New Windsor, NY Homes

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  $87,000

  • Land
  • 9,186 Sq Ft
  • $412,518 per Acre

  12 Union Ave Lot 1 Union Ave, New Windsor, NY 12553

  Commercially zoned lot, ready, cleared land with access to electric, water, sewer easy to hook up/connect. Just off 9W. Great for offices, spa and more.

  Maureen Arias Keller Williams Realty Partner

  12 Union Ave Lot 1 Union Ave, New Windsor, NY 12553
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  $460,000 Sold Oct 30, 2025

  28 Hillcrest Dr, Salisbury Mills, NY 12577

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1955

  Last Sold Summary

  • $304/SF
  • 51 Days On Market

  Current Estimated Value $465,060

  Last Listing Agent Melissa Forsyth Hudson Valley Home Connection

  28 Hillcrest Dr, Salisbury Mills, NY 12577
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  Est $720,002 Not Listed For Sale

  2625 Liberty Ridge, New Windsor, NY 12553

  • 5 Beds
  • 2.5 Baths
  • 3,922 Sq Ft
  • Built 2003

  2625 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 3% Above List Price
  • $178/SF
  • 40 Days On Market

  • Last Sold Price $699,900
  • Aug 21, 2024

  Last Listing Agent Betsy Estrella-Mejia eXp Realty
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  $460,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,762 Sq Ft

  400 Philo St, New Windsor, NY 12553

  Welcome to this beautifully maintained 3-bedroom, 1.5-bathroom residence, ideally located in the highly sought-after Woodwind community of New Windsor.Situated on an expansive corner lot, this exceptional home offers a rare blend of space, privacy, and charm — enhanced by the natural beauty of pear and peach trees and a serene backyard bordered by woods. Inside, an open and airy floor plan

  Bladimir Ledesma eXp Realty

  400 Philo St, New Windsor, NY 12553
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  $60,000 Sold Oct 27, 2025

  305 Brittany Terrace Unit 305, Rock Tavern, NY 12575

  • 2 Beds
  • 1.5 Baths
  • 1,296 Sq Ft
  • Built 1980

  Last Sold Summary

  • 50% Below List Price
  • $46/SF
  • 141 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  305 Brittany Terrace Unit 305, Rock Tavern, NY 12575
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  Est $704,441 Not Listed For Sale

  2723 Colonial Dr, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,488 Sq Ft
  • Built 2003

  2723 Colonial Dr, New Windsor, NY 12553

  Last Sold Summary

  • 7% Above List Price
  • $265/SF
  • 20 Days On Market

  • Last Sold Price $660,000
  • Sep 19, 2023

  Last Listing Agent Frank Gerbes RE/MAX Benchmark Realty Group
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  $324,999

  • 3 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  256 Quassaick Ave Unit 13, New Windsor, NY 12553

  FULLY AVAILABLE! Welcome to this well-maintained, move-in ready 2-story townhouse in Windshire Village featuring 3 bedrooms and 2.5 bathrooms. The first floor offers a bright living room, dining area, kitchen, and half bath, with sliding doors leading to a private rear patio—perfect for relaxing or outdoor dining. Upstairs features 3 bedrooms and 2 full bathrooms, including a primary bedroom with

  Umesh Shrestha BHHS Hudson Valley Properties

  256 Quassaick Ave Unit 13, New Windsor, NY 12553
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  $460,000 Sold Jan 30, 2026

  35 Guernsey Dr, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,640 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $280/SF
  • 23 Days On Market

  Current Estimated Value $460,701

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  35 Guernsey Dr, New Windsor, NY 12553
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  Est $670,087 Not Listed For Sale

  2626 Liberty Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,608 Sq Ft
  • Built 2003

  2626 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 3% Above List Price
  • $249/SF
  • 82 Days On Market

  • Last Sold Price $650,000
  • Aug 21, 2024

  Last Listing Agent Frank Gerbes RE/MAX Benchmark Realty Group
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  $530,000 Sold Sep 30, 2025

