New Windsor, NY Homes

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  /32

  $290,000

  • 3 Beds
  • 1.5 Baths
  • 1,736 Sq Ft

  82 Vails Gate Heights Dr, New Windsor, NY 12553

  Tidy three-bedroom townhome with private parking and an easy-to-maintain backyard in the convenient Vails Gate neighborhood of New Windsor. With nearly 1800 square feet of living space, the home offers a galley kitchen, two separate living areas, three bedrooms, and two baths across two levels. Laundry and mechanicals are located on the main living levels, with no basement to worry about

  Sarah Beckham ReAttached

  82 Vails Gate Heights Dr, New Windsor, NY 12553
• 

  $400,000

  Sold Jul 15, 2026

  19 Split Tree Dr, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1965

  Last Sold Summary

  • 14% Below List Price
  • $218/SF
  • 82 Days On Market

  Current Estimated Value $426,516

  Last Listing Agent Jade Oliverio Howard Hanna Rand Realty

  19 Split Tree Dr, New Windsor, NY 12553
• 

  Est $439,105

  Not Listed For Sale

  2014 John Jay Ct, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,221 Sq Ft
  • Built 2004

  2014 John Jay Ct, New Windsor, NY 12553

  Last Sold Summary

  • 97 Days On Market

  Last Listing Agent Daniel Balassone VYLLA Home
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  /33

  $769,967

  Pending

  • 3 Beds
  • 2.5 Baths
  • 3,516 Sq Ft

  50 Waterview Terrace, New Windsor, NY 12553

  Panoramic and spectacular Beaver Dam views from your beautiful Trex deck make every day of every season your own piece paradise!! 358' of lakefront make this one of the best lakefront properties anywhere! Oh yeah - the house - well that's awesome too. Lake views from almost every room, large kitchen with nook and double pantries, open family room with fireplace and turret style room full of

  Penny Alper Your Move Matters LLC

  50 Waterview Terrace, New Windsor, NY 12553
• 

  $535,000

  Sold Feb 27, 2026

  6 Farmstead Rd, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 2,768 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Above List Price
  • $193/SF
  • 92 Days On Market

  Current Estimated Value $547,885

  Last Listing Agent Hayley Butterfield LPT Realty Tri-State, LLC

  6 Farmstead Rd, New Windsor, NY 12553
• 

  Est $452,639

  Not Listed For Sale

  2002 John Jay Ct, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,801 Sq Ft
  • Built 2004

  2002 John Jay Ct, New Windsor, NY 12553

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent William Bergin RE/MAX Benchmark Realty Group
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  /15

  $357,000

  $41K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,408 Sq Ft

  237 Windsor Hwy, New Windsor, NY 12553

  Charming 3-bedroom Dutch Colonial built in 1930, offering timeless character and original details. Featuring beautiful hardwood floors, 1,404 sq. ft. of living space, side porch, a full walk-out basement, and a spacious high-pitched unfinished attic providing abundant storage opportunities. Situated on a generous lot with mature trees, including a stately magnolia, this home offers both charm and

  Gina De Cerbo RE/MAX Benchmark Realty Group

  237 Windsor Hwy, New Windsor, NY 12553
• 

  $770,000

  Sold May 26, 2026

  107 Denniston Dr, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 3,065 Sq Ft
  • Built 2002

  Last Sold Summary

  • 9% Below List Price
  • $251/SF
  • 43 Days On Market

  Current Estimated Value $779,110

  Last Listing Agent Brittany Barry HV Premier Properties Realty

  107 Denniston Dr, New Windsor, NY 12553
• 

  Est $648,892

  Not Listed For Sale

  37 Red Maple Way, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,444 Sq Ft
  • Built 2004

  37 Red Maple Way, New Windsor, NY 12553

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Joanne Finochio Howard Hanna Rand Realty
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  /17

  $269,000

  $20K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  79 Silver Spring Rd, New Windsor, NY 12553

  Charming 2-Bedroom Ranch offers a simple, functional layout with plenty of potential. The perfect chance to customize and make it your own. Whether you’re looking to downsize or step into homeownership, this property is a smart and affordable option with room to add value. Don’t miss it!

