VANGUARD NEW YORK INSURED TAX FREE FUND
N-30D, 1996-07-22
Previous: AMERICAN ENTERTAINMENT GROUP INC, 8-K, 1996-07-22
Next: CORNERCAP GROUP OF FUNDS /VA/, 485BPOS, 1996-07-22



<PAGE>   1

                           A MESSAGE TO SHAREHOLDERS

DEAR SHAREHOLDER:

         The declining interest rate environment that prevailed for most of
fiscal 1995 reversed course during the first six months of our current fiscal
year. Short-term tax-exempt yields, after falling through late February,
stabilized and then abruptly rose to end the six-month period slightly higher
than where they began. Long-term tax-exempt yields also moved lower at the
outset of the period, before creeping higher to end above their starting point.
This overall increase in interest rates resulted in lower prices for municipal
bonds.

         During the past twelve months, the net asset values of our Insured
Longer-Term Portfolios were negatively impacted by rising rates, but each
Portfolio's income component more than compensated for any decrease in
principal. Our Money Market Portfolios all gave good accounts of themselves,
providing returns that fully reflect the current level of interest rates. The
table on page 3 of this Report provides detailed results for each of our State
Tax-Free Portfolios, including per share net asset values, dividend and capital
gains distributions, and total returns over the past six and twelve months, as
well as current yields. In summary form, here are the Portfolio highlights:

THE STATE MONEY MARKET PORTFOLIOS--provided total returns ranging from +3.4% to
+3.6% for the past year. As expected, net asset values remained at $1.00 per
share. As the following table illustrates, current yields are in the area of
3.4%, moderately lower than they were twelve months ago:

<TABLE>
<CAPTION>
- -----------------------------------------------------------------
                                           SEVEN-DAY
                                       ANNUALIZED YIELD      
                              -----------------------------------
MONEY MARKET                  MAY 31,      NOV. 30,       MAY 31,
PORTFOLIO                      1996          1995          1995
- -----------------------------------------------------------------
<S>                            <C>           <C>           <C>
CALIFORNIA                     3.39%         3.61%         3.80%
PENNSYLVANIA                   3.44          3.64          3.80
NEW JERSEY                     3.30          3.57          3.71
OHIO                           3.43          3.71          3.92
- -----------------------------------------------------------------
</TABLE>

THE STATE INSURED LONGER-TERM PORTFOLIOS--earned sufficient income to offset
the modest decrease in long-term municipal bond prices, providing total returns
(capital change plus reinvested dividends) ranging from +3.4% to +5.0% for the
twelve months. Despite the swings in interest rates during the period, the
current yields on the Insured Longer-Term Portfolios (roughly 5.2%) are nearly
identical to their levels of twelve months ago.

         To provide some perspective on how our Insured Longer-Term Portfolios
performed during the past year, the table below breaks out the two components
of total return--income return and capital return. As you can see, the positive
contribution of each Portfolio's income return was marginally reduced by its
negative capital return.

<TABLE>
<CAPTION>
- ----------------------------------------------------------------
                                      INVESTMENT RETURNS     
                              ----------------------------------
                                      TWELVE MONTHS ENDED
                                         MAY 31, 1996        
                              ----------------------------------
INSURED LONGER-TERM
PORTFOLIO                     INCOME        CAPITAL        TOTAL
- ----------------------------------------------------------------
<S>                            <C>           <C>           <C>
CALIFORNIA
 INTERMEDIATE-TERM             +5.1%         -0.1%         +5.0%
CALIFORNIA LONG-TERM           +5.5          -1.7          +3.8
NEW YORK                       +5.4          -1.6          +3.8
PENNSYLVANIA                   +5.6          -1.3          +4.3
NEW JERSEY                     +5.3          -1.9          +3.4
OHIO                           +5.4          -1.6          +3.8
FLORIDA                        +5.2          -1.4          +3.8
- ---------------------------------------------------------------
</TABLE>

FIXED-INCOME MARKET REVIEW

Although the Federal Reserve lowered short-term interest rates in December and
January, the bond market fretted over the apparent strength of the U.S. economy
and the possibility of an increase in inflation. During the past six months,
the yield on the long-term U.S. Treasury bond, the benchmark for the bond
market, rose from 6.1% to 6.9%, engendering a price decline of approximately
- -10% (excluding interest income).

         The long-term municipal bond market fared much better. On balance for
the six-month period, yields on high-grade municipal bonds increased less
dramatically (5.5% to 5.9%), resulting in a price



                                      1
<PAGE>   2
decline of only -6%. Yields on top-grade (MIG 1) municipal notes remained
essentially unchanged on balance at 3.7%.

         Although the future direction of interest rate movements is virtually
impossible to predict with any level of accuracy and consistency, the relative
performance of bond funds with comparable quality and maturity guidelines is
surprisingly predictable.  That is to say, bond funds holding similar types of
securities--say, high-quality, long-term municipal bonds--should, on average,
earn roughly equivalent gross returns. What that absolute return will be,
however, is anyone's guess. On the other hand, what can be predicted with some
semblance of accuracy is the relative performance differential due to the
expense ratios of the funds. The average Vanguard Insured Longer-Term
Portfolio, for example, operates with an annual expense ratio of 0.2%, compared
to 0.9% for our average competitor. Therefore, holding all other factors equal,
a typical Vanguard Insured Longer-Term Portfolio begins with an annual income
advantage of +0.7% over a comparable municipal bond fund.

IN SUMMARY

As you may know, one of the benefits of Vanguard's Insured Longer-Term
Portfolios is their municipal bond insurance, which guarantees the timely
payment of principal and interest. These insurance provisions provide
protection against deteriorating creditworthiness within the various
municipalities and add an important level of enhanced safety.

         There are, of course, "costs" associated with insuring our Portfolios
against potential default. First, bonds that are issued with insurance
typically offer slightly lower yields than non-insured bonds. A second cost is
the explicit expense of purchasing insurance on non-insured bonds. Despite
these costs, however, our top-quality Portfolios continue to benefit from our
expense ratio advantage and provide yields that are fully competitive with
those of uninsured municipal bond portfolios.

         Over time, given our high-quality, low-cost advantage, Vanguard State
Tax-Free Portfolios should remain attractive relative to our competitors'
funds. We look forward to reporting to you in further detail in our 1996 Annual
Report six months hence.

Sincerely,

/s/ JOHN C. BOGLE
- -----------------
John C. Bogle
Chairman of the Board

/s/ JOHN J. BRENNAN
- -------------------
John J. Brennan
President

June 8, 1996

Note: Mutual fund data from Lipper Analytical Services, Inc.





