...................        $3,622,904   $5,126,168       $6,192,444
Increase or Decrease for Performance
Adjustment                             785,658      992,760       (2,000,847)
                                       -------      -------      -----------
Total.......................        $4,408,562   $6,118,928       $4,191,597
                                    ==========   ==========       ==========




                                      B-23
<PAGE>


VANGUARD'S CORE MANAGEMENT GROUP


Since November 1, 1991, Vanguard's Core Management Group has provided investment
advisory  services  on an at-cost  basis with  respect to a portion of  Vanguard
Windsor II Fund's equity allocation  (approximately 6%, as of October 31, 1999).
The Core Management Group also provides  investment advisory services to several
other Vanguard funds. The Core Management Group is supervised by the Officers of
the Fund.

     During the fiscal years ended October 31, 1997,  1998,  and 1999,  Vanguard
Windsor  II  Fund  incurred  the  following  expenses  for  investment  advisory
services: $196,000, $287,000, and $511,000, respectively.



DURATION AND TERMINATION OF INVESTMENT ADVISORY AGREEMENTS


The Funds' present  agreements  with their advisers are renewable for successive
one-year periods if specifically  approved by a vote of the Board of Trustees at
a  meeting  called  for the  purpose  of  considering  such  approval.  (The one
exception is that Windsor Fund's  agreement with Bernstein is effective  through
June 1, 2001 and  thereafter  renewable  at  one-year  intervals.)  The  Board's
approval  must include the  affirmative  votes of a majority of the Trustees who
are neither parties to the contract or "interested  persons" of such parties (as
defined in the 1940 Act).

     Each investment advisory agreement is automatically terminated if assigned,
and may be terminated without penalty at any time (1) by majority vote of either
the Board of Trustees  or the Fund's  outstanding  shares upon 60 days'  written
notice to the adviser, or (2) by the adviser upon 90 days' written notice to the
Fund.

     The Fund's Board of Trustees  may,  without the  approval of  shareholders,
provide for:


 .    The employment of a new investment  adviser  pursuant to the terms of a new
     advisory  agreement,  either as a replacement for an existing adviser or as
     an additional adviser;

 .    A change in the terms of an advisory agreement; or

 .    The  continued  employment  of an existing  adviser,  on the same  advisory
     contract terms,  where a contract has been assigned  because of a change in
     control of the adviser.

  Any such change will be communicated to shareholders in writing.




                             PORTFOLIO TRANSACTIONS


Wellington Management,  Bernstein, Barrow Hanley, Equinox, Tukman and Vanguard's
Core  Management  Group are  authorized  to (with the  approval  of the Board of
Trustees)  select the brokers or dealers  that will  execute the  purchases  and
sales of portfolio  securities for the respective Fund . The investment advisory
agreements  direct the  advisers  to use their  best  efforts to obtain the best
available  price  and most  favorable  execution  as to all  transactions.  Each
investment  adviser has undertaken to execute each  investment  transaction at a
price and commission  which  provides the most favorable  total cost or proceeds
reasonably obtainable under the circumstances.

     In placing  portfolio  transactions,  each investment  adviser will use its
best  judgment  to choose the broker most  capable of  providing  the  brokerage
services  necessary  to  obtain  the best  available  price  and most  favorable
execution.  The full range and quality of brokerage  services  available will be
considered  in  making  these  determinations.  In those  instances  where it is
reasonably determined that more than one broker can offer the brokerage services
needed  to  obtain  the  best  available  price  and most  favorable  execution,
consideration may be given to those brokers which supply investment research and
statistical  information  and provide  other  services in addition to  execution
services to the Fund and/or the  investment  adviser.  Each  investment  adviser
considers such  information  useful in the performance of its obligations  under
the agreement,  but is unable to determine the amount by which such services may
reduce its expenses.


