VANGUARD NEW YORK INSURED TAX FREE FUND
N-30D, 1995-07-26
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<PAGE>   1

                              CHAIRMAN'S LETTER

DEAR SHAREHOLDER:

During the six months ended May 31, 1995--the first half of the fiscal year for
Vanguard State Tax-Free Portfolios--a fairly substantial decline in long-term
interest rates resulted in higher prices for long-term tax-exempt bonds. These
price increases pushed the six-month total returns (capital change plus income)
of all our Insured Longer-Term Portfolios well into double-digit territory.
While long rates declined during the past six months, shorter-term interest
rates actually increased marginally. In this environment, the yields of our
Money Market Portfolios increased nicely and remained comfortably ahead of the
yields offered by comparable funds.

THE STATE INSURED LONG-TERM PORTFOLIOS

In the wake of repeated interest rate increases by the Federal Reserve during
1994, long-term municipal bond yields peaked in November 1994 at 7.1%. As these
rate hikes seemed to slow the economy's growth, concerns about future inflation
were allayed, and rates began to decline. By the end of May, municipal bond
yields had fallen to 5.8%, a decline of 130 basis points.

         In this environment, longer-term municipal bond funds enjoyed
outstanding returns. Indeed, each of Vanguard's Insured Long-Term Portfolios
provided six-month total returns (capital change plus income) in the area of
+14%. This sharp price rally overwhelmed the negative returns of the prior six
months, bringing our total returns for the twelve months strongly into positive
territory. Although fluctuating net asset values are part and parcel of bond
fund investing, the recent swings in market value demonstrate the benefit of
remaining committed to a long-term investment strategy.

         The table opposite shows the Longer-Term Portfolios' twelve-month
returns, reflecting a full year's income. To provide some perspective on how
fluctuating interest rates have impacted our Insured Longer-Term Portfolios
over this period, the table breaks down our Portfolios' total returns into
their income and capital components. I would emphasize that the table conceals
the fact that the full period was composed of two vastly different six-month
sub-periods, one in which returns were sharply negative, the other strongly
positive.

<TABLE>
<CAPTION>
- -------------------------------------------------------------------------------
                                                         Investment Returns
                                                         Twelve Months Ended
                                                             May 31,1995
                                                     --------------------------
Insured Longer-Term Portfolio                        Income    Capital  Total
- -------------------------------------------------------------------------------
<S>                                                   <C>       <C>       <C>
CALIFORNIA INTERMEDIATE-TERM                          +5.2%     +2.2%     +7.4%
CALIFORNIA LONG-TERM                                  +6.1      +3.8      +9.9
NEW YORK LONG-TERM                                    +6.0      +3.0      +9.0
PENNSYLVANIA LONG-TERM                                +6.2      +2.1      +8.3
NEW JERSEY LONG-TERM                                  +6.0      +3.5      +9.5
OHIO LONG-TERM                                        +5.9      +3.2      +9.1
FLORIDA LONG-TERM                                     +5.8      +3.6      +9.4
- --------------------------------------------------------------------------------
</TABLE>

The current tax-exempt yields on our Insured Longer-Term Portfolios are
presently in the area of 5.2%, compared with 6.3% six months ago. The yield for
each Portfolio is presented in the table on page 3 of this report, which also
includes per share net asset values, dividends, and total returns over the past
six and twelve months.

THE STATE MONEY MARKET PORTFOLIOS

As noted earlier, the Federal Reserve Board has remained relatively
tight-fisted in its monetary policy during the past six months, bringing some
stability to money market yields. This stability is a stark contrast to fiscal
1994, when the Board raised the Fed funds rate (at which banks borrow from one
another) on fully six separate occasions. It would appear that the Fed's tough
policy is bearing fruit: inflation so far remains quite subdued, and business
activity has slowed to a more normal growth rate.

         While rates have been stable in recent months, the table below shows
the impact of the dramatic surge in short-term rates on our annualized yields
over the past year and one-half. You will note that, during this period, the
yields on our Money Market Portfolios have risen by more than 60%.

<TABLE>
<CAPTION>
- ---------------------------------------------------------------------------------
                                                 Seven-Day Annualized Yield
                                          ---------------------------------------
Money Market                              May 31,  Nov. 30,    May 31,   Nov. 30,
Portfolio                                   1995     1994        1994      1993
- ---------------------------------------------------------------------------------
<S>                                          <C>      <C>         <C>      <C>
CALIFORNIA                                   3.8%     3.4%        2.6%     2.3%
PENNSYLVANIA                                 3.8      3.5         2.6      2.3
NEW JERSEY                                   3.7      3.3         2.5      2.2
OHIO                                         3.9      3.5         2.6      2.4
- ---------------------------------------------------------------------------------
</TABLE>

                                                                     (continued)





                                       1
<PAGE>   2
Regardless of future interest rate movements, the yield advantage of our
Vanguard State Money Market Portfolios is virtually certain to remain
attractive relative to other comparable money market funds. The principal
reason for this advantage, as you know, is that our operating expenses are so
much lower than industry norms. Our Portfolios, for example, operate at an
annual expense ratio of about 0.2%, compared with 0.6% for our average
competitor. This advantage of 0.4% carries directly to the bottom line: the
yield you receive. Thus, in a market in which gross yields are, say, 4.0%, our
Portfolios should provide a net yield of 3.8%, compared with 3.4% for other
comparable money market portfolios.

         I want to underscore that our higher yields do not arise from the
ownership of lower quality money market instruments.  The quality of our
Portfolios is, we believe, as high as any tax-exempt money market fund in the
field. Funds which stinted on quality last year ran the risk that their net
asset values might fall below the $1.00 value that investors have come to take
for granted. Our focus on quality--along with, we acknowledge, some good
luck--spared us the consequences of this risk, and we owned no direct
obligations of Orange County, California, the most troubled credit of the
period. Each of our Money Market Portfolios' net asset values remained at $1.00
per share, which as you know, is our objective, but is not guaranteed.