                                       2
<PAGE>   3
                              PORTFOLIO STATISTICS

<TABLE>
<CAPTION>                                                                                                                
- -----------------------------------------------------------------------------------------------------------------------------------
                                                         NET ASSET VALUE             INCOME
                       TOTAL                                PER SHARE               DIVIDENDS             TOTAL RETURN
                  NET ASSETS                           -------------------      ------------------      -----------------
                  (MILLIONS)      AVERAGE   AVERAGE    NOV. 30,    MAY 31,       SIX        TWELVE        SIX      TWELVE   CURRENT
PORTFOLIO       MAY 31, 1996     MATURITY   QUALITY*     1995        1996       MONTHS      MONTHS      MONTHS     MONTHS   YIELD**
- -----------------------------------------------------------------------------------------------------------------------------------
<S>                           <C>             <C>      <C>         <C>          <C>          <C>          <C>        <C>       <C>
MONEY MARKET
  CALIFORNIA .......  $1,276      42 DAYS     MIG 1    $ 1.00      $ 1.00       $.017        $.034        +1.7%       +3.5%    3.39%
  PENNSYLVANIA .....   1,306      32 DAYS     MIG 1      1.00        1.00        .017         .035        +1.7        +3.5     3.44
  NEW JERSEY .......     888      57 DAYS     MIG 1      1.00        1.00        .016         .033        +1.6        +3.4     3.30
  OHIO .............     199      60 DAYS     MIG 1      1.00        1.00        .017         .035        +1.7        +3.6     3.43
- -----------------------------------------------------------------------------------------------------------------------------------
INSURED INTERMEDIATE-TERM
  CALIFORNIA .......  $  264    7.4 YEARS       Aaa    $10.44      $10.25       $.254        $.512        +0.6%       +5.0%    4.77%
INSURED LONG-TERM 
  CALIFORNIA .......     978   14.1 YEARS       Aaa     11.27       10.87        .299         .600        -0.9        +3.8     5.33
  NEW YORK .........     879   11.7 YEARS       Aaa     11.01       10.57        .286         .574        -0.8+       +3.8+    5.23
  PENNSYLVANIA .....   1,565   11.4 YEARS       Aaa     11.28       10.90        .304         .608        -0.4+       +4.3+    5.28
  NEW JERSEY .......     796   11.9 YEARS       Aaa     11.78       11.29        .310         .617        -1.1+       +3.4+    5.23
  OHIO .............     203   10.9 YEARS       Aaa     11.63       11.25        .302         .605        -0.7        +3.8     5.29
  FLORIDA ..........     453   14.2 YEARS       Aaa     10.94       10.60        .275         .554        -0.6        +3.8     5.22
- -----------------------------------------------------------------------------------------------------------------------------------
</TABLE>

 * MIG 1 and Aaa are Moody's highest ratings for short-term and long-term
   municipal bonds, respectively.

** Money Market Portfolios' yields are 7-day annualized yields; others are
   30-day SEC yields.

 + Includes capital gains distributions of $.065 for New York, $.037 for
   Pennsylvania, and $.058 for New Jersey.

   Note: The shares of each of the Vanguard "single-state" Portfolios are
   available for purchase solely by residents of the designated states.





                                       3
<PAGE>   4
                          AVERAGE ANNUAL TOTAL RETURNS

THE CURRENT YIELDS QUOTED IN THE MESSAGE TO SHAREHOLDERS ARE CALCULATED IN
ACCORDANCE WITH SEC GUIDELINES. THE AVERAGE ANNUAL TOTAL RETURNS FOR THE
PORTFOLIOS (PERIODS ENDED MARCH 31, 1996) ARE AS FOLLOWS:

<TABLE>
<CAPTION>
                                                                                       SINCE INCEPTION
                                                                              ---------------------------------
                                      INCEPTION                                TOTAL        INCOME      CAPITAL
                                        DATE        1 YEAR       5 YEARS      RETURN        RETURN       RETURN
                                      ---------     ------       -------      ------        ------       ------
<S>                                   <C>            <C>          <C>          <C>           <C>          <C>
CALIFORNIA INSURED INTERMEDIATE-TERM   3/4/94        +7.60%          --        +6.56%        +5.08%       +1.48%
CALIFORNIA INSURED LONG-TERM           4/7/86        +7.73        +8.17%       +7.75         +6.47        +1.28
CALIFORNIA MONEY MARKET                6/1/87        +3.57        +3.12        +4.11         +4.11         0.00
NEW YORK INSURED TAX-FREE              4/7/86        +7.50        +8.37        +7.32         +6.44        +0.88
PENNSYLVANIA INSURED LONG-TERM         4/7/86        +7.15        +8.41        +7.95         +6.64        +1.31
PENNSYLVANIA MONEY MARKET             6/13/88        +3.62        +3.12        +4.11         +4.11         0.00
NEW JERSEY INSURED LONG-TERM           2/3/88        +7.13        +8.10        +8.39         +6.43        +1.96
NEW JERSEY MONEY MARKET                2/3/88        +3.50        +3.08        +4.09         +4.09         0.00
OHIO INSURED LONG-TERM                6/18/90        +7.13        +8.08        +8.50         +5.97        +2.53
OHIO MONEY MARKET                     6/18/90        +3.72        +3.17        +3.49         +3.49         0.00
FLORIDA INSURED TAX-FREE               9/1/92        +7.50           --        +7.62         +5.43        +2.19
</TABLE>

ALL OF THESE DATA REPRESENT PAST PERFORMANCE. THE INVESTMENT RETURN AND
PRINCIPAL VALUE OF AN INVESTMENT WILL FLUCTUATE SO THAT INVESTORS' SHARES, WHEN
REDEEMED, MAY BE WORTH MORE OR LESS THAN THEIR ORIGINAL COST.

PLEASE NOTE THAT AN INVESTMENT IN A MONEY MARKET FUND, SUCH AS THE MONEY MARKET
PORTFOLIOS OF VANGUARD STATE TAX-FREE FUNDS, IS NEITHER INSURED NOR GUARANTEED
BY THE U.S. GOVERNMENT, AND THERE IS NO ASSURANCE THAT THE FUND WILL BE ABLE TO
MAINTAIN A STABLE NET ASSET VALUE OF $1.00 PER SHARE.





                                       4
<PAGE>   5
                       REPORT FROM THE INVESTMENT ADVISER

The two major factors affecting the Longer-Term Insured Portfolios over the
last six months were the sharp rise in interest rates and the relatively better
performance of municipal bonds versus their taxable counterparts. The yield on
the 30-year U.S. Treasury bond increased 0.8 percentage points (from 6.1% to
6.9%). This was a decidedly unpleasant turn of events for bondholders and their
total returns. The increase in interest rates was prompted by signs of an
improving economy and investor concerns about inflation.  During the same
period, the yield on high-grade, long-term municipal bonds rose 0.4 percentage
points (from 5.5% to 5.9%). The question of tax reform first raised by Senator
Armey (R-TX) and later championed by Steve Forbes in the Republican
Presidential primaries seemed to have been, at least in part, answered. The
reduced intensity of the rhetoric around the question of tax reform was a
contributing factor in explaining why the municipal market performed better
than the Treasury market.

