View 41 Guernsey Drive New Windsor, NY MLS# 1017153
    1 of 25
    OPEN HOUSE: Saturday 6/27 12:00 PM - 2:00 PM
    $539,999
    4

    Beds

    3.0

    Baths

    2,004

    Sq.Ft.

    41 Guernsey Drive

    New Windsor, NY

    Courtesy of EXP REALTY
    View 4 Shaker Court New Windsor, NY MLS# 1013401
    • Recently Listed
    1 of 49
    $549,900
    4

    Beds

    3.1

    Baths

    2,452

    Sq.Ft.

    4 Shaker Court

    New Windsor, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 15 Guernsey Drive New Windsor, NY MLS# 1014088
    • Recently Listed
    1 of 34
    $525,000
    4

    Beds

    2.1

    Baths

    2,052

    Sq.Ft.

    15 Guernsey Drive

    New Windsor, NY

    Courtesy of KELLER WILLIAMS VILLAGE SQ RLT
    The time to sell is now! THE TIME TO SELL IS NOW!
    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
    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 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 29 Purdys Lane New Windsor, NY MLS# 1010298
    • Recently Listed with Virtual Tour
    1 of 49
    $599,900
    3

    Beds

    2.1

    Baths

    2,352

    Sq.Ft.

    29 Purdys Lane

    New Windsor, NY

    Courtesy of Weichert Realtors - Monroe
    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
    $547,500
    4

    Beds

    2.1

    Baths

    1,512

    Sq.Ft.

    584 Shore Drive

    New Windsor, NY

    Courtesy of UNITED RE HUDSON VALLEY EDGE
    View 10 Ona Lane New Windsor, NY MLS# 1006010
    $499,900
    3

    Beds

    2.1

    Baths

    1,818

    Sq.Ft.

    10 Ona Lane

    New Windsor, NY

    Courtesy of CRONIN & COMPANY REAL ESTATE
    View 28 Park Hill Drive New Windsor, NY MLS# 1003023
    $499,900
    3

    Beds

    2.1

    Baths

    1,513

    Sq.Ft.

    28 Park Hill Drive

    New Windsor, NY

    Courtesy of RE-MAX EXPERIENCE
    View 116 Chestnut Drive New Windsor, NY MLS# 1001314
    $575,000
    3

    Beds

    2.1

    Baths

    1,900

    Sq.Ft.

    116 Chestnut Drive

    New Windsor, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 158 Sycamore Drive New Windsor, NY MLS# 1005897
    $600,000
    3

    Beds

    2.1

    Baths

    2,118

    Sq.Ft.

    158 Sycamore Drive

    New Windsor, NY

    Courtesy of AMERICAN DREAM HOMES 110 INC
    View 37 Guernsey Drive New Windsor, NY MLS# 1003311
    $625,000
    4

    Beds

    2.1

    Baths

    2,910

    Sq.Ft.

    37 Guernsey Drive

    New Windsor, NY

    Courtesy of RE/MAX BENCHMARK REALTY GROUP
    View 512 Riley Road New Windsor, NY MLS# 1001952
    • Virtual Tour
    1 of 46
    $525,000
    3

    Beds

    1.0

    Baths

    960

    Sq.Ft.

    512 Riley Road

    New Windsor, NY

    Courtesy of BHG REAL ESTATE GREEN TEAM
    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 263 Riley Road New Windsor, NY MLS# 000031
    $519,900
    4

    Beds

    2.0

    Baths

    2,432

    Sq.Ft.

    263 Riley Road

    New Windsor, NY

    Courtesy of CURASI REALTY, INC.
    View 233 Blooming Grove Turnpike New Windsor, NY MLS# 983636
    $475,000
    3

    Beds

    2.0

    Baths

    1,734

    Sq.Ft.

    233 Blooming Grove Turnpike

    New Windsor, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 14 Creamery Drive New Windsor, NY MLS# 993436
    $499,900
    3

    Beds

    2.1

    Baths

    2,020

    Sq.Ft.

    14 Creamery Drive

    New Windsor, NY

    Courtesy of KELLER WILLIAMS PRESTIGE PROP

    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

    152

    Estimated median home price

    $469,750
    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 - 100K12
    $100K - 200K7
    $200K - 300K16
    $300K - 400K23
    $400K - 500K31
    $500K - 600K23
    $600K - 700K3
    $700K - 800K11
    $800K - 900K13
    $900K - 1M2
    $1M - Max11

    Homes for Sale by Type in New Windsor, NY

    Property TypeCount
    Single Family98
    Townhouse0
    Condo15
    Commercial16
    Rental40
    Lots and Land9
    Condo/Town/CoOp0
    CoOp7
    Multi Family6
    Mobile Home1
    Farms0

    (Data as of 6/26/2026)

    Information deemed reliable but not guaranteed.

    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.