New Windsor, NY Homes

• 

  $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
• 

  

  

  /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

  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
• 

  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
• 

  

  /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
• 

  $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 $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
• 

  

  /50

  $870,000

  $65K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,509 Sq Ft

  131 Winding Brook Ct, New Windsor, NY 12553

  Stately Colonial on a Prestigious Cul-de-sac with Resort-Style Backyard Oasis! Boasting with 3,509 sqft, and additional 1,484sqft finished walk out lower level brings it to almost 5000 sqft in Cornwall Central School District! 4-5 bedrooms, 3 full baths, one 1/2 bath. Exceptional combination of elegance, privacy and style. Dramatic two story entry welcomes you with designer chandelier and wrought

  Brenda Guttenberg RE/MAX Benchmark Realty Group

  131 Winding Brook Ct, 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 $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
• 

  

  /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
• 

  $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 $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
• 

  

  /50

  $749,900

  $50K PRICE DROP

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

  8 Oak Dr, New Windsor, NY 12553

  Amazing price reduction! A truly unique and incredible property offering 2 separate homes on one parcel! 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 to offset

  Rose Daversa Hudson Valley Home Connection

  8 Oak Dr, 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 $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

  $875,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,903 Sq Ft

  28 Bethlehem Rd, New Windsor, NY 12553

  Set way back on 2.5 beautifully landscaped acres, within the sought-after Cornwall Central School District, this custom Center Hall Colonial offers the rare combination of timeless architecture, quality craftsmanship, and modern comfort. Built in 2011 and spanning just under 3,000 square feet, the home is thoughtfully designed with generous living spaces, refined finishes, and an ideal layout for

  Vincent Nastro Howard Hanna Rand Realty

  28 Bethlehem 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 $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
• 

  

  /11

  $335,000

  $65K PRICE DROP Pending

  • 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
• 

  $410,000

  Sold Jan 16, 2026

  44 Cedar Ave, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Above List Price
  • $244/SF
  • 91 Days On Market

  Current Estimated Value $365,667

  Last Listing Agent Gloria Merino RE/MAX Town & Country

  44 Cedar Ave, 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
• 

  

  /6

  $619,900

  Coming Soon

  • 5 Beds
  • 2 Baths

  110-112 S Jacqueline St, New Windsor, NY 12553

  **NEWLY LISTED LEGAL 2-FAMILY IN THE TOWN OF CORNWALL!**Set on **1.4 private acres**, this well-maintained Ranch-style home offers a wonderful opportunity for an owner-occupant or investor. Let your tenant help supplement your mortgage while you enjoy all this property has to offerThe main residence features a **large formal living room with a wood-burning fireplace**, creating a

  Kathleen Milich RE/MAX Benchmark Realty Group

  110-112 S Jacqueline St, New Windsor, NY 12553
• 

  $555,000

  Sold Dec 08, 2025

  17 Purdys Ln, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 3,012 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $184/SF
  • 109 Days On Market

  Current Estimated Value $618,677

  Last Listing Agent Kristen Velez RE/MAX Benchmark Realty Group

  17 Purdys Ln, New Windsor, NY 12553
• 

  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
• 

  

  /36

  $429,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,436 Sq Ft

  21 Stonecrest Dr, New Windsor, NY 12553

  Welcome to 21 Stonecrest Drive in the heart of New Windsor — a well-maintained and inviting 3-bedroom, 1 full bathroom home offering 1,436 square feet of comfortable living space. Featuring beautiful hardwood floors throughout the main level, this home offers warmth and character along with a practical layout perfect for everyday living. Enjoy the convenience of a one-car attached garage, a large

  Steve Moreau Tactical Realty LLC

  21 Stonecrest Dr, New Windsor, NY 12553
• 

  $350,000

  Sold Jul 29, 2026

  309 Windsor Hwy, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,470 Sq Ft
  • Built 1920

  Last Sold Summary

  • 11% Below List Price
  • $238/SF
  • 45 Days On Market

  Current Estimated Value $395,639

  Last Listing Agent Steve Esposito HomeSmart Homes & Estates

  309 Windsor Hwy, New Windsor, NY 12553
• 

  Est $344,807

  Not Listed For Sale

  502 Bayberry Ct, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,222 Sq Ft
  • Built 1993

  502 Bayberry Ct, New Windsor, NY 12553

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Colin Seitz RE/MAX Benchmark Realty Group
• 

  