  Danielle Siltz RE/MAX Prime Properties

  79 Silver Spring Rd, New Windsor, NY 12553
• 

  $380,000

  Sold Dec 01, 2025

  5 Buttermilk Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,700 Sq Ft
  • Built 1983

  Last Sold Summary

  • 9% Above List Price
  • $224/SF
  • 0 Days On Market

  Current Estimated Value $397,159

  Last Listing Agent Federico Prada Curasi Realty, Inc.

  5 Buttermilk Dr, New Windsor, NY 12553
• 

  Est $722,634

  Not Listed For Sale

  11 Lisa Ln, New Windsor, NY 12553

  • 4 Beds
  • 3.5 Baths
  • 3,461 Sq Ft
  • Built 2000

  11 Lisa Ln, New Windsor, NY 12553

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty
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  /38

  $537,999

  $37K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,764 Sq Ft

  105 Shaker Ct N, New Windsor, NY 12553

  Tucked away on a quiet cul-de-sac in the sought-after Butter Hill Estates of New Windsor, this lovingly cared for home offers the perfect blend of comfort, space, and Hudson valley charm. Conveniently located near 9W and the Palisades Parkway, commuting to NYC is a breeze while still enjoying the peace & beauty of the Hudson Valley living. Step through the double doors into a bright and inviting

  Rebecca Bonhomme Howard Hanna Rand Realty

  105 Shaker Ct N, New Windsor, NY 12553
• 

  $380,000

  Sold Jan 16, 2026

  3 Saint Anne Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,392 Sq Ft
  • Built 1959

  Last Sold Summary

  • 5% Below List Price
  • $273/SF
  • 104 Days On Market

  Current Estimated Value $397,726

  Last Listing Agent Penny Alper Your Move Matters LLC

  3 Saint Anne Dr, New Windsor, NY 12553
• 

  Est $557,600

  Not Listed For Sale

  114 Windsor Hwy, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,664 Sq Ft
  • Built 1900

  114 Windsor Hwy, New Windsor, NY 12553

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty
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  /21

  $389,900

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  20 Hilltop Dr, New Windsor, NY 12553

  Welcome to 20 Hilltop Dr in New Windsor—an excellent opportunity for both investors and owner-occupants alike. Conveniently located with easy access to Interstate 84, the New York State Thruway, and Route 9W, this property offers an ideal location for commuters traveling throughout the Hudson Valley and beyond. Inside, you’ll find hardwood floors throughout much of the home, along with two full

  Martin Krakower eXp Realty

  20 Hilltop Dr, New Windsor, NY 12553
• 

  $260,000

  Sold Mar 19, 2026

  276 Temple Hill Rd Unit 2604, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Above List Price
  • $221/SF
  • 30 Days On Market

  Last Listing Agent Jahnny Crespo RE/MAX Town & Country

  276 Temple Hill Rd Unit 2604, New Windsor, NY 12553
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  Est $838,989

  Not Listed For Sale

  1016 Rolling Ridge, New Windsor, NY 12553

  • 4 Beds
  • 3 Baths
  • 2,962 Sq Ft
  • Built 2005

  1016 Rolling Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Sharon Salameh BHHS River Towns Real Estate
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  /20

  $499,900

  Pending

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

  69 Silver Spring Rd, New Windsor, NY 12553

  Welcome to this beautifully updated home in the heart of New Windsor offering comfort, style, and exceptional outdoor living. This well-maintained property features 3 bedrooms and 2 fully renovated bathrooms, along with a recently updated kitchen designed with modern finishes and functionality in mind. Gleaming hardwood floors run throughout the home, adding warmth and character to every room.