         The Federal Reserve Board's last action on January 31, 1996, was to
reduce the Federal funds rate and the discount rate by 0.25 percentage points.
At that time, the economy appeared to be struggling, a situation further
exacerbated by the severity of the winter. Unfortunately for bond investors,
the release of February's economic statistics showed a much stronger than
anticipated economy. Concurrently, an increase in the prices of oil, gasoline,
wheat, and corn prodded some investors to become concerned about the specter of
higher inflation. The combined effects caused the yield on the 30-year U.S.
Treasury bond to increase sharply. The beginning of the Presidential primary
season added an extra degree of uncertainty to the market.

         While bear markets are never pleasant, they often offer investment
opportunities that can be exploited to the shareholders' eventual benefit.
First, the Portfolios' dividend distribution can be positively impacted by
swapping bonds with lower yields to maturity for bonds with higher yields to
maturity. Second, capital gains distributions can usually be reduced by
realizing offsetting capital losses. Finally, bear markets are generally the
best time to buy bonds that have superior protection from early redemption. As
interest rates rise, bonds which are noncallable or have long periods before
they are callable are often available at close to the same price as bonds with
less desirable characteristics. When the time comes for interest rates to
reverse course and fall, these bonds will furnish excellent capital returns
while providing a more stable dividend.

         The past six months have been a very volatile period of time. The
future remains unknown, but the State Insured Longer-Term Portfolios will
continue to focus on their objectives. It is through this commitment to
high-quality Federal and state tax-exempt municipal bonds and low-cost, prudent
management that superior and durable investment results can be achieved.


MONEY MARKETS

The volatility experienced in the Treasury market over the past six months has
had little impact on yields in the short-term municipal bond market. Yields on
one-year municipal notes ended the period very close to where they began,
despite a 0.3% rise in yields on one-year Treasury bills. Nevertheless, there
were two issues which had a substantial impact on the short-term market.
First, seasonal supply constraints that typically plague the short-term
municipal market in the spring dampened the average weighted maturities of
money market funds. Second, and most notably, the Securities and Exchange
Commission (SEC) announced changes in the regulations governing money market
funds which became effective June 3, 1996.

         In April, the SEC adopted amendments to rule 2a-7 under the Investment
Company Act of 1940. Section 2a-7 contains regulations that protect the quality
and safety of money market funds. For the most part, the changes emphasize
higher quality and increased diversification. The new guidelines were designed
to tighten the regulations imposed on tax-exempt money market funds and improve
the likelihood that the funds maintain a stable net asset value. Compliance
with the amendments may prove challenging for the industry. Many of our
competitors operate under somewhat lower quality standards and, as a result,
may be forced to significantly restructure their funds in order to meet the
standards. In contrast, our Money Market Portfolios have





                                       5
<PAGE>   6
always been managed quite conservatively with credit quality our most important
consideration. Consequently, we expect the impact of the changes on Vanguard's
State Tax-Free Money Market Portfolios to be minimal.

         The scarcity of new issue supply in the short-term municipal market
contributed to the relative stability in yields over the period. The supply of
short-term municipals tends to be quite seasonal, the timing of which depends
upon an issuer's fiscal year. The vast majority of issuers have fiscal years
beginning July 1 and ending June 30, causing new issue supply to decline in the
months leading up to June and increase dramatically in July. Looking forward,
the glut of new issue supply should provide ample opportunities for us to
extend our average maturities, increase our diversification, and further
enhance our overall quality.

         In conclusion, the months ahead should be challenging for the
industry, with tighter regulations governing tax-free money market funds coming
at a time when short-term issuance is at its peak. Hopefully, the new
amendments adopted by the SEC will "level the playing field," bringing
competitors closer to Vanguard's already conservative style of management,
thereby further enhancing the performance advantage that arises from our "rock
bottom" expense ratios.

Sincerely,

Ian A. MacKinnon           David E. Hamlin
Senior Vice President      Principal

Pamela W. Tynan            Danine A. Mueller
Principal                  Principal

Reid O. Smith              Jerome J. Jacobs
Principal                  Principal

Vanguard Fixed Income Group

June 18, 1996





                                       6
<PAGE>   7
                            STATEMENT OF NET ASSETS

                                                FINANCIAL STATEMENTS (unaudited)
                                                                    May 31, 1996