                                      B-24
<PAGE>



     The investment advisory agreements also incorporate the concepts of Section
28(e) of the Securities  Exchange Act of 1934 by providing that,  subject to the
approval of the Board of Trustees, each investment adviser may cause the Fund to
pay a  broker-dealer  which furnishes  brokerage and research  services a higher
commission  than that  which  might be  charged  by  another  broker-dealer  for
effecting  the  same  transaction;  provided  that  such  commission  is  deemed
reasonable  in  terms of  either  that  particular  transaction  or the  overall
responsibilities of the adviser to the Funds and the other funds in the Group.

     Currently,  it is each Fund's  policy that each  investment  adviser may at
times pay higher commissions in recognition of brokerage services felt necessary
for the achievement of better execution of certain securities  transactions that
otherwise  might not be  available.  An  investment  adviser  will only pay such
higher  commissions  if it believes this to be in the best interest of the Fund.
Some brokers or dealers who may receive such higher  commissions  in recognition
of brokerage  services related to execution of securities  transactions are also
providers of research  information  to an  investment  adviser  and/or the Fund.
However, the investment advisers have informed the Fund that they generally will
not pay higher  commission  rates  specifically  for the  purpose  of  obtaining
research services.

     Some securities considered for investment by a Fund may also be appropriate
for the other Fund and for other funds and/or  clients  served by the investment
adviser.  If  purchase  or sale of  securities  consistent  with the  investment
policies of the Fund and one or more of these  other funds or clients  served by
the investment adviser are considered at or about the same time, transactions in
such  securities  will be  allocated  among the  several  funds and clients in a
manner deemed  equitable by the  investment  adviser.  Although  there may be no
specified formula for allocating such transactions, the allocation methods used,
and the results of such  allocations,  will be subject to periodic review by the
Funds' Board of Trustees.

     During the fiscal years ended October 31, 1997,  1998,  and 1999, the Funds
paid the following in brokerage commissions.


FUND                                   1997            1998            1999
- ----                                   ----            ----            ----
Vanguard Windsor Fund           $28,780,109     $27,915,402     $25,355,164
Vanguard Windsor Fund II        $15,272,207     $21,836,954     $15,327,874





                              COMPARATIVE INDEXES

Vanguard may use reprinted  material  discussing The Vanguard Group, Inc. or any
of the member funds of The Vanguard Group of Investment Companies.

     Each of the investment  company  members of The Vanguard  Group,  including
Vanguard  Windsor Fund and Vanguard  Windsor II Fund,  may from time to time use
one or more of the  following  unmanaged  indexes  for  comparative  performance
purposes.


STANDARD AND POOR'S 500 COMPOSITE STOCK PRICE INDEX--includes stocks selected by
Standard & Poor's  Index  Committee  to  include  leading  companies  in leading
industries and to reflect the U.S. stock market.

STANDARD  AND  POOR'S  500/BARRA  VALUE  INDEX--consists  of the  stocks  in the
Standard  and Poor's 500  Composite  Stock Price Index (S&P 500) with the lowest
price-to-book  ratios,  comprising 50% of the market  capitalization  of the S&P
500.

STANDARD & POOR'S  MIDCAP 400  INDEX--is  composed of 400 medium sized  domestic
stocks.

STANDARD & POOR'S  SMALLCAP  600/BARRA VALUE  INDEX--contains  stocks of the S&P
SmallCap 600 Index which have a lower than average price-to-book ratio.

STANDARD & POOR'S SMALLCAP  600/BARRA GROWTH  INDEX--contains  stocks of the S&P
SmallCap 600 Index which have a higher than average price-to-book ratio.

                                      B-25
<PAGE>


RUSSELL  1000  VALUE  INDEX--consists  of the stocks in the  Russell  1000 Index
(comprising  the 1,000  largest  U.S.-based  companies  measured by total market
capitalization)  with the lowest  price-to-book  ratios,  comprising  50% of the
market capitalization of the Russell 1000.

WILSHIRE  5000  EQUITY   INDEX--consists   of  more  than  7,000  common  equity
securities,  covering  all  stocks  in the  U.S.  for  which  daily  pricing  is
available.

WILSHIRE 4500 EQUITY  INDEX--consists  of all stocks in the Wilshire 5000 except
for the 500 stocks in the Standard and Poor's 500 Index.

