VANGUARD/WINDSOR FUNDS INC
N-30D, 2000-12-22
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Vanguard Windsor(TM)Fund

Annual Report October 31, 2000

[SHIP]
[THE VANGUARD GROUP LOGO]
<PAGE>


OUR REPORTS TO
THE OWNERS

At Vanguard,  we regard our investors not as mere customers but as owners of the
enterprise.  For that's exactly what a mutual fund shareholder is--part owner of
an investment company.

In our  reports  to you on how the  company  is doing,  we have  tried to convey
information  without  hyperbole  and in the context of broad  market  trends and
relevant benchmarks.

We've introduced several changes to this year's annual reports to make them even
more useful. Among the changes:

     - Larger  type  and redesigned graphics to make the reports easier to read.

     - An  at-a-glance  summary of key points  about  fund  performance  and the
financial markets.

     - A  table--included  for  many  funds--in  which  the  investment  adviser
highlights significant changes in holdings.

     - Comparisons of fund performance and characteristics  against both a broad
market index and a "best fit" benchmark.

     We hope  you'll  find  that  these  changes  make  the  reports  even  more
accessible and informative.

SUMMARY

* Vanguard  Windsor Fund earned  11.6%  during the 12 months  ended  October 31,
2000,  surpassing  returns  for  both  its  average  peer  fund  and  its  index
benchmarks.

* Value  stocks in general,  and  Windsor's  holdings in  particular,  rebounded
during the second half of the fiscal year.

* The fund benefited from strong stock picks in several sectors,  especially the
financial services and consumer discretionary groups.


CONTENTS

 1 Letter from the Chairman

 6 Notice to Shareholders

 7 Adviser's Report

 9 Fund Profile

10 Glossary of Investment Terms

11 Performance Summary

12 Report on After-Tax Returns

13 Financial Statements

22 Report of Independent Accountants
<PAGE>



LETTER
 from the Chairman

Fellow Shareholders,

VANGUARD  WINDSOR FUND earned  11.6% in the fiscal year ended  October 31, which
was a turbulent period for stocks.  Windsor outpaced the broad market as well as
our benchmarks:  the average multi-cap value fund, the Russell 1000 Value Index,
and the Standard & Poor's 500 Index.
     We thank our  shareholders  for their  patience in recent  years when value
stocks generated  returns well below those of growth issues.  It took discipline
to stick with value investing when price momentum--buying  stocks mainly because
their prices had risen--was a driving force on Wall Street.  However, it appears
that pundits who declared the death of value investing were off target.

2000 TOTAL RETURNS               FISCAL YEAR ENDED
                                        OCTOBER 31
--------------------------------------------------
Vanguard Windsor Fund                        11.6%
Average Multi-Cap Value Fund*                10.9
Russell 1000 Value Index                      5.5
S&P 500 Index                                 6.1
--------------------------------------------------
*Derived from data provided by Lipper Inc.

     The  table  above  presents  the  12-month  returns  of the  fund  and  its
benchmarks.  The fund's total return (capital change plus reinvested  dividends)
is based on a decrease  in net asset  value from $16.91 per share on October 31,
1999,  to $16.44 per share on October 31, 2000,  and is adjusted  for  dividends
totaling $0.29 per share paid from net investment  income and a distribution  of
$1.90 per share  paid  from net  realized  capital  gains.
     If you  own  Vanguard  Windsor  Fund in a  taxable  account,  we call  your
attention to a review of the fund's after-tax returns on page 12.

MARKET BAROMETER                                    AVERAGE ANNUAL TOTAL RETURNS
                                                  PERIODS ENDED OCTOBER 31, 2000

                                                 ONE        THREE          FIVE
                                                YEAR        YEARS         YEARS
--------------------------------------------------------------------------------
STOCKS

S&P 500 Index (Large-caps)                       6.1%        17.6%         21.7%
Russell 2000 Index (Small-caps)                 17.4          5.9          12.4
Wilshire 5000 Index (Entire market)              8.1         16.0          20.1
MSCI EAFE Index (International)                 -2.7          9.7           8.9
--------------------------------------------------------------------------------
BONDS

Lehman Aggregate Bond Index (Entire market)      7.3%         5.7%          6.3%
Lehman 10 Year Municipal Bond Index              8.2          5.0           5.7
Salomon Smith Barney 3-Month
   U.S. Treasury Bill Index                      5.7          5.2           5.2
================================================================================
CPI

Consumer Price Index                             3.4%         2.5%          2.5%
--------------------------------------------------------------------------------


FINANCIAL MARKETS IN REVIEW

The U.S.  stock  market  began the fiscal  year like a  skyrocket  as  investors
targeted technology-related stocks. In the first two months of the

                                       1
<PAGE>

period,  the broad  market  gained  more than 11%.  Fueling  the  increase  were
favorable economic data: Production rose rapidly,  unemployment fell below 4% of
the   workforce,   long-term   interest  rates   declined,   and  inflation  was
well-behaved, aside from a rise in energy prices.

     But as the period  progressed,  the effects of higher  short-term  interest
rates--engineered by the Federal Reserve Board to slow the economy and forestall
inflation--began  to show.  Data  suggested  that the  economy's  expansion  was
decelerating  to a moderate  pace.  And despite  solid  increases  in  corporate
earnings,  doubts  grew that  companies  could  sustain  the growth  pace amid a
slowing economy.

     Investors  seemed to grow wary of the lofty  prices of many tech  stocks in
relation to their earnings and other fundamentals.  Value  stocks--those  issues
characterized by relatively low prices in relation to earnings,  book value, and
dividends--  generally benefited from the market's increased emphasis on current
earnings.



TOTAL RETURNS
                           OCT. 31, 1999, TO      APR. 30, 2000, TO       FISCAL
                               APR. 30, 2000          OCT. 31, 2000         2000
--------------------------------------------------------------------------------
Russell 1000 Growth Index              18.7%                  -7.9%         9.3%
Russell 1000 Value Index               -1.0                    6.6          5.5
--------------------------------------------------------------------------------

The result was a significant  split between first- and  second-half  results for
growth and value stocks, as the table above shows.

     For the full 12 months,  the overall  market,  as measured by the  Wilshire
5000  Total  Market  Index,   returned  8.1%--a  decent  result  but  below  the
double-digit gains investors have seen in recent years. For a change, small- and
mid-capitalization  stocks outpaced their large-cap counterparts:  The small-cap
Russell 2000 Index  returned  17.4% for the 12 months,  11.3  percentage  points
ahead of the return of the large-cap S&P 500 Index.

     The year saw huge  variations in returns of various  industry  groups.  For
example,  higher oil and natural  gas prices  boosted  the oil  exploration  and
services companies in the "other energy" group to a 49% return,  making this the
top-performing  sector within the S&P 500 Index.  Other strong sectors  included
producer  durables (31%),  health care (16%), and financial  services (15%). The
year's big losers were  telephone  companies,  which  weighed down the utilities
group (-15%),  and retailers,  apparel  makers,  and other firms in the consumer
discretionary sector (-13%).

     Short-term  interest  rates rose  substantially  during the year,  with the
yield on 3-month U.S.  Treasury  bills  increasing 1.3  percentage  points.  The
increase  essentially  matched the  1.25-point  boost in the federal  funds rate
accomplished in four steps by the Federal Reserve.

     Yields were relatively flat, on balance, for most longer-term securities. A
rising federal budget surplus shrank the supply of U.S. Treasury bonds, and

                                       2

<PAGE>

their yields declined slightly for the fiscal year: The 30-year Treasury's yield
fell  from  6.16%  to  5.79%.  Yields  on  10-year  Treasuries  fell by  about a
quarter-point.  In general,  bonds turned in solid results during the 12 months.
The Lehman Brothers  Aggregate Bond Index, a proxy for taxable  investment-grade
bonds,  returned 7.3%, outpacing the S&P 500 Index.  Mortgage-backed  securities
and  high-quality  corporate bonds  performed  well,  benefiting from investors'
shift toward  high-quality  bonds and away from  speculative  issues.  Prices of
high-yield  bonds fell by more than 10%, on  average,  and the Lehman High Yield
Index returned -1.6%.

FISCAL 2000 PERFORMANCE OVERVIEW

Vanguard  Windsor  Fund's  11.6%  return in the  fiscal  year  ended  October 31
represented a remarkable comeback.  After declining -10.4% from November through
February, the fund generated a 24.6% return during the final eight months of our
fiscal year.  Windsor's  full-year  gain placed it modestly ahead of the average
multi-cap value fund and far in advance of the Russell 1000 Value Index. We also
finished the year well ahead of the broad market indexes.

     The  turnabout  was not the  result  of some  sudden  brilliant  change  in
strategy by our advisers--Wellington Management Company and Sanford C. Bernstein
& Co. They have  continued to follow their  disciplined  approaches to selecting
stocks.  Rather,  it seemed that the market began to  recognize  the merits of a
number of stocks that our advisers had selected.

     The standout group for Windsor was financial  services  stocks--the  fund's
largest industry  concentration at about one-quarter of assets on average. (This
group  accounted for more than 30% of the Russell 1000 Value  Index.)  Windsor's
financial stocks earned an average of 26% during the fiscal year,  nearly double
the  average  return  for the  sector  in the  Russell  index.  In the  consumer
discretionary group, Windsor's holdings earned about 14% during the fiscal year,
compared  with a -6% return for this group in the index.  Windsor's  health care
and materials & processing stocks also  significantly  outperformed those in the
index.  On the other  hand,  our  fund's  overall  return  was hurt by very poor
results  from its  utilities  stocks  (down nearly -30%) and by having more than
triple the market  weighting  in the  materials &  processing  sector,  a poorly
performing segment of the market.

--------------------------------------------------------------------------------
The standout group for Windsor Fund was financial services stocks.
--------------------------------------------------------------------------------

     The past year showed that patience and  perspective  are necessary  virtues
for value  investors,  who by definition are choosing  securities that have been
shunned by many other  investors  (that's why their prices are relatively low in
comparison with earnings and other measures).

     We note that many  individuals  who gave into the temptation to alter their
investment allocations paid a heavy price. Consider that the largest flows

                                       3
<PAGE>


of cash into technology-related mutual funds and out of value funds like Windsor
occurred in February  and March 2000.  The timing of these flows  couldn't  have
been worse.

     That said, we don't pretend to know what the market has in store next,  and
we continue to believe that long-term investors should maintain exposure to both
value stocks and growth stocks. As fiscal 2000  demonstrated,  market leadership
can switch  suddenly and decisively  from growth to value and back again.  As we
said in our letter one year ago, we believe that Windsor's  disciplined approach
to seeking  value gives the fund a good chance to achieve our goal of  providing
superior long-term returns.

TOTAL ASSETS MANAGED                                            OCTOBER 31, 2000

                                                        $ MILLION     PERCENTAGE
--------------------------------------------------------------------------------
Wellington Management Company, llp                        $11,799            74%
Sanford C. Berstein & Co., LLC                              3,867            24
Cash Investments*                                             269             2
--------------------------------------------------------------------------------
Total                                                     $15,935           100%
--------------------------------------------------------------------------------
*This cash is invested by The Vanguard Group in equity index futures to simulate
investment in stocks; each adviser also maintains a modest cash position.

     The table above shows the current allocation of Windsor Fund assets between
our two advisers.

LONG-TERM PERFORMANCE OVERVIEW

We're pleased by Windsor Fund's strong relative  results during fiscal 2000, but
we believe that performance is best measured over the long haul. The table below
presents the average annual returns for your fund, the average  multi-cap  value
fund,  and two market  benchmarks  over the past  decade.  It also  presents the
results of hypothetical $10,000 investments made ten years ago in each.

     Windsor  Fund's  edge over its  average  competitor  amounted  to more than
$5,000 over the decade.  Our record versus the index benchmarks  wasn't as good.
The Russell 1000 Value Index is a good yardstick for us,  although not a precise
fit,  since  some  of its  constituent  stocks  are  fairly  pricey  by  Windsor
standards.  The S&P 500  Index,  of  course,  contains  both  value  and  growth
stocks--a  big  advantage  during the 1990s,  when  growth  stocks were the best
performers.

     Our low  operating  costs  explain  much of our  margin  over our peer fund
group. Windsor Fund's expense ratio is a slender 0.31%, or


TOTAL RETURNS                                                    TEN YEARS ENDED
                                                                OCTOBER 31, 2000

                                      AVERAGE                     FINAL VALUE OF
                                       ANNUAL                          A $10,000
                                       RETURN                 INITIAL INVESTMENT
--------------------------------------------------------------------------------
Vanguard Windsor Fund                   17.5%                           $50,084
Average Multi-Cap Value Fund            16.2                             44,732
Russell 1000 Value Index                18.3                             53,805
S&P 500 Index                           19.4                             59,083
--------------------------------------------------------------------------------

                                       4
<PAGE>

$3.10 per $1,000 of assets,  versus the 1.39% ($13.90 per $1,000) charged by the
average  multi-cap  value fund,  according  to data from  Lipper Inc.  This cost
advantage gives our advisers a head start versus  competitors,  year after year,
in our quest to provide superior returns. (In comparison with indexes, all funds
are at a  disadvantage,  since indexes exist only on paper and incur no costs at
all.)

     Of course, our goal is to provide long-term returns that beat those of both
our peer funds and our index benchmark.  We hope to improve our relative returns
in future years,  but stress that it's unlikely that we or the market will match
the absolute  returns  recorded  during the past ten years.  The stock  market's
performance  during the 1990-2000 decade was one of its best ever;  returns were
far above the 11% to 12% annual average for stocks over the past 75 years or so.
We suggest  that in making your  investment  plans,  you assume no more than the
long-term average return of about 11%. After all, if you make modest assumptions
and the market  exceeds them,  the result is not bad:  You'll merely get to your
objectives sooner.


IN SUMMARY

The  financial  markets  during  the past 12  months  certainly  reinforced  the
importance of  diversification.  Just when it seemed that a single hot sector of
the stock market was the only place to be, technology-related stocks swooned and
value stocks came to the fore. And bonds--the  asset class many investors forgot
in the excitement of the bull market in stocks--posted solid results.

     Perhaps the one safe prediction for the next 12 months is that markets will
continue to be quite unpredictable. But uncertainty and volatility--risk, to use
a four-letter word--are constant companions for investors. A balanced investment
program--a  mix of  short-term  investments,  bonds,  and both  value and growth
stocks--can help you manage risk. Once you've built such a program in accordance
with your  objectives,  time  horizon,  financial  situation,  and tolerance for
market fluctuations, we recommend staying the course.

Sincerely,
/S/ JOHN J. BRENNAN
November 13, 2000


JOHN J. BRENNAN
Chairman and
Chief Executive Officer

                                       5
<PAGE>
--------------------------------------------------------------------------------
NOTICE TO SHAREHOLDERS: CHANGE IN OWNERSHIP
FOR SANFORD C. BERNSTEIN & CO., INC.
On June 20, 2000,  Alliance Capital Management L.P. (Alliance Capital) announced
that it had agreed to acquire Sanford C. Bernstein & Co., Inc. (Bernstein),  one
of the  advisers  to  Vanguard  Windsor  Fund.  The change in  ownership  is not
expected to have any  practical  effect on the  management or operations of your
fund.  However,  your fund's  advisory  contract  with  Bernstein  automatically
terminated when the change in ownership occurred.  This automatic termination is
required by the Investment Company Act of 1940.

     Alliance Capital's  acquisition of Bernstein became effective on October 2,
2000.  Following the  completion  of that  transaction,  Bernstein's  investment
professionals,  including  those  responsible  for the management of your fund's
assets, now provide investment  management services through Sanford C. Bernstein
& Co.,  LLC  (Bernstein  LLC),  a  subsidiary  of Alliance  Capital and Alliance
Capital's  Bernstein  Investment Research and Management Unit.  Accordingly,  on
September  14,  2000,  your fund's board of trustees  approved a new  investment
advisory  contract with  Bernstein LLC to take effect when the ownership  change
was  completed.  All of the  key  terms  of the  new  contract,  except  for its
commencement  and  termination  dates,  are the same as  those  in the  previous
contract. Your board believes that, like the previous advisory contract, the new
advisory  contract  will enable the fund to obtain  services of high  quality at
reasonable  cost  and  that it is in the  best  interests  of the  fund  and its
shareholders.  The board's  unanimous vote to approve the new contract  included
all of the trustees who are not "interested persons" of the fund or of Bernstein
LLC.

     In 1993, the Windsor Fund received  permission from the U.S. Securities and
Exchange Commission and the fund's shareholders for the trustees to enter into a
new advisory agreement without the delay and expense of a shareholder vote. This
special  permission  was made  subject  to  several  conditions,  including  the
requirement  that  shareholders be notified of changes to the fund's  investment
advisory agreement.

     Bernstein LLC is located at 767 Fifth Avenue, New York, NY 10153. Bernstein
LLC is registered as an investment adviser with the U.S. Securities and Exchange
Commission.  Bernstein began providing private  investment  advisory services in
1967  and  has  provided  such  services  to  both  domestic  and  international
investment portfolios for corporate, government, and union benefit plans; mutual
funds; individuals;  endowments; and foundations. As of June 30, 2000, Bernstein
had total assets under management of approximately $82.7 billion.


                                       6
<PAGE>

ADVISER'S
   Report                                     WELLINGTON MANAGEMENT COMPANY, LLP

After  appreciating  a  staggering  245% from the end of 1997  through the first
quarter  of  2000,  the  technology  sector  in the S&P 500  Index  has  finally
undergone  some  correction,  dropping  about 25% in the final  seven  months of
vanguard  windsor  fund's  fiscal  year  ended  October  31.  Given our  obvious
underweighting in these mostly high-P/E stocks,  which at their peak represented
close to one-third of the market's value,  this correction  provided an improved
backdrop for Windsor-style investing in the second half of the year.

     For the entire fiscal year, our outperformance of the S&P 500 Index was led
by three sectors--energy, financials, and health care. In each of these, we were
doubly blessed:  Our portion of the fund was overweighted  versus the index in a
sector  that  outperformed  the  market  and our  holdings  outpaced  the sector
average. And, believe it or not, our technology  stocks--low-P/E tech stocks, to
be sure--were up 30%,  outperforming  both the market as a whole and the average
return from the tech sector.

--------------------------------------------------------------------------------
INVESTMENT PHILOSOPHY

The fund reflects a belief that  superior  long-term  investment  results can be
achieved by emphasizing common stocks that are generally  misunderstood,  out of
favor, or undervalued by fundamental  measures such as  price/earnings  ratio or
dividend  yield.  The fund may  concentrate  a large  portion of assets in those
securities or industries the advisers believe offer the best return potential.
--------------------------------------------------------------------------------

     A notable event that  contributed  importantly to performance  for the year
was the September  announcement  that Citigroup was acquiring  Associates  First
Capital--our  second-largest  holding  at the  time--at  a 53%  premium.  On the
negative  side  of  things,  our  long-distance  telephone   holdings--AT&T  and
WorldCom--were very poor performers. We still hold these stocks and believe that
they have significant upside potential, although we've reduced our price targets
for them due to significantly reduced earnings forecasts.

     The U.S.  economy is  transitioning  from the  too-high  GDP growth rate of
about  5.5%  that  we saw in  1999  and in the  first  half  of  2000  to a more
sustainable  growth rate of 3.0% to 3.5% for the second half of the year and, we
expect, for the next two or three years. We think that the odds are against this
slowdown  turning  into a recession.  The  underlying  productivity  of the U.S.
economy is strong, which should keep inflation well contained,  and there are no
broad  inventory  or other  imbalances  that might get us in  trouble.  When end
demand slows,  as it has lately,  you do get inventory  imbalances in individual
sectors. However, in our modern economy such imbalances typically get recognized
and dealt with in two or three quarters.