  47 Clintonwood Dr, New Windsor, NY 12553

  • 5 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • Built 1966

  Last Sold Summary

  • 4% Below List Price
  • $251/SF
  • 34 Days On Market

  Current Estimated Value $551,705

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group

  47 Clintonwood Dr, New Windsor, NY 12553
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  Est $665,248 Not Listed For Sale

  2811 Cherry Tree Way, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,435 Sq Ft
  • Built 2004

  2811 Cherry Tree Way, New Windsor, NY 12553

  Last Sold Summary

  • 16% Above List Price
  • $236/SF
  • 21 Days On Market

  • Last Sold Price $575,000
  • Jun 06, 2023

  Last Listing Agent Ines Cruz eXp Realty
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  $885,000 Sold Jul 18, 2025

  14 Cooper Ct, New Windsor, NY 12553

  • 4 Beds
  • 3.5 Baths
  • 4,185 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Above List Price
  • $211/SF
  • 23 Days On Market

  Current Estimated Value $889,071

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  14 Cooper Ct, New Windsor, NY 12553
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  Est $683,802 Not Listed For Sale

  2652 Liberty Ridge, New Windsor, NY 12553

  • 4 Beds
  • 3 Baths
  • 3,601 Sq Ft
  • Built 2004

  2652 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 6% Above List Price
  • $179/SF
  • 13 Days On Market

  • Last Sold Price $645,000
  • Jul 10, 2024

  Last Listing Agent Brenda Guttenberg RE/MAX Benchmark Realty Group
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  $360,000 Sold Jun 09, 2025

  2 Elizabeth Ln, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1963

  Last Sold Summary

  • 13% Above List Price
  • $385/SF
  • 21 Days On Market

  Current Estimated Value $372,276

  Last Listing Agent Simone Edwards Edwards Properties

  2 Elizabeth Ln, New Windsor, NY 12553
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  Est $675,647 Not Listed For Sale

  2824 Cherry Tree Way, New Windsor, NY 12553

  • 4 Beds
  • 3 Baths
  • 2,488 Sq Ft
  • Built 2004

  2824 Cherry Tree Way, New Windsor, NY 12553

  Last Sold Summary

  • 4% Above List Price
  • $261/SF
  • 21 Days On Market

  • Last Sold Price $650,000
  • Dec 19, 2024

  Last Listing Agent Jonathan Minerick HomeCoin.com
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  $219,950 Sold Dec 16, 2025

  14 Coffey Ave, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 1,001 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $220/SF
  • 37 Days On Market

  Current Estimated Value $223,069

  Last Listing Agent Alexander Panet Real Broker NY LLC

  14 Coffey Ave, New Windsor, NY 12553
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  Est $684,320 Not Listed For Sale

  2656 Liberty Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,808 Sq Ft
  • Built 2004

  2656 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 7% Above List Price
  • $228/SF
  • 16 Days On Market

  • Last Sold Price $640,000
  • Jan 07, 2025

  Last Listing Agent Federico Prada RE/MAX Benchmark Realty Group
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  $700,000 Sold Jul 22, 2025

  49 Swan Hollow Rd, New Windsor, NY 12553

  • 4 Beds
  • 3 Baths
  • 2,900 Sq Ft
  • Built 2020

  Last Sold Summary

  • 15% Below List Price
  • $241/SF
  • 228 Days On Market

  Current Estimated Value $738,025

  Last Listing Agent Christina Wilger RE/MAX Benchmark Realty Group

  49 Swan Hollow Rd, New Windsor, NY 12553
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  Est $727,964 Not Listed For Sale

  2638 Liberty Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 3,443 Sq Ft
  • Built 2004

  2638 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 7% Above List Price
  • $198/SF
  • 29 Days On Market

  • Last Sold Price $680,000
  • Jun 07, 2023

  Last Listing Agent Courtney Tablante Keller Williams Realty
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  $205,000 Sold Oct 21, 2025

  120 John St, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,044 Sq Ft
  • Built 1920

  Last Sold Summary

  • 4% Below List Price
  • $196/SF
  • 21 Days On Market

  Current Estimated Value $225,086

  Last Listing Agent Jane Alfidi Howard Hanna Rand Realty

  120 John St, New Windsor, NY 12553
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  Est $739,758 Not Listed For Sale