MORGAN  STANLEY  CAPITAL  INTERNATIONAL  EAFE  INDEX--is an  arithmetic,  market
value-weighted  average of the performance of over 900 securities  listed on the
stock exchanges of countries in Europe, Australia, Asia, and the Far East.

GOLDMAN SACHS 100  CONVERTIBLE  BOND  INDEX--currently  includes 71 bonds and 29
preferreds.   The  original  list  of  names  was  generated  by  screening  for
convertible  issues of $100  million or greater  in market  capitalization.  The
index is priced monthly.

SALOMON BROTHERS GNMA  INDEX--includes  pools of mortgages originated by private
lenders and guaranteed by the mortgage pools of the Government National Mortgage
Association.

SALOMON BROTHERS HIGH-GRADE  CORPORATE BOND  INDEX--consists of publicly issued,
non-convertible  corporate bonds rated AA or AAA. It is a value-weighted,  total
return index, including  approximately 800 issues with maturities of 12 years or
greater.


LEHMAN  LONG-TERM  TREASURY BOND INDEX--is a market weighted index that contains
individually  priced U.S.  Treasury  securities  with  maturities of 10 years or
greater.


MERRILL LYNCH  CORPORATE & GOVERNMENT  BOND  INDEX--consists  of over 4,500 U.S.
Treasury Agency and investment grade corporate bonds.


LEHMAN   CORPORATE   (BAA)  BOND   INDEX--all   publicly   offered   fixed-rate,
non-convertible  domestic  corporate  bonds rated Baa by Moody's with a maturity
longer  than 1 year and with more  than $100  million  outstanding.  This  index
includes over 1,500 issues.

LEHMAN  BROTHERS  LONG-TERM  CORPORATE  BOND  INDEX--is  a subset of the  Lehman
Corporate  Bond Index  covering  all  corporate,  publicly  issued,  fixed-rate,
non-convertible U.S. debt issues rated at least Baa, with at least $100 million
principal outstanding and maturity greater than 10 years.


BOND BUYER  MUNICIPAL BOND INDEX--is a yield index on current coupon  high-grade
general obligation municipal bonds.

STANDARD & POOR'S PREFERRED INDEX--is a yield index based upon the average yield
for four high-grade, noncallable preferred stock issues.

NASDAQ INDUSTRIAL INDEX--is composed of more than 3,000 industrial issues. It is
a  value-weighted  index  calculated  on price  change only and does not include
income.

COMPOSITE  INDEX--70%  Standard  & Poor's  500 Index and 30%  NASDAQ  Industrial
Index.

COMPOSITE  INDEX--65%  Standard  & Poor's  500  Index and 35%  Lehman  Long-Term
Corporate AA or Better Bond Index.

COMPOSITE  INDEX--65%  Lehman Long-Term  Corporate AA or Better Bond Index and a
35% weighting in a blended equity  composite (75% Standard & Poor's/BARRA  Value
Index, 12.5% Standard & Poor's Utilities Index and 12.5% Standard & Poor's
Telephone Index).

LEHMAN  LONG-TERM  CORPORATE AA OR BETTER BOND  INDEX--consists  of all publicly
issued,  fixed  rate,  non-convertible  investment  grade,   dollar-denominated,
SEC-registered corporate debt rated AA or AAA.

                                      B-26
<PAGE>



LEHMAN  BROTHERS  AGGREGATE BOND INDEX--is a market weighted index that contains
individually priced U.S. Treasury,  agency, corporate, and mortgage pass-through
securities  corporate rated BBB- or better. The Index has a market value of over
$5 trillion.


LEHMAN BROTHERS MUTUAL FUND SHORT (1-5) GOVERNMENT/CORPORATE  INDEX--is a market
weighted index that contains  individually  priced U.S.  Treasury,  agency,  and
corporate  investment grade bonds rated BBB or better with maturities  between 1
and 5 years. The index has a market value of over $1.6 trillion.


LEHMAN BROTHERS MUTUAL FUND INTERMEDIATE (5-10) GOVERNMENT/CORPORATE INDEX--is a
market weighted index that contains  individually priced U.S. Treasury,  agency,
and corporate  securities rated BBB- or better with maturities  between 5 and 10
years. The index has a market value of over $800 billion.