                                       7
<PAGE>

     Importantly,  we see real  (inflation-adjusted)  consumer  spending growing
3.0% to 3.5%  next  year,  about in line with real  disposable  income.  And the
consumer is, after all, about  two-thirds of the economy.  The increase in oil's
price--from  around $12 a barrel in early 1999 to around $35  now--has  dampened
consumer spending,  but we expect the price to retrace its steps to the low $20s
over the next 12  months,  as  OPEC's  production  now is  clearly  outstripping
annualized  demand.  The recent  decline in mortgage  rates is another  positive
factor in the outlook for consumer  spending,  and we have already seen a bounce
in home buying from spring and summer levels.

     While we see the  economy in a positive  light,  the market is not so sure.
This has created good value  opportunities in cyclical stocks.  Accordingly,  we
are somewhat overweighted in cyclical stocks--particularly Alcoa and other basic
materials producers, retailers, specialty chemicals, and transportation.
     We are still  considerably  underweighted in both consumer  nondurables and
technology.  Consumer  nondurables  have been poor performers for a year or two,
and  we  don't  see  them   outperforming  the  market  given  their  still-high
valuations,  their low unit-volume  growth,  and the lack of their  once-vaunted
pricing power.

     And despite a 25% drop in tech stocks  since  March,  the S&P's tech sector
still  sports a 32  price/earnings  multiple  based on  estimates of next year's
earnings. This is a high price relative to the 11% long-term growth rate for the
information  technology sector as a whole--especially  if we are wrong about the
economy and we wind up in a recession.  In recessions,  technology spending gets
deferred,  and tech stocks  would be no fun at all. As it is, the group is being
buffeted  by  decelerating  growth in a number  of  technology  sub-sectors--  a
development that we envisioned in our report to you at midyear. Again, we do not
forecast  a  recession.  If we have one,  it will be short and  shallow.  In any
event,  we think  the  prices  of  cyclicals,  where we are  overweighted,  have
factored in such a possibility better than tech prices have.

     We   continue   to  invest   your   money  in  the   longstanding   Windsor
tradition--emphasizing  low-P/E stocks,  staying price  opportunistic on the buy
side and price  disciplined  on the sell side,  and being  willing  to  sensibly
concentrate--while  keeping an eye on the  ever-changing  world of business  and
contemporary trends.

     Indeed,  as tech stocks have weakened,  we've used the  opportunity to take
starting positions in select tech stocks (Dell Computer and Hewlett-Packard, for
example) at our kind of prices.  Even so, we're still way  underweighted in tech
stocks overall.  Other important new positions established in the latter half of
the fiscal year include  Staples,  Cox  Communications,  and Petrobras,  the big
Brazilian oil company.  We continue to forage--in  our usual  opportunistic  and
entrepreneurial fashion--for undervalued stocks with significant (30% or better)
upside potential as we try to provide unusual returns to you, the shareholder.

Charles T. Freeman, Portfolio Manager                          November 17, 2000

                                       8
<PAGE>

FUND PROFILE                                              As of October 31, 2000
  for Windsor Fund

This Profile provides a snapshot of the fund's  characteristics,  compared where
appropriate  to both an  unmanaged  index that we  consider a "best fit" for the
fund and a broad market index. Key terms are defined on page 10.

---------------------------------------------------------------
PORTFOLIO CHARACTERISTICS
                                                       WILSHIRE
                          FUND         BEST FIT*           5000
---------------------------------------------------------------
Number of Stocks           175               740          6,768
Median Market Cap        $8.9B            $41.6B         $46.1B
Price/Earnings Ratio     15.0x             19.8x          29.8x
Price/Book Ratio          2.2x              3.3x           4.5x
Yield                     1.6%              1.8%           1.1%
Return on Equity         15.3%             20.8%          22.8%
Earnings Growth Rate     12.2%             10.9%          16.8%
Foreign Holdings          7.3%              0.0%           0.0%
Turnover Rate              41%               ---            ---
Expense Ratio            0.31%               ---            ---
Cash Investments          0.6%               ---            ---
---------------------------------------------------------------


--------------------------------------------
TEN LARGEST HOLDINGS
   (% of total net assets)

Associates First Capital Corp.          5.4%
   (financial services)
Alcoa Inc.                              4.4
   (aluminum)
TJX Cos., Inc.                          3.3
   (retail)
WorldCom, Inc.                          3.1
   (telecommunications)
Citigroup, Inc.                         2.9
   (financial services)
Pharmacia Corp.                         2.8
   (pharmaceuticals)
Washington Mutual, Inc.                 2.4
   (savings & loan)
CIGNA Corp.                             2.1
   (insurance)
Air Products & Chemicals, Inc.          2.1
   (chemicals)
Eaton Corp.                             1.7
   (auto parts)
--------------------------------------------
Top Ten                                30.2%
--------------------------------------------


----------------------------------------------
VOLATILITY MEASURES

                                      Wilshire
              Fund  Best Fit*    Fund     5000
----------------------------------------------
R-Squared     0.89    1.00       0.53     1.00
Beta          1.15    1.00       0.88     1.00
----------------------------------------------


--------------------------------------------------------------------
SECTOR DIVERSIFICATION
   (% OF COMMON STOCKS)
                                                            WILSHIRE
                                     FUND       BEST FIT*       5000
--------------------------------------------------------------------
Auto & Transportation                7.3%           3.1%        1.7%
Consumer Discretionary               9.4            9.2        12.0
Consumer Staples                     1.1            7.8         5.3
Financial Services                  25.1           31.3        17.0
Health Care                          6.5            8.6        12.4
Integrated Oils                      5.7            7.2         3.1
Other Energy                         3.6            2.5         2.6
Materials & Processing              19.6            3.8         2.5
Producer Durables                    3.0            3.5         3.3
Technology                           6.1            4.7        26.4
Utilities                           11.0           15.7         8.7
Other                                1.6            2.6         5.0
--------------------------------------------------------------------
*Russell 1000 Value Index.


------------------------------
INVESTMENT FOCUS

MARKET CAP             Medium
STYLE                  Value
------------------------------


                                                           [PICTURE OF COMPUTER]
                                                               VISIT OUR WEBSITE
                                                                WWW.VANGUARD.COM
                                                           FOR REGULARLY UPDATED
                                                               FUND INFORMATION.

                                       9
<PAGE>

GLOSSARY
   of Investment Terms

BETA. A measure of the magnitude of a fund's past  share-price  fluctuations  in
relation to the ups and downs of the fund's  "best fit" index  benchmark  and an
overall  market  index.  Each index is assigned a beta of 1.00.  Compared with a
given index,  a fund with a beta of 1.20 would have seen its share price rise or
fall by 12% when the index rose or fell by 10%.
--------------------------------------------------------------------------------
CASH  INVESTMENTS.  The  percentage  of a fund's  net assets  invested  in "cash
equivalents"--highly  liquid,  short-term,  interest-bearing  instruments.  This
figure does not include cash  invested in futures  contracts  to simulate  stock
investment.
--------------------------------------------------------------------------------
EARNINGS  GROWTH RATE.  The average  annual rate of growth in earnings  over the
past five years for the stocks now in a fund.
--------------------------------------------------------------------------------
EXPENSE  RATIO.  The  percentage of a fund's  average net assets used to pay its
annual  administrative  and advisory  expenses.  These expenses  directly reduce
returns to investors.
--------------------------------------------------------------------------------
FOREIGN HOLDINGS. The percentage of a fund's equity assets represented by stocks
or American Depositary Receipts of companies based outside the United States.
--------------------------------------------------------------------------------
MEDIAN  MARKET  CAP.  An  indicator  of the  size of  companies  in which a fund
invests;  the  midpoint  of  market   capitalization   (market  price  x  shares
outstanding) of a fund's stocks, weighted by the proportion of the fund's assets
invested  in each  stock.  Stocks  representing  half of the fund's  assets have
market capitalizations above the median, and the rest are below it.
--------------------------------------------------------------------------------
PRICE/BOOK  RATIO.  The share price of a stock divided by its net worth, or book
value,  per share.  For a fund,  the weighted  average  price/book  ratio of the
stocks it holds.
--------------------------------------------------------------------------------
PRICE/EARNINGS  RATIO.  The ratio of a stock's  current  price to its  per-share
earnings over the past year. For a fund, the weighted  average P/E of the stocks
it holds. P/E is an indicator of market expectations about corporate  prospects;
the higher the P/E, the greater the expectations for a company's future growth.
--------------------------------------------------------------------------------
R-SQUARED.  A measure of how much of a fund's past  returns can be  explained by
the  returns  from the market in general,  as measured by the fund's  "best fit"
index  benchmark and by an overall market index.  If a fund's total returns were
precisely  synchronized with an index's returns, its R-squared would be 1.00. If
the fund's returns bore no  relationship to the index's  returns,  its R-squared
would be 0.
--------------------------------------------------------------------------------
RETURN ON  EQUITY.  The annual  average  rate of return  generated  by a company
during the past five years for each dollar of  shareholder's  equity (net income
divided by  shareholder's  equity).  For a fund, the weighted  average return on
equity for the companies whose stocks it holds.
--------------------------------------------------------------------------------
TURNOVER  RATE. An indication of trading  activity  during the past year.  Funds
with high turnover rates incur higher  transaction  costs and are more likely to
distribute capital gains (which are taxable to investors).
--------------------------------------------------------------------------------
YIELD.  A snapshot of a fund's  income from interest and  dividends.  The yield,
expressed  as a  percentage  of the fund's net asset  value,  is based on income
earned over the past 30 days and is  annualized,  or  projected  forward for the
coming  year.  The  index  yield  is  based on the  current  annualized  rate of
dividends paid on stocks in the index.
--------------------------------------------------------------------------------

                                       10
<PAGE>

PERFORMANCE SUMMARY
   for Windsor Fund

All of the data on this page represent past performance, which cannot be used to
predict  future returns that may be achieved by the fund.  Note,  too, that both
share  price and  return  can  fluctuate  widely.  An  investor's  shares,  when
redeemed, could be worth more or less than their original cost.

--------------------------------------------------------------------------------
TOTAL INVESTMENT RETURNS (%)                   October 31, 1990-October 31, 2000

                      WINDSOR FUND     RUSSELL 1000 VALUE INDEX
1991                          44.7                         32.9
1992                           9.3                         10.7
1993                          28.3                         25.2
1994                           6.3                          0.8
1995                          17.8                         24.7
1996                          23.2                         23.7
1997                          27.0                         33.2
1998                          -0.8                         14.8
1999                          13.7                         16.5
2000                          11.6                          5.5
--------------------------------------------------------------------------------
See  Financial  Highlights  table  on page 19 for  dividend  and  capital  gains
information for the past five years.
--------------------------------------------------------------------------------


--------------------------------------------------------------------------------
CUMULATIVE PERFORMANCE                         OCTOBER 31, 1990-OCTOBER 31, 2000

              WINDSOR      AVERAGE  RUSSELL 1000      WILSHIRE       S&P 500
                 FUND    MULTI-CAP         VALUE    5000 INDEX         INDEX
                        VALUE FUND*        INDEX

199010         10000         10000         10000         10000         10000
199101         12228         11555         11459         11562         11420
199104         13564         12645         12494         12865         12562
199107         13938         13077         12933         13395         13087
199110         14469         13519         13289         13860         13350
199201         14962         14216         13685         14751         14011
199204         15840         14506         14412         14789         14325
199207         16390         14787         14949         15166         14760
199210         15815         14848         14706         15202         14679
199301         18001         15951         16002         16310         15493
199304         18469         16253         16835         16332         15648
199307         19393         16749         17749         16916         16049
199310         20288         17748         18406         17902         16872
199401         21581         18436         19064         18488         17488
199404         20134         17560         18067         17432         16480
199407         21294         17808         18394         17646         16877
199410         21576         18397         18549         18356         17524
199501         20711         18046         18559         18300         17581
199504         22857         19677         20339         20019         19359
199507         25482         21524         22230         22239         21283
199510         25417         22165         23128         23062         22158
199601         27194         24001         25686         25108         24378
199604         28922         25085         26421         26464         25208
199607         28171         24206         25762         25508         24810
199610         31304         26738         28617         28118         27497
199701         35471         29346         31769         31252         30800
199704         35551         29229         32382         31131         31543
199707         41597         34654         38340         37538         37745
199710         39767         34438         38113         36990         36327
199801         40712         35400         40381         39123         39089
199804         46782         39386         46041         44600         44497
199807         42618         37294         45129         43961         45024
199810         39455         36091         43764         42484         44315
199901         40961         38855         47740         49829         51788
199904         48136         41217         52528         52172         54207
199907         46842         41389         51893         52018         54120
199910         44878         40321         50997         53385         55691
200001         42738         39515         49185         56994         57146
200004         46060         41085         50491         58554         59697
200007         46306         40930         49300         57832         58978
200010         50084         44732         53805         57709         59083
--------------------------------------------------------------------------------
                                  AVERAGE ANNUAL TOTAL RETURNS
                                  PERIODS ENDED OCTOBER 31, 2000     FINAL VALUE
                                 -------------------------------    OF A $10,000
                                  1 YEAR     5 YEARS   10 YEARS       INVESTMENT
--------------------------------------------------------------------------------
Windsor Fund                        11.60%      14.53%     17.48%        $50,084
Average Multi-Cap Value Fund*       10.94       15.08      16.16          44,732
Russell 1000 Value Index             5.52       18.40      18.33          53,805
Wilshire 5000 Index                  8.10       20.14      19.16          57,709
S&P 500 Index                        6.09       21.67      19.44          59,083
--------------------------------------------------------------------------------
*Derived from data provided by Lipper Inc.
--------------------------------------------------------------------------------

                                       11
<PAGE>

A REPORT
   on Your Fund's After-Tax Returns

This  table  presents  pre-tax  and  after-tax  returns  for  your  fund  and an
appropriate  peer group of mutual  funds.  The after-tax  returns  represent the
fund's past results only and cannot be used to predict future tax efficiency.
     If you  own the  fund  in a  tax-deferred  account  such  as an  individual
retirement  account or a 401(k),  this  information  does not apply to you. Such
accounts are not subject to current taxes.

     Income  taxes  can  have  a  considerable  impact  on a  fund's  return--an
important  consideration for investors who own mutual funds in taxable accounts.
While the pre-tax return is most often used to tally a fund's  performance,  the
fund's  after-tax  return,  which accounts for taxes on distributions of capital
gains and income  dividends,  is an  important  measure of the return  that many
investors actually received.

PRE-TAX AND AFTER-TAX                             PERIODS ENDED OCTOBER 31, 2000
AVERAGE ANNUAL TOTAL RETURNS

                                ONE YEAR        FIVE YEARS     TEN YEARS
                           -----------------------------------------------------
                           PRE-TAX AFTER-TAX PRE-TAX AFTER-TAX PRE-TAX AFTER-TAX
--------------------------------------------------------------------------------
Vanguard Windsor Fund        11.6%      7.8%   14.5%     10.7%   17.5%     13.8%
Average Mid-Cap Value Fund*  17.0      14.1    14.7      11.4    16.1      13.5
--------------------------------------------------------------------------------
*Based on data from  Morningstar,  Inc.  Elsewhere in this  report,  returns for
comparable funds are derived from data provided by Lipper Inc., which may differ
somewhat.

     The after-tax  return  calculations use the top federal income tax rates in
effect at the time of each  distribution.  The tax burden would be less, and the
after-tax return higher, for those in lower tax brackets.
     We  must  stress  that  because  many   interrelated   factors  affect  how
tax-friendly  a fund may be, it's very  difficult to predict tax  efficiency.  A
fund's tax  efficiency  can be  influenced  by its turnover  rate,  the types of
securities it holds, the accounting  practices it uses when selling shares,  and
the net cash flow it receives.
     Finally, it's important to understand that our calculation does not reflect
the tax effect of your own investment  activities.  Specifically,  you may incur
additional capital gains  taxes--thereby  lowering your after-tax return--if you
decide to sell all or some of your shares.
--------------------------------------------------------------------------------
A  NOTE  ABOUT  OUR   CALCULATIONS:   Pre-tax  total  returns  assume  that  all
distributions   received  (income  dividends,   short-term  capital  gains,  and
long-term  capital  gains) are  reinvested  in new shares,  while our  after-tax
returns assume that  distributions  are reduced by any taxes owed on them before
reinvestment.  When  calculating  the taxes due, we used the highest  individual
federal  income  tax  rates at the time of the  distributions.  Those  rates are
currently 39.6% for dividends and short-term capital gains and 20% for long-term
capital gains. State and local income taxes were not considered. The competitive
group returns provided by Morningstar are calculated in a manner consistent with
that used for Vanguard funds.

                                                           [PICTURE OF COMPUTER]
                                         You can use Vanguard's online after-tax
                                                            return calculator at
                                                      www.vanguard.com/?aftertax
                                                    to customize the calculation
                                                       of your after-tax return.

                                       12
<PAGE>

FINANCIAL STATEMENTS
   October 31, 2000

STATEMENT OF NET ASSETS

This Statement  provides a detailed list of the fund's holdings,  including each
security's market value on the last day of the reporting period.  Securities are
grouped  and  subtotaled  by asset  type  (common  stocks,  bonds,  etc.) and by
industry sector. Other assets are added to, and liabilities are subtracted from,
the value of Total Investments to calculate the fund's Net Assets.  Finally, Net
Assets are divided by the outstanding  shares of the fund to arrive at its share
price, or Net Asset Value (NAV) Per Share.

     At the end of the Statement of Net Assets, you will find a table displaying
the  composition of the fund's net assets on both a dollar and per-share  basis.
Because all income and any realized gains must be  distributed  to  shareholders
each year, the bulk of net assets consists of Paid in Capital (money invested by
shareholders).  The amounts shown for  Undistributed  Net Investment  Income and
Accumulated  Net  Realized  Gains  usually  approximate  the  sums  the fund had
available to distribute to shareholders as income  dividends or capital gains as
of  the  statement  date,  but  may  differ  because   certain   investments  or
transactions  may  be  treated  differently  for  financial  statement  and  tax
purposes.  Any Accumulated  Net Realized  Losses,  and any cumulative  excess of
distributions  over net income or net  realized  gains,  will appear as negative
balances.  Unrealized Appreciation  (Depreciation) is the difference between the
market value of the fund's  investments  and their cost,  and reflects the gains
(losses) that would be realized if the fund were to sell all of its  investments
at their statement-date values.

