Windham, NY Homes

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  /72

  $1,311,000 Sold Dec 30, 2025

  61 Cambridge Heights Rd, Windham, NY 12496

  • 5 Beds
  • 3.5 Baths
  • 4,214 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Above List Price
  • $311/SF
  • 30 Days On Market

  Current Estimated Value $1,074,369

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  61 Cambridge Heights Rd, Windham, NY 12496
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  /7

  Est $217,034 Not Listed For Sale

  32 Hickory Hill Rd, Windham, NY 12496

  • 2 Beds
  • Built 1953

  32 Hickory Hill Rd, Windham, NY 12496

  Last Sold Summary

  • 102% Above List Price
  • $101/SF
  • 7 Days On Market

  Last Sold Price $107,500

  Last Listing Agent Kathy Marino Bunce Realty
• 

  

  

  /55

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,448 Sq Ft

  5376 State Route 23, Windham, NY 12496

  Prime location and versatility make this Main Street Windham offering an outstanding opportunity. High visibility at one of the town's busiest intersections is not only great exposure but a rare find. For decades, this building was the home and shop of the local barber. In recent years the street level space served as the main office for a local builder. Currently vacant, this property has great

  Sharri Cunningham Bunce Realty

  5376 State Route 23, Windham, NY 12496
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  /30

  $1,400,000 Sold Sep 18, 2025

  4 The Loop, Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 2,536 Sq Ft
  • Built 1974

  Last Sold Summary

  • 6% Below List Price
  • $552/SF
  • 121 Days On Market

  Current Estimated Value $1,377,285

  Last Listing Agent Patricia Charbonneau Brainard Ridge Management

  4 The Loop, Windham, NY 12496
• 

  

  

  /19

  Est $882,667 Not Listed For Sale

  12 Mount View Estates Rd, Windham, NY 12496

  • 4 Beds
  • 4 Baths
  • 4,000 Sq Ft
  • Built 2006

  12 Mount View Estates Rd, Windham, NY 12496

  Last Sold Summary

  • 2% Below List Price
  • $225/SF
  • 5 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Brandon Oot Core Real Estate Team
• 

  

  /31

  $159,900

  • Land
  • 8.33 Acres
  • $19,196 per Acre

  Tbd, Windham, NY 12496

  Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

  Kyla Thomas Howard Hanna Rand Realty

  Tbd, Windham, NY 12496
• 

  

  /25

  $1,200,000 Sold Apr 30, 2025

  5344 Main St, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 6,400 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Below List Price
  • $188/SF

  Last Listing Agent Phil Uhrik Win Morrison Realty - W

  5344 Main St, Windham, NY 12496
• 

  

  /18

  Est $744,305 Not Listed For Sale

  13 Huckleberry Ln, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,978 Sq Ft
  • Built 1986

  13 Huckleberry Ln, Windham, NY 12496

  Last Sold Summary

  • 50% Above List Price
  • $251/SF
  • 102 Days On Market

  Last Sold Price $497,000

  Last Listing Agent Pieta Williams Halter Associates Realty
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  /31

  $525,000

  • 3 Beds
  • 1.5 Baths
  • 2,084 Sq Ft

  34 Old Rd, Windham, NY 12496

  Discover an exceptional Windham, NY mountain retreat just ~2 miles from Windham Mountain, offering both lifestyle appeal and income potential. This spacious, rustic 3-bedroom, 1.5-bath home features two separate living rooms—one on the first floor and one on the second floor—providing flexible space for entertaining, relaxing, or multi-group living. A cozy fireplace, open living areas, modern

  Michael Mariani Patricia Forgione's Realty

  34 Old Rd, Windham, NY 12496
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  /29

  $1,675,000 Sold May 12, 2025

  21 - 4A Stonewall Ln, Windham, NY 12496

  • 5 Beds
  • 4.5 Baths
  • 3,148 Sq Ft
  • Built 2024

  Last Sold Summary

  • 12% Below List Price
  • $532/SF
  • 0 Days On Market

  Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

  21 - 4A Stonewall Ln, Windham, NY 12496
• 

  

  /10

  Est $1,174,917 Not Listed For Sale

  99 Buckskin Loop, Windham, NY 12496

  • 5 Beds
  • 2.5 Baths
  • 3,596 Sq Ft
  • Built 2002

  99 Buckskin Loop, Windham, NY 12496

  Last Sold Summary

  • $0/SF
  • 68 Days On Market

  Last Listing Agent Jacqueline Coyle Coldwell Banker Village GreenW
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  /28

