New Windsor, NY Homes

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  /29

  $285,000

  $30K PRICE DROP

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

  276 Temple Hill Rd Unit 2414, New Windsor, NY 12553

  Beautiful 2 Bedroom, 2 Full Bath open floor condo in the sought after Continental Manor community. Gorgeous kitchen with granite countertops, beautiful cabinets, custom backsplash, food pantry, and stainless steel appliances plus laundry. From the dining room, step onto the balcony with awesome views. Large master bedroom includes ensuite. Spacious second bedroom with walk-in closet. Newer

  Tremaine Selby Weichert Realtors

  276 Temple Hill Rd Unit 2414, New Windsor, NY 12553
• 

  $255,000

  Sold Apr 30, 2026

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

  • 1 Bed
  • 1 Bath
  • 1,026 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Above List Price
  • $249/SF
  • 47 Days On Market

  Current Estimated Value $246,274

  Last Listing Agent Virginia Corbett eXp Realty

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

  Est $486,685

  Not Listed For Sale

  7 Buttermilk Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,846 Sq Ft
  • Built 1984

  7 Buttermilk Dr, New Windsor, NY 12553

  Last Sold Summary

  • 26 Days On Market
• 

  

  

  /50

  $850,000

  • 4 Beds
  • 3 Baths
  • 3,408 Sq Ft

  110 Winding Brook Ct, New Windsor, NY 12553

  Stunning Colonial in the highly sought-after Winding Brook community, located within the award-winning Cornwall School District, offering over 3,400 square feet of beautifully finished living space. A dramatic two-story foyer creates an unforgettable first impression, showcasing gleaming hardwood floors and elegant architectural columns that set the stage for the refined interiors throughout.

  Donna Gennaro Howard Hanna Rand Realty

  110 Winding Brook Ct, New Windsor, NY 12553
• 

  $369,900

  Sold Oct 09, 2025

  9 Kearney Dr, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $385/SF
  • 128 Days On Market

  Current Estimated Value $365,415

  Last Listing Agent Nicholas Cuomo Keller Williams Realty

  9 Kearney Dr, New Windsor, NY 12553
• 

  Est $502,558

  Not Listed For Sale

  19 Creamery Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft
  • Built 1981

  19 Creamery Dr, New Windsor, NY 12553

  Last Sold Summary

  • 34 Days On Market
• 

  

  /16

  $89,900

  • 3 Beds
  • 2 Baths
  • 980 Sq Ft

  424 Sand Gate Dr, New Windsor, NY 12553

  Beautiful home located in desirable Windemere Estates, set on a level lot and offering close to 1,000 square feet of comfortable living space. This well-maintained home features an open floor plan connecting the kitchen, dining, and living areas, along with 3 bedrooms, 2 full baths, and a 2-car driveway. The kitchen offers beautiful cabinetry with abundant cabinet and counter space. Additional

  Sandra Spector Howard Hanna Rand Realty

  424 Sand Gate Dr, New Windsor, NY 12553
• 

  $445,000

  Sold Jan 13, 2026

  20 Cedar Ln, New Windsor, NY 12553

  • 3 Beds
  • 1.5 Baths
  • 1,746 Sq Ft
  • Built 1988

  Last Sold Summary

  • $255/SF
  • 51 Days On Market

  Current Estimated Value $443,680

  Last Listing Agent Jodi Gillespie Gillespie Real Estate LLC

  20 Cedar Ln, New Windsor, NY 12553
• 

  Est $720,513

  Not Listed For Sale

  2414 Settlers Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft
  • Built 2002

  2414 Settlers Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 158 Days On Market
• 

  

  /50

  $799,999

  $25K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 3,181 Sq Ft

  64 Fox Hill Run, Rock Tavern, NY 12575

  In Person Open House-Thursday, May 7th 4:00 -6:00PM- Come walk through this beautiful property.Can’t attend in person? Join me for a Virtual Open House -Thursday, May 7th 5:45-6:00pm email gina.dudgeon@randrealty.com for the link. Welcome to your dream home in a sought-after executive development! This stunning Colonial, offering over 3,100 square feet of beautifully designed living space,