--------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
WINDSOR FUND                                        SHARES                 (000)
--------------------------------------------------------------------------------
COMMON STOCKS (97.5%)(1)
--------------------------------------------------------------------------------
AUTO & TRANSPORTATION (7.1%)

(2)   Eaton Corp.                                4,026,800               274,074
      Canadian National
        Railway Co.                              5,692,100               179,301
*(2)  Continental Airlines, Inc.
        Class B                                  2,560,800               134,442
      Compagnie Generale des
        Etablissements Michelin
        Class B                                  4,000,586               115,636
      Delta Air Lines, Inc.                      1,498,722                70,815
      Burlington Northern
        Santa Fe Corp.                           1,949,000                51,770
      Union Pacific Corp.                        1,072,300                50,264
      Delphi Automotive
        Systems Corp.                            2,937,059                46,075
      CSX Corp.                                  1,619,900                41,004
*(2)  America West Holdings
        Corp. Class B                            3,484,500                34,627
      Dana Corp.                                 1,550,200                34,395
      Genuine Parts Co.                          1,486,500                31,681
      Norfolk Southern Corp.                     1,923,600                27,171
      Ford Motor Co.                             1,011,843                26,434
      Southwest Airlines Co.                       307,000                 8,750
                                                                       ---------
                                                                       1,126,439
                                                                       ---------

--------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
--------------------------------------------------------------------------------
CONSUMER DISCRETIONARY (9.2%)
(2)   TJX Cos., Inc.                            19,511,200               531,680
*     Staples, Inc.                             14,076,300               200,587
*(2)  Republic Services, Inc.                   10,574,800               142,099
      May Department Stores Co.                  4,676,100               122,748
(2)   Ross Stores, Inc.                          8,625,000               113,742
      Target Corp.                               2,901,000                80,140
*     Jones Apparel Group, Inc.                  2,341,400                65,120
      Newell Rubbermaid, Inc.                    2,054,600                39,423
*     Federated Department
        Stores, Inc.                             1,100,300                35,829
      Gannett Co., Inc.                            500,000                29,000
      VF Corp.                                     994,300                27,157
      Whirlpool Corp.                              619,800                26,961
      Sears, Roebuck & Co.                         841,800                25,027
      Leggett & Platt, Inc.                      1,200,700                19,661
      Dillard's Inc.                               616,900                 6,477
                                                                       ---------
                                                                       1,465,651
                                                                       ---------
CONSUMER STAPLES (1.1%)
      Philip Morris Cos., Inc.                   2,502,900                91,669
      ConAgra Foods, Inc.                        2,395,800                51,210
      Tyson Foods, Inc.                          1,812,600                20,278
      SuperValu Inc.                               942,100                14,485
                                                                       ---------
                                                                         177,642
                                                                       ---------

                                       13
<PAGE>
--------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
WINDSOR FUND                                        SHARES                 (000)
--------------------------------------------------------------------------------
FINANCIAL SERVICES (24.4%)
      Associates First Capital Corp.
        Class A                                 22,995,700               853,715
      Citigroup, Inc.                            8,744,400               460,174
      Washington Mutual, Inc.                    8,743,864               384,730
      CIGNA Corp.                                2,782,500               339,326
      Golden West Financial Corp.                4,745,300               266,033
(2)   Dime Bancorp, Inc.                         7,771,300               189,911
      U.S. Bancorp                               4,971,400               120,246
(2)   Liberty Property Trust REIT                4,324,100               114,318
      Bank of America Corp.                      2,313,500               111,193
      PartnerRe Ltd.                             1,860,500               101,397
      Bank One Corp.                             2,220,900                81,063
      The Chubb Corp.                              907,500                76,627
      FleetBoston Financial Corp.                2,009,530                76,362
      UnionBanCal Corp.                          3,292,900                69,151
      First Union Corp.                          1,944,300                58,937
      MBIA, Inc.                                   803,800                58,426
      American International
        Group, Inc.                                574,350                56,286
      KeyCorp                                    2,167,600                53,513
      Charter One Financial                      2,266,740                51,993
      American General Corp.                       637,000                51,279
      National City Corp.                        2,185,700                46,719
      AMBAC Financial Group Inc.                   579,900                46,283
      TCF Financial Corp.                        1,104,100                44,647
(2)   IPC Holdings Ltd.                          2,006,000                40,904
      Torchmark Corp.                            1,061,800                35,371
      Summit Bancorp                               873,700                32,764
      Fannie Mae                                   344,600                26,534
      Morgan Stanley Dean
        Witter & Co.                               276,000                22,166
      Regions Financial Corp.                      509,450                12,004
      Old Republic International Corp.             383,800                 9,979
      Horace Mann Educators Corp.                  257,300                 4,326
                                                                       ---------
                                                                       3,896,377
                                                                       ---------
HEALTH CARE (6.3%)
      Pharmacia Corp.                            8,132,904               447,310
      Aetna Inc.                                 3,752,000               216,913
      Aventis SA ADR                             1,919,550               138,328
*     Foundation Health
        Systems Class A                          6,028,660               121,704
      Johnson & Johnson                            402,100                37,043
      Merck & Co., Inc.                            200,000                17,988
*     Pacificare Health
        Systems, Inc.                            1,336,200                13,947
      Bergen Brunswig Corp.
        Class A                                  1,017,100                 9,218
  Aventis SA Class A                                99,671                 7,181
                                                                       ---------
                                                                       1,009,632
                                                                       ---------
--------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
--------------------------------------------------------------------------------
INTEGRATED OILS (5.5%)
      USX-Marathon Group                         6,397,700               173,937
*     Petroleo Brasileiro ADR                    5,268,100               153,104
      Exxon Mobil Corp.                          1,647,104               146,901
      Phillips Petroleum Co.                     1,105,400                68,258
      Shell Transport &
        Trading Co. ADR                          1,302,300                64,057
      Texaco Inc.                                1,060,700                62,648
      Petro Canada                               2,535,800                53,252
      Occidental Petroleum Corp.                 2,623,200                52,136
      Conoco Inc. Class B                        1,831,300                49,788
      Amerada Hess Corp.                           666,700                41,335
      Repsol-YPF, SA ADR                         1,000,000                15,938
                                                                       ---------
                                                                         881,354
                                                                       ---------
OTHER ENERGY (3.6%)
      Anadarko Petroleum Corp.                   2,178,001               139,501
*     Anderson Exploration Ltd.                  6,774,134               124,196
(2)   Ultramar Diamond
        Shamrock Corp.                           4,547,400               119,369
      Devon Energy Corp.                         1,658,426                83,585
      Valero Energy Corp.                        2,401,300                79,393
      Ashland, Inc.                                607,000                19,879
                                                                       ---------
                                                                         565,923
                                                                       ---------
MATERIALS & PROCESSING (19.1%)
      Alcoa Inc.                                24,555,468               704,435
      Air Products & Chemicals, Inc.             8,831,200               329,514
(2)   Engelhard Corp.                           11,454,200               239,106
      E.I. du Pont de Nemours & Co.              3,200,000               145,200
      Rohm & Haas Co.                            4,805,400               144,462
      Willamette Industries, Inc.                3,898,100               141,550
      Abitibi-Consolidated, Inc.                15,176,789               132,797
      Jefferson Smurfit Group
        PLC ADR                                  6,918,641               125,400
*     Smurfit-Stone Container Corp.              9,126,750               123,211
*(2)  Packaging Corp. of America                 5,406,500                79,408
      Praxair, Inc.                              2,008,200                74,805
      Lyondell Chemical Co.                      4,603,203                66,171
      International Paper Co.                    1,597,281                58,500
      Dow Chemical Co.                           1,854,900                56,806
      Fort James Corp.                           1,650,800                54,373
      Pechiney SA ADR A                          2,861,128                51,500
      Lafarge Corp.                              2,587,700                48,843
      Georgia Pacific Group                      1,502,900                40,390
      Alcan Aluminium Ltd.                       1,265,600                39,946
      Sonoco Products Co.                        1,942,300                37,511
      The Mead Corp.                             1,185,000                34,291
      Sherwin-Williams Co.                       1,543,300                33,470
      AK Steel Corp.                             3,318,652                30,698

                                       14

<PAGE>

--------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
--------------------------------------------------------------------------------
*(2)  Kaiser Aluminum &
        Chemical Corp.                           6,048,434                30,620
      Nucor Corp.                                  863,400                29,949
      Temple-Inland Inc.                           607,800                27,199
*     American Standard Cos., Inc.                 591,400                27,131
(2)   Century Aluminum Co.                       2,000,000                17,500
      Cabot Corp.                                  771,300                16,969
      Great Lakes Chemical Corp.                   485,000                16,187
      Phosphate Resources
        Partners LP                              4,018,800                16,075
      Boise Cascade Corp.                          473,900                13,595
      Crown Cork & Seal Co., Inc.                1,398,300                12,759
*     Albany International Corp.                 1,017,555                10,939
*     Cabot Microelectronics Corp.                 216,329                 9,559
*     Owens-Illinois, Inc.                       1,303,800                 7,741
      Ryerson Tull, Inc.                           969,446                 7,271
*     Burlington Industries, Inc.                2,383,700                 2,980
      Archer-Daniels-Midland Co.                   189,935                 2,089
      Owens Corning                                615,500                   846
                                                                       ---------
                                                                       3,041,796
                                                                       ---------
PRODUCER DURABLES (3.0%)
      Alcatel SA ADR                             1,681,551               104,887
*(2)  Toll Brothers, Inc.                        3,029,166                98,448
 (2)  Kaufman & Broad Home Corp.                 2,098,600                62,433
      CNH Global NV                              4,362,600                42,263
      Cooper Industries, Inc.                    1,103,600                42,213
      The BFGoodrich Co.                           971,200                39,759
 (2)  MDC Holdings, Inc.                         1,156,300                31,654
*(2)  Beazer Homes USA, Inc.                       860,464                23,985
      Centex Corp.                                 464,900                17,201
      Thomas & Betts Corp.                         648,600                 9,810
                                                                       ---------
                                                                         472,653
                                                                       ---------
TECHNOLOGY (5.9%)
*(2)  Arrow Electronics, Inc.                    7,899,300               252,778
      International Business
        Machines Corp.                           1,867,100               183,909
*     Dell Computer Corp.                        6,000,000               177,000
      Hewlett-Packard Co.                        3,300,000               153,244
      Avnet, Inc.                                2,027,000                54,476
*(2)  General Semiconductor, Inc.                3,468,600                39,672
*     Quantum Corp.-DLT &
      Storage Systems                            2,168,300                32,525
*     Adaptec, Inc.                              1,658,700                26,228
*     Litton Industries, Inc.                      279,900                14,537
*     Ingram Micro, Inc.                           732,500                12,498
                                                                       ---------
                                                                         946,867
                                                                       ---------
UTILITIES (10.7%)
*     WorldCom, Inc.                            20,720,339               492,108
* Cox Communications, Inc.
        Class A                                  5,709,300               251,566


--------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
--------------------------------------------------------------------------------

      AT&T Corp.                                 8,253,116               191,369
*     Adelphia Communications
        Corp. Class A                            5,252,400               174,314
*     Comcast Corp. Special
        Class A                                  2,592,500               105,644
      Xcel Energy, Inc.                          2,116,215                54,096
      PG&E Corp.                                 1,919,100                51,696
      Ameren Corp.                               1,272,300                50,574
      American Electric
        Power Co., Inc.                          1,213,400                50,356
      Consolidated Edison Inc.                   1,376,000                48,418
      SBC Communications Inc.                      837,720                48,326
      FirstEnergy Corp.                          1,704,100                44,094
      Cinergy Corp.                              1,334,900                40,881
      GPU, Inc.                                    993,600                32,851
      Verizon Communications                       533,442                30,840
*     Comcast Corp. Class A                        705,500                28,308
      BellSouth Corp.                              174,300                 8,421
                                                                       ---------
                                                                       1,703,862
                                                                       ---------

MISCELLANEOUS (1.6%)                                                     248,828
                                                                       ---------

--------------------------------------------------------------------------------
TOTAL COMMON STOCKS
        (Cost $14,084,858)                                            15,537,024
--------------------------------------------------------------------------------
CONVERTIBLE PREFERRED STOCK (0.2%)
--------------------------------------------------------------------------------
      Kaufman & Broad Home Corp.
        8.25% Cvt. Pfd.
        (COST $23,120)                           3,163,700                28,473
--------------------------------------------------------------------------------

                                               Face Amount
                                                     (000)
--------------------------------------------------------------------------------
TEMPORARY CASH INVESTMENTS (2.9%)(1)
--------------------------------------------------------------------------------
FEDERAL HOME LOAN MORTGAGE CORP.
(3)   6.54%, 1/25/2001                              15,000                14,769
FEDERAL NATIONAL MORTGAGE ASSN.
(3) 6.49%, 11/2/2000                                 3,000                 2,999
REPURCHASE AGREEMENTS
Collateralized by U.S. Government
        Obligations in a Pooled
        Cash Account
        6.56%, 11/1/2000                           397,452               397,452
        6.58%, 11/1/2000--Note G                    45,758                45,758
--------------------------------------------------------------------------------
TOTAL TEMPORARY CASH INVESTMENTS
        (Cost $460,982)                                                  460,978
--------------------------------------------------------------------------------
TOTAL INVESTMENTS (100.6%)
        (Cost $14,568,960)                                            16,026,475
--------------------------------------------------------------------------------


                                       15
<PAGE>

--------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
WINDSOR FUND                                                               (000)
--------------------------------------------------------------------------------
OTHER ASSETS AND LIABILITIES (-0.6%)
--------------------------------------------------------------------------------
Other Assets--Note C                                                     84,624
Liabilities--Note G                                                    (176,314)

                                                                       ---------
                                                                        (91,690)
                                                                       ---------
--------------------------------------------------------------------------------
NET ASSETS (100%)
--------------------------------------------------------------------------------
      Applicable to 969,289,774 outstanding $.001
      par value shares of beneficial interest
      (unlimited authorization) $15,934,785
================================================================================
NET ASSET VALUE PER SHARE                                                 $16.44
================================================================================
*    See Note A in Notes to Financial Statements.
*    Non-income-producing security.
(1)  The fund  invests a portion of its reserves in equity  markets  through the
     use of index futures contracts. After giving effect to futures investments,
     the fund's effective  common stock and temporary cash investment  positions
     represent 99.2% and 1.2%, respectively,  of net assets. See Note F in Notes
     to Financial Statements.
(2)  Considered  an  affiliated  company  as the fund  owns  more than 5% of the
     outstanding  voting  securities of such company.  The total market value of
     investments in affiliated companies was $2,570,770,000.
(3)  Securities with an aggregate  value of $17,768,000  have been segregated as
     initial margin for open futures contracts.
ADR  --American Depositary Receipt.
REIT --Real Estate Investment Trust.

--------------------------------------------------------------------------------
                                                    AMOUNT                   PER
                                                     (000)                 SHARE
--------------------------------------------------------------------------------
AT OCTOBER 31, 2000, NET ASSETS CONSISTED OF:
--------------------------------------------------------------------------------
Paid in Capital--Note E                        $12,624,337                $13.03
Undistributed Net
      Investment Income                             80,408                   .08
Accumulated Net
      Realized Gains--Note E                     1,781,994                  1.84
Unrealized Appreciation
      (Depreciation)--Note F
      Investment Securities                      1,457,515                  1.50
      Futures Contracts                            (9,469)                 (.01)
--------------------------------------------------------------------------------
NET ASSETS                                     $15,934,785                $16.44
================================================================================

                                       16
<PAGE>

STATEMENT OF OPERATIONS
This Statement  shows dividend and interest income earned by the fund during the
reporting period,  and details the operating expenses charged to the fund. These
expenses  directly  reduce the amount of investment  income  available to pay to
shareholders  as  dividends.  This  Statement  also  shows  any Net Gain  (Loss)
realized  on the  sale of  investments,  and the  increase  or  decrease  in the
Unrealized Appreciation  (Depreciation) on investments during the period. If the
fund  invested  in futures  contracts  during the  period,  the results of these
investments are shown separately.

--------------------------------------------------------------------------------
                                                                    WINDSOR FUND
                                                     YEAR ENDED OCTOBER 31, 2000
                                                                           (000)
--------------------------------------------------------------------------------
INVESTMENT INCOME
INCOME
      Dividends*                                                      $ 290,584
      Interest                                                           27,075
      Security Lending                                                    1,712
--------------------------------------------------------------------------------
Total Income                                                            319,371
--------------------------------------------------------------------------------
EXPENSES
Investment Advisory Fees--Note B
      Basic Fee                                                          20,781
      Performance Adjustment                                            (12,827)
The Vanguard Group--Note C
      Management and Administrative                                      37,757
      Marketing and Distribution                                          1,633
Custodian Fees                                                              275
Auditing Fees                                                                19
Shareholders' Reports                                                       346
Trustees' Fees and Expenses                                                  20
--------------------------------------------------------------------------------
      Total Expenses                                                     48,004
      Expenses Paid Indirectly--Note D                                   (2,777)
--------------------------------------------------------------------------------
      Net Expenses                                                       45,227
--------------------------------------------------------------------------------
NET INVESTMENT INCOME                                                   274,144
--------------------------------------------------------------------------------
REALIZED NET GAIN
      Investment Securities Sold* 1,994,887
      Futures Contracts 18,907
--------------------------------------------------------------------------------
REALIZED NET GAIN                                                     2,013,794
--------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)
      Investment Securities                                            (605,604)
      Futures Contracts                                                 (15,737)
--------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)                       (621,341)
--------------------------------------------------------------------------------
NET INCREASE IN NET ASSETS RESULTING FROM OPERATIONS                 $1,666,597
================================================================================
*Dividend   income  and  realized  net  gain  from  affiliated   companies  were
$34,184,000 and $7,097,000, respectively.

                                       17
<PAGE>


STATEMENT OF CHANGES IN NET ASSETS

This Statement shows how the fund's total net assets changed during the two most
recent reporting periods. The Operations section summarizes information detailed
in  the  Statement  of  Operations.   The  amounts  shown  as  Distributions  to
shareholders  from the fund's net  income  and  capital  gains may not match the
amounts shown in the Operations section, because distributions are determined on
a tax  basis  and may be made in a period  different  from the one in which  the
income was earned or the gains were  realized on the financial  statements.  The
Capital Share Transactions section shows the amount shareholders invested in the
fund,  either by purchasing shares or by reinvesting  distributions,  as well as
the amounts redeemed.  The  corresponding  numbers of Shares Issued and Redeemed
are shown at the end of the Statement.

--------------------------------------------------------------------------------
                                                              WINDSOR FUND
                                                        YEAR ENDED OCTOBER 31,
                                                     ---------------------------
                                                             2000          1999
                                                            (000)         (000)
--------------------------------------------------------------------------------
INCREASE (DECREASE) IN NET ASSETS
OPERATIONS
  Net Investment Income                                $  274,144    $  277,607
  Realized Net Gain                                     2,013,794     1,940,531
  Change in Unrealized Appreciation (Depreciation)       (621,341)       42,819
--------------------------------------------------------------------------------
   Net Increase in Net Assets Resulting from Operations 1,666,597     2,260,957
--------------------------------------------------------------------------------
DISTRIBUTIONS
  Net Investment Income                                  (287,257)     (255,285)
  Realized Capital Gain                                (1,869,353)   (1,341,486)
--------------------------------------------------------------------------------
   Total Distributions                                 (2,156,610)   (1,596,771)
--------------------------------------------------------------------------------
CAPITAL SHARE TRANSACTIONS1
  Issued                                                  932,126     1,402,297
  Issued in Lieu of Cash Distributions                  2,025,871     1,504,748
  Redeemed                                             (3,356,921)   (5,102,907)
--------------------------------------------------------------------------------
   Net Decrease from Capital Share Transactions          (398,924)   (2,195,862)
--------------------------------------------------------------------------------
Total Decrease                                           (888,937)   (1,531,676)
--------------------------------------------------------------------------------
NET ASSETS
  Beginning of Year                                    16,823,722    18,355,398
--------------------------------------------------------------------------------
  End of Year                                         $15,934,785   $16,823,722
================================================================================
1Shares Issued (Redeemed)
  Issued                                                   61,020        82,191
  Issued in Lieu of Cash Distributions                    135,718       100,940
  Redeemed                                               (222,437)     (311,166)
--------------------------------------------------------------------------------
   Net Decrease in Shares Outstanding                     (25,699)     (128,035)
================================================================================

                                       18

<PAGE>

FINANCIAL HIGHLIGHTS

This table  summarizes  the  fund's  investment  results  and  distributions  to
shareholders on a per-share  basis. It also presents the fund's Total Return and
shows net  investment  income and expenses as percentages of average net assets.
These data will help you assess:  the  variability  of the fund's net income and
total returns from year to year;  the relative  contributions  of net income and
capital gains to the fund's total return; how much it costs to operate the fund;
and the extent to which the fund tends to distribute  capital  gains.  The table
also  shows the  Portfolio  Turnover  Rate,  a measure of  trading  activity.  A
turnover  rate of 100% means that the  average  security is held in the fund for
one year.