LEHMAN  BROTHERS  LONG (10+)  GOVERNMENT/CORPORATE  INDEX--is a market  weighted
index that contains  individually  priced U.S.  Treasury,  agency, and corporate
securities rated BBB- or better with maturities greater than 10 years. The index
has a market value of over $1.1 trillion.

LIPPER BALANCED FUND  AVERAGE--an  industry  benchmark of average balanced funds
with similar  investment  objectives  and  policies,  as measured by Lipper Inc.
LIPPER  NON-GOVERNMENT  MONEY  MARKET FUND  AVERAGE--an  industry  benchmark  of
average non-government money market funds with similar investment objectives and
policies, as measured by Lipper Inc.

LIPPER  GOVERNMENT MONEY MARKET FUND AVERAGE--an  industry  benchmark of average
government money market funds with similar  investment  objectives and policies,
as measured by Lipper Inc.

LIPPER GENERAL EQUITY FUND  AVERAGE--an  industry  benchmark of average  general
equity funds with similar  investment  objectives  and policies,  as measured by
Lipper Inc.

LIPPER FIXED INCOME FUND AVERAGE--an  industry benchmark of average fixed income
funds with similar  investment  objectives  and policies,  as measured by Lipper
Inc.



                              FINANCIAL STATEMENTS


Each Fund's Financial  Statements for the year ended October 31, 1999, including
the financial  highlights  for each of the five fiscal years in the period ended
October 31, 1999, appearing in the Vanguard Windsor Fund and Vanguard Windsor II
Fund  1999  Annual  Reports  to   Shareholders,   and  the  reports  thereon  of
PricewaterhouseCoopers LLP, independent accountants, also appearing therein, are
incorporated  by reference in this  Statement of Additional  Information.  For a
more  complete  discussion  of the  performance,  please see each Fund's  Annual
Report to Shareholders, which may be obtained without charge.






















                                      B-27
<PAGE>













































































                                                             SAI022-02/18/2000



                                      B-28


<PAGE>


                                     PART C

                             VANGUARD WINDSOR FUNDS
                               OTHER INFORMATION


ITEM 23. EXHIBITS

(a)    Declaration of Trust**
(b)    By-Laws**
(c)    Reference is made to Articles III and V of the Registrant's Declaration
       of Trust
(d)    Investment Advisory Contracts**
(e)    Not applicable

(f)    Reference is made to the section entitled  "Management of the Funds" in
       the Registrant's Statement of Additional Information

(g)    Custodian Agreement**
(h)    Amended and Restated Funds' Service Agreement**
(i)    Legal Opinion**
(j)    Consent of Independent Accountants*
(k)    Not Applicable
(l)    Not Applicable
(m)    Not Applicable

(n)    Not Applicable


(o)    Not Applicable

 * Filed herewith
 ** Filed previously

ITEM 24. PERSONS CONTROLLED BY OR UNDER COMMON CONTROL WITH REGISTRANT

Registrant is not controlled by or under common control with any person.


ITEM 25. INDEMNIFICATION

The  Registrant's   organizational  documents  contain  provisions  indemnifying
Trustees and officers  against  liability  incurred in their official  capacity.
Article VII,  Section 2 of the Declaration of Trust provides that the Registrant
may  indemnify  and hold  harmless  each and every  Trustee and officer from and
against  any and all  claims,  demands,  costs,  losses,  expenses,  and damages
whatsoever  arising out of or related to the performance of his or her duties as
a Trustee or officer.  However,  this  provision does not cover any liability to
which a Trustee  or  officer  would  otherwise  be  subject by reason of willful
misfeasance,  bad faith,  gross negligence,  or reckless disregard of the duties
involved  in  the  conduct  of  his or her  office.  Article  VI of the  By-Laws
generally provides that the Registrant shall indemnify its Trustees and officers
from  any  liability  arising  out of  their  past or  present  service  in that
capacity.  Among other things,  this provision excludes any liability arising by
reason of willful  misfeasance,  bad faith,  gross  negligence,  or the reckless
disregard  of the duties  involved in the conduct of the  Trustee's or officer's
office with the Registrant.


