New Windsor, NY Homes

• 

  $77,900 Sold Jan 07, 2026

  412 Sand Gate Dr, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • Built 2018

  Last Sold Summary

  • 13% Below List Price
  • $107/SF
  • 127 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  412 Sand Gate Dr, New Windsor, NY 12553
• 

  Est $434,415 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

  • 13% Above List Price
  • $173/SF
  • 97 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Daniel Balassone VYLLA Home
• 

  

  

  /11

  $289,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  32 Blanche Ave, New Windsor, NY 12553

  Welcome to 32 Blanche Ave, a delightful 2-bedroom, 1-bathroom home nestled in the heart of New Windsor. This charming residence sits on a generous 6,000 square-foot lot and offers 864 square feet of cozy living space, perfect for a small family or first-time homebuyers. As you approach, you'll be greeted by a charming covered porch, ideal for enjoying your morning coffee or relaxing with a good

  Avi Samet Avion

  32 Blanche Ave, New Windsor, NY 12553
• 

  $300,000 Sold Mar 12, 2025

  1133 Washington Green, New Windsor, NY 12553

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

  Last Sold Summary

  • 2% Below List Price
  • $292/SF
  • 99 Days On Market

  Current Estimated Value $311,021

  Last Listing Agent Elizabeth Nemeth John J Lease REALTORS Inc

  1133 Washington Green, New Windsor, NY 12553
• 

  Est $447,035 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

  • 12% Above List Price
  • $222/SF
  • 20 Days On Market

  Last Sold Price $400,000

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

  

  /20

  $235,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 575 Sq Ft

  24 Quassaick Ave, New Windsor, NY 12553

  This well-maintained and updated 2-bedroom, 1-bath home is truly move-in ready. Situated on a 50 x 100 lot, the property features a functional and inviting front yard, ideal for outdoor enjoyment. The updated kitchen is equipped with stainless steel appliances and offers a practical layout for everyday living. An enclosed front deck, built approximately three years ago, provides additional living

  Jonathon Lee Keller Williams Hudson Valley

  24 Quassaick Ave, New Windsor, NY 12553
• 

  $475,000 Sold Dec 22, 2025

  1802 Hawthorn Way, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft
  • Built 2012

  Last Sold Summary

  • $222/SF
  • 32 Days On Market

  Current Estimated Value $476,155

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  1802 Hawthorn Way, New Windsor, NY 12553
• 

  Est $621,481 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

  • 11% Above List Price
  • $229/SF
  • 62 Days On Market

  Last Sold Price $560,000

  Last Listing Agent Joanne Finochio Howard Hanna Rand Realty
• 

  

  /46

  $895,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,440 Sq Ft

  106 Fox Hill Run, Rock Tavern, NY 12575

  Welcome to 106 Fox Hill Run, a beautifully maintained original-owner Colonial set on 4.1 private acres in one of Rock Tavern’s most desirable locations. Built in 2008 and offering over 3,380 sq. ft. of living space, this home features an updated eat-in kitchen completed in 2023 with custom cabinetry, stainless appliances, and quartz counters, sliders leading to a Trex deck, a spacious family room

  Donna Brunell RE/MAX Benchmark Realty Group

  106 Fox Hill Run, Rock Tavern, NY 12575
• 

  $255,500 Sold May 21, 2025

  3 Jennifer Ct, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 1,076 Sq Ft
  • Built 1881

  Last Sold Summary

  • 2% Below List Price
  • $237/SF
  • 132 Days On Market

  Current Estimated Value $273,138

  Last Listing Agent Win Morrison Win Morrison Realty

  3 Jennifer Ct, New Windsor, NY 12553
• 

  Est $691,797 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

  • 2% Above List Price
  • $196/SF
  • 61 Days On Market

  Last Sold Price $680,000

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty
• 

  

  /32

  $310,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,309 Sq Ft

  307 Gazebo Ct, New Windsor, NY 12553

  Welcome to this bright and spacious move-in ready 2-bedroom, 2-bathroom condo located in the sought-after Windsor Crest community in New Windsor! This 2nd floor unit features an open-concept living and dining area with plenty of room for a large sectional and big-screen TV—perfect for relaxing or entertaining. The NEWLY RENOVATED kitchen features brand-new cabinets, countertops, microwave and

  Thomas Lawrenson Howard Hanna Rand Realty

  307 Gazebo Ct, New Windsor, NY 12553
• 

  $320,000 Sold Sep 16, 2025

  505 Barberry Ln Unit 91, New Windsor, NY 12553

  • 2 Beds
  • 1.5 Baths
  • 1,312 Sq Ft
  • Built 1988

  Last Sold Summary

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

  Current Estimated Value $328,103

  Last Listing Agent JOHN SCARANO Keller Williams Realty

  505 Barberry Ln Unit 91, New Windsor, NY 12553
• 

  Est $544,000 Not Listed For Sale

  46 Hillside Ave, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,740 Sq Ft
  • Built 1972

  46 Hillside Ave, New Windsor, NY 12553

  Last Sold Summary

  • 4% Above List Price
  • $302/SF
  • 145 Days On Market

  Last Sold Price $525,300

  Last Listing Agent Kerri Stretch Howard Hanna Rand Realty
• 

  