  Gina Dudgeon Howard Hanna Rand Realty

  64 Fox Hill Run, Rock Tavern, NY 12575
• 

  $550,000

  Sold Jan 29, 2026

  168 Toleman Rd, Washingtonville, NY 10992

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Above List Price
  • $277/SF
  • 35 Days On Market

  Current Estimated Value $547,898

  Last Listing Agent Christina Rowan Howard Hanna Rand Realty

  168 Toleman Rd, Washingtonville, NY 10992
• 

  Est $685,446

  Not Listed For Sale

  2410 Settlers Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft
  • Built 2002

  2410 Settlers Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 26 Days On Market
• 

  

  /33

  $259,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  35 Union Ave, New Windsor, NY 12553

  Full of timeless character, this 3-bd/1-ba home offers a wonderful opportunity in the heart of New Windsor. The layout features functional living space with the right amount of indoor & outdoor space to enjoy. Built in 1911, this home carries the charm and craftsmanship of a bygone era — including a stunning stained glass window & original woodwork that serves as a true architectural showpiece

  Anne DiDomenico Keller Williams Hudson Valley

  35 Union Ave, New Windsor, NY 12553
• 

  $143,000

  Sold Aug 13, 2025

  16 Bivona Ln Unit 11, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2015

  Last Sold Summary

  • 11% Below List Price
  • $115/SF
  • 28 Days On Market

  Last Listing Agent Jennifer Orantes Coldwell Banker Realty

  16 Bivona Ln Unit 11, New Windsor, NY 12553
• 

  Est $743,217

  Not Listed For Sale

  2625 Liberty Ridge, New Windsor, NY 12553

  • 5 Beds
  • 2.5 Baths
  • 3,922 Sq Ft
  • Built 2003

  2625 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 40 Days On Market
• 

  

  /13

  $225,000

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft

  276 Temple Hill Rd Unit 1516, New Windsor, NY 12553

  Affordable homeownership opportunity in desirable Continental Manor! This 2-bedroom, second-floor condo offers comfortable living in a prime New Windsor location with easy access to I-84, I-87, West Point, Stewart International Airport, Metro-North train service, and New York City commuting options. Enjoy maintenance-free exterior living and community amenities including a pool. The unit offers

  Gina De Cerbo RE/MAX Benchmark Realty Group

  276 Temple Hill Rd Unit 1516, New Windsor, NY 12553
• 

  $300,000

  Sold Oct 09, 2025

  1183 State Route 94, New Windsor, NY 12553

  • 4 Beds
  • 1.5 Baths
  • 1,106 Sq Ft
  • Built 1951

  Last Sold Summary

  • $271/SF
  • 61 Days On Market

  Current Estimated Value $321,481

  Last Listing Agent Lisa Wade-Sebring Hudson Valley Home Connection

  1183 State Route 94, New Windsor, NY 12553
• 

  Est $695,515

  Not Listed For Sale

  2626 Liberty Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,608 Sq Ft
  • Built 2003

  2626 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 82 Days On Market
• 

  

  /50

  $699,999

  Pending

  • 5 Beds
  • 4 Baths
  • 3,858 Sq Ft

  254 Orrs Mills Rd, New Windsor, NY 12553

  This custom-built Contemporary Colonial captures breathtaking mountain views from every direction and features cathedral-style ceilings, a gas fireplace in the great room, and gorgeous daily sunset views. Set on a private 2-acre property, the home offers over 4,000 sq ft of sunlit living space with vaulted ceilings, skylights, Andersen windows, three fireplaces, two dens with Brazilian hardwood

  Bryan Dale eXp Realty

  254 Orrs Mills Rd, New Windsor, NY 12553
• 

  $405,000

  Sold Jul 17, 2025

  253 Tamerisk Ln, New Windsor, NY 12553

  • 2 Beds
  • 2.5 Baths
  • 2,192 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Above List Price
  • $185/SF
  • 18 Days On Market

