Recently Sold New Windsor, NY Homes

• 

  $350,000

  Sold Jan 17, 2026

  263 Quassaick Ave, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 1,117 Sq Ft
  • Built 1930

  Last Sold Summary

  • 9% Below List Price
  • $313/SF
  • 130 Days On Market

  Current Estimated Value $361,992

  Last Listing Agent Anthony Cassase HomeSmart Homes & Estates

  263 Quassaick Ave, New Windsor, NY 12553
• 

  $397,500

  Sold Sep 17, 2025

  57 Harth Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Above List Price
  • $253/SF
  • 70 Days On Market

  Current Estimated Value $416,514

  Last Listing Agent Steve Moreau Tactical Realty LLC

  57 Harth Dr, New Windsor, NY 12553
• 

  $835,000

  Sold Apr 02, 2026

  100 Pleasant Hill Rd, New Windsor, NY 12553

  • 6 Beds
  • 5 Baths
  • 4,522 Sq Ft
  • Built 1850

  Last Sold Summary

  • 7% Below List Price
  • $185/SF
  • 301 Days On Market

  Current Estimated Value $890,335

  Last Listing Agent Jade Oliverio Howard Hanna Rand Realty

  100 Pleasant Hill Rd, New Windsor, NY 12553
• 

  $605,000

  Sold Jan 29, 2026

  2 Dimiceli St, New Windsor, NY 12553

  • 5 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Above List Price
  • $202/SF
  • 85 Days On Market

  Current Estimated Value $591,023

  Last Listing Agent MARIA FUERTES K. Fortuna Realty, Inc.

  2 Dimiceli St, New Windsor, NY 12553
• 

  $390,000

  Sold Dec 19, 2025

  12 Provost Dr, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Above List Price
  • $301/SF
  • 19 Days On Market

  Current Estimated Value $404,343

  Last Listing Agent Michael Bussa K. Fortuna Realty, Inc.

  12 Provost Dr, New Windsor, NY 12553
• 

  $470,000

  Sold Oct 28, 2025

  1721 Hawthorn Way, New Windsor, NY 12553

  • 2 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2013

  Last Sold Summary

  • 2% Above List Price
  • $235/SF
  • 32 Days On Market

  Current Estimated Value $474,275

  Last Listing Agent Danielle Oliva Serhant LLC

  1721 Hawthorn Way, New Windsor, NY 12553
• 

  $245,000

  Sold Mar 27, 2026

  810 Blooming Grove Turnpike Unit 3, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Above List Price
  • $194/SF
  • 12 Days On Market

  Last Listing Agent Kerri Stretch Howard Hanna Rand Realty

  810 Blooming Grove Turnpike Unit 3, New Windsor, NY 12553
• 

  $176,000

  Sold Feb 06, 2026

  810 Blooming Grove Turnpike Unit 113, New Windsor, NY 12553

  • 1 Bed
  • 1 Bath
  • 952 Sq Ft
  • Built 1965

  Last Sold Summary

  • 5% Below List Price
  • $185/SF
  • 18 Days On Market

  Last Listing Agent Lorri Miller 1st Independent Realty Grp

  810 Blooming Grove Turnpike Unit 113, New Windsor, NY 12553
• 

  $680,000

  Sold Jan 13, 2026

  38 Panorama Dr, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,808 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $242/SF
  • 160 Days On Market

  Current Estimated Value $712,763

  Last Listing Agent Kim O'Neil Hudson Valley Home Connection

  38 Panorama Dr, New Windsor, NY 12553
• 

  $460,000

  Sold Jul 30, 2026

  532 Shore Dr, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1949

  Last Sold Summary

  • 2% Above List Price
  • $323/SF
  • 25 Days On Market

  Current Estimated Value $445,905

  Last Listing Agent Erica Soutar eXp Realty

  532 Shore Dr, New Windsor, NY 12553
• 

  $126,000

  Sold Feb 13, 2026

  125 King George Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $90/SF
  • 53 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  125 King George Dr, New Windsor, NY 12553
• 

  $238,000

  Sold Nov 05, 2025

  276 Temple Hill Rd Unit 2710, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $232/SF
  • 49 Days On Market

  Current Estimated Value $245,863

  Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group

  276 Temple Hill Rd Unit 2710, New Windsor, NY 12553
• 

  $999,000

  Sold May 15, 2026

  1016 Forest Glen, New Windsor, NY 12553

  • 4 Beds
  • 4.5 Baths
  • 4,834 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Above List Price
  • $207/SF
  • 28 Days On Market

