New Windsor, NY Homes

• 

  $487,500

  Sold Feb 06, 2026

  14 Windsor Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 1952

  Last Sold Summary

  • 3% Above List Price
  • $262/SF
  • 53 Days On Market

  Current Estimated Value $482,302

  Last Listing Agent Michael Cahill HomeSmart Homes & Estates

  14 Windsor Dr, New Windsor, NY 12553
• 

  Est $344,391

  Not Listed For Sale

  166 Vails Gate Heights Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft
  • Built 1973

  166 Vails Gate Heights Dr, New Windsor, NY 12553

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Catherine Eichner Eichner Realty Group Inc.
• 

  $465,000

  Sold Jul 15, 2026

  15 Riley Rd, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1920

  Last Sold Summary

  • 4% Above List Price
  • $245/SF
  • 385 Days On Market

  Current Estimated Value $446,720

  Last Listing Agent Inna Sobel Atelier Properties LLC

  15 Riley Rd, New Windsor, NY 12553
• 

  Est $323,716

  Not Listed For Sale

  124 Vails Gate Heights Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft
  • Built 1970

  124 Vails Gate Heights Dr, New Windsor, NY 12553

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Nicole Gold RE/MAX Benchmark Realty Group
• 

  $352,000

  Sold Aug 26, 2026

  610 Mount Airy Rd, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1984

  Last Sold Summary

  • 17% Above List Price
  • $297/SF
  • 38 Days On Market

  Current Estimated Value $356,582

  Last Listing Agent Keith Sumner John J Lease REALTORS Inc

  610 Mount Airy Rd, New Windsor, NY 12553
• 

  Est $506,997

  Not Listed For Sale

  119 Vails Gate Heights Dr, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Built 1972

  119 Vails Gate Heights Dr, New Windsor, NY 12553

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Waldina Almazan RE/MAX Benchmark Realty Group
• 

  $340,000

  Sold Jul 17, 2026

  69 Cedar Ave, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,350 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 19 Days On Market

  Current Estimated Value $350,790

  Last Listing Agent Manuel Galan eXp Realty

  69 Cedar Ave, New Windsor, NY 12553
• 

  Est $470,594

  Not Listed For Sale

  87 Vails Gate Heights Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft
  • Built 1970

  87 Vails Gate Heights Dr, New Windsor, NY 12553

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Kristen Velez RE/MAX Benchmark Realty Group
• 

  $599,900

  Sold Sep 11, 2026

  29 Purdys Ln, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,352 Sq Ft
  • Built 1999

  Last Sold Summary

  • $255/SF
  • 29 Days On Market

  Current Estimated Value $599,523

  Last Listing Agent Rosalie Cook Weichert Realtors

  29 Purdys Ln, New Windsor, NY 12553
• 

  Est $326,647

  Not Listed For Sale

  83 Vails Gate Heights Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft
  • Built 1970

  83 Vails Gate Heights Dr, New Windsor, NY 12553

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty
• 

  $280,000

  Sold Nov 19, 2025

  1121 Washington Green, New Windsor, NY 12553

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

  Last Sold Summary

  • 7% Below List Price
  • $272/SF
  • 206 Days On Market

  Current Estimated Value $292,903

  Last Listing Agent Frank Gerbes RE/MAX Benchmark Realty Group

  1121 Washington Green, New Windsor, NY 12553
• 

  Est $474,359

  Not Listed For Sale

  11 Truex Dr, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 1958

  11 Truex Dr, New Windsor, NY 12553

  Last Sold Summary

  • 108 Days On Market

  Last Listing Agent Frank Gerbes RE/MAX Benchmark Realty Group
• 

  $550,000

  Sold Aug 12, 2026

  17 Shaker Ct, New Windsor, NY 12553

  • 5 Beds
  • 2.5 Baths
  • 2,431 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $226/SF
  • 64 Days On Market

  Current Estimated Value $549,671

  Last Listing Agent Olivia Cappelli Donna Ruffino Realty Corp

  17 Shaker Ct, New Windsor, NY 12553
• 

  Est $454,046

  Not Listed For Sale

  3 Truex Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,104 Sq Ft
  • Built 1958

  3 Truex Dr, New Windsor, NY 12553

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Laura DiMaggio RE/MAX Classic Realty
• 