<TABLE>
<CAPTION>
                                                             Face         Market
                                                           Amount          Value
                                                            (000)         (000)+
- --------------------------------------------------------------------------------
<S>                                                      <C>            <C>
MUNICIPAL BONDS (98.3%)                                                         
- --------------------------------------------------------------------------------
ISSUER INSURED (80.9%)
  Albany County NY GO
    5.00%, 10/1/05 (3)                                   $  2,000       $  1,981
    5.00%, 10/1/06 (3)                                      3,150          3,105
    5.00%, 10/1/12 (3)                                      4,400          4,040
    7.00%, 1/15/05 (2)                                      1,250          1,351
  Albany NY Municipal Water
    Finance Auth.
    7.50%, 12/1/17 (1)                                      2,080          2,254
  Broome County NY Public Safety
    Facility Project
    5.25%, 4/1/15 (1)                                       3,000          2,764
  Buffalo & Erie NY Toll Bridge Auth.
    6.00%, 1/1/15 (1)                                       4,500          4,510
  Buffalo NY General Improvement
    6.75%, 3/1/06 (1)                                       1,815          1,953
    6.75%, 3/1/07 (1)                                         390            419
    6.75%, 3/1/09 (1)                                         410            439
    6.75%, 3/1/10 (1)                                         380            407
    6.75%, 3/1/11 (1)                                         385            413
  Buffalo NY Municipal Water
    Finance Auth.
    5.75%, 7/1/19 (4)                                       8,500          8,184
  Buffalo NY Sewer Auth. System Rev.
    5.00%, 7/1/12 (3)                                       2,400          2,161
    5.25%, 7/1/08 (3)                                       3,500          3,445
  Duchess County NY Resource
    Recovery Solid Waste System
    7.50%, 1/1/09 (3)                                       2,000          2,172
  Erie County NY GO
    6.10%, 1/15/06 (3)                                      1,865          1,991
    6.125%, 1/15/07 (3)                                     1,660          1,773
    6.125%, 1/15/09 (3)                                       735            780
    6.125%, 1/15/10 (3)                                       735            777
    6.125%, 1/15/11 (3)                                       735            775
    6.125%, 1/15/12 (3)                                       735            773
  Erie County NY Water Auth. Rev.
    0.00%, 12/1/05 (2)                                      3,000          1,877
    0.00%, 12/1/06 (2)                                      6,915          4,059
    VRDO 3.35%, 6/5/96 (2)                                    700            700
    5.00%, 12/1/04 (2)                                      5,920          5,896
    6.00%, 12/1/08 (2)                                      1,600          1,683
  Town of Hempstead NY GO
    5.375%, 8/1/96 (3)                                      1,131          1,134
    5.50%, 8/1/11 (3)                                       2,450          2,413
    5.625%, 2/1/11 (3)                                        890            888
    5.625%, 2/1/12 (3)                                      1,490          1,478
    5.625%, 2/1/13 (3)                                      1,170          1,154
  Huntington NY GO
    5.50%, 4/1/13 (3)                                       3,400          3,327
    6.70%, 2/1/10 (3)                                         375            417
    6.70%, 2/1/11 (3)                                         310            345
  City of Jamestown NY GO
    7.50%, 5/15/02 (2)                                        110            125
    7.50%, 5/15/06 (2)                                        250            295
  Metropolitan Transit Auth.
    of New York
    (Commuter Facilities Rev.)
    5.50%, 7/1/17 (1)                                       2,500          2,357
    5.625%, 7/1/15 (4)                                      5,000          4,844
    6.10%, 7/1/09 (1)                                       6,035          6,364
    6.25%, 7/1/22 (1)                                       3,000          3,053
    (Transportation Facilities Rev.)
    5.40%, 7/1/07 (3)                                      12,000         12,079
    6.00%, 7/1/11 (2)                                       2,000          2,017
    7.00%, 7/1/09 (2)                                      19,050         21,728
  Monroe County NY GO
    (Rochester Water Dist.)
    5.60%, 6/1/04 (3)                                       1,235          1,283
    5.70%, 6/1/05 (3)                                       1,350          1,408
    5.80%, 6/1/06 (3)                                       1,340          1,402
    5.90%, 2/1/07 (3)                                         550            577
  Montgomery, Ostego, Scholoharie
    Counties NY Solid Waste
    5.25%, 1/1/14 (1)                                       1,640          1,516
  Mount Sinai NY Union Free
    School Dist.
    6.20%, 2/15/14 (2)                                      1,050          1,104
    6.20%, 2/15/15 (2)                                        540            566
  Nassau County NY Combined
    Sewer Dist. GO
    4.70%, 10/1/04 (3)                                      1,805          1,759
    4.80%, 10/1/05 (3)                                      1,760          1,711
    4.90%, 10/1/06 (3)                                      1,740          1,694
    5.00%, 10/1/07 (3)                                      1,715          1,664
    5.00%, 10/1/08 (3)                                      1,695          1,626
    5.00%, 5/1/09 (3)                                       3,210          3,046
    5.00%, 5/1/10 (3)                                       2,875          2,699
    5.00%, 5/1/11 (3)                                       1,770          1,648
    5.00%, 5/1/12 (3)                                       1,760          1,622
    5.35%, 7/1/08 (1)                                       4,730          4,715
    5.35%, 1/15/09 (1)                                      3,505          3,462
    5.35%, 7/1/09 (1)                                       4,635          4,576
    5.875%, 8/1/12 (3)                                        825            836
    6.20%, 5/15/07 (1)                                        840            884
    6.20%, 5/15/08 (1)                                        835            880
    6.25%, 5/15/09 (1)                                        825            867
    6.25%, 5/15/10 (1)                                        820            853
  Nassau County NY GO
    5.00%, 11/1/97 (3)                                      7,825          7,951
    5.125%, 3/1/13 (2)                                      5,860          5,428
    5.125%, 3/1/14 (2)                                      5,900          5,420
    5.50%, 7/15/07 (1)                                      1,270          1,286
    5.50%, 7/15/08 (1)                                      1,300          1,306
    5.50%, 7/15/09 (1)                                      1,325          1,321
</TABLE>




                                       7
<PAGE>   8
                      STATEMENT OF NET ASSETS (continued)

<TABLE>
<CAPTION>
                                                             Face         Market
                                                           Amount          Value
                                                            (000)         (000)+
- --------------------------------------------------------------------------------
  <S>                                                    <C>            <C>
    5.50%, 7/15/10 (1)                                   $  1,345       $  1,332
    5.50%, 7/15/11 (1)                                      1,370          1,349
    5.70%, 8/1/11 (3)                                       2,000          2,000
    5.75%, 2/1/11 (1)                                       1,100          1,104
  New York City Cultural Resources
    (Museum of Modern Art)
    5.40%, 1/1/06 (2)                                         805            815
    5.40%, 1/1/12 (2)                                       1,400          1,357
    5.50%, 1/1/07 (2)                                         840            850
  New York City GO
    VRDO 3.65%, 6/4/96 (1)                                    200            200
    5.75%, 8/1/09 (3)                                       4,250          4,294
    6.625%, 8/1/13 (1)                                        675            720
    6.95%, 8/15/12 (1)                                      1,460          1,590
    7.10%, 2/1/09 (1)                                       5,000          5,519
  New York City Health & Hosp. Corp.
    5.625%, 2/15/13 (2)                                    23,400         22,744
  New York City IDA
    (USTA Project)
    6.375%, 11/15/14 (4)                                    2,000          2,078
  New York City Municipal Water
    Finance Auth. Water & Sewer
    System Rev.
    VRDO 3.60%, 6/4/96 (3)                                 12,800         12,800
    VRDO 3.70%, 6/4/96 (3)                                  3,300          3,300
    5.35%, 6/15/13 (1)                                      5,300          4,979
    5.875%, 6/15/12 (2)                                    20,000         20,385
    5.875%, 6/15/13 (2)                                    20,000         20,290
    8.75%, 6/15/97 (6) (Prere.)                             2,500          2,676
  New York State Dormitory Auth.
    (City Univ. of New York)
    6.25%, 7/1/19 (1)                                       4,485          4,561
    7.00%, 7/1/14 (3)                                      20,700         22,381
    (Colgate Univ.)
    6.50%, 7/1/01 (1) (Prere.)                              1,350          1,476
    (Fashion Institute Student
    Housing Corp.)
    7.10%, 7/1/96 (1) (Prere.)                                590            603
    7.20%, 7/1/96 (1) (Prere.)                              3,560          3,640
    (Fordham Univ.)
    5.50%, 7/1/23 (3)                                      10,150          9,500
    5.75%, 7/1/15 (3)                                       1,500          1,473
    7.20%, 7/1/15 (2)                                         710            777
    (Foundling Charities Corp.)
    6.50%, 7/1/12 (1)                                       6,530          6,707
    (Iona College)
    5.25%, 7/1/08 (1)                                       1,000            978
    5.35%, 7/1/09 (1)                                       1,000            976
    7.625%, 7/1/09 (1)                                      5,000          5,378
    (Ithaca College)
    6.25%, 7/1/21 (1)                                      10,000         10,159
    (Mt. Sinai School of Medicine)
    6.75%, 7/1/15 (1)                                       7,245          7,738
    (New York Public Library)
    0.00%, 7/1/06 (1)                                         910            530
    0.00%, 7/1/07 (1)                                       1,000            545
    0.00%, 7/1/08 (1)                                         910            464
    0.00%, 7/1/09 (1)                                         910            432
    0.00%, 7/1/10 (1)                                         500            221
    0.00%, 7/1/11 (1)                                         500            207
    (New York Univ.)
    6.00%, 7/1/15 (3)                                      32,165         32,091
    6.70%, 7/1/96 (1) (Prere.)                              1,250          1,278
    (Rensselaer Polytech. Institute)
    6.50%, 7/1/06 (3)                                       3,000          3,227
    (School Dist.)
    6.00%, 7/1/15 (3)                                       2,675          2,669
    (Siena College)
    6.00%, 7/1/11 (1)                                       1,500          1,520
    (State Univ.)
    5.25%, 7/1/14 (2)                                       1,000            932
    5.30%, 7/1/24 (2)                                       3,380          3,052
    5.75%, 7/1/07 (2)                                       2,250          2,319
    5.75%, 7/1/08 (2)                                       3,335          3,414
    6.00%, 7/1/09 (2)                                       1,590          1,654
    (Union College)
    5.75%, 7/1/10 (3)                                       1,800          1,810
  New York State Energy Research &
    Development Auth. PCR
    (Niagara Mohawk)
    6.625%, 10/1/13 (3)                                    10,000         10,692
  New York State Medical
    Care Facility Finance Agency
    8.00%, 8/15/97 (8) (Prere.)                             5,000          5,338
    (Mental Health Services)
    5.50%, 8/15/21 (3)                                      8,000          7,414
    6.00%, 8/15/15 (1)                                     15,000         15,034
    6.375%, 8/15/10 (3)                                     6,100          6,380
    7.40%, 8/15/07 (1)                                        890            958
    (Sisters of Charity-Buffalo)
    6.625%, 11/1/18 (2)                                     5,500          5,824
  New York State Thruway Auth. Rev.
    5.00%, 1/1/20 (1)                                       3,740          3,263
    5.50%, 1/1/23 (3)                                       6,800          6,334
    6.00%, 1/1/15 (3)                                       2,350          2,345
    6.00%, 1/1/25 (3)                                       9,250          9,100
    (Highway & Bridge Trust Fund)
    5.30%, 4/1/10 (1)                                       3,775          3,634
    5.50%, 4/1/15 (1)                                      12,480         11,916
    5.80%, 4/1/10 (2)                                      14,215         14,377
    5.80%, 4/1/11 (2)                                       8,635          8,701
    6.00%, 4/1/09 (3)                                       5,000          5,161
</TABLE>