  /24

  $499,999

  • 3 Beds
  • 1.5 Baths
  • 1,754 Sq Ft

  629 Twin Arch Rd, Rock Tavern, NY 12575

  Welcome to this beautifully updated raised ranch, where modern style meets effortless functionality. Situated on a prime corner lot, this home is flooded with abundant natural light thanks to its numerous windows and open-concept layout. The main level features a seamless flow between the living and dining areas, perfect for entertaining or quiet evenings at home.The home offers three spacious

  Samantha McCrory Exit Realty Connections

  629 Twin Arch Rd, Rock Tavern, NY 12575
• 

  $535,000 Sold Aug 27, 2025

  309 Maple Ave, New Windsor, NY 12553

  • 3 Beds
  • 3 Baths
  • 2,526 Sq Ft
  • Built 1927

  Last Sold Summary

  • 2% Above List Price
  • $212/SF
  • 47 Days On Market

  Current Estimated Value $535,501

  Last Listing Agent Jennifer Rivera Keller Williams Realty

  309 Maple Ave, New Windsor, NY 12553
• 

  Est $832,960 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

  • 2% Above List Price
  • $275/SF
  • 24 Days On Market

  Last Sold Price $815,000

  Last Listing Agent Sharon Salameh BHHS River Towns Real Estate
• 

  

  /25

  $235,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,260 Sq Ft

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

  Imagine coming home to a space where everything is already done — no projects, no stress, just comfort and ease from the moment you walk in. Welcome to Unit #3, a fully renovated, first-floor, walk-in condo offering effortless one-level living in the heart of New Windsor. This move-in-ready two-bedroom, one-bath home has been completely updated with a modern, stylish feel and a layout designed

  Kerri Stretch Howard Hanna Rand Realty

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

  $440,000 Sold Feb 02, 2026

  223 Margo St, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,691 Sq Ft
  • Built 1961

  Last Sold Summary

  • 7% Above List Price
  • $260/SF
  • 41 Days On Market

  Current Estimated Value $405,004

  Last Listing Agent Tyler Prokosch John J Lease REALTORS Inc

  223 Margo St, New Windsor, NY 12553
• 

  Est $683,798 Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 2.5 Baths
  • 3,388 Sq Ft
  • Built 2002

  Unlisted Address

  Last Sold Summary

  • 36% Above List Price
  • $148/SF
  • 33 Days On Market

  Last Sold Price $502,000

  Last Listing Agent Erin Connolly Artisan Realty
• 

  

  /33

  $850,000

  • 5 Beds
  • 4 Baths
  • 4,366 Sq Ft

  1010 Pine View, New Windsor, NY 12553

  Tucked away on a private street within the desirable Forest Glen community, this tastefully updated 5-bedroom, 4-bath modern Colonial offers the perfect balance of privacy, space, and convenience—just 6 minutes to the Salisbury/Cornwall Metro-North station and moments from major shopping and everyday amenities. Set on a beautifully level and fenced 0.51-acre property, the home features an

  Samuel Berek Serhant LLC

  1010 Pine View, New Windsor, NY 12553
• 

  $375,000 Sold Dec 23, 2025

  9 Louise Dr, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Built 1974

  Last Sold Summary

  • 23% Below List Price
  • $214/SF
  • 223 Days On Market

  Current Estimated Value $391,601

  Last Listing Agent JoCATENA HARGROVE Century 21 Hudson Valley Rlty.

  9 Louise Dr, New Windsor, NY 12553
• 

  Est $733,213 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

  • $328/SF
  • 31 Days On Market

  Last Sold Price $735,000

  Last Listing Agent Virginia Corbett eXp Realty
• 

  

  /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
• 

  $208,000 Sold Dec 08, 2025

  Lot 1 Bethlehem Rd, New Windsor, NY 12553

  • Land
  • 1.52 Acres
  • $136,842 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 348 Days On Market

  Last Listing Agent Shawn Larry SHAHAR Management LLC

  Lot 1 Bethlehem Rd, New Windsor, NY 12553
• 

  Est $702,464 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

  • 24% Above List Price
  • $208/SF
  • 29 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Dean Nugent Mary Jane Pastor Realty
• 

  