  Current Estimated Value $989,670

  Last Listing Agent Monica Whitney Exit Realty Connections

  1016 Forest Glen, New Windsor, NY 12553
• 

  $165,000

  Sold Nov 04, 2025

  102 Brittany Terrace Unit 102, Rock Tavern, NY 12575

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Below List Price
  • $132/SF
  • 3 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  102 Brittany Terrace Unit 102, Rock Tavern, NY 12575
• 

  $400,000

  Sold Dec 17, 2025

  1003 Ethan Allen Dr, New Windsor, NY 12553

  • 2 Beds
  • 2.5 Baths
  • 1,485 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Above List Price
  • $269/SF
  • 32 Days On Market

  Current Estimated Value $406,114

  Last Listing Agent Lyra Blumenthal RE/MAX Benchmark Realty Group

  1003 Ethan Allen Dr, New Windsor, NY 12553
• 

  $428,000

  Sold Feb 18, 2026

  527 Toleman Rd, Rock Tavern, NY 12575

  • 3 Beds
  • 2.5 Baths
  • 2,268 Sq Ft
  • Built 1984

  Last Sold Summary

  • 1% Above List Price
  • $189/SF
  • 44 Days On Market

  Current Estimated Value $516,110

  Last Listing Agent JANICE CARRASCO Nexthome NOVACARR Realty

  527 Toleman Rd, Rock Tavern, NY 12575
• 

  $235,000

  Sold Dec 15, 2025

  810 Blooming Grove Turnpike Unit 84, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Built 1965

  Last Sold Summary

  • 7% Below List Price
  • $187/SF
  • 177 Days On Market

  Last Listing Agent Lindsay Knowles Howard Hanna Rand Realty

  810 Blooming Grove Turnpike Unit 84, New Windsor, NY 12553
• 

  $319,900

  Sold Sep 30, 2025

  1047 Washington Green Unit 1047, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft
  • Built 1989

  Last Sold Summary

  • $311/SF
  • 40 Days On Market

  Current Estimated Value $322,866

  Last Listing Agent Lyra Blumenthal RE/MAX Benchmark Realty Group

  1047 Washington Green Unit 1047, New Windsor, NY 12553
• 

  $400,000

  Sold Jul 14, 2026

  239 Leslie Ave, New Windsor, NY 12553

  • 4 Beds
  • 1 Bath
  • 1,335 Sq Ft
  • Built 1946

  Last Sold Summary

  • $300/SF
  • 21 Days On Market

  Current Estimated Value $396,873

  Last Listing Agent Juan Bautista Serhant LLC

  239 Leslie Ave, New Windsor, NY 12553
• 

  $565,000

  Sold Dec 10, 2025

  40 Clara Ave, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 3,070 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Below List Price
  • $184/SF
  • 27 Days On Market

  Current Estimated Value $587,069

  Last Listing Agent Eric Staub Keller Williams NY Realty

  40 Clara Ave, New Windsor, NY 12553
• 

  $720,000

  Sold Nov 10, 2025

  395 Toleman Rd, Rock Tavern, NY 12575

  • 4 Beds
  • 2.5 Baths
  • 2,480 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $290/SF
  • 49 Days On Market

  Current Estimated Value $732,709

  Last Listing Agent Jessica Evans KW Hudson Valley United

  395 Toleman Rd, Rock Tavern, NY 12575
• 

  $490,000

  Sold Jul 10, 2026

  335 Oak Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,664 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Above List Price
  • $294/SF
  • 32 Days On Market

  Current Estimated Value $468,364

  Last Listing Agent Michael Scimeca Howard Hanna Rand Realty

  335 Oak Dr, New Windsor, NY 12553
• 

  $350,000

  Sold Apr 30, 2026

  614 Crab Apple Ln, New Windsor, NY 12553

  • 2 Beds
  • 1.5 Baths
  • 1,228 Sq Ft
  • Built 1994

  Last Sold Summary

  • $285/SF
  • 25 Days On Market

  Current Estimated Value $348,182

  Last Listing Agent Alan Scheiner A.B.S. Realty Corp

  614 Crab Apple Ln, New Windsor, NY 12553
• 

  $255,000

  Sold Apr 30, 2026

  276 Temple Hill Rd Unit 1506, New Windsor, NY 12553

  • 1 Bed
  • 1 Bath
  • 1,026 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Above List Price
  • $249/SF
  • 47 Days On Market

  Current Estimated Value $249,881

  Last Listing Agent Virginia Corbett eXp Realty

  276 Temple Hill Rd Unit 1506, New Windsor, NY 12553
• 

  $369,900

  Sold Oct 09, 2025

  9 Kearney Dr, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $385/SF
  • 128 Days On Market

  Current Estimated Value $368,625

  Last Listing Agent Nicholas Cuomo Keller Williams Realty

  9 Kearney Dr, New Windsor, NY 12553
• 

  $450,000

  Sold Jul 09, 2026

  804 Hawthorn Way, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 2013

  Last Sold Summary

  • 5% Below List Price
  • $236/SF
  • 41 Days On Market

  Current Estimated Value $472,007

  Last Listing Agent Brian Smith River Realty Services, Inc.