<TABLE>
<CAPTION>

------------------------------------------------------------------------------------------------------------
                                                                                     WINDSOR FUND
                                                                                YEAR ENDED OCTOBER 31,
                                                            ------------------------------------------------
<S>                                                              <C>      <C>       <C>      <C>       <C>
FOR A SHARE OUTSTANDING THROUGHOUT EACH YEAR                     2000     1999      1998     1997      1996
------------------------------------------------------------------------------------------------------------
NET ASSET VALUE, BEGINNING OF YEAR                             $16.91   $16.34    $19.55   $16.99    $15.55
------------------------------------------------------------------------------------------------------------
INVESTMENT OPERATIONS
  Net Investment Income                                           .28      .27       .23      .36       .43
  Net Realized and Unrealized Gain (Loss)on Investments          1.44     1.77      (.32)    3.94      2.85
------------------------------------------------------------------------------------------------------------
   Total from Investment Operations                              1.72     2.04      (.09)    4.30      3.28
------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS
  Dividends from Net Investment Income                           (.29)    (.24)     (.24)    (.41)     (.46)
  Distributions from Realized Capital Gains                     (1.90)   (1.23)    (2.88)   (1.33)    (1.38)
------------------------------------------------------------------------------------------------------------
   Total Distributions                                          (2.19)   (1.47)    (3.12)   (1.74)    (1.84)
------------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF YEAR                                   $16.44   $16.91    $16.34   $19.55    $16.99
============================================================================================================
Total Return                                                   11.60%   13.74%    -0.78%   27.04%    23.16%
============================================================================================================

Ratios/Supplemental Data
  Net Assets, End of Year (Millions)                          $15,935  $16,824   $18,355  $20,678   $15,841
  Ratio of Total Expenses to Average Net Assets                 0.31%    0.28%     0.27%    0.27%     0.31%
  Ratio of Net Investment Income to Average Net Assets          1.75%    1.56%     1.31%    1.89%     2.75%
  Portfolio Turnover Rate                                         41%      56%       48%      61%       34%
============================================================================================================
</TABLE>

                                       19
<PAGE>

NOTES TO FINANCIAL STATEMENTS

Vanguard Windsor Fund is registered under the Investment  Company Act of 1940 as
a diversified open-end investment company, or mutual fund.

A. The following  significant  accounting policies conform to generally accepted
accounting  principles for U.S. mutual funds. The fund consistently follows such
policies in preparing its financial statements.

     1. SECURITY  VALUATION:  Equity  securities are valued at the latest quoted
sales  prices  as of the  close  of  trading  on the  New  York  Stock  Exchange
(generally  4:00 p.m.  Eastern time) on the valuation  date; such securities not
traded on the valuation date are valued at the mean of the latest quoted bid and
asked  prices.  Prices are taken from the primary  market in which each security
trades.  Temporary cash investments acquired over 60 days to maturity are valued
using the latest bid prices or using  valuations based on a matrix system (which
considers such factors as security  prices,  yields,  maturities,  and ratings),
both  as  furnished  by  independent  pricing  services.  Other  temporary  cash
investments  are valued at amortized  cost,  which  approximates  market  value.
Securities for which market  quotations are not readily  available are valued by
methods deemed by the board of trustees to represent fair value.

     2.  FEDERAL  INCOME  TAXES:  The fund  intends to  continue to qualify as a
regulated   investment  company  and  distribute  all  of  its  taxable  income.
Accordingly,  no provision for federal income taxes is required in the financial
statements.

     3.  REPURCHASE  AGREEMENTS:  The fund,  along  with  other  members  of The
Vanguard  Group,  transfers  uninvested  cash balances to a pooled cash account,
which  is  invested  in  repurchase   agreements  secured  by  U.S.   government
securities.  Securities pledged as collateral for repurchase agreements are held
by a custodian bank until the agreements  mature.  Each agreement  requires that
the market value of the  collateral be sufficient to cover  payments of interest
and principal; however, in the event of default or bankruptcy by the other party
to  the  agreement,  retention  of  the  collateral  may  be  subject  to  legal
proceedings.

     4. FUTURES CONTRACTS:  The fund uses S&P 500 Index and S&P MidCap 400 Index
futures  contracts to a limited extent,  with the objective of maintaining  full
exposure to the stock market while maintaining liquidity.  The fund may purchase
or sell futures  contracts to achieve a desired level of investment,  whether to
accommodate  portfolio  turnover or cash flows from capital share  transactions.
The primary  risks  associated  with the use of futures  contracts are imperfect
correlation  between changes in market values of stocks held by the fund and the
prices of futures contracts, and the possibility of an illiquid market.

     Futures contracts are valued at their quoted daily settlement  prices.  The
aggregate  principal  amounts of the contracts are not recorded in the financial
statements.  Fluctuations  in the value of the  contracts  are  recorded  in the
Statement  of Net  Assets  as an  asset  (liability)  and in  the  Statement  of
Operations as  unrealized  appreciation  (depreciation)  until the contracts are
closed, when they are recorded as realized futures gains (losses).

     5.  DISTRIBUTIONS:  Distributions  to  shareholders  are  recorded  on  the
ex-dividend  date.  Distributions  are  determined on a tax basis and may differ
from net investment  income and realized  capital gains for financial  reporting
purposes.

     6. OTHER:  Dividend  income is recorded on the ex-dividend  date.  Security
transactions  are accounted for on the date securities are bought or sold. Costs
used to determine  realized gains (losses) on the sale of investment  securities
are those of the specific securities sold.

B.  Wellington  Management  Company,  llp, and Sanford C.  Bernstein & Co., LLC,
provide  investment  advisory  services  to the fund for fees  calculated  at an
annual  percentage  rate of  average  net  assets.  The basic fee of  Wellington
Management  Company,   llp,  is  subject  to  quarterly   adjustments  based  on
performance  relative to the S&P 500 Index for the  preceding  three years.

                                       20
<PAGE>

The basic fee of Sanford  C.  Bernstein  & Co.,  LLC,  is  subject to  quarterly
adjustments  based on performance  relative to the Russell 1000 Value Index. For
the  year  ended  October  31,  2000,  the  aggregate  investment  advisory  fee
represented  an effective  annual basic rate of 0.13% of the fund's  average net
assets before a decrease of $12,827,000 (0.08%) based on performance.
     The  Vanguard  Group  manages  the cash  reserves of the fund on an at-cost
basis.

C. The Vanguard Group  furnishes at cost corporate  management,  administrative,
marketing,  and distribution  services. The costs of such services are allocated
to the fund  under  methods  approved  by the  board of  trustees.  The fund has
committed to provide up to 0.40% of its net assets in capital  contributions  to
Vanguard. At October 31, 2000, the fund had contributed capital of $2,914,000 to
Vanguard  (included in Other Assets),  representing 0.02% of net assets and 2.9%
of  Vanguard's  capitalization.  The  fund's  trustees  and  officers  are  also
directors and officers of Vanguard.

D. The fund has asked its investment advisers to direct certain security trades,
subject to obtaining the best price and execution, to brokers who have agreed to
rebate to the fund part of the  commissions  generated.  Such  rebates  are used
solely to reduce the fund's management and administrative  expenses.  The fund's
custodian  bank has also agreed to reduce its fees when the fund  maintains cash
on  deposit  in the  non-interest-bearing  custody  account.  For the year ended
October 31, 2000,  directed  brokerage  and  custodian  fee offset  arrangements
reduced  expenses by $2,670,000  and $107,000,  respectively.  The total expense
reduction  represented  an effective  annual rate of 0.02% of the fund's average
net assets.

E. During the year ended October 31, 2000, the fund purchased  $6,269,347,000 of
investment  securities and sold $8,552,278,000 of investment  securities,  other
than temporary cash investments.

     The fund used a tax accounting  practice to treat a portion of the price of
capital shares redeemed during the year as  distributions  from realized capital
gains. Accordingly,  the fund has reclassified $221,667,000 from accumulated net
realized gains to paid in capital.

F. At October 31, 2000, net unrealized appreciation of investment securities for
financial   reporting  and  federal  income  tax  purposes  was  $1,457,515,000,
consisting of unrealized gains of $3,270,144,000 on securities that had risen in
value since their purchase and $1,812,629,000 in unrealized losses on securities
that had fallen in value since their purchase.
     At  October  31,  2000,  the  aggregate  settlement  value of open  futures
contracts  expiring in December  2000 and the  related  unrealized  depreciation
were:

--------------------------------------------------------------------------------
                                                                (000)
                                                    ----------------------------
                                                    AGGREGATE
                            NUMBER OF              SETTLEMENT         UNREALIZED
FUTURES CONTRACTS      LONG CONTRACTS                   VALUE       DEPRECIATION
--------------------------------------------------------------------------------
S&P 500 Index                     695                $250,235           $(8,475)
S&P MidCap 400 Index              104                  27,105              (994)
--------------------------------------------------------------------------------

Unrealized  depreciation on open futures  contracts is required to be treated as
realized loss for tax purposes.

G. The market value of securities on loan to broker/dealers at October 31, 2000,
was  $44,340,000,  for which the fund held cash collateral of  $45,758,000.  The
fund invests cash collateral  received in repurchase  agreements,  and records a
liability for the return of the collateral, during the period the securities are
on loan.

                                       21
<PAGE>

REPORT
 of Independent Accountants

To the Shareholders and Trustees of Vanguard Windsor Fund

In our  opinion,  the  accompanying  statement  of net  assets  and the  related
statements  of  operations  and of  changes  in net  assets  and  the  financial
highlights present fairly, in all material  respects,  the financial position of
Vanguard  Windsor  Fund (the  "Fund") at October  31,  2000,  the results of its
operations  for the year then  ended,  the changes in its net assets for each of
the two years in the period then ended and the financial  highlights for each of
the  five  years  in the  period  then  ended,  in  conformity  with  accounting
principles  generally accepted in the United States of America.  These financial
statements  and  financial  highlights  (hereafter  referred  to  as  "financial
statements") are the responsibility of the Fund's management; our responsibility
is to express an opinion on these financial  statements based on our audits.  We
conducted our audits of these  financial  statements in accordance with auditing
standards generally accepted in the United States of America, which require that
we plan and perform the audit to obtain  reasonable  assurance about whether the
financial  statements  are free of  material  misstatement.  An  audit  includes
examining,  on a test basis,  evidence supporting the amounts and disclosures in
the  financial   statements,   assessing  the  accounting  principles  used  and
significant  estimates made by management,  and evaluating the overall financial
statement presentation.  We believe that our audits, which included confirmation
of  securities  at October 31, 2000 by  correspondence  with the  custodian  and
brokers, provide a reasonable basis for our opinion.

PricewaterhouseCoopers LLP
Philadelphia, Pennsylvania

November 29, 2000

--------------------------------------------------------------------------------
SPECIAL 2000 TAX INFORMATION (UNAUDITED) FOR VANGUARD WINDSOR FUND

This  information  for the fiscal  year ended  October  31,  2000,  is  included
pursuant to provisions of the Internal Revenue Code.

     The fund  distributed  $1,687,633,000  as capital gain dividends  (from net
long-term capital gains) to shareholders during the fiscal year, all of which is
designated as a 20% rate gain distribution.

     For corporate  shareholders,  86.4% of investment  income  (dividend income
plus short-term gains, if any) qualifies for the dividends-received deduction.

                                       22
<PAGE>

THE VANGUARD(R)
  Family of Funds

STOCK FUNDS

500 Index Fund
Calvert Social Index(TM) Fund
Capital Opportunity Fund
Convertible Securities Fund
Developed Markets Index Fund
Emerging Markets Stock
 Index Fund
Energy Fund
Equity Income Fund
European Stock Index Fund
Explorer(TM) Fund
Extended Market Index Fund
Global Equity Fund
Gold and Precious Metals Fund
Growth and Income Fund
Growth Equity Fund
Growth Index Fund
Health Care Fund
Institutional Developed Markets
 Index Fund
Institutional Index Fund
International Growth Fund
International Value Fund
Mid-Cap Index Fund
Morgan(TM) Growth Fund
Pacific Stock Index Fund
PRIMECAP Fund
REIT Index Fund
Selected Value Fund
Small-Cap Growth Index Fund
Small-Cap Index Fund
Small-Cap Value Index Fund
Strategic Equity Fund
Tax-Managed Capital
 Appreciation Fund
Tax-Managed Growth and
 Income Fund
Tax-Managed International Fund
Tax-Managed Small-Cap Fund
Total International Stock
 Index Fund
Total Stock Market Index Fund
U.S. Growth Fund
U.S. Value Fund
Utilities Income Fund
Value Index Fund
Windsor(TM) Fund
Windsor(TM) II Fund


BALANCED FUNDS

Asset Allocation Fund
Balanced Index Fund
Global Asset Allocation Fund
LifeStrategy(R) Conservative
 Growth Fund
LifeStrategy(R) Growth Fund
LifeStrategy(R) Income Fund
LifeStrategy(R) Moderate
 Growth Fund
STAR(TM) Fund
Tax-Managed Balanced Fund
Wellesley(R) Income Fund
Wellington(TM) Fund


BOND FUNDS

Admiral(TM) Intermediate-Term
 Treasury Fund
Admiral(TM) Long-Term
 Treasury Fund
Admiral(TM) Short-Term
 Treasury Fund
GNMA Fund
High-Yield Corporate Fund
High-Yield Tax-Exempt Fund
Inflation-Protected Securities Fund
Insured Long-Term
 Tax-Exempt Fund
Intermediate-Term Bond
 Index Fund
Intermediate-Term Corporate Fund
Intermediate-Term
 Tax-Exempt Fund
Intermediate-Term Treasury Fund
Limited-Term Tax-Exempt Fund
Long-Term Bond Index Fund
Long-Term Corporate Fund
Long-Term Tax-Exempt Fund
Long-Term Treasury Fund
Preferred Stock Fund
Short-Term Bond Index Fund
Short-Term Corporate Fund
Short-Term Federal Fund
Short-Term Tax-Exempt Fund
Short-Term Treasury Fund
State Tax-Exempt Bond Funds
 (California, Florida,
 Massachusetts, New Jersey,
 New York, Ohio, Pennsylvania)
Total Bond Market Index Fund


MONEY MARKET FUNDS

Admiral(TM) Treasury Money
 Market Fund
Federal Money Market Fund
Prime Money Market Fund
State Tax-Exempt Money Market Funds
 (California, New Jersey,
 New York, Ohio, Pennsylvania)
Tax-Exempt Money Market Fund
Treasury Money Market Fund


VARIABLE ANNUITY PLAN

Balanced Portfolio
Diversified Value Portfolio
Equity Income Portfolio
Equity Index Portfolio
Growth Portfolio
High-Grade Bond Portfolio
High Yield Bond Portfolio
International Portfolio
Mid-Cap Index Portfolio
Money Market Portfolio
REIT Index Portfolio
Short-Term Corporate Portfolio
Small Company Growth Portfolio




For information  about Vanguard funds and our variable  annuity plan,  including
charges and  expenses,  obtain a prospectus  from The Vanguard  Group,  P.O. Box
2600,  Valley Forge, PA 19482-2600.  Read it carefully before you invest or send
money.

                                       23

<PAGE>

THE PEOPLE
Who Govern Your Fund

The  trustees of your mutual fund are there to see that the fund is operated and
managed in your best interests  since,  as a shareholder,  you are part owner of
the fund.  Your  fund  trustees  also  serve on the  board of  directors  of The
Vanguard  Group,  which is owned by the  funds  and  exists  solely  to  provide
services to them on an at-cost basis.

     Six of Vanguard's  seven board members are  independent,  meaning that they
have no  affiliation  with  Vanguard or the funds they  oversee,  apart from the
sizable personal investments they have made as private  individuals.  They bring
distinguished  backgrounds  in business,  academia,  and public service to their
task of working with Vanguard officers to establish the policies and oversee the
activities of the funds.

     Among board members' responsibilities are selecting investment advisers for
the  funds;  monitoring  fund  operations,  performance,  and  costs;  reviewing
contracts;  nominating  and  selecting  new  trustees/  directors;  and electing
Vanguard officers.

     The list below provides a brief description of each trustee's  professional
affiliations.  The year in which the trustee  joined the Vanguard board is noted
in parentheses.

TRUSTEES

JOHN J. BRENNAN  (1987)  Chairman of the Board,  Chief  Executive  Officer,  and
Director/Trustee  of The Vanguard  Group,  Inc.,  and of each of the  investment
companies in The Vanguard Group.

JOANN HEFFERNAN HEISEN (1998) Vice President,  Chief Information  Officer, and a
member of the  Executive  Committee of Johnson & Johnson;  Director of Johnson &
Johnson*Merck Consumer Pharmaceuticals Co., The Medical Center at Princeton, and
Women's Research and Education Institute.

BRUCE K.  MACLAURY  (1990)  President  Emeritus  of The  Brookings  Institution;
Director of  American  Express  Bank Ltd.,  The St. Paul  Companies,  Inc.,  and
National Steel Corp.

BURTON G. MALKIEL  (1977)  Chemical  Bank  Chairman's  Professor  of  Economics,
Princeton  University;  Director of Prudential  Insurance Co. of America,  Banco
Bilbao  Argentaria,  Gestion,  BKF Capital,  The Jeffrey Co., NeuVis,  Inc., and
Select Sector SPDR Trust.

ALFRED M. RANKIN, Jr. (1993) Chairman,  President,  Chief Executive Officer, and
Director of NACCO Industries, Inc.; Director of The BFGoodrich Co.

JAMES O. WELCH,  JR.  (1971)  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 (1985) Retired Chairman and Chief Executive Officer of Rohm &
Haas Co.; Director of AmeriSource  Health  Corporation,  Cummins Engine Co., and
The Mead Corp.; Trustee of Vanderbilt University.

--------------------------------------------------------------------------------
OTHER FUND OFFICERS

RAYMOND J. KLAPINSKY, Secretary; Managing Director and Secretary of The Vanguard
Group,  Inc.;  Secretary  of each of the  investment  companies  in The Vanguard
Group.

THOMAS J. HIGGINS,  Treasurer;  Principal of The Vanguard Group, Inc.; Treasurer
of each of the  investment  companies  in The Vanguard  Group.
--------------------------------------------------------------------------------
VANGUARD  MANAGING DIRECTORS.

GREGORY BARTON, Legal Department.

ROBERT A. DISTEFANO, Information Technology.

JAMES H. GATELY, Direct Investor Services.

KATHLEEN C. GUBANICH, Human Resources.

IAN A. MACKINNON, Fixed Income Group.

F. WILLIAM MCNABB, III, Institutional Investor Group.

MICHAEL S. MILLER, Planning and Development.

RALPH K. PACKARD, Chief Financial Officer.

GEORGE U. SAUTER, Quantitative Equity Group.
--------------------------------------------------------------------------------
                                 JOHN C. BOGLE
               Founder; Chairman and Chief Executive, 1974-1996.

<PAGE>

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


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

Q220 122000
<PAGE>

Vanguard Windsor(TM)II Fund
Annual Report October 31, 2000


OUR REPORTS TO
THE OWNERS

At Vanguard,  we regard our investors not as mere customers but as owners of the
enterprise.  For that's exactly what a mutual fund shareholder is--part owner of
an investment company.

In our  reports  to you on how the  company  is doing,  we have  tried to convey
information  without  hyperbole  and in the context of broad  market  trends and
relevant benchmarks.

We've introduced several changes to this year's annual reports to make them even
more useful. Among the changes:

     **Larger type and redesigned graphics to  make  the reports easier to read.

     **An  at-a-glance  summary of key points  about  fund  performance  and the
financial markets.

     **A  table--included  for  many  funds--in  which  the  investment  adviser
highlights significant changes in holdings.

     **Comparisons of fund performance and characteristics  against both a broad
market index and a "best fit" benchmark.  We hope you'll find that these changes
make the reports even more accessible and informative.