  

  /60

  $900,000

  Sold May 11, 2026

  106 Station Rd, Rock Tavern, NY 12575

  • 3 Beds
  • 5 Baths
  • 3,000 Sq Ft
  • Built 1750

  Last Sold Summary

  • 18% Below List Price
  • $300/SF
  • 114 Days On Market

  Current Estimated Value $958,059

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc

  106 Station Rd, Rock Tavern, NY 12575
• 

  Est $518,989

  Not Listed For Sale

  12 Truex Cir, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,874 Sq Ft
  • Built 1975

  12 Truex Cir, New Windsor, NY 12553

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Deborah Meurlin Exit Realty Connections
• 

  $210,000

  Sold Sep 03, 2026

  43 Lafayette Dr, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 715 Sq Ft
  • Built 1954

  Last Sold Summary

  • 7% Below List Price
  • $294/SF
  • 48 Days On Market

  Current Estimated Value $228,043

  Last Listing Agent Sammy Zambrano Keller Williams Realty

  43 Lafayette Dr, New Windsor, NY 12553
• 

  Est $410,035

  Not Listed For Sale

  6 Park Hill Dr, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1958

  6 Park Hill Dr, New Windsor, NY 12553

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Federico Prada Curasi Realty, Inc.
• 

  $465,000

  Sold Apr 24, 2026

  81 Blooming Grove Turnpike, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 1945

  Last Sold Summary

  • 4% Below List Price
  • $209/SF
  • 48 Days On Market

  Current Estimated Value $475,309

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  81 Blooming Grove Turnpike, New Windsor, NY 12553
• 

  Est $522,913

  Not Listed For Sale

  6 Herbert Hoover Dr, New Windsor, NY 12553

  • 5 Beds
  • 2.5 Baths
  • 2,356 Sq Ft
  • Built 1966

  6 Herbert Hoover Dr, New Windsor, NY 12553

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Annalisa Badstein eXp Realty
• 

  $510,000

  Sold May 14, 2026

  16 Faye Ave, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 2,319 Sq Ft
  • Built 1952

  Last Sold Summary

  • $220/SF
  • 128 Days On Market

  Current Estimated Value $501,190

  Last Listing Agent Alexandra Zinko Century 21 Realty Center

  16 Faye Ave, New Windsor, NY 12553
• 

  Est $385,142

  Not Listed For Sale

  1 Park Hill Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,542 Sq Ft
  • Built 1957

  1 Park Hill Dr, New Windsor, NY 12553

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group
• 

  $385,000

  Sold Nov 27, 2025

  1068 River Rd, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Above List Price
  • $231/SF
  • 61 Days On Market

  Current Estimated Value $382,881

  Last Listing Agent Yidel Rosenberg MS Realty Group USA, Inc

  1068 River Rd, New Windsor, NY 12553
• 

  Est $550,304

  Not Listed For Sale

  502 Union Ave, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 2,014 Sq Ft
  • Built 1950

  502 Union Ave, New Windsor, NY 12553

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Lyra Blumenthal RE/MAX Benchmark Realty Group
• 

  $385,000

  Sold Feb 16, 2026

  221 Tamerisk Ln, New Windsor, NY 12553

  • 2 Beds
  • 2.5 Baths
  • 1,895 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $203/SF
  • 37 Days On Market

  Current Estimated Value $397,879

  Last Listing Agent Naomi Streicher Q Home Sales

  221 Tamerisk Ln, New Windsor, NY 12553
• 

  Est $361,707

  Not Listed For Sale

  1089 State Route 94, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 778 Sq Ft
  • Built 1940

  1089 State Route 94, New Windsor, NY 12553

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Tremaine Selby Weichert Realtors
• 