IN SUMMARY

The recent swings in total returns we have witnessed help to demonstrate that
"staying the course"--even in the face of turbulent markets--will more often
than not lead to a successful long-term investment program. In contrast,
attempting to jump into and out of mutual funds in hopes of timing the
movements of the market is almost certain to result in failure.

         Whether rates remain volatile or not, the benefits of investing in
Vanguard State Tax-Free Portfolios endure: high quality, low cost, and
professional management. Along with these advantages, the Portfolios distribute
income that is 100% exempt from both Federal and state income taxes. Together,
these factors should ensure our ability to provide shareholders with efficient
and effective Portfolios in the years to come.

         I look forward to reporting to you on our results for the full year in
our 1995 Annual Report six months hence.

Sincerely,

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

June 9, 1995

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





                                       2
<PAGE>   3
A FEW WORDS ABOUT POSSIBLE CHANGES IN THE TAX LAW

The uncertainties related to a variety of new tax proposals seem to have
unnerved some participants in the tax-exempt bond market.  Of the options which
have been considered, perhaps the most significant to municipal bond investors
is the "flat tax." Indeed, under one proposed version, municipal bond yields
would have no advantage over taxable yields. Because of this uncertainty, the
rise in municipal bond prices has been significantly less than the rise in U.S.
Treasury bond prices over the past few months.

         As a result, the yield on high-quality long-term municipal bonds is at
94% of the yield on taxable U.S. Treasuries giving municipal bonds their
largest after-tax yield advantage in recent years. What this means is that an
investor in the highest marginal tax bracket (40%) would currently earn an
after-tax yield of about 3.8% on a U.S. Treasury bond (60% of 6.4%). A
high-grade municipal bond, on the other hand, would provide a tax-exempt yield
of 6.0%--fully 58% higher. Thus, it would appear that tax uncertainty has
created unusual yield opportunity.

         In any event, the flat tax option is no longer high on the legislative
agenda, and neither of the tax bills adopted by the Senate or the House of
Representatives would disturb the existing tax-exempt status of municipal bond
interest. Until the details of any tax law changes become clearer, we would
caution municipal bond investors to give careful consideration before making
any shifts in their holdings of municipal bonds. In the meantime, we will keep
you abreast of our views on the possible effects of any proposed legislation
that could materially impact the tax status of your municipal bond fund
holdings.

<TABLE>
- ----------------------------------------------------------------------------------------------------------------------------------
                                                              Net Asset Value
                            Total                                Per Share             Dividends          Total Return
                       Net Assets                            ------------------     ----------------    ----------------
                       (millions)       Average   Average    Nov. 30,   May 31,      Six      Twelve     Six      Twelve   Current
Portfolio            May 31, 1995      Maturity   Quality*     1994       1995      Months    Months    Months    Months   Yield**
- ----------------------------------------------------------------------------------------------------------------------------------
<S>                       <C>        <C>          <C>       <C>        <C>         <C>       <C>       <C>       <C>        <C>
MONEY MARKET
  CALIFORNIA    . . . .    $1,114       24 days    MIG 1     $  1.00     $ 1.00     $.019     $.033     + 1.9%      +3.3%     3.80%
  PENNSYLVANIA    . . .     1,148       26 days    MIG 1        1.00       1.00      .018      .033     + 1.9       +3.3      3.80
  NEW JERSEY    . . . .       818       51 days    MIG 1        1.00       1.00      .018      .032     + 1.8       +3.2      3.71
  OHIO    . . . . . . .       166       60 days    MIG 1        1.00       1.00      .019      .033     + 1.9       +3.4      3.92
- ----------------------------------------------------------------------------------------------------------------------------------
INSURED LONG-TERM
  CALIFORNIA
   INTERMEDIATE-TERM       $  171     6.6 years     Aaa      $  9.64     $10.26     $.253     $.499     + 9.2%      +7.4%     4.86%
  CALIFORNIA    . . . .       936    12.7 years     Aaa         9.92      11.06      .301      .606     +14.7       +9.9      5.29
  NEW YORK    . . . . .       799    11.1 years     Aaa         9.70      10.80      .293      .587     +14.5       +9.0      5.18
  PENNSYLVANIA    . . .     1,482    12.8 years     Aaa        10.07      11.08      .308      .625     +13.2       +8.3      5.28
  NEW JERSEY    . . . .       742    10.5 years     Aaa        10.40      11.57      .316      .628     +14.4       +9.5      5.12
  OHIO    . . . . . . .       175     9.5 years     Aaa        10.28      11.43      .307      .611     +14.3       +9.1      5.22
  FLORIDA   . . . . . .       362    13.1 years     Aaa         9.61      10.75      .281      .562     +14.9       +9.4      5.27
- ----------------------------------------------------------------------------------------------------------------------------------
</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.

    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 NOTED IN THE CHAIRMAN'S LETTER ARE CALCULATED IN ACCORDANCE
WITH SEC GUIDELINES. THE AVERAGE ANNUAL TOTAL RETURNS FOR THE PORTFOLIOS
(PERIODS ENDED MARCH 31, 1995) 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         +6.72%           --       +5.61%      +4.96%       +0.65%
CALIFORNIA INSURED LONG-TERM                         4/7/86         +8.14         +8.33%      +7.75       +6.55        +1.20
CALIFORNIA MONEY MARKET                              6/1/87         +3.09         +3.47       +4.18       +4.18         0.00
NEW YORK INSURED TAX-FREE                            4/7/86         +7.84         +8.72       +7.30       +6.54        +0.76
PENNSYLVANIA INSURED LONG-TERM                       4/7/86         +7.54         +8.73       +8.04       +6.75        +1.29
PENNSYLVANIA MONEY MARKET                           6/13/88         +3.04         +3.52       +4.19       +4.19         0.00
NEW JERSEY INSURED LONG-TERM                         2/3/88         +8.06         +8.69       +8.57       +6.55        +2.02
NEW JERSEY MONEY MARKET                              2/3/88         +2.96         +3.48       +4.17       +4.17         0.00
OHIO INSURED LONG-TERM                              6/18/90         +7.57            --       +8.80       +6.08        +2.72
OHIO MONEY MARKET                                   6/18/90         +3.08            --       +3.44       +3.44         0.00
FLORIDA INSURED TAX-FREE                             9/1/92         +8.74            --       +7.68       +5.44        +2.24
</TABLE>

ALL OF THESE DATA REPRESENT PAST PERFORMANCE. THE INVESTMENT RETURN AND
PRINCIPAL VALUE OF AN INVESTMENT WILL FLUCTUATE SO THAT AN INVESTOR'S 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

Two significant events occurred during the first six months of the fiscal year.
The first was the stunning market rally that drove long-term municipal yields
approximately -1.1 percentage points lower. The second was the turmoil
surrounding the bankruptcy of Orange County, California.