  Christina Biagini Weichert Realtors

  69 Silver Spring Rd, New Windsor, NY 12553
• 

  $508,000

  Sold Aug 15, 2025

  12 Truex Cir, New Windsor, NY 12553

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

  Last Sold Summary

  • 2% Below List Price
  • $271/SF
  • 57 Days On Market

  Current Estimated Value $518,989

  Last Listing Agent Deborah Meurlin Exit Realty Connections

  12 Truex Cir, New Windsor, NY 12553
• 

  Est $748,038

  Not Listed For Sale

  1008 Pine View, New Windsor, NY 12553

  • 4 Beds
  • 3.5 Baths
  • 2,242 Sq Ft
  • Built 2001

  1008 Pine View, New Windsor, NY 12553

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Virginia Corbett eXp Realty
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  /32

  $524,999

  Pending

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

  8 Shaker Ct, New Windsor, NY 12553

  Nestled in prestigious Butter Hill Estates of New Windsor, in the heart of the Hudson Valley, 8 Shaker Court is waiting for you! Surrounded by majestic mountains, come home to this expansive, captivating colonial! Enjoy early mornings and late evenings on the large front patio, and plenty of fun to be had in the fenced in backyard! Also featuring a full basement, spacious driveway and 2-car

  Irena Lulashi Keller Williams Rlty Integrity

  8 Shaker Ct, New Windsor, NY 12553
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  /60

  $900,000

  Sold May 11, 2026

  106 Station Rd, Salisbury Mills, NY 12577

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

  Last Sold Summary

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

  Current Estimated Value $958,059

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc.

  106 Station Rd, Salisbury Mills, NY 12577
• 

  Est $718,819

  Not Listed For Sale

  1047 Rolling Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft
  • Built 2005

  1047 Rolling Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Dean Nugent Mary Jane Pastor Realty
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  /24

  $299,000

  $126K PRICE DROP Pending

  • 3 Beds
  • 1 Bath
  • 1,896 Sq Ft

  12 Elizabeth Ln, New Windsor, NY 12553

  NEW PRICE PENDING BANK APPROVAL!!! Welcome to 12 Elizabeth Lane in New Windsor — a well-maintained 3-bedroom, 1-bath ranch offering comfortable single-level living on a beautifully manicured 0.23-acre lot. Set on an elevated property with attractive curb appeal, this home features a spacious and functional layout with bright living spaces and generous storage throughout. The main living area

  Arya Rabinovits eRealty Advisors, Inc

  12 Elizabeth Ln, New Windsor, NY 12553
• 

  $240,000

  Sold Mar 27, 2026

  276 Temple Hill Rd Unit 2513, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $204/SF
  • 42 Days On Market

  Current Estimated Value $255,739

  Last Listing Agent Tameeka Williams KFortuna All Aspects Realty

  276 Temple Hill Rd Unit 2513, New Windsor, NY 12553
• 

  Est $857,340

  Not Listed For Sale

  1021 Rolling Ridge, New Windsor, NY 12553

  • 5 Beds
  • 3 Baths
  • 3,232 Sq Ft
  • Built 2004

  1021 Rolling Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
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  /48

  $824,999

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,425 Sq Ft

  35 Briarwood Ln, New Windsor, NY 12553

  Welcome to this stunning custom ranch located in the highly sought-after Briarwood Estates community within the Cornwall School District. Built in 2018 by Olympia Development, this beautifully maintained 3-bedroom, 2.5-bath home offers 2,425 square feet of thoughtfully designed one-level living space with exceptional indoor and outdoor amenities. Step inside to an open floor plan featuring

  Erin Talarico Howard Hanna Rand Realty

  35 Briarwood Ln, New Windsor, NY 12553
• 

  $485,000

  Sold Dec 05, 2025

  117 Holly Dr, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,731 Sq Ft
  • Built 1941

  Last Sold Summary

  • 4% Above List Price
  • $280/SF
  • 19 Days On Market

  Current Estimated Value $488,519

  Last Listing Agent Gina De Cerbo RE/MAX Benchmark Realty Group

  117 Holly Dr, New Windsor, NY 12553
• 

  Est $403,719

  Not Listed For Sale

  705 Driftwood Ln, New Windsor, NY 12553

  • 2 Beds
  • 2.5 Baths
  • 2,028 Sq Ft
  • Built 1998

  705 Driftwood Ln, New Windsor, NY 12553

  Last Sold Summary

  • 14 Days On Market

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

  

  /50

  $785,000

  $15K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 4,407 Sq Ft

  8 Oak Dr, New Windsor, NY 12553

  PRICE IMPROVED! This incredible property offers 2 separate homes on one parcel! Privacy yet the bonus of 2 dwellings! Live in your spacious beautiful home of over 3100 square feet, and have the luxury of an adorable guest house next door or generate rental income or space for extended family. This amazing property also includes the possible option to assume the remaining VA loan at 2.25% interest

