View 15 Guernsey Drive New Windsor, NY MLS# 1014088
    1 of 34
    OPEN HOUSE: Saturday 6/20 12:00 PM - 2:30 PM
    $525,000
    4

    Beds

    2.1

    Baths

    2,052

    Sq.Ft.

    15 Guernsey Drive

    New Windsor, NY

    Courtesy of KELLER WILLIAMS VILLAGE SQ RLT
    View 21 Continental Drive New Windsor, NY MLS# 1013279
    • Recently Listed
    1 of 32
    $469,500
    3

    Beds

    1.1

    Baths

    1,344

    Sq.Ft.

    21 Continental Drive

    New Windsor, NY

    Courtesy of RE/MAX BENCHMARK REALTY GROUP
    View 20 Hudson Drive New Windsor, NY MLS# 1014237
    • Recently Listed
    1 of 44
    $470,000
    3

    Beds

    1.2

    Baths

    1,410

    Sq.Ft.

    20 Hudson Drive

    New Windsor, NY

    Courtesy of TACTICAL REALTY LLC
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 16 Bivona Lane Lot 136 New Windsor, NY MLS# 20263289
    $110,000
    3

    Beds

    2.0

    Baths

    1,152

    Sq.Ft.

    16 Bivona Lane Lot 136

    New Windsor, NY

    UlsterCountyNY
    Courtesy of AMODIO REAL ESTATE & PROP
    View 5 Oak Ridge Drive New Windsor, NY MLS# 999959
    • Recently Listed with Virtual Tour
    1 of 40
    $480,000
    3

    Beds

    1.1

    Baths

    1,350

    Sq.Ft.

    5 Oak Ridge Drive

    New Windsor, NY

    Courtesy of HUDSON VALLEY HOME CONNECTION
    View 20 Hilltop Drive New Windsor, NY MLS# 979998
    • Recently Listed
    1 of 21
    $389,900
    2

    Beds

    2.0

    Baths

    1,152

    Sq.Ft.

    20 Hilltop Drive

    New Windsor, NY

    Courtesy of EXP REALTY
    View 10 Oakwood Terrace 101 New Windsor, NY MLS# 1012422
    $270,000
    2

    Beds

    1.1

    Baths

    1,200

    Sq.Ft.

    10 Oakwood Terrace 101

    New Windsor, NY

    Courtesy of KRISTINA OLSEN
    View 6 Lannis Avenue New Windsor, NY MLS# 1011969
    • Recently Listed
    1 of 12
    $389,000
    3

    Beds

    2.1

    Baths

    2,148

    Sq.Ft.

    6 Lannis Avenue

    New Windsor, NY

    Courtesy of EREALTY ADVISORS, INC
    View 140 Mount Airy Road New Windsor, NY MLS# 1010746
    • Recently Listed
    1 of 3
    $72,500
    Studio

    Beds

    0.0

    Baths

    56,628

    Sq.Ft.

    140 Mount Airy Road

    New Windsor, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 13 Clarkview Road New Windsor, NY MLS# 1010649
    • Recently Listed
    1 of 43
    $489,000
    4

    Beds

    2.0

    Baths

    1,320

    Sq.Ft.

    13 Clarkview Road

    New Windsor, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 150 Mount Airy Road New Windsor, NY MLS# 1010275
    • Recently Listed
    1 of 48
    $549,900
    5

    Beds

    4.0

    Baths

    2,790

    Sq.Ft.

    150 Mount Airy Road

    New Windsor, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 18 Square Hill Lot 48 Road 48 New Windsor, NY MLS# 1008800
    $99,000
    2

    Beds

    2.0

    Baths

    1,344

    Sq.Ft.

    18 Square Hill Lot 48 Road 48

    New Windsor, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 2898 Route 9W, Lot 15 New Windsor, NY MLS# 986238
    • Recently Listed
    1 of 13
    $84,900
    2

    Beds

    1.0

    Baths

    784

    Sq.Ft.

    2898 Route 9W, Lot 15

    New Windsor, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 1505 Balsam Drive New Windsor, NY MLS# 1010026
    • Recently Listed with Virtual Tour
    1 of 50
    $450,000
    2

    Beds

    3.0

    Baths

    2,020

    Sq.Ft.

    1505 Balsam Drive

    New Windsor, NY

    Courtesy of EXP REALTY
    View 8 Shaker Court New Windsor, NY MLS# 1009500
    • Recently Listed
    1 of 32
    $524,999
    5

    Beds

    2.1

    Baths

    2,821

    Sq.Ft.

    8 Shaker Court

    New Windsor, NY

    Courtesy of KELLER WILLIAMS RLTY INTEGRITY
    View 584 Shore Drive New Windsor, NY MLS# 1009591
    • Recently Listed
    1 of 35
    $550,000
    4

    Beds

    2.1

    Baths

    1,512

    Sq.Ft.

    584 Shore Drive

    New Windsor, NY

    Courtesy of UNITED RE HUDSON VALLEY EDGE
    View 333 Oak Drive New Windsor, NY MLS# 1001297
    • Recently Listed
    1 of 46
    $385,000
    2

    Beds

    1.0

    Baths

    942

    Sq.Ft.

    333 Oak Drive

    New Windsor, NY

    Courtesy of RE/MAX BENCHMARK REALTY GROUP
    View 1103 Washington Green New Windsor, NY MLS# 1007338
    • Recently Listed with Virtual Tour
    1 of 21
    $325,000
    2

    Beds

    2.0

    Baths

    1,029

    Sq.Ft.

    1103 Washington Green

    New Windsor, NY

    Courtesy of RE/MAX BENCHMARK REALTY GROUP
    View 28 Park Hill Drive New Windsor, NY MLS# 1003023
    • Recently Listed with Virtual Tour
    1 of 50
    $499,900
    3

    Beds

    2.1

    Baths

    1,513

    Sq.Ft.

    28 Park Hill Drive

    New Windsor, NY

    Courtesy of RE-MAX EXPERIENCE
    View 12 Elizabeth Lane New Windsor, NY MLS# 999345
    $299,000
    3

    Beds

    1.0

    Baths

    1,896

    Sq.Ft.

    12 Elizabeth Lane

    New Windsor, NY

    Courtesy of EREALTY ADVISORS, INC

    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

    148

    Estimated median home price

    $467,000
    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 - 100K13
    $100K - 200K7
    $200K - 300K16
    $300K - 400K23
    $400K - 500K26
    $500K - 600K22
    $600K - 700K4
    $700K - 800K12
    $800K - 900K12
    $900K - 1M2
    $1M - Max11

    Homes for Sale by Type in New Windsor, NY

    Property TypeCount
    Single Family94
    Townhouse0
    Condo16
    Commercial15
    Rental44
    Lots and Land10
    Condo/Town/CoOp0
    CoOp7
    Multi Family5
    Mobile Home1
    Farms0

    (Data as of 6/17/2026)

    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.