MONEY MARKETS

The aggressive tightening of monetary policy by the Federal Reserve Board in
1994 slowed down dramatically in the first half of fiscal year 1995. The only
intervention occurred on February 1, 1995, when the Federal Reserve Board
increased the discount and Federal funds rates 0.5%. Participants in the
short-term municipal market reacted favorably to this relative stability in
interest rates and 1-year notes rallied roughly +1%. While yields on 1-year
notes declined, yields on shorter-term variable rate instruments moved in the
opposite direction, resulting in what is known as a flattening of the
short-term municipal yield curve.  The average weighted maturities of the
Portfolios were positioned at the lower end of their maturity spectrum, and
consequently benefited from this flattening. During the fiscal half, the
average monthly yield on all non-institutional state-specific money funds rose
+0.78%.

         In the upcoming months, increased supply of short-term municipal
issuance should present an opportunity for our Money Market Portfolios to
extend their average maturities, but not at the expense of sacrificing quality.

BOND MARKETS

For the first half of the fiscal year, investors pushed long-term interest
rates lower as economic indices pointed increasingly to slower domestic
economic growth. Investors viewed the slowing as beneficially affecting
inflation. Long-term interest rates declined for virtually the entire six
months. For example, the benchmark 30-year U.S. Treasury bond began the fiscal
year yielding 8.0%, and by the end of May, the yield had fallen -1.4% to 6.6%.
Long-term tax-exempt bond yields followed suit, however, not in quite the same
magnitude as the taxable market. The Bond Buyer 20 Municipal Bond Index yield
declined -1.1% (from 6.9% to 5.8%) over the same period.

         The Florida, New Jersey, New York, Ohio, California, and Pennsylvania
Insured Long-Term Portfolios performed well over the six-month period. The
Portfolios benefited from an extension in their average weighted maturity that
began in the fourth quarter of the last fiscal year. Additionally, the
Portfolios' structure, with superior protection from early calls, aided in
maintaining the price responsiveness of the Portfolios during the market rally.

         Looking ahead there are three main strategies that we expect to pursue
regarding the management of the money invested in the Florida, New Jersey, New
York, Ohio, California, and Pennsylvania Insured Long-Term Portfolios. The
first is a continued focus on improvements in call protection to enhance the
durability of dividends; second is investing to minimize taxable capital gains
distributions when it does not interfere with superior total return potential;
and third is a focus on higher coupon bonds that would position the Portfolios
more defensively should interest rates reverse direction and move higher.

ORANGE COUNTY

During the afternoon of December 1, 1994, reports began to appear in the media
that Orange County, California, had experienced massive losses from its
investment pool in the range of $1.5 billion. Several days later, a news
conference convened by county officials confirmed the losses. On December 6,
acting to prevent creditors from forcing the county to become insolvent, the
officials filed for bankruptcy protection under Chapter 9 of the Federal
Bankruptcy Code. This was the first municipal bankruptcy filing by a major
government since the Great Depression. So far, there have been no major
defaults on bonds by the county or the other 187 government pool participants
(mainly from Orange County). However, if plans for a financial rescue of the
County are not completed before the end of June 1995, a series of defaults
could occur which would rival the $2.5 billion default by the Washington Public
Power Supply System in 1984. Importantly, Vanguard has no direct exposure to
losses stemming from Orange County.

         How this debacle happened is still being discussed and investigated.
The County Treasurer used reverse repurchase agreements to leverage the





                                       5
<PAGE>   6
portfolio to roughly three times the value of the underlying investments. He
then invested about a quarter of the pool in exotic derivative securities which
had coupons that reset inversely to changes in interest rates. As rates rose
rapidly during 1994, the portfolio suffered massive unrealized market value
losses. Orange County was not the only jurisdiction to have experienced massive
investment losses in 1994. Highly publicized, but less serious problems
occurred in the investments of the State of Wisconsin, Cuyahoga County (Ohio),
and Odessa (Texas) Junior College District. As a result, state and local
government investments, investment policies, and investment oversight will be
more carefully scrutinized in the future.

         Nevertheless, the aftershock of the bankruptcy extended well beyond
the boundaries of California, and consequently, all municipal money market
funds experienced its effects. The immediate reaction in the short-term
municipal market resulted in a rise in yields of +0.75 percentage points on all
general market notes. Orange County Tax and Revenue Anticipation Notes, and any
related credits, faced a much more severe crisis with virtually no bid for
these securities. Since then, liquidity for general market notes has returned,
and yields have rallied through their December levels. However, illiquidity
persists for Orange County investors as bondholders negotiate payment on the
notes that are due in July.

         The Orange County bankruptcy underscores the benefit of the additional
layer of credit protection provided by the AAA-rated insurance policies
attached to the bonds that are owned by the State Insured Long-Term Portfolios.
As the bankruptcy story unfolded, most uninsured Orange County investment pool
related bonds were illiquid. In contrast, while insured Orange County related
bonds underperformed other insured bonds by three points, the insured market
was liquid. By late December, much of that underperformance had disappeared,
and at the end of the fiscal half, insured Orange County related bonds were
trading at prices just slightly lower than other insured bonds.

CONCLUSION

The Orange County bankruptcy has reinforced our commitment to rigorous credit
evaluation of the municipal securities in which we invest. This conservative
approach to assessing credit quality combined with Vanguard's low expenses
provides a high-quality investment that is exempt from both Federal and state
income taxes.

