New Windsor, NY Homes

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  /22

  $350,000 Pending

  • Land
  • 2.69 Acres
  • $130,112 per Acre

  524 MacNary Rd, New Windsor, NY 12553

  NEW WINDSOR LOTS FOR SALE...7 parcels, 6 possible lots always with town approvals to verify how many lots can be buildable in the heart of New Windsor with possible municipal water, sewer plus natural gas. First photo in MLS is the access from Knox Drive and the second photo is the access from Macnary Road. Additional Information: Soil Type: Unknown,

  George Koudounas RE/MAX Benchmark Realty Group

  524 MacNary Rd, 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 $332,685

  Last Listing Agent JOHN SCARANO Keller Williams Realty

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

  Est $434,502 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

  • 9% Above List Price
  • $222/SF
  • 20 Days On Market

  • Last Sold Price $400,000
  • Feb 26, 2024

  Last Listing Agent William Bergin RE/MAX Benchmark Realty Group
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  /14

  $84,900

  • 2 Beds
  • 2 Baths
  • 784 Sq Ft

  3146 Route 9w Unit 6A, New Windsor, NY 12553

  Brand New Home on Lot #6A! Imagine your bright and modern new home! This lovely home offers comfort, convenience and affordability. The home features an open layout, a kitchen with tons of cabinets and appliances. You'll find two nice bedrooms situated on opposite ends of the home, offering privacy. The primary bedrooms features its own private bathroom. Enjoy a super convenient location – just a

  Sandra Spector Howard Hanna Rand Realty

  3146 Route 9w Unit 6A, New Windsor, NY 12553
• 

  $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 $555,588

  Last Listing Agent Jennifer Rivera Keller Williams Realty

  309 Maple Ave, New Windsor, NY 12553
• 

  Est $609,820 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

  • 9% Above List Price
  • $229/SF
  • 62 Days On Market

  • Last Sold Price $560,000
  • Feb 07, 2024

  Last Listing Agent Joanne Finochio Howard Hanna Rand Realty
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  /18

  $310,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 1.5 Baths
  • 1,296 Sq Ft

  276 Temple Hill Rd Unit 704, New Windsor, NY 12553

  Welcome to this beautifully updated and move-in ready unit located in the highly desirable Temple Hill community in New Windsor. This spacious residence offers the perfect blend of comfort, style, and convenience—ideal for today’s buyer looking for low-maintenance living without sacrificing quality. Step inside to discover a bright and inviting layout featuring generous living space, abundant

  Julius Cooper eXp Realty

  276 Temple Hill Rd Unit 704, 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 $428,800

  Last Listing Agent Tyler Prokosch John J Lease REALTORS Inc

  223 Margo St, New Windsor, NY 12553
• 

  Est $682,949 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

  • $196/SF
  • 61 Days On Market

  • Last Sold Price $680,000
  • Dec 20, 2024

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty
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  /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
• 

  $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 $396,861

  Last Listing Agent JoCATENA HARGROVE Century 21 Hudson Valley Rlty.

  9 Louise Dr, New Windsor, NY 12553
• 

  Est $806,915 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

  • 1% Below List Price
  • $275/SF
  • 24 Days On Market

  • Last Sold Price $815,000
  • Aug 30, 2024

  Last Listing Agent Sharon Salameh BHHS River Towns Real Estate
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  /39

  $399,900

  • 3 Beds
  • 1.5 Baths
  • 996 Sq Ft

  19 Valewood Dr, New Windsor, NY 12553

  Welcome to this well-maintained home nestled on a quiet, tree-lined street in desirable New Windsor. Offering comfortable living spaces, a functional layout, and thoughtful updates, this home is ideal for everyday living and easy entertaining. A new roof installed in 2021 adds peace of mind for the next owner.Inside, you’ll find bright and inviting rooms filled with natural light, along with

  Janet Rendle Weichert Realtors

  19 Valewood Dr, New Windsor, NY 12553
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  $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
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  Est $687,588 Not Listed For Sale

  Unlisted Address

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

  Unlisted Address

  Last Sold Summary

  • 37% Above List Price
  • $148/SF
  • 33 Days On Market

  • Last Sold Price $502,000
  • Jul 25, 2023

  Last Listing Agent Erin Connolly-Frontino Artisan Realty
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  /24

  $479,999 Pending

  • 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
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  $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 $539,634

  Last Listing Agent Jacqueline Manzolillo-Blais Keller Williams Realty

  491 Toleman Rd, Rock Tavern, NY 12575
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  Est $712,783 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

  • 3% Below List Price
  • $328/SF
  • 31 Days On Market

  • Last Sold Price $735,000
  • Oct 02, 2024

  Last Listing Agent Virginia Corbett eXp Realty
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  /34

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  217 Brittany Terrace Unit 217, Rock Tavern, NY 12575

  Welcome to this beautiful home located in the highly sought-after Brittany Terrace community in Rock Tavern, offering the ease of one-level living in a peaceful, nature-filled setting. Perfectly positioned with wooded views in the front and a tranquil lake backdrop, this charming 3-bedroom home offers nearly 1,400 square feet of living space and a fantastic open floor plan ideal for both everyday

