$6,500,000
4.9 Acres4.9 ac
70 Pleasant Hill Road
New Windsor, NY 12553
Listed with KW Hudson Valley United
102listings found· showing 1–50
$6,500,000
4.9 Acres4.9 ac
70 Pleasant Hill Road
New Windsor, NY 12553
Listed with KW Hudson Valley United
$1,050,000
5 Bed • 4.5 Bath • 4,499 Sq. Ft.5 bd · 4.5 ba · 4,499 sqft
102 Pleasant Hill Road
New Windsor, NY 12553
Listed with Howard Hanna Rand Realty
$679,000
4 Bed • 2.5 Bath • 2,376 Sq. Ft.4 bd · 2.5 ba · 2,376 sqft
2508 Constitution Way
New Windsor, NY 12553
Listed with Howard Hanna Rand Realty
$160,000
1.2 Acres1.2 ac
126 Dean Hill Road
New Windsor, NY 12553
Listed with Four Seasons Sothebys Intl
$1,100,000
4 Bed • 3 Bath • 3,100 Sq. Ft.4 bd · 3 ba · 3,100 sqft
4 Jefferson Avenue
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$700,000
3 Bed • 2 Bath • 2,165 Sq. Ft.3 bd · 2 ba · 2,165 sqft
20 Ivy Rock Lane
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$458,000
3 Bed • 2 Bath • 1,456 Sq. Ft.3 bd · 2 ba · 1,456 sqft
3 Hilltop Drive
New Windsor, NY 12553
Listed with Corcoran Country Living
$1,650,000
1.1 Acres1.1 ac
929 Little Britain Road
New Windsor, NY 12553
Listed with Curasi Realty, Inc.
$795,000
4 Bed • 3 Bath • 3,160 Sq. Ft.4 bd · 3 ba · 3,160 sqft
1964 State Route 32
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$439,900
4 Bed • 2.5 Bath • 1,296 Sq. Ft.4 bd · 2.5 ba · 1,296 sqft
40 Birchwood Drive
New Windsor, NY 12553
Listed with Howard Hanna Rand Realty
$1,500,000
29 Acres29 ac
Mt Airy Road
New Windsor, NY 12553
Listed with Keller Williams Valley Realty
$816,000
4 Bed • 2.5 Bath • 2,552 Sq. Ft.4 bd · 2.5 ba · 2,552 sqft
45 Frank Street
New Windsor, NY 12553
Listed with Keller Williams Village Sq Rlt
$370,000
3 Bed • 1.5 Bath • 1,296 Sq. Ft.3 bd · 1.5 ba · 1,296 sqft
1 Rocky Lane
New Windsor, NY 12553
Listed with eXp Realty
$1,200,000
4 Bed • 3.5 Bath • 3,100 Sq. Ft.4 bd · 3.5 ba · 3,100 sqft
8 Jefferson Avenue
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$820,000
4 Bed • 2.5 Bath • 2,661 Sq. Ft.4 bd · 2.5 ba · 2,661 sqft
79 Frank Street
New Windsor, NY 12553
Listed with Keller Williams Village Sq Rlt
$450,000
3 Bed • 2.5 Bath • 1,994 Sq. Ft.3 bd · 2.5 ba · 1,994 sqft
160 Highwood Drive
New Windsor, NY 12553
Listed with Compass Greater NY, LLC
$1,275,000
15.5 Acres15.5 ac
Silver Stream Road
New Windsor, NY 12553
Listed with Sage Realty Center LLC
$826,000
4 Bed • 2.5 Bath • 2,772 Sq. Ft.4 bd · 2.5 ba · 2,772 sqft
16 McDonald Court
New Windsor, NY 12553
Listed with Keller Williams Village Sq Rlt
$490,000
3 Bed • 2.5 Bath • 2,302 Sq. Ft.3 bd · 2.5 ba · 2,302 sqft
202 Iron Forge Lane
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$549,000
4 Bed • 2.5 Bath • 2,028 Sq. Ft.4 bd · 2.5 ba · 2,028 sqft
5 Jennifer Court
New Windsor, NY 12553
Listed with eXp Realty
$70,000
1 Bed • 1 Bath • 1,662 Sq. Ft.1 bd · 1 ba · 1,662 sqft
2 Mazies Lane
New Windsor, NY 12553
Listed with Epique Realty
$590,000
0.28 Acres0.28 ac
16 Sloop Hill Road
New Windsor, NY 12553
Listed with Tactical Realty LLC
$69,900
2 Bed • 2 Bath • 784 Sq. Ft.2 bd · 2 ba · 784 sqft
3146 Route 9w #6A
New Windsor, NY 12553
Listed with Howard Hanna Rand Realty
$599,900
0.55 Acres0.55 ac
69 Old Temple Hill Road
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$370,000
3 Bed • 2.5 Bath • 1,633 Sq. Ft.3 bd · 2.5 ba · 1,633 sqft
120 Highwood Drive
New Windsor, NY 12553
Listed with River Realty Services, Inc.