  2058 Independence Dr, New Windsor, NY 12553

  • 5 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2006

  2058 Independence Dr, New Windsor, NY 12553

  Last Sold Summary

  • 10% Above List Price
  • $243/SF
  • 33 Days On Market

  • Last Sold Price $675,000
  • Dec 07, 2023

  Last Listing Agent Christina Wilger RE/MAX Benchmark Realty Group
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  $679,000 Sold Oct 31, 2025

  195 Pleasant Hill Rd, New Windsor, NY 12553

  • 4 Beds
  • 3 Baths
  • 2,405 Sq Ft
  • Built 2019

  Last Sold Summary

  • 4% Above List Price
  • $282/SF
  • 44 Days On Market

  Current Estimated Value $702,427

  Last Listing Agent Martin Remo RE/MAX Prime Properties

  195 Pleasant Hill Rd, New Windsor, NY 12553
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  Est $683,909 Not Listed For Sale

  3042 Molly Pitcher Dr, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,808 Sq Ft
  • Built 2007

  3042 Molly Pitcher Dr, New Windsor, NY 12553

  Last Sold Summary

  • 5% Above List Price
  • $232/SF
  • 176 Days On Market

  • Last Sold Price $650,760
  • Jan 30, 2025

  Last Listing Agent Verria Hairston Opendoor Brokerage LLC
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  $745,380 Sold Apr 25, 2025

  4 Trotter Ln, Rock Tavern, NY 12575

  • 4 Beds
  • 2.5 Baths
  • 2,960 Sq Ft
  • Built 2009

  Last Sold Summary

  • 3% Above List Price
  • $252/SF
  • 23 Days On Market

  Current Estimated Value $761,000

  Last Listing Agent Denise Clancy Curasi Realty, Inc.

  4 Trotter Ln, Rock Tavern, NY 12575
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  Est $496,758 Not Listed For Sale

  352 Shelly Rd, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,996 Sq Ft
  • Built 1976

  352 Shelly Rd, New Windsor, NY 12553

  Last Sold Summary

  • 7% Above List Price
  • $233/SF
  • 74 Days On Market

  • Last Sold Price $465,000
  • Feb 12, 2025

  Last Listing Agent Nicole Gold RE/MAX Benchmark Realty Group
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  $430,000 Sold Mar 11, 2026

  76 Creamery Dr, New Windsor, NY 12553

  • 3 Beds
  • 3 Baths
  • 2,004 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $215/SF
  • 110 Days On Market

  Current Estimated Value $457,287

  Last Listing Agent Jeanette Santory Howard Hanna Rand Realty

  76 Creamery Dr, New Windsor, NY 12553
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  Est $569,648 Not Listed For Sale

  322 Burroughs Ln, New Windsor, NY 12553

  • 5 Beds
  • 2.5 Baths
  • 2,502 Sq Ft
  • Built 1978

  322 Burroughs Ln, New Windsor, NY 12553

  Last Sold Summary

  • 1% Below List Price
  • $230/SF
  • 156 Days On Market

  • Last Sold Price $575,000
  • Jan 08, 2025

  Last Listing Agent Anna Mantovi Harbor Gray Real Estate LLC
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  $200,000 Sold Oct 24, 2025

  276 Temple Hill Rd Unit 1604, New Windsor, NY 12553

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Built 1986

  Last Sold Summary

  • $250/SF
  • 60 Days On Market

  Current Estimated Value $199,802

  Last Listing Agent Desiree Beecham River Realty Services, Inc.

  276 Temple Hill Rd Unit 1604, New Windsor, NY 12553
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  Est $503,019 Not Listed For Sale

  59 Keats Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 1978

  59 Keats Dr, New Windsor, NY 12553

  Last Sold Summary

  • 2% Below List Price
  • $302/SF
  • 26 Days On Market

  • Last Sold Price $515,000
  • Jan 03, 2025

  Last Listing Agent Virginia Corbett eXp Realty
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  $375,000 Sold Apr 13, 2026

  320 Walnut Ave, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 1,147 Sq Ft
  • Built 1960

  Last Sold Summary

  • 7% Above List Price
  • $327/SF
  • 19 Days On Market

  Current Estimated Value $349,165

  Last Listing Agent Thomas Pellegrino Curasi Realty, Inc.