  Sandra Spector Howard Hanna Rand Realty

  217 Brittany Terrace Unit 217, Rock Tavern, NY 12575
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  $238,000 Sold Mar 31, 2026

  810 Blooming Grove Turnpike Unit 36, New Windsor, NY 12553

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

  Last Sold Summary

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

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  810 Blooming Grove Turnpike Unit 36, New Windsor, NY 12553
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  Est $711,068 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

  • 26% Above List Price
  • $208/SF
  • 29 Days On Market

  • Last Sold Price $565,000
  • Dec 13, 2023

  Last Listing Agent Dean Nugent Mary Jane Pastor Realty
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  /46

  $965,000 Pending

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

  1016 Forest Glen, New Windsor, NY 12553

  Experience refined living in the beautiful Forest Glen community. This impeccably maintained custom built residence showcases timeless elegance paired with modern comfort. From the moment you enter, you are welcomed by sun-drenched living spaces, thoughtfully designed for both sophisticated entertaining and everyday luxury. The main living level offers radiant heated floors and 5 zone surround

  Monica Whitney Exit Realty Connections

  1016 Forest Glen, 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 $529,657

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

  6 Farmstead Rd, New Windsor, NY 12553
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  Est $841,106 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

  • 12% Above List Price
  • $232/SF
  • 61 Days On Market

  • Last Sold Price $750,000
  • Dec 21, 2023

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
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  /33

  $850,000 Pre-Foreclosure

  • 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
• 

  $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 $391,758

  Last Listing Agent Federico Prada RE/MAX Benchmark Realty Group

  5 Buttermilk Dr, New Windsor, NY 12553
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  Est $404,382 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

  • 23% Above List Price
  • $163/SF
  • 14 Days On Market

  • Last Sold Price $330,000
  • Mar 13, 2024

  Last Listing Agent Desiree Beecham River Realty Services, Inc.
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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
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  $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 $386,204

  Last Listing Agent Penny Alper Your Move Matters LLC

  3 Saint Anne Dr, New Windsor, NY 12553
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  Est $381,700 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

  • 11% Above List Price
  • $206/SF
  • 99 Days On Market

  • Last Sold Price $345,000
  • Apr 23, 2024

  Last Listing Agent Melissa Forsyth Hudson Valley Home Connection
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  /35

  $499,000

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

  129 Vails Gate Heights Dr, New Windsor, NY 12553

  Welcome to this well-maintained raised ranch located in the desirable New Windsor area of the Hudson Valley. This inviting home offers 3 spacious bedrooms and 2 full bathrooms, providing comfortable living for a variety of lifestyles. The main level features a bright and functional layout with generous living space and natural light throughout. The lower level includes a large family room and

  Waldina Almazan RE/MAX Benchmark Realty Group

  129 Vails Gate Heights Dr, New Windsor, NY 12553
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  $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 $261,019

  Last Listing Agent Joy Gallagher Weichert Realtors

  8 E Green Rd, Rock Tavern, NY 12575
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  Est $421,221 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

  • 8% Above List Price
  • $178/SF
  • 29 Days On Market

  • Last Sold Price $389,900
  • Feb 02, 2024

  Last Listing Agent Diane Blanton Howard Hanna Rand Realty
• 

  

  /35

  $469,000

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

  335 Oak Dr, New Windsor, NY 12553

  Charming, well-maintained Colonial located in the sought-after Beaver Dam Lake Community. The home provides Lake Rights, Private Beach access, community center and park area. The home features 3 bedrooms including a large primary and two additional bedrooms with water views. Cozy living room with a working fireplace and a feature wall that is great for entertaining. Kitchen has granite

  Michael Scimeca Howard Hanna Rand Realty

  335 Oak 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 $393,913 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

  • 6% Above List Price
  • $161/SF
  • 36 Days On Market

  • Last Sold Price $370,000
  • Aug 06, 2024

  Last Listing Agent Marilynn Shultz BHHS Hudson Valley Properties
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  /24

  $349,900 Pending

  • 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
• 

  $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 $518,137

  Last Listing Agent Deborah Meurlin Exit Realty Connections

  12 Truex Cir, New Windsor, NY 12553
• 

  Est $342,886 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

  • 7% Above List Price
  • $261/SF
  • 5 Days On Market

  • Last Sold Price $319,000
  • Feb 28, 2024

  Last Listing Agent Colin Seitz RE/MAX Benchmark Realty Group
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  /28

  $245,000 Pending

  • 1 Bed
  • 1 Bath
  • 1,026 Sq Ft

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

  Welcome to this bright and inviting Junior 4 condominium, offering a flexible layout that includes one bedroom plus an additional room that can easily function as a home office, den, or guest space. Situated on the second floor, this home provides 1,026 sq. ft. of thoughtfully designed living space, featuring a stunning eat-in kitchen, a spacious living area with new luxury vinyl plank flooring,

  Virginia Corbett eXp Realty

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

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