SUMMARY

* Vanguard Windsor II Fund posted a 7.2% return, just ahead of its average peer.

* Value stocks outperformed growth stocks during the second half of fiscal 2000.

* Windsor II's concentration in the financial  services,  utilities,  and "other
energy" sectors contributed to the fund's turnaround in performance.

CONTENTS

 1 Letter from the Chairman

 6 Notice to Shareholders

 7 Adviser's Report

10 Fund Profile

11 Glossary of Investment Terms

12 Performance Summary

13 Report on After-Tax Returns

14 Financial Statements

24 Report of Independent Accountants
<PAGE>


LETTER
 from the Chairman

Fellow Shareholders,

Long-neglected  value  stocks came back in favor  during a volatile 12 months in
the  financial  markets,  propelling  vanguard  windsor ii fund to a fiscal-year
return of 7.2%, which outpaced the returns of our two value-focused  comparative
standards.


2000 TOTAL RETURNS                           FISCAL YEAR ENDED
                                                    OCTOBER 31
--------------------------------------------------------------
Vanguard Windsor II Fund                                  7.2%
Average Large-Cap Value Fund*                             7.1
Russell 1000 Value Index                                  5.5
Wilshire 5000 Index                                       8.1
--------------------------------------------------------------
*Derived from data provided by Lipper Inc.

     The  adjacent  table  pre-sents  the total  returns  (capital  change  plus
reinvested  dividends)  for the 12 months ended October 31, 2000,  for the fund,
its average peer, and the unmanaged  Russell 1000 Value Index,  the benchmark we
consider the best fit for Windsor II, as well as the Wilshire  5000 Total Market
Index, a proxy for the overall U.S. stock market.

     The fund's  return is based on a change in net asset  value from $29.03 per
share on October  31,  1999,  to $27.58 per share on October  31,  2000,  and is
adjusted for dividends  totaling $0.67 per share paid from net investment income
and a distribution of $2.50 per share paid from net realized capital gains.

     If you own Vanguard Windsor II Fund in a taxable  account,  you may wish to
review our report on the fund's after-tax returns on page 13.

FINANCIAL MARKETS IN REVIEW

The U.S.  stock  market  began the fiscal year like a  skyrocket,  as  investors
exhibited  extreme  enthusiasm for  technology-related  stocks. In the first two
months of the  period,  the broad  market  gained  more  than 11%.  Fueling  the
increase were favorable


MARKET BAROMETER                                Average Annual Total Returns
                                              Periods Ended October 31, 2000

                                              One        Three          Five
                                             Year        Years         Years
----------------------------------------------------------------------------
STOCKS

S&P 500 Index (Large-caps)                   6.1%        17.6%         21.7%
Russell 2000 Index (Small-caps)             17.4          5.9          12.4
Wilshire 5000 Index (Entire market)          8.1         16.0          20.1
MSCI EAFE Index (International)             -2.7          9.7           8.9
----------------------------------------------------------------------------
BONDS

Lehman Aggregate Bond Index (Entire market)  7.3%         5.7%          6.3%
Lehman 10 Year Municipal Bond Index          8.2          5.0           5.7
Salomon Smith Barney 3-Month
 U.S. Treasury Bill Index                    5.7          5.2           5.2
============================================================================
CPI

Consumer Price Index                         3.4%         2.5%          2.5%
----------------------------------------------------------------------------

                                       1
<PAGE>

economic  data:  Production  rose  rapidly,  unemployment  fell  below 4% of the
workforce,  long-term  interest rates declined,  and inflation was well-behaved,
save for a rise in energy prices.

     But as the period  progressed,  the effects of higher  short-term  interest
rates--engineered by the Federal Reserve Board to slow the economy and forestall
inflation--began  to show.  Data  suggested  that the  economy's  expansion  was
decelerating  to a moderate  pace.  And,  despite  solid  increases in corporate
earnings,  doubts  grew that  companies  could  sustain  the growth  pace amid a
slowing economy.

     Investors  seemed to grow wary of the lofty  prices of many tech  stocks in
relation to their earnings and other fundamentals.  Value  stocks--those  issues
characterized by relatively low prices in relation to earnings,  book value, and
dividends--  generally benefited from the market's increased emphasis on current
earnings.  The result was a  significant  split between  first- and  second-half
results for growth and value stocks, as the table above shows.


TOTAL RETURNS

                           OCT. 31, 1999, TO   APR. 30, 2000 TO    FISCAL
                           APR. 30, 2000          OCT. 31, 2000      2000
--------------------------------------------------------------------------
Russell 1000 Growth Index               18.7%              -7.9%      9.3%
Russell 1000 Value Index                -1.0                6.6       5.5
--------------------------------------------------------------------------

     For the full 12 months,  the overall  market,  as measured by the  Wilshire
5000 Index,  returned 8.1%--a decent result but one below the double-digit gains
investors   have  seen  in  recent  years.   For  a  change,   small-  and  mid-
capitalization  stocks  outpaced  their  large-cap  counterparts:  The small-cap
Russell 2000 Index  returned  17.4% for the 12 months,  11.3  percentage  points
ahead of the return of the large-cap S&P 500 Index,  which  accounts for roughly
three-fourths of the market value of U.S. stocks.

     The year saw huge variations in returns of various industry groups.  Higher
oil and natural gas prices helped the oil exploration and services  companies in
the "other energy" group to a 49% return,  making this the top-performing sector
within  the S&P 500 Index.  Other  strong  sectors  included  producer  durables
(+31%),  health care  (+16%),  and  financial  services  (+15%).  Technology,  a
standout  during the first  half of the year,  fell  during the second  half but
still  provided a 12-month  return of 15%. The year's big losers were  telephone
companies, which weighed down the utilities group (-15%), and retailers, apparel
makers, and other firms in the consumer discretionary sector (-13%).

THE FIXED INCOME MARKETS

Short-term  interest rates rose  substantially  during the fiscal year, with the
yield of 3-month U.S. Treasury bills rising 1.3 percentage  points. The

                                       2
<PAGE>

increase  essentially matched the 1.25-point increase in the federal funds rate,
accomplished in four steps by the Federal Reserve.

     Yields were relatively flat, on balance,  for most longer-term  securities,
however.  A rising federal  budget  surplus  shrank the supply of U.S.  Treasury
securities,  and their yields declined slightly for the fiscal year: The 30-year
Treasury's yield fell from 6.16% to 5.79%.  Yields on 10-year Treasuries fell by
about a quarter-point.  In general,  bonds turned in solid results during the 12
months.  The Lehman  Aggregate Bond Index, a proxy for taxable  investment-grade
bonds,  returned 7.3%, outpacing the S&P 500 Index.  Mortgage-backed  securities
and  high-quality  corporate bonds  performed  well,  benefiting from investors'
shift toward  high-quality bonds and away from speculative issues. The prices of
high-yield  bonds fell by more than 10% on  average,  and the Lehman  High Yield
Index returned -1.6%.

FISCAL 2000 PERFORMANCE OVERVIEW

What a difference a year makes.  In fiscal 1999,  the Windsor II Fund lagged its
benchmarks.  The fund  performed  poorly in an  environment  that punished value
investing.  Fiscal  2000  began in a similar  fashion,  but the  trend  reversed
suddenly during the spring.  Windsor II earned 25.2% in the last eight months of
the period,  regaining ground it lost early on and ending with a 12-month return
of 7.2%.  Although  our  return  was only  slightly  ahead of the  result of our
average peer, we arrived at the same destination via very different routes.  Our
average  peer built a big lead early in the fiscal year,  but returned  11.7% in
the last  eight  months,  less than half of  Windsor  II's gain  during the same
period.

--------------------------------------------------------------------------------
Windsor II gained 25.2% in the last eight months, making up for a poor beginning
to the fiscal year.
--------------------------------------------------------------------------------

     Three  sectors  played major roles in the fund's  turnaround.  The fund had
more than one-quarter of its assets in financial services companies. While those
holdings fared poorly initially,  they returned 27.8% in the fiscal second half.
In the "other energy" sector--the market's best performer during fiscal 2000 due
to rising oil and natural gas  prices--Windsor  II's stake of about 10% was more
than  triple the sector  weighting  in the  Russell  1000  Value  Index.  In the
utilities  sector,  our holdings of electric  companies  performed  well even as
telephone companies slumped badly.

     One notable  shortcoming  during the period was the fund's stock selections
in the  consumer  discretionary  sector,  which  is home to many  retailing  and
restaurant  stocks  that were hurt by tough  competition  and  concerns  about a
possible slowdown in consumer spending.

     We recognize that Windsor II Fund's strong  performance over the past eight
months was  overdue in the eyes of our  shareholders,  and we thank you for your
patience  during the preceding  months,  when value stocks were decidedly out of
favor and our performance was well below par.

                                       3
<PAGE>

We note that  many  individuals  who gave in to the  temptation  to alter  their
investment  allocations  in  pursuit of hot growth  stocks  paid a heavy  price.
Consider that the largest flows of cash into technology-related mutual funds and
the  largest  outflows  of cash from value  funds like  Windsor II  occurred  in
February  and March 2000.  The timing of these flows  couldn't  have been worse.



TOTAL ASSETS MANAGED                                     OCTOBER 31, 2000

                                                $ MILLION      PERCENTAGE
--------------------------------------------------------------------------
Barrow, Hanley, Mewhinney &
 Strauss, Inc.                                    $14,723              62%
Equinox Capital Management, Inc.                    3,682              15
Tukman Capital Management, Inc.                     3,233              13
Vanguard Quantitative Equity Group                  1,442               6
Cash Investments*                                     990               4
--------------------------------------------------------------------------
Total                                             $24,070             100%
--------------------------------------------------------------------------
*This cash is invested by The Vanguard Group in equity index futures to simulate
 investment in stocks; each adviser also maintains a modest cash position.


     That said, we don't pretend to know what the market has in store next,  but
we continue to believe that  long-term  investors are  well-advised  to maintain
exposure to both value stocks and growth  stocks.  As fiscal 2000  demonstrated,
market  leadership can switch  suddenly and decisively  from growth to value and
back again.

     As you know, the fund's assets are divided among four  managers.  The table
at left shows the  allocation  among  managers as of the end of the fiscal year.
For  further  details on the fund's  performance  and  holdings,  please see the
Adviser's Report on page 7.

LONG-TERM PERFORMANCE OVERVIEW

A single  year's  performance  hardly  provides an adequate  picture of a fund's
merits.  We've always  believed a long-term  view is important.  The table below
shows that a  hypothetical  $10,000  investment a decade ago in Windsor II would
have grown to $50,395,  or about  $1,400 more than a similar  investment  in the
average  large-cap value fund.  However,  during the past decade the fund lagged
both the Russell 1000 Value and the  Wilshire  5000  Indexes.  As a total market
benchmark,  the  Wilshire  5000 also  includes  growth  stocks,  which  were the
market's  leaders in recent years. Of course,  indexes have a big advantage over
real-world  funds because they are theoretical  constructs that do not incur the
actual operating and transaction costs that funds must bear.


TOTAL RETURNS                                             TEN YEARS ENDED
                                                         OCTOBER 31, 2000

                                       AVERAGE             FINAL VALUE OF
                                        ANNUAL                  A $10,000
                                        RETURN         INITIAL INVESTMENT
-------------------------------------------------------------------------
Vanguard Windsor II Fund                  17.6%                   $50,395
Average Large-Cap Value Fund              17.2                     49,016
Russell 1000 Value Index                  18.3                     53,805
Wilshire 5000 Index                       19.2                     57,709
-------------------------------------------------------------------------

     Nevertheless,                 our                fund's             expense

                                       4
<PAGE>

ratio  (average  expenses as a  percentage  of average net assets) of 0.37% is a
fraction of the average  peer's  1.28%,  according to data from Lipper Inc. This
gap may seem  inconsequential,  but we assure you that over time it is extremely
important,  giving our advisers a head start each year in their quest to provide
superior  returns.  Over  time,  costs  matter,  since  operating  expenses  and
transaction costs reduce the returns that a fund passes on to its shareholders.

     While we hope to improve our relative  returns versus  competitors  and our
index benchmark in the future,  we doubt that either the fund or the market will
be able to match the absolute  returns seen during the past ten years. The stock
market's  performance  during  the  1990-2000  decade  was one of its best ever;
returns were far above the 11% to 12% annual average for stocks over the past 75
years or so. Therefore,  we caution against extrapolating the remarkable returns
of the past decade into your investment  plans.  If you make modest  assumptions
and the market exceeds them, you'll merely get to your objectives sooner.

IN SUMMARY

The  financial  markets  during  the past 12  months  certainly  reinforced  the
importance of diversification. Just as it seemed that a single hot sector of the
stock  market was the only place to be,  technology-related  stocks  swooned and
value stocks came to the fore. And bonds--the  asset class many investors forgot
in the excitement of the bull market in  stocks--posted  solid results.

     Perhaps the one safe prediction for the next 12 months is that markets will
continue to be quite unpredictable. But uncertainty and volatility--risk, to use
a four-letter word--are constant companions for investors. A balanced investment
program--a  mix of  short-term  investments,  bonds,  and both  value and growth
stocks--can help you manage risk. Once you've built such a program in accordance
with your  objectives,  time  horizon,  financial  situation,  and tolerance for
market fluctuations, we recommend staying the course.

Sincerely,
/S/ JOHN J. BRENNAN
November 13, 2000


JOHN J. BRENNAN
Chairman and
Chief Executive Officer

                                       5
<PAGE>



--------------------------------------------------------------------------------
NOTICE OF CHANGE IN OWNERSHIP FOR BARROW, HANLEY, MEWHINNEY & STRAUSS, INC.

In July  2000,  Old  Mutual  plc  agreed  to  acquire  United  Asset  Management
Corporation  (UAM), the parent company of Barrow,  Hanley,  Mewhinney & Strauss,
Inc.  (BHMS),  an  investment  adviser for  Vanguard  Windsor II Fund.  UAM will
continue to own BHMS,  and the change in the parent  company's  ownership is not
expected to have any  practical  effect on the fund.  There will be no change in
BHMS's role as the fund's  investment  adviser,  in the personnel who advise the
fund,  or in the fees  charged  to the  fund.  However,  as is  required  by the
Investment  Company  Act of  1940,  your  fund's  advisory  contract  with  BHMS
automatically terminated with the change in ownership.

     Accordingly,  on September 14, 2000, your fund's board of trustees approved
a new investment advisory contract with BHMS that took effect when the ownership
of BHMS's parent company officially  changed in early October.  All of the terms
of the new contract,  except for its commencement and termination dates, are the
same as those in the previous contract. Your board believes that, similar to the
previous  contract,  the new  advisory  contract  will enable the fund to obtain
services of high quality at reasonable  cost and that the new contract is in the
best interests of the fund and its  shareholders.  (In 1993,  your fund received
permission  from  the  U.S.  Securities  and  Exchange  Commission  and from its
shareholders for the trustees to enter into a new advisory agreement without the
delay and  expense of a  shareholder  vote.  This  special  permission  was made
subject to several  conditions,  including the requirement that  shareholders be
notified of changes to the fund's investment  advisory  agreement.)

     In July,  Old Mutual plc  announced the terms of a tender offer under which
it  would  acquire  all  of  UAM's  outstanding  shares.  The  directors  of UAM
recommended  that its  shareholders  accept Old Mutual's offer, and UAM tendered
all of its shares.  The acquisition  became  effective on October 5, 2000.

     BHMS, which is registered as an investment  adviser with the Securities and
Exchange  Commission,  is located at One McKinney Plaza,  3232 McKinney  Avenue,
15th  Floor,  Dallas,  Texas  75204.  UAM began  providing  investment  advisory
services in December 1980.  Today the principal  operating  subsidiaries  of UAM
manage both domestic and  international  investment  portfolios  for  corporate,
government, and union benefit plans; mutual funds; individuals;  endowments; and
foundations.   Together   with  its   subsidiaries,   UAM   manages  or  advises
approximately $195 billion in assets.

                                       6
<PAGE>


ADVISER'S
 Report                               BARROW, HANLEY, MEWHINNEY & STRAUSS,  INC.

VANGUARD WINDSOR II FUND had a 7.2% return for the fiscal year ended October 31,
consisting of a poor -3.4% return for the first half-year and an excellent 10.9%
gain for the second six months.  These  results  were less a  reflection  of the
manager's  competence  than  an  illustration  of the  madness  of  the  moment,
something whose equal we are unlikely to see again.

THE INVESTMENT ENVIRONMENT

The past fiscal year should be viewed as having two  distinct  and nearly  equal
parts. Investors' attention,  and the market's performance,  were focused on one
sector--technology--to an extreme degree. A lack of tech stocks in the fund hurt
our  performance  through  February;   that  same  near-absence  of  tech  names
dramatically  helped  performance  thereafter.  Even  though  shareholders  were
clamoring for exposure to this area, most stocks were priced too high, given our
assessment of their growth  potential.  Rather than join the parade, we held our
ground.  Although  prices  in the  sector  have  fallen--dramatically,  in  many
cases--we  still believe that most of the very large names are far too pricey to
justify  purchase.  Early in the fiscal year,  talk about "new economy" and "old
economy" was in every newspaper and magazine  article,  and yet there is but one
economy. The real economy focuses on profit opportunities.

--------------------------------------------------------------------------------
INVESTMENT PHILOSOPHY

The fund reflects a belief that  superior  long-term  investment  results can be
achieved  by  holding  a  diversified  portfolio  of  out-of-favor  stocks  with
below-average  price/earnings  ratios,  above-average  dividend yields,  and the
prospect of above-average total returns.
--------------------------------------------------------------------------------

OUR SUCCESSES

Our electric utility holdings have been the fund's top contributors lately, with
names like  Entergy,  Reliant  Energy,  and American  Electric  Power  providing
leadership.  We believe the future for these and other electric utilities can be
bright despite the uncertainties of deregulation.  During the second half of the
fiscal year, our better-performing  stocks included Washington Mutual, Allstate,
and John  Hancock.  These  stocks'  returns  were  influenced  to some degree by
declining  interest  rates,  but  even  more  by a  significant  improvement  in
investors' assessments of their business prospects. We feel that these and other
holdings  are  underappreciated   and  continue  to  bear  promise.   Other  top
contributors for the fiscal second half included  Phillips  Petroleum and Philip
Morris.  Significant increases in Phillips Petroleum's revenues from oil and gas
pushed that stock up. Philip Morris  benefited  from a growing  perception  that
tobacco litigation was not a fatal threat.

                                       7
<PAGE>

OUR SHORTFALLS

Retailers, including Kmart and Sears, were weak, reflecting disappointing sales.
It seems to us that  inflation in energy  prices must affect demand for consumer
products.  These issues are quite cheap and should rebound. Newell Rubbermaid is
having problems passing along increased costs in its petroleum-based feedstocks.
Service  Corp.  International's  stock has  reacted to  financial  fears that we
regard as  unfounded.  The  company is  profitable  and,  although  the  funeral
business is changing, it is a necessary industry. Once tax-loss selling comes to
an end, the stock should rebound.  In the oil-services  sector,  Halliburton has
been  weak due to a very  slow flow of new  orders  in its  marine  construction
division.  This division  probably  will be sold,  leaving the company much less
subject to the oil industry's ups and downs.  We are confident that 2001 will be
a positive year for the entire energy industry.

THE FUND'S POSITIONING

Your fund is  significantly  overweighted,  compared  with any  relevant  market
index, in two sectors:  energy and electric  utilities.  We believe that after a
long  period  of  underinvestment  on new  production  capacity  in both  areas,
meaningful price increases are in store. Eventually, we'll see a dramatic change
in infrastructure  spending to increase  supplies.  Only then would we expect to
see excess capacity in these industries.