Respectfully,

Ian A. MacKinnon
Senior Vice President

Jerome J. Jacobs
Vice President

Pamela W. Tynan
Vice President

David E. Hamlin
Assistant Vice President

Reid O. Smith
Assistant Vice President

Danine A. Mueller
Portfolio Manager

Vanguard Fixed Income Group

June 14, 1995





                                       6
<PAGE>   7
                                                            Financial Statements
                                                                     (unaudited)
                                                                    May 31, 1995

                            STATEMENT OF NET ASSETS

<TABLE>
<CAPTION>
                                                      Face            Market
                                                    Amount             Value
                                                     (000)            (000)+
- ----------------------------------------------------------------------------
<S>                                               <C>            <C>
MUNICIPAL BONDS (98.3%)                                                     
- ----------------------------------------------------------------------------
ISSUER INSURED (77.8%)
  Albany County GO
    5.00%, 10/1/05 (3)                            $  2,000       $     1,998
    5.00%, 10/1/06 (3)                               3,150             3,120
    5.00%, 10/1/12 (3)                               4,400             4,128
    7.00%, 1/15/05 (2)                               1,250             1,387
  Albany Municipal Water
    Finance Auth.
    7.50%, 12/1/17 (1)                               2,080             2,305
  Broome County Public Safety
    Facility Project
    5.25%, 4/1/15 (1)                                3,000             2,851
  Buffalo General Improvement
    6.75%, 3/1/06 (1)                                1,815             2,004
    6.75%, 3/1/07 (1)                                  390               429
    6.75%, 3/1/09 (1)                                  410               448
    6.75%, 3/1/10 (1)                                  380               415
    6.75%, 3/1/11 (1)                                  385               419
  Buffalo Municipal Water
    Finance Auth.
    5.75%, 7/1/19 (4)                                7,450             7,411
  Buffalo Sewer Auth. System Rev.
    5.00%, 7/1/12 (3)                                2,400             2,258
    5.25%, 7/1/08 (3)                                3,500             3,487
  Duchess County Resource Recovery
    7.50%, 1/1/09 (3)                                2,000             2,234
  Erie County GO
    6.10%, 1/15/06 (3)                               1,865             2,016
    6.125%, 1/15/07 (3)                              1,660             1,793
    6.125%, 1/15/09 (3)                                735               790
    6.125%, 1/15/10 (3)                                735               788
    6.125%, 1/15/11 (3)                                735               787
    6.125%, 1/15/12 (3)                                735               785
  Erie County Water Auth.
    VRDO 3.40%, 6/7/95 (2)                           5,800             5,800
    0.00%, 12/1/05 (2)                               3,000             1,772
    0.00%, 12/1/06 (2)                               6,915             3,845
    5.00%, 12/1/04 (2)                               5,920             5,902
    6.00%, 12/1/08 (2)                               1,600             1,688
  Huntington GO
    5.50%, 4/1/13 (3)                                3,400             3,415
    6.70%, 2/1/10 (3)                                  375               424
    6.70%, 2/1/11 (3)                                  310               351
  City of Jamestown GO
    7.50%, 5/15/02 (2)                                 110               128
    7.50%, 5/15/06 (2)                                 250               301
  Metropolitan Transit Auth.
    of New York
    (Commuter Facilities Rev.)
    5.50%, 7/1/17 (1)                                2,500             2,456
    6.10%, 7/1/09 (1)                                6,035             6,448
    6.25%, 7/1/22 (1)                                3,000             3,103
    (Transportation Facilities Rev.)
    5.40%, 7/1/07 (3)                               17,330            17,622
    6.00%, 7/1/11 (2)                                2,000             2,032
    7.00%, 7/1/09 (2)                               13,650            15,872
  Monroe County GO
    (Rochester Water Dist.)
    5.60%, 6/1/04 (3)                                1,235             1,298
    5.70%, 6/1/05 (3)                                1,350             1,424
    5.80%, 6/1/06 (3)                                1,340             1,418
    5.90%, 2/1/07 (3)                                  550               583
  Montgomery, Ostego,
    Scholoharie Counties Solid Waste
    5.25%, 1/1/14 (1)                                1,640             1,581
  Mount Sinai Union Free School Dist.
    6.20%, 2/15/14 (2)                               1,050             1,138
    6.20%, 2/15/15 (2)                                 540               586
  Nassau County GO
    5.50%, 7/15/07 (1)                               1,270             1,291
    5.50%, 7/15/08 (1)                               1,300             1,311
    5.50%, 7/15/09 (1)                               1,325             1,346
    5.50%, 7/15/10 (1)                               1,345             1,355
    5.50%, 7/15/11 (1)                               1,370             1,374
    5.70%, 8/1/11 (3)                                2,000             2,042
    5.75%, 2/1/11 (1)                                1,100             1,124
  Nassau County Combined
    Sewer Dist. GO
    4.70%, 10/1/04 (3)                               1,805             1,761
    4.80%, 10/1/05 (3)                               1,760             1,718
    4.90%, 10/1/06 (3)                               1,740             1,704
    5.00%, 10/1/07 (3)                               1,715             1,682
    5.00%, 10/1/08 (3)                               1,695             1,645
    5.00%, 5/1/09 (3)                                3,210             3,082
    5.00%, 5/1/10 (3)                                2,875             2,724
    5.00%, 5/1/11 (3)                                1,770             1,670
    5.00%, 5/1/12 (3)                                1,760             1,653
    5.35%, 7/1/08 (1)                                4,730             4,747
    5.35%, 1/15/09 (1)                               3,505             3,485
    5.35%, 7/1/09 (1)                                4,635             4,608
    5.875%, 8/1/12 (3)                                 825               844
    6.20%, 5/15/07 (1)                                 840               892
    6.20%, 5/15/08 (1)                                 835               884
    6.25%, 5/15/09 (1)                                 825               875
    6.25%, 5/15/10 (1)                                 820               865
  New York City GO
    5.75%, 8/1/09 (3)                                4,250             4,316
    6.625%, 8/1/13 (1)                                 675               723
    6.95%, 8/15/12 (1)                               1,460             1,643
    7.10%, 2/1/09 (1)                                5,000             5,600
  New York City Cultural Resources
    (Museum of Modern Art)
    5.40%, 1/1/06 (2)                                  805               822
    5.40%, 1/1/12 (2)                                1,400             1,380
    5.50%, 1/1/07 (2)                                  840               858
</TABLE>