ITEM 26. BUSINESS AND OTHER CONNECTIONS OF INVESTMENT ADVISER


Wellington  Management Company,  LLP,  (Wellington  Management) is an investment
adviser  registered  under the Investment  Advisers Act of 1940, as amended (the
Advisers  Act).  The list  required by this Item 26 of officers  and partners of
Wellington  Management,  together  with  any  information  as  to  any  business
profession,  vocation or employment of a substantial  nature  engaged in by such
officers  and  partners  during the past two years,  is  incorporated  herein by
reference  from  Schedules  B and D of Form ADV filed by  Wellington  Management
pursuant to the Advisers Act (SEC File No. 801-15908).


                                      C-1
<PAGE>


     Sanford C.  Bernstein & Co.,  Inc.  (Bernstein)  is an  investment  adviser
registered under the Advisers Act. The list required by this Item 26 of officers
and partners of  Bernstein,  together  with any  information  as to any business
profession,  vocation,  or employment of a substantial nature engaged in by such
officers  and  partners  during the past two years,  is  incorporated  herein by
reference from Schedules B and D of Form ADV filed by Bernstein  pursuant to the
Advisers Act (SEC File No. 801-10488).


     Barrow, Hanley,  Mewhinney & Strauss, Inc. (Barrow Hanley) is an investment
adviser  registered under the Advisers Act. The list required by this Item 26 of
officers and directors of Barrow Hanley, together with any information as to any
business profession,  vocation, or employment of a substantial nature engaged in
by such officers and directors during the past two years, is incorporated herein
by reference from Schedules B and D of Form ADV filed by Barrow Hanley  pursuant
to the Advisers Act (SEC File No. 801-14861).


     Tukman  Capital  Management  (Tukman) is an investment  adviser  registered
under the  Advisers  Act.  The list  required  by this Item 26 of  officers  and
directors  of  Tukman,   together  with  any  information  as  to  any  business
profession,  vocation,  or employment of a substantial nature engaged in by such
officers and  directors  during the past two years,  is  incorporated  herein by
reference  from  Schedules  B and D of Form ADV filed by Tukman  pursuant to the
Advisers Act (SEC File No. 801-15279).

     Equinox Capital  Management  (Equinox) is an investment  adviser registered
under the  Advisers  Act.  The list  required  by this Item 26 of  officers  and
directors  of  Equinox,  together  with  any  information  as  to  any  business
profession,  vocation,  or employment of a substantial nature engaged in by such
officers and  directors  during the past two years,  is  incorporated  herein by
reference  from  Schedules B and D of Form ADV filed by Equinox  pursuant to the
Advisers Act (SEC File No. 801-34524).


     The Vanguard Group,  Inc.  (Vanguard) is an investment  adviser  registered
under the  Advisers  Act.  The list  required  by this Item 26 of  officers  and
directors  of  Vanguard,  together  with  any  information  as to  any  business
profession,  vocation,  or employment of a substantial nature engaged in by such
officers and  directors  during the past two years,  is  incorporated  herein by
reference from  Schedules B and D of Form ADV filed by Vanguard  pursuant to the
Advisers Act (SEC File No. 801-11953).




ITEM 27. PRINCIPAL UNDERWRITERS

(a)    Not Applicable
(b)    Not Applicable
(c)    Not Applicable

ITEM 28. LOCATION OF ACCOUNTS AND RECORDS


The books,  accounts,  and other documents  required to be maintained by Section
31(a) of the Investment Company Act and the rules promulgated thereunder will be
maintained  in the physical  possession  of  Registrant;  Registrant's  Transfer
Agent,  The Vanguard Group,  Inc.,  Valley Forge,  Pennsylvania  19482;  and the
Registrant's  Custodian,  State  Street  Bank and Trust  Company,  225  Franklin
Street, Boston, Massachusetts 02105.