  Rose Daversa Hudson Valley Home Connection

  8 Oak Dr, New Windsor, NY 12553
• 

  $610,000

  Sold Jan 27, 2026

  2033 Little Britain Rd, Rock Tavern, NY 12575

  • 3 Beds
  • 2.5 Baths
  • 2,698 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Below List Price
  • $226/SF
  • 41 Days On Market

  Current Estimated Value $625,063

  Last Listing Agent Steve Esposito HomeSmart Homes & Estates

  2033 Little Britain Rd, Rock Tavern, NY 12575
• 

  Est $404,058

  Not Listed For Sale

  175 Highwood Dr, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,672 Sq Ft
  • Built 1995

  175 Highwood Dr, New Windsor, NY 12553

  Last Sold Summary

  • 99 Days On Market

  Last Listing Agent Melissa Forsyth Hudson Valley Home Connection
• 

  

  /21

  $325,000

  Pending

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

  1103 Washington Green, New Windsor, NY 12553

  This First Floor Unit in Washington Green is a rare find. It is one of the few with an oversized storage closet in unit off living room + a concrete walkway from the back patio stretching around to the parking lot, leaving almost no stairs. This End-unit living space backs up to the woods for complete privacy + tranquility, where you can enjoy your own gardening space and lawn. The Washington

  Lauren Racanelli RE/MAX Benchmark Realty Group

  1103 Washington Green, New Windsor, NY 12553
• 

  $300,000

  Sold Jun 26, 2026

  276 Temple Hill Rd Unit 2808, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,530 Sq Ft
  • Built 1986

  Last Sold Summary

  • 12% Below List Price
  • $196/SF
  • 87 Days On Market

  Current Estimated Value $319,267

  Last Listing Agent Kelly Roebuck Curasi Realty, Inc.

  276 Temple Hill Rd Unit 2808, New Windsor, NY 12553
• 

  Est $416,678

  Not Listed For Sale

  609 Crab Apple Ln, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft
  • Built 1993

  609 Crab Apple Ln, New Windsor, NY 12553

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Diane Blanton Howard Hanna Rand Realty
• 

  

  /3

  $72,500

  Pending

  • Land
  • 1.3 Acres
  • $55,769 per Acre

  140 Mount Airy Rd, New Windsor, NY 12553

  Over One Acre of Beautiful Wooded Land for SaleBuild your dream home on this stunning parcel of over one acre, located in a highly desirable and established neighborhood. Zoned for a single-family residence, this property offers the perfect blend of privacy, natural beauty, and convenience.The lot is heavily wooded, allowing you to preserve as many trees as you wish to create your own

  Jane Alfidi Howard Hanna Rand Realty

  140 Mount Airy Rd, New Windsor, NY 12553
• 

  $849,900

  Sold Nov 03, 2025

  558 Beattie Rd, Rock Tavern, NY 12575

  • 3 Beds
  • 2 Baths
  • 1,798 Sq Ft
  • Built 2010

  Last Sold Summary

  • $473/SF
  • 38 Days On Market

  Current Estimated Value $845,209

  Last Listing Agent Christina Wilger RE/MAX Benchmark Realty Group

  558 Beattie Rd, Rock Tavern, NY 12575
• 

  Est $415,725

  Not Listed For Sale

  187 Highwood Dr, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Built 1995

  187 Highwood Dr, New Windsor, NY 12553

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Marilynn Shultz BHHS Hudson Valley Properties
• 

  

  /11

  $335,000

  $65K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  7 Columbus St, New Windsor, NY 12553

  Investor opportunity in the heart of New Windsor! This two-family property offers two 1-bedroom apartments, with separate entrances making it an ideal addition to your investment portfolio or an excellent owner-occupant opportunity. Features include a new roof, separate electric meters, municipal water and sewer, and natural gas service. Situated on a generous lot with ample off-street parking

  Gina De Cerbo RE/MAX Benchmark Realty Group

  7 Columbus St, New Windsor, NY 12553

Showing Results 241 - 280, Page 7 of 18