$899,000
6 Bed • 4.5 Bath • 4,500 Sq. Ft.6 bd · 4.5 ba · 4,500 sqft
131 Riley Road
New Windsor, NY 12553
Listed with Luciano Rios Property Grp, Inc
$499,900
3 Bed • 2.5 Bath • 2,148 Sq. Ft.3 bd · 2.5 ba · 2,148 sqft
6 Lannis Avenue
New Windsor, NY 12553
Listed with eRealty Advisors, Inc
$695,000
4 Bed • 2.5 Bath • 2,488 Sq. Ft.4 bd · 2.5 ba · 2,488 sqft
2723 Colonial Drive
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$77,999
2 Bed • 1 Bath • 1,152 Sq. Ft.2 bd · 1 ba · 1,152 sqft
118 King George Drive
New Windsor, NY 12553
Listed with Keller Williams Realty
$159,000
2 Bed • 1 Bath • 880 Sq. Ft.2 bd · 1 ba · 880 sqft
50 Cromwell Terrace #6
New Windsor, NY 12553
Listed with Artisan Realty
$489,000
3 Bed • 2.5 Bath • 1,934 Sq. Ft.3 bd · 2.5 ba · 1,934 sqft
67 Steele Road
New Windsor, NY 12553
Listed with Hollingsworth Real Estate Grp.
$425,000
3 Bed • 1.5 Bath • 1,384 Sq. Ft.3 bd · 1.5 ba · 1,384 sqft
8 Mark Street
New Windsor, NY 12553
Listed with eXp Realty
$415,000
2 Bed • 1.5 Bath • 1,464 Sq. Ft.2 bd · 1.5 ba · 1,464 sqft
713 Hewitt Lane
New Windsor, NY 12553
Listed with Quinn Realty Group Inc
$225,000
2 Bed • 1 Bath • 879 Sq. Ft.2 bd · 1 ba · 879 sqft
5 Ora Street
New Windsor, NY 12553
Listed with SHAHAR Management LLC
$245,000
1 Bed • 1 Bath • 800 Sq. Ft.1 bd · 1 ba · 800 sqft
276 Temple Hill Road #1519
New Windsor, NY 12553
Listed with eXp Realty
$469,000
4 Bed • 2.5 Bath • 1,872 Sq. Ft.4 bd · 2.5 ba · 1,872 sqft
41 Ona Lane
New Windsor, NY 12553
Listed with Exit Realty Connections
$465,000
3 Bed • 2.5 Bath • 1,630 Sq. Ft.3 bd · 2.5 ba · 1,630 sqft
206 Tamerisk Lane
New Windsor, NY 12553
Listed with Howard Hanna Rand Realty
$339,900
2 Bed • 1.5 Bath • 1,056 Sq. Ft.2 bd · 1.5 ba · 1,056 sqft
7 Kearney Drive
New Windsor, NY 12553
Listed with Keller Williams Realty
$449,900
3 Bed • 1.5 Bath • 1,488 Sq. Ft.3 bd · 1.5 ba · 1,488 sqft
12 Barclay Road
New Windsor, NY 12553
Listed with Coldwell Banker Realty
$285,000
3 Bed • 2 Bath • 1,176 Sq. Ft.3 bd · 2 ba · 1,176 sqft
245 Quassaick Avenue
New Windsor, NY 12553
Listed with Curasi Realty, Inc.
$450,000
3 Bed • 2.5 Bath • 1,610 Sq. Ft.3 bd · 2.5 ba · 1,610 sqft
406 Hawthorn Way
New Windsor, NY 12553
Listed with eXp Realty
$320,000
2 Bed • 2 Bath • 1,029 Sq. Ft.2 bd · 2 ba · 1,029 sqft
1015 Washington Green Green #1015
New Windsor, NY 12553
Listed with eXp Realty
$270,000
2.87 Acres2.87 ac
Moore's Hill Road
New Windsor, NY 12553
Listed with Keller Williams Valley Realty
$228,000
3 Bed • 2 Bath • 1,344 Sq. Ft.3 bd · 2 ba · 1,344 sqft
128 Brittany Terrace #128
New Windsor, NY 12575
Listed with KW Hudson Valley United
$65,000
0.22 Acres0.22 ac
21 Coffey Avenue
New Windsor, NY 12553
Listed with John J Lease REALTORS Inc
$456,654
0.19 Acres0.19 ac
11 Quassaick Avenue
New Windsor, NY 12553
Listed with Your Move Matters LLC
$285,000
2 Bed • 2 Bath • 1,176 Sq. Ft.2 bd · 2 ba · 1,176 sqft
276 Temple Hill Road #2414
New Windsor, NY 12553
Listed with Weichert Realtors
$369,900
2 Bed • 2 Bath • 1,152 Sq. Ft.2 bd · 2 ba · 1,152 sqft
20 Hilltop Drive
New Windsor, NY 12553
Listed with eXp Realty
$344,999
3 Bed • 1.5 Bath • 1,512 Sq. Ft.3 bd · 1.5 ba · 1,512 sqft
276 Temple Hill Road #2001
New Windsor, NY 12553
Listed with National Veterans Realty Group
$134,900
1 Bed • 1 Bath • 960 Sq. Ft.1 bd · 1 ba · 960 sqft
10 Oakwood Terrace #65
New Windsor, NY 12553
Listed with Keller Williams Realty
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Nov 2, 2026, 2:08 PM ET. ©2026 One Key MLS.