                                       8
<PAGE>   9

<TABLE>
<CAPTION>
                                                             Face         Market
                                                           Amount          Value
                                                            (000)         (000)+
- --------------------------------------------------------------------------------
<S>                                                      <C>            <C>
  New York State Urban
    Development Corp.
    5.375%, 1/1/12 (1)                                   $ 21,375       $ 20,492
  Niagara Falls NY Bridge Comm.
    5.25%, 10/1/15 (3)                                      5,000          4,682
    6.25%, 10/1/20 (3)                                      8,685          9,132
    6.25%, 10/1/21 (3)                                      9,230          9,714
  North Hempstead NY GO
    6.30%, 4/1/08 (3)                                       2,055          2,222
    6.40%, 4/1/10 (3)                                       1,500          1,626
    6.40%, 4/1/11 (3)                                       2,075          2,247
  North Hempstead NY Solid
    Waste Auth.
    5.00%, 2/1/12 (1)                                       3,370          3,066
  Oyster Bay Public Improvement
    5.40%, 2/15/03 (1)                                      1,475          1,518
    5.60%, 2/15/05 (1)                                      1,000          1,036
    5.70%, 2/15/07 (1)                                        805            832
    5.70%, 2/15/09 (1)                                        980          1,000
    5.70%, 2/15/11 (1)                                        300            303
  Rochester NY GO
    4.25%, 9/15/97 (2)                                      6,730          6,774
    5.70%, 8/15/03 (2)                                      2,330          2,456
    5.70%, 8/15/04 (2)                                      2,180          2,297
  Smithtown NY GO
    5.25%, 4/1/06 (1)                                       1,000          1,000
    5.45%, 4/1/08 (1)                                         400            400
  Suffolk County NY GO
    4.50%, 8/1/97 (2)                                       1,390         1,402
    5.00%, 4/1/06 (1)                                       2,255          2,215
    5.00%, 7/15/06 (3)                                      1,000            982
    5.10%, 7/15/07 (3)                                      1,280          1,254
    5.20%, 7/15/08 (3)                                      1,100          1,076
  Suffolk County NY Water Auth.
    5.10%, 6/1/07 (1)                                       7,110          6,986
    5.25%, 6/1/04 (2) (Prere.)                             21,305         21,443
    5.25%, 6/1/10 (2) (ETM)                                 3,790          3,738
    5.25%, 6/1/11 (2) (ETM)                                 2,380          2,334
    5.25%, 6/1/12 (2) (ETM)                                 4,290          4,181
    5.25%, 6/1/17 (2)                                       1,695          1,587
    5.75%, 6/1/02 (2) (Prere.)                              1,100          1,170
    5.75%, 6/1/13 (2)                                       7,340          7,316
  Triborough Bridge & Tunnel Auth.
    5.50%, 1/1/17 (2)                                      18,485         17,442
  City of Yonkers NY School Dist. GO
    5.375%, 8/1/96 (3)                                        695            697
    5.375%, 8/1/97 (3)                                        685            698
    5.60%, 8/1/09 (3)                                         565            566
    5.70%, 8/1/10 (3)                                         545            547
    5.75%, 8/1/11 (3)                                         500            502
    5.80%, 8/1/12 (3)                                         500            502
  OUTSIDE NEW YORK:
  Puerto Rico Electric Power
    Auth. Rev.
    6.50%, 7/1/06 (1)                                      10,000         11,068
  Puerto Rico Public Building Auth.
    0.00%, 7/1/03 (3)                                       4,000          2,853
                                                                        --------
        GROUP TOTAL                                                      710,731
                                                                        --------
- --------------------------------------------------------------------------------
PORTFOLIO INSURED (.9%)
  New York State Dormitory Auth.
    (Cornell Univ.)
    6.875%, 7/1/14                                          6,825          6,974
  New York State Energy
    Research & Development
    (Niagara Mohawk Power Corp.)
    8.875%, 11/1/25                                         1,100          1,128
                                                                        --------
        GROUP TOTAL                                                        8,102
                                                                        --------
- --------------------------------------------------------------------------------
SECONDARY MARKET INSURED (8.2%)
  Municipal Assistance Corp. for
    New York City
    6.00%, 7/1/08 (3)                                      22,350         22,928
  New York City Municipal Water
    Finance Auth. Water & Sewer
    System Rev.
    5.00%, 6/15/17 (3)                                      4,000          3,521
  New York State Dormitory Auth.
    (City Univ.)
    5.75%, 7/1/09 (3)                                       3,750          3,826
    5.75%, 7/1/11 (3)                                       5,950          6,010
    (Cornell Univ.)
    7.25%, 7/1/12 (1)                                       1,175          1,286
    (State Univ.)
    6.00%, 5/15/17 (2)                                      5,600          5,554
  New York State Medical
    Care Facilities
    5.375%, 2/15/14 (1)                                     5,000          4,682
  Port Auth. of New York &
    New Jersey
    6.50%, 1/15/26 (1)                                      1,500          1,550
  Triborough Bridge & Tunnel Auth.
    5.00%, 1/1/17 (2)                                         105             93
    5.00%, 1/1/17 (3)                                         395            349
    5.50%, 1/1/19 (2)                                       4,000          3,745
    6.00%, 1/1/12 (1)                                       7,805          8,110
    6.75%, 1/1/09 (2)                                       3,000          3,337
    6.875%, 1/1/15 (3)                                      7,000          7,482
                                                                        --------
        GROUP TOTAL                                                       72,473
                                                                        --------
- --------------------------------------------------------------------------------
</TABLE>