  Current Estimated Value $442,019

  Last Listing Agent Tina Cardona RE/MAX Benchmark Realty Group

  253 Tamerisk Ln, New Windsor, NY 12553
• 

  Est $663,576

  Not Listed For Sale

  2101 Patriots Ct, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft
  • Built 2001

  2101 Patriots Ct, New Windsor, NY 12553

  Last Sold Summary

  • 49 Days On Market
• 

  

  /13

  $299,900

  Pending

  • 4 Beds
  • 3 Baths
  • 1,930 Sq Ft

  34 Birchwood Dr, New Windsor, NY 12553

  **Multiple offer situation. Seller requesting highest, best and final offers 5pm 5/20/2026.** Cute 4 bedroom ranch on a great corner lot in the Town of New Windsor. Hardwood floors throughout, eat-in kitchen, living room, central air and roomy enclosed patio right off the kitchen overlooking your yard. Bring your vision and bring this great property back to life! Sold as-is. Buyer to pay NYS and

  Brian Smith River Realty Services, Inc.

  34 Birchwood Dr, New Windsor, NY 12553
• 

  $460,000

  Sold Oct 30, 2025

  28 Hillcrest Dr, Salisbury Mills, NY 12577

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1955

  Last Sold Summary

  • $304/SF
  • 51 Days On Market

  Current Estimated Value $458,244

  Last Listing Agent Melissa Forsyth Hudson Valley Home Connection

  28 Hillcrest Dr, Salisbury Mills, NY 12577
• 

  Est $708,573

  Not Listed For Sale

  2652 Liberty Ridge, New Windsor, NY 12553

  • 4 Beds
  • 3 Baths
  • 3,601 Sq Ft
  • Built 2004

  2652 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 13 Days On Market
• 

  

  /28

  $399,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,436 Sq Ft

  62 Union Ave, New Windsor, NY 12553

  Welcome to 62 Union Ave in New Windsor — a beautifully renovated home that’s move-in ready and packed with updates buyers are looking for. Step inside to find refinished hardwood floors that bring warmth and character throughout the main living spaces. The home features a brand-new kitchen with modern finishes, perfect for both everyday living and entertaining. The bathroom has been fully updated

  Matthew Skowronski HomeSmart Homes & Estates

  62 Union Ave, New Windsor, NY 12553
• 

  $60,000

  Sold Oct 27, 2025

  305 Brittany Terrace Unit 305, Rock Tavern, NY 12575

  • 2 Beds
  • 1.5 Baths
  • 1,296 Sq Ft
  • Built 1980

  Last Sold Summary

  • 50% Below List Price
  • $46/SF
  • 141 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  305 Brittany Terrace Unit 305, Rock Tavern, NY 12575
• 

  Est $695,459

  Not Listed For Sale

  2824 Cherry Tree Way, New Windsor, NY 12553

  • 4 Beds
  • 3 Baths
  • 2,488 Sq Ft
  • Built 2004

  2824 Cherry Tree Way, New Windsor, NY 12553

  Last Sold Summary

  • 21 Days On Market
• 

  

  /22

  $226,900

  $8K PRICE DROP

  • 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
• 

  $460,000

  Sold Jan 30, 2026

  35 Guernsey Dr, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 1,640 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $280/SF
  • 23 Days On Market

  Current Estimated Value $461,429

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  35 Guernsey Dr, New Windsor, NY 12553
• 

  Est $709,294

  Not Listed For Sale

  2808 Cherry Tree Way, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft
  • Built 2004

  2808 Cherry Tree Way, New Windsor, NY 12553

  Last Sold Summary

  • 29 Days On Market
• 

  

  /37

  $799,999

  • 5 Beds
  • 2.5 Baths
  • 3,452 Sq Ft

  2041 Independence Dr, New Windsor, NY 12553

  Welcome to 2041 Independence Drive, a beautifully maintained extended colonial—the largest model in The Reserve community in New Windsor. Offering 5 bedrooms and 2.5 baths, this expansive home delivers both space and sophistication. Proudly offered by the original owners, it has been meticulously cared for and thoughtfully upgraded throughout. Step into a stunning two-story foyer with granite