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

<TABLE>
<CAPTION>
                                                      Face            Market
                                                    Amount             Value
                                                     (000)            (000)+
- ----------------------------------------------------------------------------
  <S>                                              <C>            <C>
  New York City Health &
    Hosp. Corp.
    5.625%, 2/15/13 (2)                            $23,400        $   23,203
  New York City Industrial
    Development Auth.
    (USTA Proj.)
    6.375%, 11/15/14 (2)                             2,000             2,099
  New York City Municipal Water
    Finance Auth. Water & Sewer
    System Rev.
    VRDO 4.00%, 6/2/95 (3)                           2,100             2,100
    VRDO 4.10%, 6/2/95 (3)                          21,600            21,600
    5.875%, 6/15/12 (2)                             20,000            20,576
    5.875%, 6/15/13 (2)                             20,000            20,527
  New York State Dormitory Auth.
    (City Univ. of New York)
    5.75%, 7/1/11 (3)                                5,950             6,082
    6.25%, 7/1/19 (1)                                4,485             4,651
    7.00%, 7/1/14 (3)                               20,700            22,909
    (Colgate Univ.)
    6.50%, 7/1/21 (1)                                1,350             1,432
    (Fashion Institute Student
    Housing Corp.)
    7.10%, 7/1/03 (1)                                  590               618
    7.20%, 7/1/05 (1)                                1,705             1,787
    7.20%, 7/1/06 (1)                                1,855             1,944
    (Fordham Univ.)
    5.50%, 7/1/23 (2)                               10,150             9,936
    7.20%, 7/1/15 (2)                                  710               792
    (Foundling Charities Corp.)
    6.50%, 7/1/12 (1)                                6,530             6,871
    (Iona College)
    7.625%, 7/1/09 (1)                               5,000             5,519
    (Ithaca College)
    6.25%, 7/1/21 (1)                               10,000            10,332
    (Mt. Sinai School of Medicine)
    6.75%, 7/1/15 (1)                                7,245             7,847
    8.375%, 7/1/95 (3) (Prere.)                        650               665
    (New York Public Library)
    0.00%, 7/1/06 (1)                                  910               509
    0.00%, 7/1/07 (1)                                1,000               525
    0.00%, 7/1/08 (1)                                  910               448
    0.00%, 7/1/09 (1)                                  910               419
    0.00%, 7/1/10 (1)                                  500               216
    0.00%, 7/1/11 (1)                                  500               202
    (New York Univ.)
    6.00%, 7/1/15 (3)                               32,165            32,698
    6.70%, 7/1/96 (1) (Prere.)                       1,250             1,311
    (Rensselaer Polytech. Inst.)
    6.50%, 7/1/06 (3)                                3,000             3,263
    (Siena College)
    6.00%, 7/1/11 (1)                                1,500             1,544
    (Special Act)
    6.00%, 7/1/15 (3)                                2,675             2,705
    (Union College)
    5.75%, 7/1/10 (3)                                1,800             1,829
  New York State Energy Research &
    Development Auth. PCR
    (Niagara Mohawk)
    6.625%, 10/1/13 (3)                             10,000            10,769
  New York State Medical
    Care Facility Finance Agency
    (Mental Health Services)
    5.50%, 8/15/21 (3)                               8,000             7,741
    6.00%, 8/15/95 (1)                              15,000            15,340
    6.375%, 8/15/10 (3)                              6,100             6,465
    7.40%, 8/15/07 (1)                                 890               987
    (St. Mary's Hosp.)
    8.375%, 11/1/95 (2)(Prere.)                      2,200             2,285
    (Sisters of Charity--Buffalo)
    6.625%, 11/1/18 (2)                              5,500             5,882
  New York State Thruway Auth.
    (Highway & Bridge Trust Fund)
    5.80%, 4/1/10 (2)                               14,215            14,523
    6.00%, 4/1/09 (3)                                5,000             5,193
    (GO Rev.)
    5.50%, 1/1/23 (3)                                6,800             6,575
    6.00%, 1/1/15 (3)                                2,350             2,399
    6.00%, 1/1/25 (3)                               10,000            10,192
  New York State Urban
    Development Corp.
    5.375%, 1/1/12 (1)                              14,000            13,706
  Niagara Falls Bridge Comm.
    5.25%, 10/1/15 (3)                               5,000             4,800
    6.25%, 10/1/20 (3)                               8,685             9,468
    6.25%, 10/1/21 (3)                               9,230            10,077
  North Hempstead GO
    6.30%, 4/1/08 (3)                                2,055             2,263
    6.40%, 4/1/10 (3)                                1,500             1,655
    6.40%, 4/1/11 (3)                                2,075             2,284
  North Hempstead Solid
    Waste Auth.
    5.00%, 2/1/12 (1)                                3,370             3,166
  Oyster Bay Public Improvement
    5.40%, 2/15/03 (1)                               1,475             1,531
    5.60%, 2/15/05 (1)                               1,000             1,053
    5.70%, 2/15/07 (1)                                 805               846
    5.70%, 2/15/09 (1)                                 980             1,012
    5.70%, 2/15/11 (1)                                 300               309
  Rochester GO
    5.70%, 8/15/03 (2)                               2,330             2,493
    5.70%, 8/15/04 (2)                               2,180             2,333
</TABLE>