                                       9
<PAGE>   10
                      STATEMENT OF NET ASSETS (continued)

<TABLE>
<CAPTION>
                                                             Face         Market
                                                           Amount          Value
                                                            (000)         (000)+
- --------------------------------------------------------------------------------
<S>                                                      <C>            <C>
NON-INSURED (8.3%)
  Half Hollow Hills NY Central
    School Dist. TAN
    4.25%, 6/28/96                                       $  3,000       $  3,001
  Manhasset NY Union Free School
    Dist. TAN
    4.50%, 6/27/96                                          5,800          5,803
  Metropolitan Transit Auth.
    of New York
    8.375%, 7/1/96 (Prere.)                                 2,590          2,652
  New York City Cultural
    Resources VRDO
    (Carnegie Hall)
    3.35%, 6/5/96 LOC                                         600            600
  New York City GO VRDO
    3.60%, 6/5/96 LOC                                      15,600         15,600
    3.75%, 6/4/96 LOC                                         700            700
    3.80%, 6/5/96 LOC                                       6,100          6,100
  New York Environmental
    Facilities Water PCR
    5.20%, 5/15/14                                          1,500          1,432
  New York Local Govt.
    Assistance Corp. VRDO
    3.45%, 6/5/96 LOC                                       5,200          5,200
  New York State Dormitory Auth.
    (Columbia Univ.)
    5.75%, 7/1/15                                          11,965         11,707
  New York State Power Auth.
    7.00%, 1/1/09                                           6,000          6,332
  Onondaga County NY Public
    Improvements
    5.875%, 2/15/06                                         1,580          1,651
    5.875%, 2/15/08                                         2,475          2,558
  Westchester County NY GO
    6.70%, 11/1/08                                          3,250          3,650
    6.70%, 11/1/09                                          3,645          4,085
  OUTSIDE NEW YORK:
  Puerto Rico Govt. Development Bank
    VRDO 3.25%, 6/5/96 LOC                                  1,500          1,500
                                                                        --------
        GROUP TOTAL                                                       72,571
                                                                        --------
- --------------------------------------------------------------------------------
TOTAL MUNICIPAL BONDS
  (Cost $836,945)                                                        863,877
- --------------------------------------------------------------------------------
OTHER ASSETS AND LIABILITIES (1.7%)                                             
- --------------------------------------------------------------------------------
  Other Assets--Note B                                                    17,731
  Liabilities                                                             (3,095)
                                                                        --------
                                                                          14,636
- --------------------------------------------------------------------------------
NET ASSETS (100%)                                                               
- --------------------------------------------------------------------------------
  Applicable to 83,130,905 outstanding
    shares of beneficial interest
    (unlimited authorization--no par value)                             $878,513
- --------------------------------------------------------------------------------
NET ASSET VALUE PER SHARE                                                 $10.57
================================================================================
</TABLE>

+ See Note A to Financial Statements.

<TABLE>
<CAPTION>
- --------------------------------------------------------------------------------
AT MAY 31, 1996, NET ASSETS CONSISTED OF:                                       
- --------------------------------------------------------------------------------
                                                           Amount            Per
                                                            (000)          Share
                                                         --------        -------
<S>                                                      <C>              <C>
  PAID IN CAPITAL                                        $852,055         $10.25
  Undistributed Net
    Investment Income                                          --             --
  Accumulated Net
    Realized Gains                                             30             --
  Unrealized Appreciation
    (Depreciation)--Note E
    Investment Securities                                  26,932            .33
    Futures Contracts                                        (504)          (.01)
- --------------------------------------------------------------------------------
NET ASSETS                                               $878,513         $10.57
- --------------------------------------------------------------------------------
</TABLE>

BAN=Bond Anticipation Note
COP=Certificate of Participation
CP=Commercial Paper
GO=General Obligation
IDA=Industrial Development Authority Bond
PCR=Pollution Control Revenue
RAN=Revenue Anticipation Note
TAN=Tax Anticipation Note
TOB=Tender Option Bond
TRAN=Tax Revenue Anticipation Note
VRDO=Variable Rate Demand Obligation
(ETM)=Escrowed to Maturity
(Prere.)=Prerefunded

Scheduled principal and interest payments are guaranteed by:
(1) MBIA (Municipal Bond Insurance Association)
(2) AMBAC (AMBAC Indemnity Corporation)
(3) FGIC (Financial Guaranty Insurance Company)
(4) FSA (Financial Security Assurance)
(5) CGI (Capital Guaranty Insurance)
(6) BIGI (Bond Investors Guaranty Insurance)
(7) Connie Lee Inc.
(8) FHA (Federal Housing Authority)
The insurance does not guarantee the market value of the
municipal bonds.

LOC=Scheduled principal and interest payments are guaranteed by
bank letter of credit.





                                       10
<PAGE>   11
                            STATEMENT OF OPERATIONS

<TABLE>
<CAPTION>
                                                                                               Six Months Ended
                                                                                                   May 31, 1996
                                                                                                          (000)
- ---------------------------------------------------------------------------------------------------------------
<S>                                                                                         <C>       <C>
INVESTMENT INCOME
   INCOME . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
      Interest  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                       $  24,033
- ---------------------------------------------------------------------------------------------------------------
            Total Income  . . . . . . . . . . . . . . . . . . . . . . . . . . .                          24,033
- ---------------------------------------------------------------------------------------------------------------
   EXPENSES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
      The Vanguard Group--Note B
         Investment Advisory Services . . . . . . . . . . . . . . . . . . . . .             $ 51
         Management and Administrative  . . . . . . . . . . . . . . . . . . . .              731
         Marketing and Distribution . . . . . . . . . . . . . . . . . . . . . .              101            883
                                                                                            ----               
      Insurance Expense . . . . . . . . . . . . . . . . . . . . . . . . . . . .                              11
      Custodian Fees  . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                              10
      Auditing Fees . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                               4
      Shareholders' Reports . . . . . . . . . . . . . . . . . . . . . . . . . .                              20
      Annual Meeting and Proxy Costs  . . . . . . . . . . . . . . . . . . . . .                               4
      Trustees' Fees and Expenses . . . . . . . . . . . . . . . . . . . . . . .                               1
- ---------------------------------------------------------------------------------------------------------------
            Total Expenses  . . . . . . . . . . . . . . . . . . . . . . . . . .                             933
            Expenses Paid Indirectly--Note C  . . . . . . . . . . . . . . . . .                             (10)
- --------------------------------------------------------------------------------------------------------------- 
               Net Expenses . . . . . . . . . . . . . . . . . . . . . . . . . .                             923
- ---------------------------------------------------------------------------------------------------------------
               Net Investment Income  . . . . . . . . . . . . . . . . . . . . .                          23,110
- ---------------------------------------------------------------------------------------------------------------
REALIZED NET GAIN
      Investment Securities Sold  . . . . . . . . . . . . . . . . . . . . . . .                             537
      Futures Contracts . . . . . . . . . . . . . . . . . . . . . . . . . . . .                             380
- ---------------------------------------------------------------------------------------------------------------
               Realized Net Gain  . . . . . . . . . . . . . . . . . . . . . . .                             917
- ---------------------------------------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)
      Investment Securities . . . . . . . . . . . . . . . . . . . . . . . . . .                         (31,516)
      Futures Contracts . . . . . . . . . . . . . . . . . . . . . . . . . . . .                            (670)
- --------------------------------------------------------------------------------------------------------------- 
               Change in Unrealized Appreciation (Depreciation) . . . . . . . .                         (32,186)
- --------------------------------------------------------------------------------------------------------------- 
               Net Decrease in Net Assets Resulting from Operations . . . . . .                       $  (8,159)
=============================================================================================================== 
</TABLE>