  320 Walnut Ave, New Windsor, NY 12553
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  Est $519,275 Not Listed For Sale

  73 Keats Dr, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,347 Sq Ft
  • Built 1978

  73 Keats Dr, New Windsor, NY 12553

  Last Sold Summary

  • 13% Above List Price
  • $196/SF
  • 48 Days On Market

  • Last Sold Price $460,000
  • Oct 11, 2023

  Last Listing Agent Jeffrey Miller Howard Hanna Rand Realty
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  $530,000 Sold Mar 03, 2026

  293 Garden St, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft
  • Built 1993

  Last Sold Summary

  • $269/SF
  • 65 Days On Market

  Current Estimated Value $531,398

  Last Listing Agent Ann Margaret Bolton eRealty Advisors, Inc

  293 Garden St, New Windsor, NY 12553
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  Est $574,744 Not Listed For Sale

  31 Keats Dr, New Windsor, NY 12553

  • 4 Beds
  • 3.5 Baths
  • 2,875 Sq Ft
  • Built 1979

  31 Keats Dr, New Windsor, NY 12553

  Last Sold Summary

  • 3% Above List Price
  • $195/SF
  • 34 Days On Market

  • Last Sold Price $560,000
  • Oct 25, 2023

  Last Listing Agent Jackie Siracuse Absolute Real Estate of NY Inc
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  $322,500 Sold Apr 24, 2025

  276 Temple Hill Rd, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Above List Price
  • $213/SF
  • 33 Days On Market

  Last Listing Agent Bob Donnelly eRealty Advisors, Inc

  276 Temple Hill Rd, New Windsor, NY 12553
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  Est $460,697 Not Listed For Sale

  222 Melville Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1975

  222 Melville Dr, New Windsor, NY 12553

  Last Sold Summary

  • 1% Above List Price
  • $287/SF
  • 34 Days On Market

  • Last Sold Price $454,000
  • Feb 21, 2025

  Last Listing Agent William Giannico Keller Williams Realty
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  $451,000 Sold Sep 15, 2025

  21 Harth Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,324 Sq Ft
  • Built 1960

  Last Sold Summary

  • 5% Above List Price
  • $341/SF
  • 47 Days On Market

  Current Estimated Value $451,614

  Last Listing Agent Suzanne Hallisey RE/MAX Benchmark Realty Group

  21 Harth Dr, New Windsor, NY 12553
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  Est $505,565 Not Listed For Sale

  52 Keats Dr, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,707 Sq Ft
  • Built 1976

  52 Keats Dr, New Windsor, NY 12553

  Last Sold Summary

  • 5% Above List Price
  • $283/SF
  • 23 Days On Market

  • Last Sold Price $482,500
  • Oct 23, 2023

  Last Listing Agent Suzanne Sweeney RE/MAX Benchmark Realty Group
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  $450,000 Sold Dec 16, 2025

  32 Valley Dr, Salisbury Mills, NY 12577

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1975

  Last Sold Summary

  • 5% Below List Price
  • $285/SF
  • 55 Days On Market

  Current Estimated Value $452,412

  Last Listing Agent George Koudounas RE/MAX Benchmark Realty Group

  32 Valley Dr, Salisbury Mills, NY 12577
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  Est $448,379 Not Listed For Sale

  44 Keats Dr, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 1,532 Sq Ft
  • Built 1977

  44 Keats Dr, New Windsor, NY 12553

  Last Sold Summary

  • 14% Above List Price
  • $258/SF
  • 26 Days On Market

  • Last Sold Price $395,000
  • Mar 18, 2024

  Last Listing Agent Angela Danosky Picture It Sold, LLC
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  $415,000 Sold Nov 07, 2025

  206 Tamerisk Ln, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,630 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $255/SF
  • 30 Days On Market

  Current Estimated Value $433,603

  Last Listing Agent Jennifer Lucas Keller Williams Realty

  206 Tamerisk Ln, New Windsor, NY 12553

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