                                       8
<PAGE>   9
<TABLE>
<CAPTION>
                                                      Face            Market
                                                    Amount             Value
                                                     (000)            (000)+
- ----------------------------------------------------------------------------
<S>                                              <C>             <C>
  Smithtown
    5.25%, 4/1/06 (1)                            $   1,000       $     1,011
    5.45%, 4/1/08 (1)                                  400               404
  Suffolk County GO
    5.00%, 4/1/06 (1)                                2,255             2,234
    5.00%, 7/15/06 (3)                               1,000               991
    5.10%, 7/15/07 (3)                               1,280             1,267
    5.20%, 7/15/08 (3)                               1,100             1,089
  Suffolk County Southwest
    Sewer Dist. GO
    6.40%, 2/1/03 (3)                                1,190             1,230
  Suffolk County Water Auth.
    5.10%, 6/1/07 (1)                                7,110             7,041
    5.25%, 6/1/02 (2) (Prere.)                      21,305            22,078
    5.25%, 6/1/10 (2) (ETM)                          3,790             3,713
    5.25%, 6/1/11 (2) (ETM)                          2,380             2,315
    5.25%, 6/1/12 (2) (ETM)                          4,290             4,163
    5.25%, 6/1/17 (2)                                1,695             1,627
    5.75%, 6/1/02 (2) (Prere.)                       1,100             1,188
    5.75%, 6/1/13 (2)                                7,340             7,422
  Triborough Bridge & Tunnel Auth.
    5.50%, 1/1/17 (2)                               18,485            18,197
OUTSIDE NEW YORK:
  Puerto Rico Public Building Auth.
    0.00%, 7/1/03 (3)                                4,000             2,681
                                                                   ---------
          GROUP TOTAL                                                622,221
                                                                   ---------
- ----------------------------------------------------------------------------
PORTFOLIO INSURED (1.1%)
  New York State Dormitory Auth.
    (Cornell Univ.)
    6.875%, 7/1/14                                   6,825             7,107
  New York State Energy
    Research & Development
    (Niagara Mohawk Power Corp.)
    8.875%, 11/1/25                                  1,100             1,142
  Port Auth. of New York &
    New Jersey
    8.70%, 7/15/20                                     750               780
                                                                   ---------
          GROUP TOTAL                                                  9,029
                                                                   ---------
- ----------------------------------------------------------------------------
SECONDARY MARKET INSURED (7.9%)
  Municipal Assistance Corp. for
    New York City
    6.00%, 7/1/08 (3)                               22,350            23,141
  New York City Municipal Water
    Finance Auth. Water & Sewer
    System Rev.
    5.00%, 6/15/17 (3)                               4,000             3,660
  New York State Dormitory Auth.
    (City Univ. of New York)
    5.75%, 7/1/09 (3)                                3,750             3,874
    (Cornell Univ.)
    7.25%, 7/1/12 (1)                                1,175             1,304
    (State Univ.)
    6.00%, 5/15/17 (2)                               5,600             5,655
  Port Auth. of New York &
    New Jersey
    6.50%, 1/15/26 (1)                               1,500             1,580
  Triborough Bridge &
    Tunnel Auth.
    5.00%, 1/1/17 (2)                                  105                97
    5.00%, 1/1/17 (3)                                  395               366
    5.50%, 1/1/19 (2)                                4,000             3,922
    6.00%, 1/1/12 (1)                                7,805             8,191
    6.75%, 1/1/09 (2)                                3,000             3,386
    6.875%, 1/1/15 (3)                               7,000             7,642
                                                                   ---------
          GROUP TOTAL                                                 62,818
                                                                   ---------
- ----------------------------------------------------------------------------
NON-INSURED (11.5%)
  Erie County BAN
    4.75%, 8/15/95                                   7,000             7,011
  Metropolitan Transit Auth.
    of New York
    (Transit Auth. Rev.)
    8.375%, 7/1/96 (Prere.)                          2,590             2,757
  New York City GO VRDO
    3.90%, 6/7/95 (LOC)                              4,800             4,800
    4.02%, 6/7/95 (LOC)                              7,100             7,100
    4.05%, 6/2/95 (LOC)                             11,800            11,800
    4.10%, 6/2/95 (LOC)                             10,000            10,000
  New York Environmental
    Facilities PCR
    5.20%, 5/15/14                                   1,500             1,388
  New York Local Govt.
    Assistance Corp. VRDO
    3.30%, 6/7/95 (LOC)                              3,100             3,100
  New York State Dormitory Auth.
    (Columbia Univ.)
    5.75%, 7/1/15                                   11,965            11,964
  New York State Energy Research
    & Development Auth. PCR
    (Long Island Lighting Co.)
    4.70%, 3/1/96 (LOC)*                             5,000             5,029
  New York State Power Auth.
    7.00%, 1/1/09                                    6,000             6,419
  Onondaga County Public
    Improvements
    5.875%, 2/15/06                                  1,580             1,668
    5.875%, 2/15/08                                  2,475             2,607
  Triborough Bridge & Tunnel Auth.
    TOB VRDO
    4.00%, 6/8/95                                    3,200             3,200
</TABLE>





                                       9
<PAGE>   10
                      STATEMENT OF NET ASSETS (continued)
                                       
<TABLE>
<CAPTION>
                                                      Face            Market
                                                    Amount             Value
                                                     (000)            (000)+
- ----------------------------------------------------------------------------
<S>                                               <C>             <C>
  Westchester County GO
    6.70%, 11/1/08                                $  3,250        $    3,734
    6.70%, 11/1/09                                   3,645             4,175
OUTSIDE NEW YORK:
  Puerto Rico Govt. Development
    Bank VRDO
    3.45%, 6/7/95 (LOC)                              5,000             5,000
                                                                  ----------
          GROUP TOTAL                                                 91,752
                                                                  ----------
- ----------------------------------------------------------------------------
TOTAL MUNICIPAL BONDS
  (Cost $743,576)                                                    785,820
- ----------------------------------------------------------------------------
OTHER ASSETS AND LIABILITIES (1.7%)                                         
- ----------------------------------------------------------------------------
  Other Assets--Note B                                                15,645
  Liabilities                                                         (2,037)
                                                                  ---------- 
                                                                      13,608
- ----------------------------------------------------------------------------
NET ASSETS (100%)                                                           
- ----------------------------------------------------------------------------
  Applicable to 74,028,652 outstanding
    shares of beneficial interest
    (unlimited authorization--no par value)                         $799,428
- ----------------------------------------------------------------------------
NET ASSET VALUE PER SHARE                                             $10.80
============================================================================
</TABLE>

+See Note A to Financial Statements.