     Windsor  II  continues  to have very  little  exposure  to the  technology,
telecommunications,  and media sectors, whereas many indexes and portfolios have
weightings of 10% to 30% in these industries. We see a real potential for excess
capacity  in these areas of the  economy,  as they have had large  increases  in
investment in the past five years.  If we are right,  the very high relative and
absolute  prices of these stocks could create an  opportunity  for capital loss.
The fund has a significant position in financial services, which is generally in
line with our benchmarks.

     It  is  important  to  know  that  the  fund's  holdings  have  a  weighted
price/earnings ratio of 19.8, based on trailing 12-month earnings, which is only
two-thirds  of the P/E of the overall  market,  as measured by the Wilshire 5000
Index. At some point,  investors will again care about dividends,  and this fund
has a significant yield advantage over most equity portfolios.

James P. Barrow, Portfolio Manager

November 10, 2000

                                       8
<PAGE>



PORTFOLIO CHANGES                             FISCAL YEAR ENDED OCTOBER 31, 2000

                                        COMMENTS
--------------------------------------------------------------------------------
ADDITIONS

Conoco  Class A*                        Bought this domestic oil stock with cash
                                        from sales of some oil-services stocks.
--------------------------------------------------------------------------------
Emerson Electric                        Good company, cheap stock.
--------------------------------------------------------------------------------
Watson Pharmaceuticals*                 Dynamic  company   that  had  a  falling
                                        stock price.
--------------------------------------------------------------------------------
Bristol-Myers Squibb                    Stock became cheap due to worries about
                                        expiring patents.
--------------------------------------------------------------------------------
Newell Rubbermaid                       Added  to  holdings  after price fell on
                                        earnings shortfall.
================================================================================
REDUCTIONS

Citigroup                               Stock seems ahead of itself.
--------------------------------------------------------------------------------
Ford Motor                              Earnings are peaking as autos are at the
                                        top of their cycle.
--------------------------------------------------------------------------------
Washington Mutual                       Reduced a large holding.
--------------------------------------------------------------------------------
Baker Hughes                            Reduced a large holding.
--------------------------------------------------------------------------------
Phillips Petroleum                      Reduced a large holding.
--------------------------------------------------------------------------------
SBC Communications                      Reduced a large holding.
--------------------------------------------------------------------------------
*New holding in portfolio.

                                                                     SEE PAGE 14
                                                                  FOR A COMPLETE
                                                                  LISTING OF THE
                                                               FUND'S  HOLDINGS.
                                       9
<PAGE>


FUND PROFILE                                              As of October 31, 2000
 for Windsor II Fund

This Profile provides a snapshot of the fund's  characteristics,  compared where
appropriate  to both an  unmanaged  index that we  consider a "best fit" for the
fund and a broad market index. Key terms are defined on page 11.

-------------------------------------------------------------------------
PORTFOLIO CHARACTERISTICS
                                                                 WILSHIRE
                                        FUND        BEST FIT*        5000
-------------------------------------------------------------------------
Number of Stocks                         272              740       6,768
Median Market Cap                     $29.6B           $41.6B      $46.1B
Price/Earnings Ratio                   19.8x            19.8x       29.8x
Price/Book Ratio                        3.0x             3.3x        4.5x
Yield                                   2.1%             1.8%        1.1%
Return on Equity                       19.6%            20.8%       22.8%
Earnings Growth Rate                    9.7%            10.9%       16.8%
Foreign Holdings                        4.3%             0.0%        0.0%
Turnover Rate                            26%               --          --
Expense Ratio                          0.37%               --          --
Cash Investments                        2.6%               --          --
-------------------------------------------------------------------------


--------------------------------------------
TEN LARGEST HOLDINGS
 (% of total net assets)

Allstate Corp.
 (insurance)                           3.0%
Entergy Corp.
 (electrical utilities)                2.6
Philip Morris Cos., Inc.
 (tobacco)                             2.6
American Electric Power Co., Inc.
 (electrical utilities)                2.5
Phillips Petroleum Co.
 (oil)                                 2.4
BP Amoco PLC ADR
 (oil)                                 2.3
Washington Mutual, Inc.
 (savings & loan)                      2.3
SBC Communications Inc.
(telecommunications)                   2.2
Schlumberger Ltd.
 (oil)                                 2.1
Citigroup, Inc.
 (financial services)                  2.1
-------------------------------------------
Top Ten                               24.1%
-------------------------------------------


----------------------------------------------------
VOLATILITY MEASURES

                                            WILSHIRE
               FUND     BEST FIT*     FUND      5000


R-Squared      0.93          1.00     0.41      1.00
Beta           0.99          1.00     0.66      1.00
----------------------------------------------------



----------------------------------------------------------
SECTOR DIVERSIFICATION
 (% OF COMMON STOCKS)
                                                 WILSHIRE
                         FUND      BEST FIT*         5000

Auto & Transportation      0.7%          3.1%         1.7%
Consumer Discretionary    11.8           9.2         12.0
Consumer Staples           8.9           7.8          5.3
Financial Services        26.5          31.3         17.0
Health Care                5.3           8.6         12.4
Integrated Oils            9.5           7.2          3.1
Other Energy               8.9           2.5          2.6
Materials & Processing     4.0           3.8          2.5
Producer Durables          1.5           3.5          3.3
Technology                 3.1           4.7         26.4
Utilities                 15.4          15.7          8.7
Other                      4.4           2.6          5.0
----------------------------------------------------------
*Russell 1000 Value Index.


------------------------
INVESTMENT FOCUS

MARKET CAP         Large
STYLE              Value
------------------------
                                                           [PICTURE OF COMPUTER]
                                                               VISIT OUR WEBSITE
                                                                WWW.VANGUARD.COM
                                                           FOR REGULARLY UPDATED
                                                                FUND INFORMATION


                                       10
<PAGE>

GLOSSARY
 of Investment Terms

BETA. A measure of the magnitude of a fund's past  share-price  fluctuations  in
relation to the ups and downs of the fund's  "best fit" index  benchmark  and an
overall  market  index.  Each index is assigned a beta of 1.00.  Compared with a
given index,  a fund with a beta of 1.20 would have seen its share price rise or
fall by 12% when the index rose or fell by 10%.
--------------------------------------------------------------------------------
CASH  INVESTMENTS.  The  percentage  of a fund's  net assets  invested  in "cash
equivalents"--highly  liquid,  short-term,   interest-bearing  securities.  This
figure does not include cash  invested in futures  contracts  to simulate  stock
investment.
--------------------------------------------------------------------------------
EARNINGS  GROWTH RATE.  The average  annual rate of growth in earnings  over the
past five years for the stocks now in a fund.
--------------------------------------------------------------------------------
EXPENSE  RATIO.  The  percentage of a fund's  average net assets used to pay its
annual  administrative  and advisory  expenses.  These expenses  directly reduce
returns to investors.
--------------------------------------------------------------------------------
FOREIGN HOLDINGS. The percentage of a fund's equity assets represented by stocks
or American Depositary Receipts of companies based outside the United States.
--------------------------------------------------------------------------------
MEDIAN  MARKET  CAP.  An  indicator  of the  size of  companies  in which a fund
invests;  the  midpoint  of  market   capitalization   (market  price  x  shares
outstanding) of a fund's stocks, weighted by the proportion of the fund's assets
invested  in each  stock.  Stocks  representing  half of the fund's  assets have
market capitalizations above the median, and the rest are below it.
--------------------------------------------------------------------------------
PRICE/BOOK  RATIO.  The share price of a stock divided by its net worth, or book
value,  per share.  For a fund,  the weighted  average  price/book  ratio of the
stocks it holds.
--------------------------------------------------------------------------------
PRICE/EARNINGS  RATIO.  The ratio of a stock's  current  price to its  per-share
earnings over the past year. For a fund, the weighted  average P/E of the stocks
it holds. P/E is an indicator of market expectations about corporate  prospects;
the higher the P/E, the greater the expectations for a company's future growth.
--------------------------------------------------------------------------------
R-SQUARED.  A measure of how much of a fund's past  returns can be  explained by
the  returns  from the market in general,  as measured by the fund's  "best fit"
index  benchmark and by an overall market index.  If a fund's total returns were
precisely  synchronized with an index's returns, its R-squared would be 1.00. If
the fund's returns bore no  relationship to the index's  returns,  its R-squared
would be 0.
--------------------------------------------------------------------------------
RETURN ON  EQUITY.  The annual  average  rate of return  generated  by a company
during the past five years for each dollar of  shareholder's  equity (net income
divided by  shareholder's  equity).  For a fund, the weighted  average return on
equity for the companies whose stocks it holds.
--------------------------------------------------------------------------------
TURNOVER  RATE. An indication of trading  activity  during the past year.  Funds
with high turnover rates incur higher  transaction  costs and are more likely to
distribute capital gains (which are taxable to investors).
--------------------------------------------------------------------------------
YIELD.  A snapshot of a fund's  income from interest and  dividends.  The yield,
expressed  as a  percentage  of the fund's net asset  value,  is based on income
earned over the past 30 days and is  annualized,  or  projected  forward for the
coming  year.  The  index  yield  is  based on the  current  annualized  rate of
dividends paid on stocks in the index.
--------------------------------------------------------------------------------

                                       11
<PAGE>

PERFORMANCE SUMMARY
for Windsor II Fund

All of the data on this page represent past performance, which cannot be used to
predict  future returns that may be achieved by the fund.  Note,  too, that both
share  price and  return  can  fluctuate  widely.  An  investor's  shares,  when
redeemed, could be worth more or less than their original cost.

--------------------------------------------------------------------------------
TOTAL INVESTMENT RETURNS (%)                   October 31, 1990-October 31, 2000

               WINDSOR FUND        RUSSELL 1000 VALUE INDEX

1991                   36.6                            32.9
1992                   12.5                            10.7
1993                   19.5                            25.2
1994                    2.2                             0.8
1995                   23.1                            24.7
1996                   27.2                            23.7
1997                   31.3                            33.2
1998                   16.5                            14.8
1999                    4.6                            16.5
2000                    7.2                             5.5
--------------------------------------------------------------------------------
See  Financial  Highlights  table  on page 21 for  dividend  and  capital  gains
information for the past five years.
--------------------------------------------------------------------------------


--------------------------------------------------------------------------------
CUMULATIVE PERFORMANCE                         OCTOBER 31, 1990-OCTOBER 31, 2000

             WINDSOR       AVERAGE       RUSSELL      WILSHIRE       S&P 500
             II FUND     LARGE-CAP    1000 VALUE    5000 INDEX         INDEX
                       VALUE FUND*         INDEX

199010         10000         10000         10000         10000         10000
199101         11795         11629         11459         11562         11420
199104         13062         12665         12494         12865         12562
199107         13534         13105         12933         13395         13087
199110         13661         13504         13289         13860         13350
199201         14281         14185         13685         14751         14011
199204         14803         14446         14412         14789         14325
199207         15447         14683         14949         15166         14760
199210         15369         14644         14706         15202         14679
199301         16392         15592         16002         16310         15493
199304         16795         15906         16835         16332         15648
199307         17509         16288         17749         16916         16049
199310         18367         17271         18406         17902         16872
199401         18864         17906         19064         18488         17488
199404         17890         16969         18067         17432         16480
199407         18298         17212         18394         17646         16877
199410         18774         17754         18549         18356         17524
199501         18657         17655         18559         18300         17581
199504         20492         19299         20339         20019         19359
199507         22060         20921         22230         22239         21283
199510         23108         21666         23128         23062         22158
199601         25941         23704         25686         25108         24378
199604         27044         24587         26421         26464         25208
199607         26563         23965         25762         25508         24810
199610         29387         26482         28617         28118         27497
199701         32534         29303         31769         31252         30800
199704         32886         29671         32382         31131         31543
199707         38722         35022         38340         37538         37745
199710         38577         34021         38113         36990         36327
199801         40618         35910         40381         39123         39089
199804         47002         40160         46041         44600         44497
199807         45830         39341         45129         43961         45024
199810         44948         38910         43764         42484         44315
199901         48251         43577         47740         49829         51788
199904         52710         46092         52528         52172         54207
199907         50678         45557         51893         52018         54120
199910         47003         45762         50997         53385         55691
200001         43548         45634         49185         56994         57146
200004         45426         47212         50491         58554         59697
200007         45718         46267         49300         57832         58978
200010         50395         49016         53805         57709         59083
--------------------------------------------------------------------------------
                                  AVERAGE ANNUAL TOTAL RETURNS
                                  PERIODS ENDED OCTOBER 31, 2000     FINAL VALUE
                                 -------------------------------    OF A $10,000
                                  1 YEAR     5 YEARS   10 YEARS       INVESTMENT
--------------------------------------------------------------------------------
Windsor II Fund                     7.22%      16.88%     17.55%         $50,395
Average Large-Cap Value Fund*       7.11       17.74      17.23           49,016
Russell 1000 Value Index            5.52       18.40      18.33           53,805
Wilshire 5000 Index                 8.10       20.14      19.16           57,709
S&P 500 Index                       6.09       21.67      19.44           59,083
--------------------------------------------------------------------------------
*Derived from data provided by Lipper Inc.
--------------------------------------------------------------------------------

                                       12
<PAGE>

A REPORT
 on Your Fund's After-Tax Returns

This  table  presents  pre-tax  and  after-tax  returns  for  your  fund  and an
appropriate  peer group of mutual  funds.  The after-tax  returns  represent the
fund's  past  results  only  and  should  not be  used  to  predict  future  tax
efficiency.

     If you  own the  fund  in a  tax-deferred  account  such  as an  individual
retirement  account or a 401(k),  this  information  does not apply to you. Such
accounts are not subject to current taxes.

     Income  taxes  can  have  a  considerable  impact  on a  fund's  return--an
important  consideration for investors who own mutual funds in taxable accounts.
While the pre-tax return is most often used to tally a fund's  performance,  the
fund's  after-tax  return,  which accounts for taxes on distributions of capital
gains and income  dividends,  is an  important  measure of the return  that many
investors actually received.

PRE-TAX AND AFTER-TAX                             PERIODS ENDED OCTOBER 31, 2000
AVERAGE ANNUAL TOTAL RETURNS

                                ONE YEAR        FIVE YEARS     TEN YEARS
                           -----------------------------------------------------
                           PRE-TAX AFTER-TAX PRE-TAX AFTER-TAX PRE-TAX AFTER-TAX
--------------------------------------------------------------------------------
Vanguard Windsor II Fund      7.2%      3.9%   16.9%     13.8%   17.6%     14.9%
Average Large Value Fund*     7.6       5.5    15.4      12.6    16.0      13.3
--------------------------------------------------------------------------------
*Based on data from  Morningstar,  Inc.  Elsewhere in this  report,  returns for
comparable funds are derived from data provided by Lipper Inc., which may differ
somewhat.

     The after-tax  return  calculations use the top federal income tax rates in
effect at the time of each  distribution.  The tax burden would be less, and the
after-tax return higher, for those in lower tax brackets.

     We  must  stress  that  because  many   interrelated   factors  affect  how
tax-friendly  a fund may be, it is very difficult to predict tax  efficiency.  A
fund's tax  efficiency  can be  influenced  by its turnover  rate,  the types of
securities it holds, the accounting  practices it uses, and the net cash flow it
receives.

     Finally, it's important to understand that our calculation does not reflect
the tax effect of your own investment  activities.  Specifically,  you may incur
additional capital gains  taxes--thereby  lowering your after-tax return--if you
decide to sell all or some of your shares.
--------------------------------------------------------------------------------
A  NOTE  ABOUT  OUR   CALCULATIONS:   Pre-tax  total  returns  assume  that  all
distributions   received  (income  dividends,   short-term  capital  gains,  and
long-term  capital  gains) are  reinvested  in new shares,  while our  after-tax
returns assume that  distributions  are reduced by any taxes owed on them before
reinvestment.  When  calculating  the taxes due, we used the highest  individual
federal  income  tax  rates at the time of the  distributions.  Those  rates are
currently 39.6% for dividends and short-term capital gains and 20% for long-term
capital gains. State and local income taxes were not considered. The competitive
group returns provided by Morningstar are calculated in a manner consistent with
that used for Vanguard funds.

                                                           [PICTURE OF COMPUTER]
                                         You can use Vanguard's online after-tax
                                                            return calculator at
                                                      www.vanguard.com/?aftertax
                                                    to customize the calculation
                                                       of your after-tax return.

                                       13
<PAGE>

FINANCIAL STATEMENTS
 October 31, 2000

STATEMENT OF NET ASSETS

This Statement  provides a detailed list of the fund's holdings,  including each
security's market value on the last day of the reporting period.  Securities are
grouped  and  subtotaled  by asset  type  (common  stocks,  bonds,  etc.) and by
industry sector. Other assets are added to, and liabilities are subtracted from,
the value of Total Investments to calculate the fund's Net Assets.  Finally, Net
Assets are divided by the outstanding  shares of the fund to arrive at its share
price, or Net Asset Value (NAV) Per Share.

     At the end of the Statement of Net Assets, you will find a table displaying
the  composition of the fund's net assets on both a dollar and per-share  basis.
Because all income and any realized gains must be  distributed  to  shareholders
each year, the bulk of net assets consists of Paid in Capital (money invested by
shareholders).  The amounts shown for  Undistributed  Net Investment  Income and
Accumulated  Net  Realized  Gains  usually  approximate  the  sums  the fund had
available to distribute to shareholders as income  dividends or capital gains as
of  the  statement  date,  but  may  differ  because   certain   investments  or
transactions  may  be  treated  differently  for  financial  statement  and  tax
purposes.  Any Accumulated  Net Realized  Losses,  and any cumulative  excess of
distributions  over net income or net  realized  gains,  will appear as negative
balances.  Unrealized Appreciation  (Depreciation) is the difference between the
market value of the fund's  investments  and their cost,  and reflects the gains
(losses) that would be realized if the fund were to sell all of its  investments
at their statement-date values.