  Philip Szumlaski Keller Williams Realty

  2041 Independence Dr, New Windsor, NY 12553
• 

  $525,000

  Sold Jun 15, 2026

  114 Chestnut Dr, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft
  • Built 1941

  Last Sold Summary

  • $354/SF
  • 42 Days On Market

  Current Estimated Value $525,120

  Last Listing Agent Jade Oliverio Howard Hanna Rand Realty

  114 Chestnut Dr, New Windsor, NY 12553
• 

  Est $713,773

  Not Listed For Sale

  2656 Liberty Ridge, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,808 Sq Ft
  • Built 2004

  2656 Liberty Ridge, New Windsor, NY 12553

  Last Sold Summary

  • 16 Days On Market
• 

  

  /33

  $420,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 1 Bath
  • 1,424 Sq Ft

  178 Mount Airy Rd, New Windsor, NY 12553

  This welcoming, 3-bedroom ranch in the Cornwall School District, offers the perfect combination of comfort, functionality, and flexible living space. Recent updates include a new roof (2024)! Inside, you enter an open-concept living and dining area that flows seamlessly into the kitchen, where you'll have all you need with your counter space, cabinetry, and appliances, including a stainless steel

  Nicole Gold RE/MAX Benchmark Realty Group

  178 Mount Airy Rd, New Windsor, NY 12553
• 

  $489,999

  Sold May 15, 2026

  1210 Hawthorn Way, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Above List Price
  • $240/SF
  • 37 Days On Market

  Current Estimated Value $481,371

  Last Listing Agent Elsie Nunez Keller Williams Realty

  1210 Hawthorn Way, New Windsor, NY 12553
• 

  Est $723,880

  Not Listed For Sale

  3042 Molly Pitcher Dr, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 2,808 Sq Ft
  • Built 2007

  3042 Molly Pitcher Dr, New Windsor, NY 12553

  Last Sold Summary

  • 176 Days On Market
• 

  

  /45

  $350,000

  Pending

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

  714 Hewitt Ln, New Windsor, NY 12553

  Plum Point End Unit Townhouse with River Views! This 2 bedroom 1.5 bath townhouse with attached garage is tucked away in the desirable Plum Point Complex with manicured grounds, pool, clubhouse, tennis courts, and close to all amenities. The paver front patio and covered porch welcome you. Spacious living room with wood burning fireplace, a formal dining room with built in bookshelves and sliders

  Brenda Guttenberg RE/MAX Benchmark Realty Group

  714 Hewitt Ln, New Windsor, NY 12553
• 

  $530,000

  Sold Sep 30, 2025

  47 Clintonwood Dr, New Windsor, NY 12553

  • 5 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • Built 1966

  Last Sold Summary

  • 4% Below List Price
  • $251/SF
  • 34 Days On Market

  Current Estimated Value $539,517

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group

  47 Clintonwood Dr, New Windsor, NY 12553
• 

  Est $507,530

  Not Listed For Sale

  352 Shelly Rd, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,996 Sq Ft
  • Built 1976

  352 Shelly Rd, New Windsor, NY 12553

  Last Sold Summary

  • 74 Days On Market
• 

  

  /4

  $259,000

  Pending

  • Land
  • 4.1 Acres
  • $63,171 per Acre

  1103 Little Britain Rd, Rock Tavern, NY 12575

  Less then one mile from New York Stewart International Airport. Over 4 commercial acres with 493 feet of frontage along Little Britain Road, aka Rte 207, and 496 feet of frontage along Mt Airy Road. Municipal water and sewer along Mt Airy Road. LC zoning allows for Retail, Service Establishments, Professional Business, restaurants, Hotels, Repair Garages, Car Washes & more.

  Robert Vitanza Rand Commercial

  1103 Little Britain Rd, Rock Tavern, NY 12575

Showing Results 441 - 480, Page 12 of 18