- ----------------------------------------------------------------------------
AT MAY 31, 1995, NET ASSETS CONSISTED OF:                 
- ----------------------------------------------------------------------------
<TABLE>
<CAPTION>
                                                    Amount               Per
                                                     (000)             Share
                                                 ---------         ---------
<S>                                               <C>                 <C>
  Paid in Capital                                 $753,366            $10.17
  Undistributed Net
    Investment Income                                   --                --
  Accumulated Net
    Realized Gains                                   4,155               .06
  Unrealized Appreciation
    of Investments--Note D                          41,907               .57
- ----------------------------------------------------------------------------
NET ASSETS                                        $799,428            $10.80
- ----------------------------------------------------------------------------
</TABLE>

BAN=Bond Anticipation Note

COP=Certificate of Participation

CP=Commercial Paper

GO=General Obligation

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

*Put Option Obligation.


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, 1995
                                                                                                             (000)
- ------------------------------------------------------------------------------------------------------------------
<S>                                                                                       <C>              <C>
INVESTMENT INCOME
  INCOME
    Interest  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                              $21,890
- ------------------------------------------------------------------------------------------------------------------
          Total Income  . . . . . . . . . . . . . . . . . . . . . . . . . . .                               21,890
- ------------------------------------------------------------------------------------------------------------------
  EXPENSES
    The Vanguard Group--Note B
      Investment Advisory Services  . . . . . . . . . . . . . . . . . . . . .             $   47
      Management and Administrative   . . . . . . . . . . . . . . . . . . . .                669
      Marketing and Distribution  . . . . . . . . . . . . . . . . . . . . . .                 82               798
                                                                                          ------                  
    Insurance Expense   . . . . . . . . . . . . . . . . . . . . . . . . . . .                                   13
    Auditing Fees   . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                                    4
    Shareholders' Reports   . . . . . . . . . . . . . . . . . . . . . . . . .                                   19
    Annual Meeting and Proxy Costs  . . . . . . . . . . . . . . . . . . . . .                                    2
    Trustees' Fees and Expenses   . . . . . . . . . . . . . . . . . . . . . .                                    1
- ------------------------------------------------------------------------------------------------------------------
          Total Expenses  . . . . . . . . . . . . . . . . . . . . . . . . . .                                  837
- ------------------------------------------------------------------------------------------------------------------
            Net Investment Income   . . . . . . . . . . . . . . . . . . . . .                               21,053
- ------------------------------------------------------------------------------------------------------------------
REALIZED NET GAIN
    Investment Securities Sold  . . . . . . . . . . . . . . . . . . . . . . .                                2,531
    Futures Contracts   . . . . . . . . . . . . . . . . . . . . . . . . . . .                                  123
- ------------------------------------------------------------------------------------------------------------------
            Realized Net Gain   . . . . . . . . . . . . . . . . . . . . . . .                                2,654
- ------------------------------------------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION
  (DEPRECIATION)
    Investment Securities   . . . . . . . . . . . . . . . . . . . . . . . . .                               74,595
    Futures Contracts   . . . . . . . . . . . . . . . . . . . . . . . . . . .                                1,599
- ------------------------------------------------------------------------------------------------------------------
          Change in Unrealized
            Appreciation (Depreciation)   . . . . . . . . . . . . . . . . . .                               76,194
- ------------------------------------------------------------------------------------------------------------------
          Net Increase in Net Assets
            Resulting from Operations   . . . . . . . . . . . . . . . . . . .                              $99,901
==================================================================================================================
</TABLE>





                                      11
<PAGE>   12
                      STATEMENT OF CHANGES IN NET ASSETS

<TABLE>
<CAPTION>
                                                                                SIX MONTHS ENDED        Year Ended
                                                                                         MAY 31,      November 30,
                                                                                            1995              1994
                                                                                           (000)             (000)
- ------------------------------------------------------------------------------------------------------------------
<S>                                                                                    <C>              <C>
INCREASE (DECREASE) IN NET ASSETS
OPERATIONS
  Net Investment Income   . . . . . . . . . . . . . . . . . . . . . . . . . .           $ 21,053         $  43,141
  Realized Net Gain   . . . . . . . . . . . . . . . . . . . . . . . . . . . .              2,654             1,995
  Change in Unrealized Appreciation (Depreciation)  . . . . . . . . . . . . .             76,194           (95,745)
- ------------------------------------------------------------------------------------------------------------------ 
      Net Increase (Decrease) in Net Assets Resulting from Operations   . . .             99,901           (50,609)
- ------------------------------------------------------------------------------------------------------------------ 
DISTRIBUTIONS (1)
  Net Investment Income   . . . . . . . . . . . . . . . . . . . . . . . . . .            (21,053)          (43,141)
  Realized Net Gain   . . . . . . . . . . . . . . . . . . . . . . . . . . . .                 --              (855)
- ------------------------------------------------------------------------------------------------------------------ 
      Total Distributions   . . . . . . . . . . . . . . . . . . . . . . . . .            (21,053)          (43,996)
- ------------------------------------------------------------------------------------------------------------------ 
CAPITAL SHARE TRANSACTIONS (2)
  Issued    --Regular   . . . . . . . . . . . . . . . . . . . . . . . . . . .             67,279           144,207
            --In Lieu of Cash Distributions   . . . . . . . . . . . . . . . .             15,408            32,859
            --Exchange  . . . . . . . . . . . . . . . . . . . . . . . . . . .             33,616            49,547
  Redeemed  --Regular   . . . . . . . . . . . . . . . . . . . . . . . . . . .            (44,653)         (129,929)
            --Exchange  . . . . . . . . . . . . . . . . . . . . . . . . . . .            (45,997)         (114,519)
- ------------------------------------------------------------------------------------------------------------------ 
      Net Increase (Decrease) from Capital Share Transactions   . . . . . . .             25,653           (17,835)
- ------------------------------------------------------------------------------------------------------------------ 
      Total Increase (Decrease)     . . . . . . . . . . . . . . . . . . . . .            104,501          (112,440)
- ------------------------------------------------------------------------------------------------------------------ 
NET ASSETS
  Beginning of Period   . . . . . . . . . . . . . . . . . . . . . . . . . . .            694,927           807,367
- ------------------------------------------------------------------------------------------------------------------
  End of Period   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .           $799,428         $ 694,927
==================================================================================================================
  (1) Distributions Per Share
      Net Investment Income   . . . . . . . . . . . . . . . . . . . . . . . .              $.293             $.588
      Realized Net Gain   . . . . . . . . . . . . . . . . . . . . . . . . . .                 --             $.012
- ------------------------------------------------------------------------------------------------------------------
  (2) Shares Issued and Redeemed
      Issued  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              9,767            18,358
      Issued in Lieu of Cash Distributions  . . . . . . . . . . . . . . . . .              1,480             3,139
      Redeemed  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .             (8,893)          (23,433)
- ------------------------------------------------------------------------------------------------------------------ 
                                                                                           2,354            (1,936)
- ------------------------------------------------------------------------------------------------------------------ 
</TABLE>