--------------------------------------------------------------------
                                                              MARKET
                                                              VALUE*
WINDSOR II FUND                                     SHARES     (000)
--------------------------------------------------------------------
COMMON STOCKS (93.1%)(1)
--------------------------------------------------------------------
AUTO & TRANSPORTATION (0.7%)
   General Motors Corp.                          1,963,068  $  121,956
   Ford Motor Co.                                  451,453      11,794
   Delta Air Lines, Inc.                           123,800       5,850
   Burlington Northern
    Santa Fe Corp.                                 200,800       5,334
   PACCAR, Inc.                                    105,500       4,438
   TRW, Inc.                                        96,700       4,061
*  Navistar International Corp.                    121,600       4,020
   Union Pacific Corp.                              71,000       3,328
*  Continental Airlines, Inc.
    Class B                                         19,800       1,040
   Delphi Automotive
    Systems Corp.                                   50,400         791
*  Northwest Airlines Corp.
    Class A                                         19,000         542
   Kansas City Southern
    Industries, Inc.                                11,500         100
                                                          ------------
                                                            $  163,254
                                                          ------------
CONSUMER DISCRETIONARY (11.0%)
   Waste Management, Inc.                       24,746,597     494,932
   Sears, Roebuck & Co.                         12,742,100     378,823
*(2)Kmart Corp.                                 39,811,200     236,379
   Gannett Co., Inc.                             3,791,100     219,884
   Wal-Mart Stores, Inc.                         4,314,800     195,784
*  Cendant Corp.                                13,650,200     163,802
   Newell Rubbermaid, Inc.                       8,479,200     162,695
   The Walt Disney Co.                           4,253,832     152,340
   Target Corp.                                  5,090,000     140,611
   Tribune Co.                                   3,105,500     115,098
*  AT&T Corp.-Liberty Media
    Class A                                      5,250,000      94,500
   Kimberly-Clark Corp.                          1,295,000      85,470
   J.C. Penney Co., Inc.                         5,646,800      65,997
*(2)Service Corp. International                 24,745,700      57,224
   McDonald's Corp.                                254,800       7,899
   Eastman Kodak Co.                               132,800       5,959
   Darden Restaurants Inc.                         227,300       5,114
*  Toys R Us, Inc.                                 274,500       4,718
*  Convergys Corp.                                 105,000       4,574
   R.R. Donnelley & Sons Co.                       187,300       4,027
   Reader's Digest Assn., Inc.
    Class A                                        103,900       3,812
   Hasbro, Inc.                                    349,700       3,759
*  Viacom Inc. Class B                              65,991       3,753
*  Outback Steakhouse                              128,300       3,657
   Galileo International, Inc.                     175,800       3,472
   Wendy's International, Inc.                     151,200       3,289
   Whirlpool Corp.                                  74,000       3,219
*  Mandalay Resort Group                           146,300       3,045
*  AutoNation, Inc.                                447,100       3,018
*  Clear Channel
    Communications, Inc.                            38,100       2,288

                                       14
<PAGE>
----------------------------------------------------------------------
                                                                MARKET
                                                                VALUE*
                                                    SHARES       (000)
----------------------------------------------------------------------
*  AutoZone Inc.                                    81,400  $    2,183
   Time Warner, Inc.                                28,500       2,163
   May Department Stores Co.                        74,037       1,943
*  Jones Apparel Group, Inc.                        62,300       1,733
   Circuit City Stores, Inc.                       121,900       1,615
*  International Game Technology                    31,000       1,135
   Gillette Co.                                     19,400         677
*  Tricon Global Restaurants, Inc.                  21,300         639
   Hertz Corp. Class A                              16,400         539
   Harcourt General, Inc.                            7,700         432
   VF Corp.                                         14,300         391
                                                          ------------
                                                            $2,642,592
                                                          ------------
CONSUMER STAPLES (8.3%)
   Philip Morris Cos., Inc.                     16,906,400     619,197
   Anheuser-Busch Cos., Inc.                     8,416,800     385,069
   Procter & Gamble Co.                          4,498,800     321,383
   Imperial Tobacco Group ADR                   14,840,000     289,380
   PepsiCo, Inc.                                 3,643,300     176,472
   H.J. Heinz Co.                                2,536,900     106,391
   Sara Lee Corp.                                2,380,900      51,338
   The Coca-Cola Co.                               104,600       6,315
   Ralston Purina Group                            213,400       5,175
   IBP, Inc.                                       249,700       5,134
   R.J. Reynolds Tobacco
    Holdings, Inc.                                 140,200       5,012
   Brown-Forman Corp. Class B                       80,700       4,913
   Nabisco Holdings Corp. Class A                   74,400       4,022
   Nabisco Group Holdings Corp.                    105,000       3,032
   SuperValu Inc.                                  157,000       2,414
   McCormick & Co., Inc.                            71,200       2,256
   Tyson Foods, Inc.                               195,500       2,187
*  Safeway, Inc.                                    30,800       1,684
                                                          ------------
                                                            $1,991,374
                                                          ------------
FINANCIAL SERVICES (24.7%)
   Allstate Corp.                               18,172,344     731,437
   Washington Mutual, Inc.                      12,397,230     545,478
   Citigroup, Inc.                               9,691,239     510,001
   Bank of America Corp.                         9,828,612     472,388
   American International
    Group, Inc.                                  4,676,241     458,272
   Bank One Corp.                               11,435,605     417,400
   The Chase Manhattan Corp.                     7,988,084     363,458
   First Union Corp.                            11,213,402     339,906
   Wells Fargo & Co.                             7,061,300     327,026
   Fannie Mae                                    4,215,700     324,609
   Aon Corp.                                     6,736,062     279,126
*  John Hancock Financial
    Services, Inc.                               7,512,300     237,576
   American General Corp.                        2,128,600     171,352
   PNC Financial Services Group                  2,381,022     159,231
   Morgan Stanley Dean
   Witter & Co.                                  1,614,300     129,648
   U.S. Bancorp                                  4,324,900     104,609
   J.P. Morgan & Co., Inc.                         614,100     101,634
   National City Corp.                             961,500      20,552
   American Express Co.                            236,700      14,202
   Conseco Inc.                                  2,024,000      14,042
   Merrill Lynch & Co., Inc.                       189,800      13,286
   The Bank of New York Co., Inc.                  181,600      10,453
   Mellon Financial Corp.                          197,900       9,549
   CIGNA Corp.                                      77,600       9,463
   FleetBoston Financial Corp.                     230,584       8,762
   Freddie Mac                                     126,300       7,578
   Marsh & McLennan Cos., Inc.                      49,300       6,446
   St. Paul Cos., Inc.                             122,200       6,263
   MGIC Investment Corp.                            91,700       6,247
   Golden West Financial Corp.                     109,800       6,156
   Nationwide Financial
    Services, Inc.                                 118,600       5,767
   Loews Corp.                                      63,000       5,729
   Bear Stearns Co., Inc.                           94,100       5,705
   SouthTrust Corp.                                173,300       5,611
   Dime Bancorp, Inc.                              218,400       5,337
   First Data Corp.                                104,200       5,223
   The Hartford Financial Services
    Group Inc.                                      69,400       5,166
   Golden State Bancorp Inc.                       196,700       5,139
   Countrywide Credit
    Industries, Inc.                               135,555       5,075
   A.G. Edwards & Sons, Inc.                        97,950       4,971
   The PMI Group Inc.                               66,350       4,902
   Hibernia Corp. Class A                          365,800       4,367
   Compass Bancshares Inc.                         223,400       4,063
   Heller Financial, Inc.                          138,800       4,060
   Deluxe Corp.                                    174,500       3,937
   State Street Corp.                               31,400       3,917
   UnionBanCal Corp.                               185,790       3,902
   Dow Jones & Co., Inc.                            66,000       3,886
   Northern Trust Corp.                             45,000       3,842
   Huntington Bancshares Inc.                      211,860       3,045
   First Virginia Banks, Inc.                       70,500       2,917
   Equity Residential Properties
    Trust REIT                                      59,000       2,777
   The Goldman Sachs Group, Inc.                    24,900       2,485
   Associates First Capital Corp.                   66,500       2,469
   GATX Corp.                                       58,400       2,456
   Stilwell Financial, Inc.                         46,000       2,061
*  CNA Financial Corp.                              54,700       1,997
   Associated Banc-Corp.                            82,940       1,996
   Duke Realty Investments,
    Inc. REIT                                       80,100       1,897
   Lehman Brothers Holdings, Inc.                   29,400       1,896
   Equity Office Properties
    Trust REIT                                      61,900       1,865
   Archstone Communities
    Trust REIT                                      66,400       1,565
   ProLogis Trust REIT                              70,900       1,489
   Mercantile Bankshares Corp.                      37,300       1,403

                                       15
<PAGE>
----------------------------------------------------------------------
                                                                MARKET
                                                                VALUE*
WINDSOR II FUND                                     SHARES       (000)
----------------------------------------------------------------------
   Public Storage, Inc. REIT                        61,800  $    1,391
   Commerce Bancshares, Inc.                        36,603       1,315
   Household International, Inc.                    26,000       1,308
   Automatic Data Processing, Inc.                  17,800       1,163
*  DST Systems, Inc.                                15,400         949
   Simon Property Group, Inc. REIT                  40,800         910
   SunTrust Banks, Inc.                             16,700         815
   Comdisco, Inc.                                   64,600         795
   Spieker Properties, Inc. REIT                    12,800         709
   M & T Bank Corp.                                 14,000         703
   MBNA Corp.                                       17,100         642
   Firstar Corp.                                    23,600         465
   Erie Indemnity Co. Class A                        5,700         159
   Charter One Financial                             2,415          55
                                                          ------------
                                                            $5,940,446
                                                          ------------
HEALTH CARE (4.9%)
   Bristol-Myers Squibb Co.                      6,402,300     390,140
   American Home
    Products Corp.                               4,129,500     262,223
*  Watson Pharmaceuticals, Inc.                 2,987,000      186,874
   HCA-The Healthcare Co.                        3,563,500     142,317
   Johnson & Johnson                             1,527,500     140,721
   Merck & Co., Inc.                               269,400      24,229
   Abbott Laboratories                             282,300      14,909
   UnitedHealth Group Inc.                          74,300       8,127
   Tenet Healthcare Corp.                          165,000       6,487
   Baxter International, Inc.                       45,000       3,698
*  Chiron Corp.                                    69,100        2,993
   C.R. Bard, Inc.                                  48,500       2,031
   Pharmacia Corp.                                  35,272       1,940
   DENTSPLY International Inc.                      52,400       1,818
                                                          ------------
                                                            $1,188,507
                                                          ------------
INTEGRATED OILS (8.8%)
   Phillips Petroleum Co.                        9,484,400     585,662
   BP Amoco PLC ADR                             11,098,572     565,334
   Occidental Petroleum Corp.                   18,342,300     364,553
(2)Conoco Inc. Class A                           9,900,000     255,544
   Exxon Mobil Corp.                             1,955,928     174,444
   Unocal Corp.                                  4,222,600     144,096
   Chevron Corp.                                   157,300      12,918
   Texaco Inc.                                     145,200       8,576
   Kerr-McGee Corp.                                 77,600       5,068
(2)Conoco Inc. Class B                             135,900       3,695
   Amerada Hess Corp.                               53,700       3,329
                                                          ------------
                                                            $2,123,219
                                                          ------------

OTHER ENERGY (8.2%)
 Schlumberger Ltd.                               6,775,600     515,793
 Baker Hughes, Inc.                             14,796,000     508,612
 Halliburton Co.                                11,555,700     428,283
 Williams Cos., Inc.                             6,191,546     258,884
 Enron Corp.                                     1,723,100     141,402
 Transocean Sedco Forex Inc.                     2,232,631     118,329
 Apache Corp.                                       81,200       4,491
 Ultramar Diamond
  Shamrock Corp.                                   145,700       3,825
 EOG Resources, Inc.                                81,700       3,217
 Anadarko Petroleum Corp.                           15,424         988
                                                          ------------
                                                            $1,983,824
                                                          ------------
MATERIALS & PROCESSING (3.7%)
(2)Fort James Corp.                             13,072,100     430,562
   Dow Chemical Co.                              4,372,400     133,905
(2)Millennium Chemicals, Inc.                    7,368,142     118,811
   Hanson PLC ADR                                3,995,350     104,878
(2)Crompton Corp.                                6,238,569      49,909
   E.I. du Pont de Nemours & Co.                   172,387       7,822
   Archer-Daniels-Midland Co.                      605,850       6,664
   Praxair, Inc.                                   129,000       4,805
*  American Standard Cos., Inc.                    103,900       4,766
   Boise Cascade Corp.                             148,600       4,263
   The Timber Co.                                  143,900       4,074
   Engelhard Corp.                                 190,100       3,968
   Lafarge Corp.                                   171,800       3,243
   Eastman Chemical Co.                             74,500       3,194
   Fluor Corp.                                      77,200       2,702
   Johns Manville Corp.                            220,000       2,021
   Alcoa Inc.                                       70,400       2,020
   Temple-Inland Inc.                               32,000       1,432
   Westvaco Corp.                                   18,500         527
   International Paper Co.                           9,600         352
                                                          ------------
                                                            $  889,918
                                                          ------------
PRODUCER DURABLES (1.4%)
   Emerson Electric Co.                          4,091,000     300,433
   The Boeing Co.                                  205,500      13,935
   Northrop Grumman Corp.                           61,700       5,183
   Cooper Industries, Inc.                         134,400       5,141
   United Technologies Corp.                        72,396       5,054
   Pitney Bowes, Inc.                              121,300       3,601
   Caterpillar, Inc.                                49,200       1,725
                                                          ------------
                                                            $  335,072
                                                          ------------
TECHNOLOGY (2.9%)
   International Business
    Machines Corp.                               2,275,000     224,088
   Electronic Data Systems Corp.                 3,619,300     169,881
   Intel Corp.                                   2,573,000     115,785
   Compaq Computer Corp.                         3,261,500      99,182
*  Microsoft Corp.                                 527,000      36,297
   Hewlett-Packard Co.                             246,200      11,433
*  Seagate Technology Inc.                          92,700       6,477
   Motorola, Inc.                                  227,000       5,661
*  Intuit, Inc.                                     81,000       4,976
*  KEMET Corp.                                     142,500       3,972
   Rockwell International Corp.                     84,700       3,330
   AVX Corp.                                       102,200       2,925
*  Advanced Micro Devices, Inc.                    127,000       2,873
*  Computer Sciences Corp.                          41,100       2,589
*  Apple Computer, Inc.                            104,600       2,046

                                       16
<PAGE>
----------------------------------------------------------------------
                                                                MARKET
                                                                VALUE*
                                                    SHARES       (000)
----------------------------------------------------------------------
*  American Management
    Systems, Inc.                                   23,400  $      506
*  3Com Corp.                                       13,900         247
                                                          ------------
                                                            $  692,268
                                                          ------------
UTILITIES (14.3%)
(2)Entergy Corp.                                16,284,200     623,888
   American Electric Power
    Co., Inc.                                   14,726,060     611,131
   SBC Communications Inc.                       9,130,047     526,690
   Verizon Communications                        7,702,654     445,310
   Reliant Energy, Inc.                         10,594,900     437,702
(2)FirstEnergy Corp.                            12,083,777     312,668
   Xcel Energy, Inc.                             4,214,500     107,733
   Public Service Enterprise
    Group, Inc.                                  2,445,400     101,484
*  WorldCom, Inc.                                4,041,172      95,978
   AT&T Corp.                                    4,010,745      92,999
   BellSouth Corp.                                 439,800      21,248
*  Comcast Corp. Special Class A                   157,000       6,398
   TXU Corp.                                       167,200       6,197
   Exelon Corp.                                    100,450       6,040
   PPL Corp.                                       132,688       5,465
   GPU, Inc.                                       155,200       5,131
   DTE Energy Co.                                  142,000       5,130
   Telephone & Data Systems, Inc.                   46,100       4,864
   Sprint Corp.                                    177,180       4,518
*  Qwest Communications
   International Inc.                               92,511       4,498
*  XO Communications Inc.                          119,500       4,031
   Duke Energy Corp.                                46,300       4,002
   Cinergy Corp.                                   121,000       3,706
   Pinnacle West Capital Corp.                      76,700       3,332
*  U.S. Cellular Corp.                              50,500       3,232
   Sempra Energy                                   154,900       3,204
   Ameren Corp.                                     79,700       3,168
   Edison International                            102,100       2,438
   CP&L, Inc.                                       50,600       2,040
   PG&E Corp.                                       72,600       1,956
   ALLTEL Corp.                                     30,200       1,946
   Kinder Morgan, Inc.                              30,000       1,157
   Southern Co.                                     12,400         364
*  Level 3 Communications, Inc.                      3,300         157
                                                          ------------
                                                            $3,459,805
                                                          ------------
OTHER (4.2%)
   General Electric Co.                          6,569,200     360,074
   Honeywell International Inc.                  6,025,362     324,240
(2)ITT Industries, Inc.                          8,916,800     290,353
   Minnesota Mining &
    Manufacturing Co.                              101,600       9,817
   Fortune Brands, Inc.                            201,300       5,926
   Johnson Controls, Inc.                           89,800       5,354
*  Thermo Electron Corp.                           154,700       4,486
*  FMC Corp.                                        38,800       2,949
   Crane Co.                                        34,200         896
                                                          ------------
                                                            $1,004,095
                                                          ------------
----------------------------------------------------------------------
TOTAL COMMON STOCKS
   (Cost $17,799,055)                                      $22,414,374
----------------------------------------------------------------------
                                                      Face
                                                    Amount
                                                     (000)
----------------------------------------------------------------------
TEMPORARY CASH INVESTMENTS (7.3%)(1)
----------------------------------------------------------------------
FEDERAL HOME LOAN MORTGAGE CORP.
(3)6.54%, 1/25/2001                               $ 25,000  $   24,615
FEDERAL NATIONAL MORTGAGE ASSN.
(3)6.54%, 1/24/2001                                 35,000  $   34,474
REPURCHASE AGREEMENTS
Collateralized by U.S. Government
   Obligations in a Pooled
   Cash Account
   6.56%, 11/1/2000                              1,698,345  $1,698,345
   6.58%, 11/1/2000--Note G                          4,120      4,120
----------------------------------------------------------------------
TOTAL TEMPORARY CASH INVESTMENTS
   (Cost $1,761,564)                                        $1,761,554
----------------------------------------------------------------------
TOTAL INVESTMENTS (100.4%)
   (Cost $19,560,619)                                      $24,175,928
----------------------------------------------------------------------
OTHER ASSETS AND LIABILITIES (-0.4%)
----------------------------------------------------------------------
Other Assets--Note C                                           216,763
Liabilities--Note G                                           (322,786)
                                                          ------------
                                                              (106,023)
                            `                             ------------
----------------------------------------------------------------------
NET ASSETS (100%)
----------------------------------------------------------------------
Applicable to 872,618,430 outstanding $.001
   par value shares of beneficial interest
   (unlimited authorization)                               $24,069,905
======================================================================

NET ASSET VALUE PER SHARE                                       $27.58
======================================================================
*See Note A in Notes to Financial Statements.
*Non-income-producing security.

(1)The fund invests a portion of its cash reserves in equity markets through the
   use of   index futures contracts. After giving effect to futures investments,
   the fund's  effective  common  stock and temporary cash investment  positions
   represent  97.4% and 3.0%, respectively,  of  net assets. See Note F in Notes
   to Financial Statements.
(2)Considered  an  affiliated  company  as the  fund  owns  more  than 5% of the
   outstanding  voting  securities  of such  company.  The total market value of
   investments in affiliated companies was $2,379,033,000.
(3)Securities with an aggregate  value of  $59,089,000  have been  segregated as
   initial margin for open futures contracts.
ADR--American Depositary Receipt.
REIT--Real Estate Investment Trust.

                                       17
<PAGE>
-----------------------------------------------------------------------
                                                    AMOUNT         PER
WINDSOR II FUND                                      (000)       SHARE
-----------------------------------------------------------------------
AT OCTOBER 31, 2000, NET ASSETS CONSISTED OF:
-----------------------------------------------------------------------
Paid in Capital--Note E                        $18,212,531      $20.87
Undistributed Net
  Investment Income                                158,735         .18
Accumulated Net
  Realized Gains--Note E                         1,135,931        1.30
Unrealized Appreciation
  (Depreciation)--Note F
  Investment Securities                          4,615,309        5.29
  Futures Contracts                                (52,601)       (.06)
-----------------------------------------------------------------------
NET ASSETS                                     $24,069,905       $27.58
=======================================================================

                                       18
<PAGE>

STATEMENT OF OPERATIONS

This Statement  shows dividend and interest income earned by the fund during the
reporting period,  and details the operating expenses charged to the fund. These
expenses  directly  reduce the amount of investment  income  available to pay to
shareholders  as  dividends.  This  Statement  also  shows  any Net Gain  (Loss)
realized  on the  sale of  investments,  and the  increase  or  decrease  in the
Unrealized Appreciation  (Depreciation) on investments during the period. If the
fund  invested  in futures  contracts  during the  period,  the results of these
investments are shown separately.