ITEM 29. MANAGEMENT SERVICES

Other than as set forth under the description of The Vanguard Group in Part B of
this   Registration   Statement,   the   Registrant   is  not  a  party  to  any
management-related service contract.


ITEM 30. UNDERTAKINGS

Not Applicable

                                      C-2

<PAGE>


                                   SIGNATURES


Pursuant to the  requirements  of the  Securities Act of 1933 and the Investment
Company  Act of  1940,  the  Registrant  hereby  certifies  that  it  meets  all
requirements for effectiveness of this Registration  Statement  pursuant to Rule
485(b) under the  Securities  Act of 1933 and has duly caused this  Registration
Statement  to be  signed  on its  behalf  by  the  undersigned,  thereunto  duly
authorized, in the Town of Valley Forge and the Commonwealth of Pennsylvania, on
the 28th day of January, 2000.


                                              VANGUARD WINDSOR FUNDS

                                   BY: _____________(signature)________________
                                   (HEIDI STAM) JOHN J. BRENNAN* CHAIRMAN AND
                                             CHIEF EXECUTIVE OFFICER


     Pursuant  to  the   requirements  of  the  Securities  Act  of  1933,  this
Post-Effective  Amendment to the Registration Statement has been signed below by
the following persons in the capacities and on the date indicated:

SIGNATURE                     TITLE                              DATE
- --------------------------------------------------------------------------------



By:/S/ JOHN J. BRENNAN        President, Chairman, Chief      January 28, 2000
   ---------------------------Executive Officer, and Trustee
       (Heidi Stam)
      John J. Brennan*


By:/S/ JOANN HEFFERNAN HEISEN Trustee                         January 28, 2000
   ---------------------------
       (Heidi Stam)
     JoAnn Heffernan Heisen*


By:/S/ BRUCE K. MACLAURY      Trustee                         January 28, 2000
   ---------------------------
       (Heidi Stam)
      Bruce K. MacLaury*


By:/S/ BURTON G. MALKIEL      Trustee                         January 28, 2000
   ---------------------------
       (Heidi Stam)
       Burton G. Malkiel*



By:/S/ ALFRED M. RANKIN, JR.  Trustee                         January 28, 2000
   ---------------------------
       (Heidi Stam)
     Alfred M. Rankin, Jr.*


By:/S/ JOHN C. SAWHILL        Trustee                         January 28, 2000
   ---------------------------
       (Heidi Stam)
      John C. Sawhill*


By:/S/ JAMES O. WELCH, JR.    Trustee                         January 28, 2000
   ---------------------------
       (Heidi Stam)
     James O. Welch, Jr.*



By:/S/ J. LAWRENCE WILSON     Trustee                         January 28, 2000
   ---------------------------
       (Heidi Stam)
     J. Lawrence Wilson*



By:/S/ THOMAS J. HIGGINS      Treasurer and Principal         January 28, 2000
   ---------------------------
       (Heidi Stam)           Financial Officer and Principal
      Thomas J. Higgins*      Accounting Officer




*By Power of  Attorney.  See File Number  33-4424,  filed on January  25,  1999.
Incorporated by Reference.

<PAGE>



                               INDEX TO EXHIBITS



Consent of Independent Accountants . . . . . . . . . . .Ex-99.BJ

<PAGE>


                       CONSENT OF INDEPENDENT ACCOUNTANTS


We hereby  consent to the  incorporation  by reference in the  Prospectuses  and
Statement of Additional  Information  constituting parts of this  Post-Effective
Amendment No. 94 to the registration  statement on Form N-1A (the  "Registration
Statement")  of our reports dated  November 30, 1999,  relating to the financial
statements  and  financial  highlights  appearing in the October 31, 1999 Annual
Reports to Shareholders of Vanguard Windsor Funds,  which are also  incorporated
by reference into the Registration  Statement. We also consent to the references
to us under the heading "Financial Highlights" in the Prospectuses and under the
headings   "Financial   Statements"   and  "Service   Providers  -   Independent
Accountants" in the Statement of Additional Information.


PricewaterhouseCoopers LLP
Philadelphia, PA


January 27, 2000



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