                                      12
<PAGE>   13
                             FINANCIAL HIGHLIGHTS

<TABLE>
<CAPTION>
                                                                                  Year Ended November 30,
                                                 SIX MONTHS ENDED    -----------------------------------------------
For a Share Outstanding Throughout Each Period       MAY 31, 1995      1994      1993       1992      1991      1990
- --------------------------------------------------------------------------------------------------------------------
<S>                                                       <C>       <C>       <C>        <C>        <C>       <C>
NET ASSET VALUE, BEGINNING OF PERIOD    . . . . . . .       $9.70    $10.97    $10.45     $10.04     $9.66     $9.73
                                                            -----    ------    ------     ------     -----     -----
INVESTMENT OPERATIONS
  Net Investment Income   . . . . . . . . . . . . . .        .293      .588      .594       .631      .639      .629
  Net Realized and Unrealized Gain (Loss)
    on Investments  . . . . . . . . . . . . . . . . .       1.100    (1.258)     .665       .410      .380     (.070)
                                                            -----    ------    ------     ------     -----     ----- 
      TOTAL FROM INVESTMENT OPERATIONS    . . . . . .       1.393     (.670)    1.259      1.041     1.019      .559
- --------------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS
  Dividends from Net Investment Income  . . . . . . .       (.293)    (.588)    (.594)     (.631)    (.639)    (.629)
  Distributions from Realized Capital Gains . . . . .          --     (.012)    (.145)        --        --        --
                                                            -----    ------    ------     ------     -----     -----
      TOTAL DISTRIBUTIONS   . . . . . . . . . . . . .       (.293)    (.600)    (.739)     (.631)    (.639)    (.629)
- -------------------------------------------------------------------------------------------------------------------- 
NET ASSET VALUE, END OF PERIOD    . . . . . . . . . .      $10.80     $9.70    $10.97     $10.45    $10.04     $9.66
====================================================================================================================
TOTAL RETURN    . . . . . . . . . . . . . . . . . . .     +14.51%    -6.37%   +12.42%    +10.63%   +10.87%    +5.99%
- --------------------------------------------------------------------------------------------------------------------
RATIOS/SUPPLEMENTAL DATA
- ------------------------
Net Assets, End of Period (Millions)  . . . . . . . .        $799      $695      $807       $574      $408      $241
Ratio of Expenses to Average Net Assets . . . . . . .       .23%*      .22%      .19%       .23%+     .27%+     .31%+
Ratio of Net Investment Income to
  Average Net Assets  . . . . . . . . . . . . . . . .      5.68%*     5.60%     5.47%      6.11%     6.48%     6.60%
Portfolio Turnover Rate . . . . . . . . . . . . . . .        15%*       20%       10%        28%       19%       17%
- --------------------------------------------------------------------------------------------------------------------
</TABLE>

+Insurance expense represents .01%, .01%, and .02%.

*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, Inc. 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, 1995, the Fund had contributed capital of $108,000 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
                   NOTES TO FINANCIAL STATEMENTS (continued)

The Fund's investment adviser may direct certain new issue portfolio trades,
subject to obtaining the best price and execution, to underwriters who have
agreed to rebate or credit to the Fund a portion of the underwriting fees
generated. Such rebates or credits are used solely to reduce the Fund's
administrative expenses. For the six months ended May 31, 1995, directed
brokerage arrangements reduced the Fund's expenses by $46,000 (an annual rate
of .01 of 1% of average net assets.)

C. During the six months ended May 31, 1995, the Fund made purchases of
$52,984,000 and sales of $58,940,000 of investment securities other than
temporary cash investments.

At November 30, 1994, the Fund had available a capital loss carryforward of
$435,000 to offset future net capital gains through November 30, 2002.

D. At May 31, 1995, unrealized appreciation of investment securities for
financial reporting and Federal income tax purposes aggregated $42,244,000 of
which $43,689,000 related to appreciated securities and $1,445,000 related to
depreciated securities.

At May 31, 1995, the aggregate settlement value of short positions in Municipal
Bond Index futures contracts expiring in June 1995, the related unrealized
depreciation, and the market value of securities deposited as an initial margin
for open futures contracts were $8,116,000, $337,000, and $5,902,000,
respectively.





                                       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/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 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]

<TABLE>
          <S>                             <C>
          Vanguard Financial Center       Valley Forge, Pennsylvania 19482

          New Account Information:        Shareholder Account Services:
                   1-(800) 662-7447       1-(800) 662-2739
</TABLE>

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.
                                      
                                   Q762-5/95



VANGUARD
NEW YORK
INSURED
TAX-FREE FUND


SEMI-ANNUAL REPORT
MAY 31, 1995


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