  $424,900

  Sold Feb 17, 2026

  11 Sunset Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,595 Sq Ft
  • Built 1952

  Last Sold Summary

  • $266/SF
  • 57 Days On Market

  Current Estimated Value $424,582

  Last Listing Agent ALDO TROPEANO Sams Realty

  11 Sunset Dr, New Windsor, NY 12553
• 

  Est $446,459

  Not Listed For Sale

  7 Dean Hill Rd, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,605 Sq Ft
  • Built 1965

  7 Dean Hill Rd, New Windsor, NY 12553

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Desiree Beecham River Realty Services, Inc.
• 

  $645,000

  Sold Jan 13, 2026

  24 Hillcrest Dr, Salisbury Mills, NY 12577

  • 4 Beds
  • 2.5 Baths
  • 2,947 Sq Ft
  • Built 1993

  Last Sold Summary

  • 2% Below List Price
  • $219/SF
  • 80 Days On Market

  Current Estimated Value $657,324

  Last Listing Agent Minnie Thomas KW Hudson Valley United

  24 Hillcrest Dr, Salisbury Mills, NY 12577
• 

  Est $379,962

  Not Listed For Sale

  738 Mount Airy Rd, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1950

  738 Mount Airy Rd, New Windsor, NY 12553

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Kathleen Milich RE/MAX Benchmark Realty Group
• 

  $499,900

  Sold Sep 11, 2026

  10 Ona Ln, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft
  • Built 1965

  Last Sold Summary

  • $275/SF
  • 22 Days On Market

  Current Estimated Value $494,926

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  10 Ona Ln, New Windsor, NY 12553
• 

  Est $387,152

  Not Listed For Sale

  721 Mount Airy Rd, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 1,010 Sq Ft
  • Built 1942

  721 Mount Airy Rd, New Windsor, NY 12553

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group
• 

  $715,000

  Sold Aug 26, 2026

  2657 Liberty Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,435 Sq Ft
  • Built 2006

  Last Sold Summary

  • 1% Above List Price
  • $294/SF
  • 54 Days On Market

  Current Estimated Value $701,745

  Last Listing Agent Alyssa Scancarello Howard Hanna Rand Realty

  2657 Liberty Ridge, New Windsor, NY 12553
• 

  Est $458,908

  Not Listed For Sale

  515 Mount Airy Rd, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft
  • Built 1965

  515 Mount Airy Rd, New Windsor, NY 12553

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Kathleen Milich RE/MAX Benchmark Realty Group
• 

  $205,000

  Sold Mar 16, 2026

  312 Brittany Terrace Unit 312, Rock Tavern, NY 12575

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $131/SF
  • 99 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  312 Brittany Terrace Unit 312, Rock Tavern, NY 12575
• 

  Est $397,348

  Not Listed For Sale

  183 Riley Rd, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1978

  183 Riley Rd, New Windsor, NY 12553

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Emelisa Mendoza RE/MAX Town & Country
• 

  $550,000

  Sold Nov 21, 2025

  40 Hillside Ave, New Windsor, NY 12553

  • 6 Beds
  • 3 Baths
  • 1,344 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Above List Price
  • $409/SF
  • 43 Days On Market

  Current Estimated Value $549,383

  Last Listing Agent Navia Mordan Unity Lux Realty LLC

  40 Hillside Ave, New Windsor, NY 12553
• 

  Est $628,924

  Not Listed For Sale

  126 Dean Hill Rd, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 2,604 Sq Ft
  • Built 1987

  126 Dean Hill Rd, New Windsor, NY 12553

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Yves Bouzaglo Four Seasons Sothebys Intl
• 

  $290,000

  Sold Dec 11, 2025

  37 Clancy Ave, New Windsor, NY 12553

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1920

  Last Sold Summary

  • 14% Above List Price
  • $242/SF
  • 41 Days On Market

  Current Estimated Value $299,968

  Last Listing Agent Carlos Bermudez 1st Independent Realty Grp

  37 Clancy Ave, New Windsor, NY 12553
• 

  Est $541,053

  Not Listed For Sale

  114 Dean Hill Rd, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft
  • Built 1979

  114 Dean Hill Rd, New Windsor, NY 12553

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Jade Oliverio Howard Hanna Rand Realty

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