                                       11
<PAGE>   12
                       STATEMENT OF CHANGES IN NET ASSETS

<TABLE>
<CAPTION>
                                                                     SIX MONTHS ENDED           Year Ended
                                                                         MAY 31, 1996    November 30, 1995
                                                                                (000)                (000)
- ----------------------------------------------------------------------------------------------------------
<S>                                                                          <C>                 <C>
INCREASE IN NET ASSETS
OPERATIONS
   Net Investment Income  . . . . . . . . . . . . . . . . . . . .            $ 23,110            $  42,840
   Realized Net Gain  . . . . . . . . . . . . . . . . . . . . . .                 917                2,683
   Change in Unrealized Appreciation (Depreciation)   . . . . . .             (32,186)              92,901
- ----------------------------------------------------------------------------------------------------------
         Net Increase (Decrease) in Net Assets
            Resulting from Operations . . . . . . . . . . . . . .              (8,159)             138,424
- ----------------------------------------------------------------------------------------------------------
DISTRIBUTIONS
   Net Investment Income  . . . . . . . . . . . . . . . . . . . .             (23,110)             (42,840)
   Realized Net Gain  . . . . . . . . . . . . . . . . . . . . . .              (5,071)                   -
- ----------------------------------------------------------------------------------------------------------
         Total Distributions  . . . . . . . . . . . . . . . . . .             (28,181)             (42,840)
- ---------------------------------------------------------------------------------------------------------- 
CAPITAL SHARE TRANSACTIONS (1)
   Issued . . . . . . . . . . . . . . . . . . . . . . . . . . . .             112,866              192,402
   Issued in Lieu of Cash Distributions . . . . . . . . . . . . .              21,052               31,309
   Redeemed . . . . . . . . . . . . . . . . . . . . . . . . . . .             (78,382)            (154,905)
- ---------------------------------------------------------------------------------------------------------- 
         Net Increase from Capital Share Transactions . . . . . .              55,536               68,806
- ----------------------------------------------------------------------------------------------------------
         Total Increase . . . . . . . . . . . . . . . . . . . . .              19,196              164,390
- ----------------------------------------------------------------------------------------------------------
NET ASSETS
   Beginning of Period  . . . . . . . . . . . . . . . . . . . . .             859,317              694,927
- ----------------------------------------------------------------------------------------------------------
   End of Period  . . . . . . . . . . . . . . . . . . . . . . . .            $878,513            $ 859,317
==========================================================================================================
   (1)Shares Issued and Redeemed
      Issued  . . . . . . . . . . . . . . . . . . . . . . . . . .              10,427               18,283
      Issued in Lieu of Cash Distributions  . . . . . . . . . . .               1,941                2,958
      Redeemed  . . . . . . . . . . . . . . . . . . . . . . . . .              (7,274)             (14,879)
- ---------------------------------------------------------------------------------------------------------- 
                                                                                5,094                6,362
- ----------------------------------------------------------------------------------------------------------
</TABLE>





                                       12
<PAGE>   13
                              FINANCIAL HIGHLIGHTS

<TABLE>
<CAPTION>
                                                                                      Year Ended November 30,            
                                                      SIX MONTHS ENDED     ----------------------------------------------
For A Share Outstanding Throughout Each Period            May 31, 1996      1995       1994      1993      1992      1991
- -------------------------------------------------------------------------------------------------------------------------
<S>                                                             <C>      <C>        <C>       <C>       <C>       <C>
NET ASSET VALUE, BEGINNING OF PERIOD  . . . . . . . . . . .     $11.01    $ 9.70     $10.97    $10.45    $10.04    $ 9.66
                                                                ------    ------     ------    ------    ------    ------
INVESTMENT OPERATIONS
   Net Investment Income  . . . . . . . . . . . . . . . . .       .286      .581       .588      .594      .631      .639
   Net Realized and Unrealized Gain (Loss)
      on Investments  . . . . . . . . . . . . . . . . . . .      (.375)    1.310     (1.258)     .665      .410      .380
                                                                ------    ------     ------    ------    ------    ------
         TOTAL FROM INVESTMENT OPERATIONS . . . . . . . . .      (.089)    1.891      (.670)    1.259     1.041     1.019
- -------------------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS
   Dividends from Net Investment Income . . . . . . . . . .      (.286)    (.581)     (.588)    (.594)    (.631)    (.639)
   Distributions from Realized Capital Gains  . . . . . . .      (.065)       --      (.012)    (.145)       --        --
                                                                ------    ------     ------    ------    ------    ------
         TOTAL DISTRIBUTIONS  . . . . . . . . . . . . . . .      (.351)    (.581)     (.600)    (.739)    (.631)    (.639)
- ------------------------------------------------------------------------------------------------------------------------- 
NET ASSET VALUE, END OF PERIOD  . . . . . . . . . . . . . .     $10.57    $11.01     $ 9.70    $10.97    $10.45    $10.04
=========================================================================================================================
TOTAL RETURN  . . . . . . . . . . . . . . . . . . . . . . .     -0.85%   +19.90%     -6.37%   +12.42%   +10.63%   +10.87%
- -------------------------------------------------------------------------------------------------------------------------
RATIOS/SUPPLEMENTAL DATA
- ------------------------
Net Assets, End of Period (Millions)  . . . . . . . . . . .       $879      $859       $695      $807      $574      $408
Ratio of Total Expenses to Average Net Assets . . . . . . .      .21%*      .22%       .22%      .19%     .23%+     .27%+
Ratio of Net Investment Income to
   Average Net Assets . . . . . . . . . . . . . . . . . . .     5.27%*     5.51%      5.60%     5.47%     6.11%     6.48%
Portfolio Turnover Rate . . . . . . . . . . . . . . . . . .        3%*       10%        20%       10%       28%       19%
- -------------------------------------------------------------------------------------------------------------------------
</TABLE>

+Insurance expense represents .01% and .01%.
*Annualized.