  /22

  $234,900

  • 2 Beds
  • 2 Baths
  • 1,680 Sq Ft

  201 Brittany Terrace, Rock Tavern, NY 12575

  Luxurious home located in the highly sought after Brittany Terrace community in Rock Tavern. Rare unit in this 55 plus community with a one car attached garage! Beautiful 2 bedroom home with a den/sitting room close to 1,700 square feet. The home is in excellent condition, meticulously maintained. Corner lot with two driveways, 2 porches, attached garage (garage has a side door to outside too)

  Sandra Spector Howard Hanna Rand Realty

  201 Brittany Terrace, Rock Tavern, NY 12575
• 

  $525,000 Sold Aug 22, 2025

  491 Toleman Rd, Rock Tavern, NY 12575

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Above List Price
  • $286/SF
  • 20 Days On Market

  Current Estimated Value $520,272

  Last Listing Agent Jacqueline Manzolillo-Blais Keller Williams Realty

  491 Toleman Rd, Rock Tavern, NY 12575
• 

  Est $831,869 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

  • 11% Above List Price
  • $232/SF
  • 61 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /24

  $349,900 Coming Soon

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

  614 Crab Apple Ln, New Windsor, NY 12553

  Discover your dream home at Windsor Crest in New Windsor, NY! This beautifully updated 2-bedroom, 2-bath townhouse features a stunning fireplace, new flooring, and a modern heating system—all in excellent condition. Enjoy top-notch amenities like a pool, tennis court, pickleball, and a clubhouse. Live the lifestyle you’ve always dreamed of!Updates to the house are as follows:Lifeproof

  Alan Scheiner A.B.S. Realty Corp

  614 Crab Apple Ln, 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 $383,033

  Last Listing Agent Federico Prada RE/MAX Benchmark Realty Group

  5 Buttermilk Dr, New Windsor, NY 12553
• 

  Est $398,120 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

  • 21% Above List Price
  • $163/SF
  • 14 Days On Market

  Last Sold Price $330,000

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

  

  /40

  $479,999 Pending

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

  1210 Hawthorn Way, New Windsor, NY 12553

  Just turn the key and move right into this meticulously maintained 3 bedroom 2.5 bath home at The Grove. 1 Year home warranty included! This elegant & bright home offers sophisticated living with features such as hardwood floors and central A/C. Featuring an enormous eat-in kitchen which is a chef's dream. It's equipped with stainless steel appliances, which include a new LG fridge 1/2026,

  Elsie Nunez Keller Williams Realty

  1210 Hawthorn Way, 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 $405,056

  Last Listing Agent Penny Alper Your Move Matters LLC

  3 Saint Anne Dr, New Windsor, NY 12553
• 

  Est $396,631 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

  • 15% Above List Price
  • $206/SF
  • 99 Days On Market

  Last Sold Price $345,000

  Last Listing Agent Melissa Forsyth Hudson Valley Home Connection
• 

  

  /21

  $139,000

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  10 Oakwood Terrace Unit 65, New Windsor, NY 12553

  Welcome to this beautifully maintained 1-bedroom co-op located in the desirable Oakwood Terrace community. This bright and clean unit offers a spacious layout with an abundance of closet space, perfect for comfortable and organized living. Step out onto your private balcony and enjoy peaceful outdoor space ideal for morning coffee or evening relaxation. The apartment features on-site laundry for

  Jennifer Lucas Keller Williams Realty

  10 Oakwood Terrace Unit 65, New Windsor, NY 12553
• 

  $256,000 Sold Sep 18, 2025

  8 E Green Rd, Rock Tavern, NY 12575

  • 5 Beds
  • 2 Baths
  • 1,962 Sq Ft
  • Built 1947

  Last Sold Summary

  • 14% Below List Price
  • $130/SF
  • 47 Days On Market

  Current Estimated Value $277,445

  Last Listing Agent Joy Gallagher Weichert Realtors

  8 E Green Rd, Rock Tavern, NY 12575
• 

  Est $423,257 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

  • 9% Above List Price
  • $178/SF
  • 29 Days On Market

  Last Sold Price $389,900

  Last Listing Agent Diane Blanton Howard Hanna Rand Realty
• 

  

  /23

  $449,900 Pending

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

  76 Creamery Dr, New Windsor, NY 12553

  Don’t miss this spacious and well-appointed 3-bedroom, 3-bath, Family Room and Fireplace home located in the desirable Butter Hill Estates neighborhood of New Windsor, NY. This property features a large inground pool perfect for summer entertaining, a 2-car garage and ample driveway parking, a cozy fireplace for relaxing evenings. Convenient location close to schools, shopping (including Woodbury

  Jeanette Santory Howard Hanna Rand Realty

  76 Creamery Dr, New Windsor, NY 12553
• 

  $640,000 Sold Mar 14, 2025

  324 Chestnut Ave, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,160 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $296/SF
  • 48 Days On Market

  Current Estimated Value $635,141

  Last Listing Agent Rebecca Bonhomme Howard Hanna Rand Realty

  324 Chestnut Ave, New Windsor, NY 12553

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