  /38

  $689,000

  • 5 Beds
  • 3.5 Baths
  • 2,776 Sq Ft

  13 James Wilkinson Rd, Rock Tavern, NY 12575

  AMAZING 1.8 ACRE LEVEL PROPERTY! Stunning setting with fully fenced in INGROUND SALT WATER POOL! Extended updated bi-level! Impressive, family room with fireplace, cathedral ceilings and access to trex deck overlooking the park-like backyard with mature trees! Spacious home featuring 5 bedrooms, 4 FULL bathrooms! Kitchen features granite countertops, abundant wood cabinetry, pantry with custom

  Sharon Kushner eXp Realty

  13 James Wilkinson Rd, Rock Tavern, NY 12575
• 

  $200,000

  Sold Feb 06, 2026

  276 Temple Hill Rd Unit 2201, New Windsor, NY 12553

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

  Last Sold Summary

  • 2% Below List Price
  • $250/SF
  • 46 Days On Market

  Current Estimated Value $202,742

  Last Listing Agent jeff farnell John J Lease REALTORS Inc

  276 Temple Hill Rd Unit 2201, New Windsor, NY 12553
• 

  Est $343,249

  Not Listed For Sale

  504 Bayberry Ct Unit 49, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,246 Sq Ft
  • Built 1991

  504 Bayberry Ct Unit 49, New Windsor, NY 12553

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Nancy Diehl Rita Levine Real Estate
• 

  

  /42

  $860,000

  $30K PRICE DROP Pending

  • 5 Beds
  • 3 Baths
  • 2,998 Sq Ft

  27 Wild Turkey Ln, Rock Tavern, NY 12575

  Welcome to 27 Wild Turkey Lane—where every wish feels within reach.This beautifully maintained five-bedroom, three-bath Colonial blends timeless charm with modern sophistication, offering a lifestyle of comfort, elegance, and possibility.Step through the grand open foyer into a flowing, open-concept design that invites you to explore. The main level features gleaming hardwood floors, a

  Carlos Infante Coldwell Banker Realty

  27 Wild Turkey Ln, Rock Tavern, NY 12575
• 

  $475,000

  Sold Aug 12, 2026

  129 Vails Gate Heights Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 2,257 Sq Ft
  • Built 1972

  Last Sold Summary

  • $210/SF
  • 28 Days On Market

  Current Estimated Value $477,417

  Last Listing Agent Waldina Almazan RE/MAX Benchmark Realty Group

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

  Est $350,709

  Not Listed For Sale

  506 Bayberry Ct, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Built 1993

  506 Bayberry Ct, New Windsor, NY 12553

  Last Sold Summary

  • 44 Days On Market

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

  

  /40

  $480,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,350 Sq Ft

  5 Oak Ridge Dr, New Windsor, NY 12553

  Welcome to 5 Oak Ridge Drive in New Windsor! This well-maintained ranch-style home offers the convenience of single-level living with 3 bedrooms, 1.5 bathrooms, and an attached garage with an automatic electric door opener. Recent improvements include a new central air conditioning system and an upgraded electrical system, providing comfort and peace of mind for years to come.The

  Pete Wolven Hudson Valley Home Connection

  5 Oak Ridge Dr, New Windsor, NY 12553
• 

  $425,000

  Sold Nov 14, 2025

  109 Pine Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • Built 1941

  Last Sold Summary

  • 3% Below List Price
  • $275/SF
  • 54 Days On Market

  Current Estimated Value $433,144

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

  109 Pine Dr, New Windsor, NY 12553
• 

  Est $392,338

  Not Listed For Sale

  400 Arbor Ln, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,486 Sq Ft
  • Built 1993

  400 Arbor Ln, New Windsor, NY 12553

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty
• 

  

  /47

  $649,000

  $10K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 3,242 Sq Ft

  2 Melissa Ln, Washingtonville, NY 10992

  Welcome to this beautifully maintained one-owner Colonial offering 3,242 square feet of living space on a picturesque 1.4-acre property just one hour from New York City. Nothing in this home is small! A U-shaped driveway creates an impressive arrival, leading to a spacious home designed for comfortable living and effortless entertaining. Enter into a grand entryway featuring two closets and an

  Martha Randazzo Howard Hanna Rand Realty

  2 Melissa Ln, Washingtonville, NY 10992
• 

  $500,000

  Sold Jan 24, 2026

  14 Cherie Ln, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,958 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Below List Price
  • $255/SF
  • 108 Days On Market

  Current Estimated Value $502,828

  Last Listing Agent Suzanne Hallisey RE/MAX Benchmark Realty Group

  14 Cherie Ln, New Windsor, NY 12553

Showing Results 241 - 280, Page 7 of 18