                                       13
<PAGE>   14
                         NOTES TO FINANCIAL STATEMENTS

Vanguard New York Insured Tax-Free Fund is registered under the Investment
Company Act of 1940 as an open-end investment company.  The Fund invests in
securities of municipal issuers whose ability to meet their obligations may be
affected by economic and political developments in the State of New York.

A.   The following significant accounting policies are in conformity with
generally accepted accounting principles for investment companies. Such
policies are consistently followed by the Fund in the preparation of financial
statements.

1. SECURITY VALUATION: Municipal bonds are valued utilizing primarily the
   latest bid prices or, if bid prices are not available, on the basis of
   valuations based on a matrix system (which considers such factors as
   security prices, yields, maturities, and ratings), both as furnished by an
   independent pricing service.

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

3. FUTURES: The Fund utilizes Municipal Bond Index, U.S. Treasury Bond, and
   U.S. Treasury Note futures contracts to a limited extent, with the
   objectives of enhancing returns, managing interest rate risk, maintaining
   liquidity, diversifying credit risk and minimizing transaction costs. The
   Fund may purchase futures contracts instead of municipal bonds when futures
   contracts are believed to be priced more attractively than municipal bonds.
   The Fund may also seek to take advantage of price differences among bond
   market sectors by simultaneously buying futures (or bonds) of one market
   sector and selling futures (or bonds) of another sector. Futures contracts
   may also be used to simulate a fully invested position in the underlying
   bonds while maintaining a cash balance for liquidity.  The primary risks
   associated with the use of futures contracts are imperfect correlation
   between changes in market values of bonds held by the Fund and the price of
   futures contracts, and the possibility of an illiquid market. Futures
   contracts are valued based upon their quoted daily settlement prices.
   Fluctuations in the values of futures contracts are recorded as unrealized
   appreciation (depreciation) until terminated at which time realized gains
   (losses) are recognized.  Unrealized appreciation (depreciation) related to
   open futures contracts is required to be treated as realized gain (loss) for
   Federal income tax purposes.

4. DISTRIBUTIONS: Distributions from net investment income are declared on a
   daily basis payable on the first business day of the following month. Annual
   distributions from realized gains, if any, are recorded on the ex-dividend
   date. Capital gain distributions are determined on a tax basis and may
   differ from realized capital gains for financial reporting purposes due to
   differences in the timing of realization of gains.

5. OTHER: Security transactions are accounted for on the date the securities
   are purchased or sold. Costs used in determining realized gains and losses
   on the sale of investment securities are those of specific securities sold.
   Premiums and original issue discounts are amortized and accreted,
   respectively, to interest income over the lives of the respective
   securities.

B.   The Vanguard Group furnishes at cost investment advisory, 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. At May 31, 1996, the Fund had contributed capital of $92,000 to
Vanguard (included in Other Assets), representing .5% of Vanguard's
capitalization. The Fund's officers and trustees are also officers and
directors of Vanguard.





                                       14
<PAGE>   15
C.   The Fund's custodian bank has agreed to reduce its fees when the Fund
maintains cash on deposit in the non-interest bearing custody account. For the
six months ended May 31, 1996, custodian fee offset arrangements reduced the
Fund's expenses by $10,000.

D.   During the six months ended May 31, 1996, the Fund made purchases of
$57,930,000 and sales of $11,876,000 of investment securities other than
temporary cash investments.

E.   At May 31, 1996, unrealized appreciation of investment securities for
financial reporting and Federal income tax purposes aggregated $26,932,000 of
which $32,005,000 related to appreciated securities and $5,073,000 related to
depreciated securities.

At May 31, 1996, the Fund had a long position in U.S. Treasury Bond futures
contracts expiring in September 1996 with an aggregate settlement value and net
unrealized depreciation of $32,582,000 and $504,000, respectively. The market
value of securities deposited as initial margin for open futures contracts was
$5,653,000.





                                       15
<PAGE>   16
                         THE VANGUARD FAMILY OF FUNDS

                               FIXED INCOME FUNDS

MONEY MARKET FUNDS
Vanguard Admiral Funds
U.S. Treasury Money
 Market Portfolio
Vanguard Money Market Reserves
TAX-EXEMPT MONEY MARKET FUNDS
Vanguard Municipal Bond Fund
Money Market Portfolio
Vanguard State Tax-Free Funds
Money Market Portfolios
 (CA, NJ, OH, PA)
TAX-EXEMPT INCOME FUNDS
Vanguard Municipal Bond Fund
Vanguard State Tax-Free Funds
Insured Longer-Term Portfolios
 (CA, FL, NJ, NY, OH, PA)
INCOME FUNDS
Vanguard Admiral Funds
Vanguard Fixed Income
 Securities Fund
Vanguard Preferred Stock Fund


                           EQUITY AND BALANCED FUNDS

GROWTH AND INCOME FUNDS
Vanguard Convertible
 Securities Fund
Vanguard Equity Income Fund
Vanguard Quantitative Portfolios
Vanguard Selected Value Portfolio
Vanguard/Trustees' Equity Fund
U.S. Portfolio
Vanguard/Windsor Fund
Vanguard/Windsor II
BALANCED FUNDS
Vanguard Asset Allocation Fund
Vanguard LifeStrategy Funds
Income Portfolio
Conservative Growth Portfolio
Moderate Growth Portfolio
Growth Portfolio
Vanguard STAR Portfolio
Vanguard/Wellesley Income Fund
Vanguard/Wellington Fund
GROWTH FUNDS
Vanguard/Morgan Growth Fund
Vanguard/PRIMECAP Fund
Vanguard U.S. Growth Portfolio
AGGRESSIVE GROWTH FUNDS
Vanguard Explorer Fund
Vanguard Horizon Fund
Global Equity Portfolio
Global Asset Allocation Portfolio
Capital Opportunity Portfolio
Aggressive Growth Portfolio
Vanguard Specialized Portfolios
INTERNATIONAL FUNDS
Vanguard International
 Growth Portfolio
Vanguard/Trustees' Equity Fund
International Portfolio


                                  INDEX FUNDS

Vanguard Index Trust
Total Stock Market Portfolio
500 Portfolio
Extended Market Portfolio
Growth Portfolio
Value Portfolio
Small Capitalization Stock Portfolio
Vanguard International Equity
 Index Fund
European Portfolio
Pacific Portfolio
Emerging Markets Portfolio
Vanguard Bond Index Fund
Vanguard Tax-Managed Fund
Vanguard Balanced Index Fund


                          [THE VANGUARD GROUP LOGO]

          Vanguard Financial Center    Valley Forge, Pennsylvania 19482
           New Account Information:    Shareholder Account Services:
                   1 (800) 662-7447    1 (800) 662-2739

    This Report has been prepared for shareholders and may be distributed
      to others only if preceded or accompanied by a current prospectus.
       All Funds in the Vanguard Family are offered by prospectus only.


                                  Q762-5/96



VANGUARD
NEW YORK
INSURED
TAX-FREE FUND

SEMI-ANNUAL REPORT
MAY 31, 1996



© 2022 IncJournal is not affiliated with or endorsed by the U.S. Securities and Exchange Commission