  804 Hawthorn Way, New Windsor, NY 12553
• 

  $445,000

  Sold Jan 13, 2026

  20 Cedar Ln, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,746 Sq Ft
  • Built 1988

  Last Sold Summary

  • $255/SF
  • 51 Days On Market

  Current Estimated Value $450,624

  Last Listing Agent Jodi Gillespie Gillespie Real Estate LLC

  20 Cedar Ln, New Windsor, NY 12553
• 

  $550,000

  Sold Jan 29, 2026

  168 Toleman Rd, Washingtonville, NY 10992

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Above List Price
  • $277/SF
  • 35 Days On Market

  Current Estimated Value $556,413

  Last Listing Agent Christina Rowan Howard Hanna Rand Realty

  168 Toleman Rd, Washingtonville, NY 10992
• 

  $586,000

  Sold Aug 14, 2026

  116 Chestnut Dr, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1941

  Last Sold Summary

  • 2% Above List Price
  • $308/SF
  • 28 Days On Market

  Current Estimated Value $504,057

  Last Listing Agent Jade Oliverio Howard Hanna Rand Realty

  116 Chestnut Dr, New Windsor, NY 12553
• 

  $530,000

  Sold Sep 03, 2026

  8 Shaker Ct, New Windsor, NY 12553

  • 5 Beds
  • 2.5 Baths
  • 2,821 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Above List Price
  • $188/SF
  • 49 Days On Market

  Current Estimated Value $532,860

  Last Listing Agent Irena Lulashi Keller Williams Rlty Integrity

  8 Shaker Ct, New Windsor, NY 12553
• 

  $655,000

  Sold Aug 06, 2026

  9 Karen Ct, Rock Tavern, NY 12575

  • 4 Beds
  • 2.5 Baths
  • 2,394 Sq Ft
  • Built 1988

  Last Sold Summary

  • 9% Above List Price
  • $274/SF
  • 23 Days On Market

  Current Estimated Value $613,125

  Last Listing Agent Kerri Stretch Howard Hanna Rand Realty

  9 Karen Ct, Rock Tavern, NY 12575
• 

  $950,000

  Sold Jul 24, 2026

  104 Winding Brook Ct, New Windsor, NY 12553

  • 5 Beds
  • 4.5 Baths
  • 3,752 Sq Ft
  • Built 2006

  Last Sold Summary

  • 17% Below List Price
  • $253/SF
  • 50 Days On Market

  Current Estimated Value $987,052

  Last Listing Agent Raquel Berrios Nine28 Realty, LLC

  104 Winding Brook Ct, New Windsor, NY 12553
• 

  $300,000

  Sold Oct 09, 2025

  1183 State Route 94, New Windsor, NY 12553

  • 4 Beds
  • 1.5 Baths
  • 1,106 Sq Ft
  • Built 1951

  Last Sold Summary

  • $271/SF
  • 61 Days On Market

  Current Estimated Value $327,719

  Last Listing Agent Lisa Wade-Sebring Hudson Valley Home Connection

  1183 State Route 94, New Windsor, NY 12553
• 

  $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 $465,504

  Last Listing Agent Melissa Forsyth Hudson Valley Home Connection

  28 Hillcrest Dr, Salisbury Mills, NY 12577
• 

  $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
• 

  $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 $468,614

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  35 Guernsey Dr, New Windsor, NY 12553
• 

  $525,000

  Sold Jun 15, 2026

  114 Chestnut Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft
  • Built 1941

  Last Sold Summary

  • $354/SF
  • 42 Days On Market

  Current Estimated Value $518,382

  Last Listing Agent Jade Oliverio Howard Hanna Rand Realty

  114 Chestnut Dr, New Windsor, NY 12553
• 

  $489,999

  Sold May 15, 2026

  1210 Hawthorn Way, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Above List Price
  • $240/SF
  • 37 Days On Market

  Current Estimated Value $482,649

  Last Listing Agent Elsie Nunez Keller Williams Realty

  1210 Hawthorn Way, New Windsor, NY 12553
• 

  $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 $549,351

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group

  47 Clintonwood Dr, New Windsor, NY 12553
• 

  $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 $237,600

  Last Listing Agent Alexander Panet Real Broker NY LLC

  14 Coffey Ave, New Windsor, NY 12553

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