-------------------------------------------------------------------------------
                                                               WINDSOR II FUND
                                                   YEAR ENDED OCTOBER 31, 2000
                                                                         (000)
-------------------------------------------------------------------------------
INVESTMENT INCOME
INCOME
 Dividends*                                                          $ 563,303
 Interest                                                               99,399
 Security Lending                                                        1,786
-------------------------------------------------------------------------------
  Total Income                                                         664,488
-------------------------------------------------------------------------------
EXPENSES
 Investment Advisory Fees--Note B
  Basic Fee                                                             30,354
  Performance Adjustment                                                (6,281)
 The Vanguard Group--Note C
  Management and Administrative                                         62,100
  Marketing and Distribution                                             3,412
 Custodian Fees                                                             85
 Auditing Fees                                                              28
 Shareholders' Reports                                                     760
 Trustees' Fees and Expenses                                                34
-------------------------------------------------------------------------------
  Total Expenses                                                        90,492
  Expenses Paid Indirectly--Note D                                      (3,825)
-------------------------------------------------------------------------------
  Net Expenses                                                          86,667
-------------------------------------------------------------------------------
NET INVESTMENT INCOME                                                  577,821
-------------------------------------------------------------------------------
REALIZED NET GAIN
 Investment Securities Sold*                                         1,389,813
 Futures Contracts                                                      84,282
-------------------------------------------------------------------------------
REALIZED NET GAIN                                                    1,474,095
-------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)
 Investment Securities                                                (793,181)
 Futures Contracts                                                     (71,695)
-------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)                      (864,876)
-------------------------------------------------------------------------------
NET INCREASE IN NET ASSETS RESULTING FROM OPERATIONS                $1,187,040
===============================================================================
*Dividend   income  and  realized  net  loss  from  affiliated   companies  were
$137,047,000 and $(802,507,000), respectively.

                                       19
<PAGE>

STATEMENT OF CHANGES IN NET ASSETS

This Statement shows how the fund's total net assets changed during the two most
recent reporting periods. The Operations section summarizes information detailed
in  the  Statement  of  Operations.   The  amounts  shown  as  Distributions  to
shareholders  from the fund's net  income  and  capital  gains may not match the
amounts shown in the Operations section, because distributions are determined on
a tax  basis  and may be made in a period  different  from the one in which  the
income was earned or the gains were  realized on the financial  statements.  The
Capital Share Transactions section shows the amount shareholders invested in the
fund,  either by purchasing shares or by reinvesting  distributions,  as well as
the amounts redeemed.  The  corresponding  numbers of Shares Issued and Redeemed
are shown at the end of the Statement.

-------------------------------------------------------------------------------
                                                         WINDSOR II FUND
                                                      YEAR ENDED OCTOBER 31,
                                                    -------------------------
                                                          2000          1999
                                                         (000)         (000)
-----------------------------------------------------------------------------
INCREASE (DECREASE) IN NET ASSETS
OPERATIONS
 Net Investment Income                               $ 577,821     $ 670,002
 Realized Net Gain                                   1,474,095     2,600,015
 Change in Unrealized Appreciation (Depreciation)     (864,876)   (1,931,112)
-----------------------------------------------------------------------------
Net Increase in Net Assets Resulting from Operations 1,187,040     1,338,905
-----------------------------------------------------------------------------
DISTRIBUTIONS
 Net Investment Income                                (642,217)     (741,695)
 Realized Capital Gain                              (2,514,938)   (2,559,664)
-----------------------------------------------------------------------------
  Total Distributions                               (3,157,155)   (3,301,359)
-----------------------------------------------------------------------------
CAPITAL SHARE TRANSACTIONS1
 Issued                                              2,976,235     6,123,676
 Issued in Lieu of Cash Distributions                3,004,773     3,148,067
 Redeemed                                          (10,481,817)   (6,407,121)
-----------------------------------------------------------------------------
  Net Increase (Decrease) from Capital
   Share Transactions                               (4,500,809)    2,864,622
-----------------------------------------------------------------------------
Total Increase (Decrease)                           (6,470,924)      902,168
-----------------------------------------------------------------------------
NET ASSETS
 Beginning of Year                                  30,540,829    29,638,661
-----------------------------------------------------------------------------
End of Year                                        $24,069,905   $30,540,829
=============================================================================

1Shares Issued (Redeemed)
 Issued                                                118,060       198,010
 Issued in Lieu of Cash Distributions                  120,577       109,009
 Redeemed                                             (417,883)     (209,049)
-----------------------------------------------------------------------------
  Net Increase (Decrease) in Shares Outstanding       (179,246)       97,970
=============================================================================

                                       20
<PAGE>


FINANCIAL HIGHLIGHTS

This table  summarizes  the  fund's  investment  results  and  distributions  to
shareholders on a per-share  basis. It also presents the fund's Total Return and
shows net  investment  income and expenses as percentages of average net assets.
These data will help you assess:  the  variability  of the fund's net income and
total returns from year to year;  the relative  contributions  of net income and
capital gains to the fund's total return; how much it costs to operate the fund;
and the extent to which the fund tends to distribute  capital  gains.  The table
also  shows the  Portfolio  Turnover  Rate,  a measure of  trading  activity.  A
turnover  rate of 100% means that the  average  security is held in the fund for
one year.



<TABLE>
---------------------------------------------------------------------------------------------------------
                                                                           Windsor II Fund
                                                                        Year Ended October 31,
                                                             --------------------------------------------
<S>                                                        <C>       <C>      <C>      <C>       <C>

FOR A SHARE OUTSTANDING THROUGHOUT EACH YEAR                  2000      1999     1998     1997      1996
---------------------------------------------------------------------------------------------------------
NET ASSET VALUE, BEGINNING OF YEAR                          $29.03    $31.07   $29.36   $24.04    $20.06
---------------------------------------------------------------------------------------------------------
INVESTMENT OPERATIONS
  Net Investment Income                                        .64       .64      .65      .64       .62
  Net Realized and Unrealized Gain (Loss) on Investments      1.08       .73     3.91     6.47      4.63
---------------------------------------------------------------------------------------------------------
    Total from Investment Operations                          1.72      1.37     4.56     7.11      5.25
---------------------------------------------------------------------------------------------------------
DISTRIBUTIONS
  Dividends from Net Investment Income                       (.67)     (.74)    (.66)    (.63)     (.58)
  Distributions from Realized Capital Gains                 (2.50)    (2.67)   (2.19)   (1.16)     (.69)
---------------------------------------------------------------------------------------------------------
    Total Distributions                                     (3.17)    (3.41)   (2.85)   (1.79)    (1.27)
---------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF YEAR                                $27.58    $29.03   $31.07   $29.36    $24.04
=========================================================================================================

TOTAL RETURN                                                 7.22%     4.57%   16.51%   31.27%    27.17%
=========================================================================================================

RATIOS/SUPPLEMENTAL DATA
  Net Assets, End of Year (Millions)                       $24,070   $30,541  $29,639  $22,568   $14,758
  Ratio of Total Expenses to Average Net Assets              0.37%     0.37%    0.41%    0.37%     0.39%
  Ratio of Net Investment Income to Average Net Assets       2.36%     2.08%    2.16%    2.49%     2.92%
  Portfolio Turnover Rate                                      26%       26%      31%      30%       32%
=========================================================================================================
</TABLE>

                                       21
<PAGE>


NOTES TO FINANCIAL STATEMENTS

Vanguard Windsor II Fund is registered under the Investment  Company Act of 1940
as a diversified open-end investment company, or mutual fund.

A. The following  significant  accounting policies conform to generally accepted
accounting  principles for U.S. mutual funds. The fund consistently follows such
policies in preparing its financial statements.

     1. SECURITY  VALUATION:  Equity  securities are valued at the latest quoted
sales  prices  as of the  close  of  trading  on the  New  York  Stock  Exchange
(generally  4:00 p.m.  Eastern time) on the valuation  date; such securities not
traded on the valuation date are valued at the mean of the latest quoted bid and
asked  prices.  Prices are taken from the primary  market in which each security
trades.  Temporary cash investments acquired over 60 days to maturity are valued
using the latest bid prices or using  valuations based on a matrix system (which
considers such factors as security  prices,  yields,  maturities,  and ratings),
both  as  furnished  by  independent  pricing  services.  Other  temporary  cash
investments  are valued at amortized  cost,  which  approximates  market  value.
Securities for which market  quotations are not readily  available are valued by
methods deemed by the board of trustees to represent fair value.

     2.  FEDERAL  INCOME  TAXES:  The fund  intends to  continue to qualify as a
regulated   investment  company  and  distribute  all  of  its  taxable  income.
Accordingly,  no provision for federal income taxes is required in the financial
statements.

     3.  REPURCHASE  AGREEMENTS:  The fund,  along  with  other  members  of The
Vanguard  Group,  transfers  uninvested  cash balances to a pooled cash account,
which  is  invested  in  repurchase   agreements  secured  by  U.S.   government
securities.  Securities pledged as collateral for repurchase agreements are held
by a custodian bank until the agreements  mature.  Each agreement  requires that
the market value of the  collateral be sufficient to cover  payments of interest
and principal; however, in the event of default or bankruptcy by the other party
to  the  agreement,  retention  of  the  collateral  may  be  subject  to  legal
proceedings.

     4. FUTURES CONTRACTS:  The fund uses S&P 500 Index and S&P MidCap 400 Index
futures  contracts to a limited extent,  with the objective of maintaining  full
exposure to the stock market while maintaining liquidity.  The fund may purchase
or sell futures  contracts to achieve a desired level of investment,  whether to
accommodate  portfolio  turnover or cash flows from capital share  transactions.
The primary  risks  associated  with the use of futures  contracts are imperfect
correlation  between changes in market values of stocks held by the fund and the
prices of futures contracts, and the possibility of an illiquid market.

     Futures contracts are valued at their quoted daily settlement  prices.  The
aggregate  principal  amounts of the contracts are not recorded in the financial
statements.  Fluctuations  in the value of the  contracts  are  recorded  in the
Statement  of Net  Assets  as an  asset  (liability)  and in  the  Statement  of
Operations as  unrealized  appreciation  (depreciation)  until the contracts are
closed, when they are recorded as realized futures gains (losses).

     5.  DISTRIBUTIONS:  Distributions  to  shareholders  are  recorded  on  the
ex-dividend  date.  Distributions  are  determined on a tax basis and may differ
from net investment  income and realized  capital gains for financial  reporting
purposes.

     6. OTHER:  Dividend  income is recorded on the ex-dividend  date.  Security
transactions  are accounted for on the date securities are bought or sold. Costs
used to determine  realized gains (losses) on the sale of investment  securities
are those of the specific securities sold.

B. Barrow, Hanley, Mewhinney & Strauss, Inc.; Equinox Capital Management,  Inc.;
and Tukman Capital Management, Inc., provide investment advisory services to the
fund for fees calculated at an annual percentage rate of average net assets. The
basic fees thus  computed for Barrow,  Hanley,  Mewhinney & Strauss,  Inc.,  are
subject to quarterly  adjustments based on performance relative to the S&P/BARRA
Value Index;  such fees for Equinox  Capital  Management,  Inc.,  are subject to
quarterly  adjustments  based on performance  relative to the Russell 1000 Value
Index; such fees

                                       22
<PAGE>

for Tukman Capital Management,  Inc., are subject to quarterly adjustments based
on performance relative to the S&P 500 Index.

     The Vanguard Group provides  investment  advisory  services to a portion of
the fund on an at-cost basis;  the fund paid Vanguard  advisory fees of $414,000
for the year ended October 31, 2000.

     For the year ended October 31, 2000, the aggregate  investment advisory fee
represented an effective annual basic rate of 0.12% of average net assets before
a decrease of $6,281,000 (0.03%) based on performance.

C. The Vanguard Group  furnishes at cost corporate  management,  administrative,
marketing,  and distribution  services. The costs of such services are allocated
to the fund  under  methods  approved  by the  board of  trustees.  The fund has
committed to provide up to 0.40% of its net assets in capital  contributions  to
Vanguard. At October 31, 2000, the fund had contributed capital of $4,415,000 to
Vanguard (included in Other Assets), representing 0.02% of the fund's net assets
and 4.4% of Vanguard's capitalization. The fund's trustees and officers are also
directors and officers of Vanguard.

D. The fund has asked its investment advisers to direct certain security trades,
subject to obtaining the best price and execution, to brokers who have agreed to
rebate to the fund part of the  commissions  generated.  Such  rebates  are used
solely to reduce the fund's management and administrative expenses. For the year
ended  October 31,  2000,  these  arrangements  reduced  the fund's  expenses by
$3,825,000 (an annual rate of 0.02% of average net assets).

E. During the year ended October 31, 2000, the fund purchased  $5,822,673,000 of
investment securities and sold $12,599,936,000 of investment  securities,  other
than temporary cash investments.

     The fund used a tax accounting  practice to treat a portion of the price of
capital shares redeemed during the year as  distributions  from realized capital
gains. Accordingly,  the fund has reclassified $321,828,000 from accumulated net
realized gains to paid in capital.

F. At October 31, 2000, net unrealized appreciation of investment securities for
financial   reporting  and  federal  income  tax  purposes  was  $4,615,309,000,
consisting of unrealized gains of $6,923,211,000 on securities that had risen in
value since their purchase and $2,307,902,000 in unrealized losses on securities
that had fallen in value since their purchase.

     At  October  31,  2000,  the  aggregate  settlement  value of open  futures
contracts  expiring in December  2000 and the  related  unrealized  depreciation
were:


--------------------------------------------------------------------------------
                                                                 (000)
                                                         -----------------------
                                                      AGGREGATE
                                    NUMBER OF        SETTLEMENT       UNREALIZED
FUTURES CONTRACTS              LONG CONTRACTS             VALUE     DEPRECIATION
--------------------------------------------------------------------------------
S&P 500 Index                           2,686          $967,094        $(48,977)
S&P MidCap 400 Index                      275            71,672          (3,624)
--------------------------------------------------------------------------------

Unrealized  depreciation on open futures  contracts is required to be treated as
realized loss for tax purposes.

G. The market value of securities on loan to broker/dealers at October 31, 2000,
was $3,999,000 for which the fund held cash  collateral of $4,120,000.  The fund
invests  cash  collateral  received  in  repurchase  agreements,  and  records a
liability for the return of the collateral, during the period the securities are
on loan.

                                       23
<PAGE>


REPORT
 of Independent Accountants

To the Shareholders and Trustees of Vanguard Windsor II Fund

In our  opinion,  the  accompanying  statement  of net  assets  and the  related
statements  of  operations  and of  changes  in net  assets  and  the  financial
highlights present fairly, in all material  respects,  the financial position of
Vanguard  Windsor II Fund (the "Fund") at October 31,  2000,  the results of its
operations  for the year then  ended,  the changes in its net assets for each of
the two years in the period then ended and the financial  highlights for each of
the  five  years  in the  period  then  ended,  in  conformity  with  accounting
principles  generally accepted in the United States of America.  These financial
statements  and  financial  highlights  (hereafter  referred  to  as  "financial
statements") are the responsibility of the Fund's management; our responsibility
is to express an opinion on these financial  statements based on our audits.  We
conducted our audits of these  financial  statements in accordance with auditing
standards generally accepted in the United States of America, which require that
we plan and perform the audit to obtain  reasonable  assurance about whether the
financial  statements  are free of  material  misstatement.  An  audit  includes
examining,  on a test basis,  evidence supporting the amounts and disclosures in
the  financial   statements,   assessing  the  accounting  principles  used  and
significant  estimates made by management,  and evaluating the overall financial
statement presentation.  We believe that our audits, which included confirmation
of  securities  at October 31, 2000 by  correspondence  with the  custodian  and
brokers, provide a reasonable basis for our opinion.


PricewaterhouseCoopers LLP
Philadelphia, Pennsylvania

November 29, 2000




--------------------------------------------------------------------------------
SPECIAL 2000 TAX INFORMATION (UNAUDITED) FOR VANGUARD WINDSOR II FUND

This  information  for the fiscal  year ended  October  31,  2000,  is  included
pursuant to provisions of the Internal Revenue Code.

The  fund  distributed  $2,439,406,000  as  capital  gain  dividends  (from  net
long-term capital gains) to shareholders during the fiscal year, all of which is
designated as a 20% rate gain distribution.

For corporate  shareholders,  92.8% of investment  income  (dividend income plus
short-term gains, if any) qualifies for the dividends-received deduction.

                                       24
<PAGE>

THE PEOPLE

Who Govern Your Fund

The  trustees of your mutual fund are there to see that the fund is operated and
managed in your best interests  since,  as a shareholder,  you are part owner of
the fund.  Your  fund  trustees  also  serve on the  board of  directors  of The
Vanguard  Group,  which is owned by the  funds  and  exists  solely  to  provide
services to them on an at-cost basis.

     Six of Vanguard's  seven board members are  independent,  meaning that they
have no  affiliation  with  Vanguard or the funds they  oversee,  apart from the
sizable personal investments they have made as private  individuals.  They bring
distinguished  backgrounds  in business,  academia,  and public service to their
task of working with Vanguard officers to establish the policies and oversee the
activities of the funds.

     Among board members' responsibilities are selecting investment advisers for
the  funds;  monitoring  fund  operations,  performance,  and  costs;  reviewing
contracts;  nominating  and  selecting  new  trustees/  directors;  and electing
Vanguard officers.

     The list below provides a brief description of each trustee's  professional
affiliations.  The year in which the trustee  joined the Vanguard board is noted
in parentheses.
--------------------------------------------------------------------------------
TRUSTEES

JOHN J. BRENNAN  (1987)  Chairman of the Board,  Chief  Executive  Officer,  and
Director/Trustee  of The Vanguard  Group,  Inc.,  and of each of the  investment
companies in The Vanguard Group.

JOANN HEFFERNAN HEISEN (1998) Vice President,  Chief Information  Officer, and a
member of the  Executive  Committee of Johnson & Johnson;  Director of Johnson &
Johnson*Merck Consumer Pharmaceuticals Co., The Medical Center at Princeton, and
Women's Research and Education Institute.

BRUCE K.  MACLAURY  (1990)  President  Emeritus  of The  Brookings  Institution;
Director of  American  Express  Bank Ltd.,  The St. Paul  Companies,  Inc.,  and
National Steel Corp.

BURTON G. MALKIEL  (1977)  Chemical  Bank  Chairman's  Professor  of  Economics,
Princeton  University;  Director of Prudential  Insurance Co. of America,  Banco
Bilbao  Argentaria,  Gestion,  BKF Capital,  The Jeffrey Co., NeuVis,  Inc., and
Select Sector SPDR Trust.

ALFRED M. RANKIN, JR. (1993) Chairman,  President,  Chief Executive Officer, and
Director of NACCO Industries, Inc.; Director of The BFGoodrich Co.

JAMES O. WELCH,  JR.  (1971)  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 (1985) Retired Chairman and Chief Executive Officer of Rohm &
Haas Co.; Director of AmeriSource  Health  Corporation,  Cummins Engine Co., and
The Mead Corp.; Trustee of Vanderbilt University.
--------------------------------------------------------------------------------
OTHER FUND OFFICERS

RAYMOND J. KLAPINSKY, Secretary; Managing Director and Secretary of The Vanguard
Group,  Inc.;  Secretary  of each of the  investment  companies  in The Vanguard
Group.

THOMAS J. HIGGINS,  Treasurer;  Principal of The Vanguard Group, Inc.; Treasurer
of each of the investment companies in The Vanguard Group.
--------------------------------------------------------------------------------
VANGUARD MANAGING DIRECTORS

R. GREGORY BARTON, Legal Department.

ROBERT A. DISTEFANO, Information Technology.

JAMES H. GATELY, Direct Investor Services.

KATHLEEN C. GUBANICH, Human Resources.

IAN A. MACKINNON, Fixed Income Group.

F. WILLIAM MCNABB, III, Institutional Investor Group.

MICHAEL S. MILLER, Planning and Development.

RALPH K. PACKARD, Chief Financial Officer.

GEORGE U. SAUTER, Quantitative Equity Group.
--------------------------------------------------------------------------------
                                 JOHN C. BOGLE
               Founder; Chairman and Chief Executive, 1974-1996.
<PAGE>


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