View 129 Vails Gate Heights Drive New Windsor, NY MLS# 1002813
$475,000
3

Beds

2.0

Baths

2,257

Sq.Ft.

129 Vails Gate Heights Drive

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 335 Oak Drive New Windsor, NY MLS# 971051
  • Virtual Tour
1 of 35
$469,000
3

Beds

1.1

Baths

1,664

Sq.Ft.

335 Oak Drive

New Windsor, NY

Courtesy of HOWARD HANNA RAND REALTY
View 400 Philo Street New Windsor, NY MLS# 969616
$460,000
3

Beds

1.1

Baths

1,762

Sq.Ft.

400 Philo Street

New Windsor, NY

Courtesy of EXP REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 11 Quassaick Avenue New Windsor, NY MLS# 964500
$456,654
3,900

Sq.Ft.

11 Quassaick Avenue

New Windsor, NY

Courtesy of YOUR MOVE MATTERS LLC
View 3 Regimental Place New Windsor, NY MLS# 987124
  • Virtual Tour
1 of 36
$450,000
3

Beds

1.2

Baths

1,900

Sq.Ft.

3 Regimental Place

New Windsor, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 532 Shore Drive New Windsor, NY MLS# 988669
$449,900
4

Beds

2.0

Baths

1,424

Sq.Ft.

532 Shore Drive

New Windsor, NY

Courtesy of EXP REALTY
View 21 Stonecrest Drive New Windsor, NY MLS# 999560
  • Recently Listed
1 of 36
$449,000
3

Beds

1.0

Baths

1,436

Sq.Ft.

21 Stonecrest Drive

New Windsor, NY

Courtesy of TACTICAL REALTY LLC
View 11 Shaker Court New Windsor, NY MLS# 964605
$445,000
3

Beds

2.1

Baths

1,492

Sq.Ft.

11 Shaker Court

New Windsor, NY

Courtesy of COMPASS GREATER NY, LLC
View 601 Crab Apple Lane New Windsor, NY MLS# 972987
$439,999
3

Beds

2.1

Baths

1,673

Sq.Ft.

601 Crab Apple Lane

New Windsor, NY

Courtesy of KELLER WILLIAMS REALTY NYC GRP
View 15 Riley Road New Windsor, NY MLS# 855497
$439,000
4

Beds

2.1

Baths

1,900

Sq.Ft.

15 Riley Road

New Windsor, NY

Courtesy of ATELIER PROPERTIES LLC
View 117 Sandpiper Lane 1B New Windsor, NY MLS# 949842
$435,000
3

Beds

2.0

Baths

1,510

Sq.Ft.

117 Sandpiper Lane 1B

New Windsor, NY

Courtesy of EASY LIFESTYLE REAL ESTATE
View 20 Cresthaven Drive New Windsor, NY MLS# 998445
    1 of 47
    OPEN HOUSE: Saturday 5/23 12:00 PM - 2:00 PM
    $429,999
    3

    Beds

    2.0

    Baths

    1,216

    Sq.Ft.

    20 Cresthaven Drive

    New Windsor, NY

    Courtesy of HUDSON VALLEY HOME CONNECTION
    View 324 Walnut Avenue New Windsor, NY MLS# 973822
    • Recently Listed
    1 of 20
    $429,000
    3

    Beds

    2.1

    Baths

    1,632

    Sq.Ft.

    324 Walnut Avenue

    New Windsor, NY

    Courtesy of CHARLES J BUSER
    View 11 Ona Lane New Windsor, NY MLS# 20261568
    $425,000
    3

    Beds

    2.1

    Baths

    1,894

    Sq.Ft.

    11 Ona Lane

    New Windsor, NY

    UlsterCountyNY
    Courtesy of CENTURY 21 ALLIANCE-NP
    View 19 Split Tree Drive New Windsor, NY MLS# 967365
    $420,000
    4

    Beds

    2.0

    Baths

    1,836

    Sq.Ft.

    19 Split Tree Drive

    New Windsor, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 1707 Hawthorn Way New Windsor, NY MLS# 995992
    • Recently Listed
    1 of 45
    $420,000
    2

    Beds

    2.1

    Baths

    1,758

    Sq.Ft.

    1707 Hawthorn Way

    New Windsor, NY

    Courtesy of ICONIC PROS
    View 3014 Patrick Henry Court 43 New Windsor, NY MLS# 974757
    $419,900
    3

    Beds

    2.1

    Baths

    2,592

    Sq.Ft.

    3014 Patrick Henry Court 43

    New Windsor, NY

    Courtesy of BHG REAL ESTATE GREEN TEAM
    View 59 Bethlehem Road New Windsor, NY MLS# 993465
    • Recently Listed
    1 of 24
    $410,000
    6

    Beds

    1.0

    Baths

    1,489

    Sq.Ft.

    59 Bethlehem Road

    New Windsor, NY

    Courtesy of KELLER WILLIAMS HUDSON VALLEY
    View 15 Queen Street New Windsor, NY MLS# 860612
    $405,000
    3

    Beds

    1.0

    Baths

    1,350

    Sq.Ft.

    15 Queen Street

    New Windsor, NY

    Courtesy of JOHN J LEASE REALTORS INC
    View 9 Hill View Road New Windsor, NY MLS# 965805
    • Virtual Tour
    1 of 28
    $405,000
    3

    Beds

    1.1

    Baths

    1,331

    Sq.Ft.

    9 Hill View Road

    New Windsor, NY

    Courtesy of REDFIN REAL ESTATE

    About New Windsor

    Located just 15 miles north of the United States Military Academy at West Point New Windsor benefits from a significant degree of tourist trade.  The community boasts a rich historic legacy that includes cultural attractions like the Knox Headquarters, the New Windsor Cantonment, Patton House,  Last Encampment, and Edmonston House.  Serving as a bedroom community as well as a center for limited business activity, this reason is home to commuters and those who are employed locally.  Among the recreational amenities are Crestview Lake, sports leagues, ball fields, playgrounds, tennis courts, a skating rink, a senior center, and supervised programs. Metro-North commuter rail service and buses are available to New York City, and several routes link to major thoroughfares: Routes 94, 32, 207, and 300. LaGuardia, Stewart, and Kennedy international airports are all accessible.

    Listings in New Windsor, NY

    138

    Estimated median home price

    $453,327
    New Windsor NY Homes for Sale & Properties

    Weichert Realtors is one of the nation's leading providers of New Windsor, New York real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in New Windsor, NY.

    Homes for Sale by Price in New Windsor, NY

    PriceCount
    $0 - 100K11
    $100K - 200K6
    $200K - 300K18
    $300K - 400K18
    $400K - 500K29
    $500K - 600K19
    $600K - 700K4
    $700K - 800K9
    $800K - 900K10
    $900K - 1M2
    $1M - Max12

    Homes for Sale by Type in New Windsor, NY

    Property TypeCount
    Single Family83
    Townhouse0
    Condo19
    Commercial15
    Rental35
    Lots and Land10
    Condo/Town/CoOp0
    CoOp6
    Multi Family4
    Mobile Home1
    Farms0

    (Data as of 5/21/2026)

    Information deemed reliable but not guaranteed.

    All information provided is deemed reliable but is not guaranteed and should be independently verified.

    Copyright 2026 by the Multiple Listing service of Ulster County, Inc. All Rights Reserved.

    The data relating to real estate on this web site comes in part from the IDX of the Multiple Listing service of Ulster County, Inc. Real estate listings held by brokerage firms other that Weichert Realtors are marked with IDX logo and the detailed information about them includes the name of the listing broker.

    The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

    The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

    Information Copyright 2021, OneKey® MLS. All Rights Reserved.