  $234,500

  • Land
  • 2.3 Acres
  • $101,957 per Acre

  0 N Ridge Extension Unit 20255019, Windham, NY 12496

  Welcome to North Ridge Estates - Build Your Catskills Dream GetawayHere's your chance to own the last remaining building lot in North Ridge Estates, an exclusive, private enclave known for its high-end vacation homes and newly built million-dollar properties. Set on 2.30 acres, this prime parcel has already been surveyed and features a driveway leading into the heart of the property with

  Lisa Jaeger Coldwell Banker Village GreenW

  0 N Ridge Extension Unit 20255019, Windham, NY 12496
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  /42

  $655,000 Sold Dec 23, 2025

  442 Mitchell Hollow Rd, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft
  • Built 1969

  Last Sold Summary

  • 6% Below List Price
  • $228/SF
  • 146 Days On Market

  Current Estimated Value $651,710

  Last Listing Agent Mark McAlpine Compass Greater New York, LLC

  442 Mitchell Hollow Rd, Windham, NY 12496
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  /35

  Est $645,290 Not Listed For Sale

  861 County Route 10, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1979

  861 County Route 10, Windham, NY 12496

  Last Sold Summary

  • 4% Below List Price
  • $438/SF
  • 5 Days On Market

  Last Sold Price $670,000

  Last Listing Agent Joseph Satto Fresh Air Realty
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  /48

  $369,000

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  110/2 Highridge Rd, Hensonville, NY 12439

  Charming 3-Bedroom Retreat in Serene Wooded Setting Nestled on a private road in a tranquil wooded haven, this newly renovated 3-bedroom, 2-bath retreat seamlessly blends modern comforts with cozy charm. Perfect as a primary residence, vacation home, or income-generating AirB&B, this property offers exceptional versatility and appeal. Key Features: Upper Level: Spacious bedroom, full bath, and an

  Fred Mazza Bunce Realty

  110/2 Highridge Rd, Hensonville, NY 12439
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  /34

  $420,000 Sold Jul 14, 2025

  296 Mitchell Hollow Rd, Windham, NY 12496

  • 3 Beds
  • 1 Bath
  • 1,486 Sq Ft
  • Built 1847

  Last Sold Summary

  • 4% Below List Price
  • $283/SF
  • 33 Days On Market

  Current Estimated Value $428,592

  Last Listing Agent Allison Morelle Coldwell Banker Village GreenK

  296 Mitchell Hollow Rd, Windham, NY 12496
• 

  Est $595,113 Not Listed For Sale

  543 N Settlement Rd, Windham, NY 12496

  • 4 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1974

  543 N Settlement Rd, Windham, NY 12496

  Last Sold Summary

  • 4% Below List Price
  • $497/SF
  • 40 Days On Market

  Last Sold Price $620,000

  Last Listing Agent Jennifer Woods Daniel Gale Sotheby's
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  /9

  $75,000

  • Land
  • 2 Acres
  • $37,500 per Acre

  0 Trailview Ln, Windham, NY 12496

  Transform Your Vision at Trail View-Dreaming of the perfect place to make your vision a reality? Trail View is where it all begins-a breathtaking 2-acre lot nestled in the heart of Windham, offering stunning slope views and endless possibilities. Whether you're planning your dream home, a cozy vacation cabin, or a chic rental property, this lot is ready to bring your ideas to life! Imagine

  Regina Tortorella Coldwell Banker Village GreenW

  0 Trailview Ln, Windham, NY 12496
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  /59

  $1,392,500 Sold Mar 06, 2026

  3 the Enclave, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 2,893 Sq Ft
  • Built 2002

  Last Sold Summary

  • 13% Below List Price
  • $481/SF
  • 116 Days On Market

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  3 the Enclave, Windham, NY 12496
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  /35

  Not Listed For Sale

  11 Whisper Unit 105g, Windham, NY 12496

  • 3 Beds
  • 4 Baths
  • 1,686 Sq Ft
  • Built 2016

  11 Whisper Unit 105g, Windham, NY 12496

  Last Sold Summary

  • $445/SF
  • 24 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW
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  /37

  $179,900

  • Land
  • 5.61 Acres
  • $32,068 per Acre

  TBD Boulder Brook Rd Unit Lot 11, Windham, NY 12496

  Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

  Kyla Thomas Howard Hanna Rand Realty

  TBD Boulder Brook Rd Unit Lot 11, Windham, NY 12496
• 

  

  /30

  $397,500 Sold Nov 25, 2025

  1020 Maplecrest Rd, Windham, NY 12439

  • 4 Beds
  • 2 Baths
  • 2,267 Sq Ft
  • Built 1980

  Last Sold Summary

  • 1% Below List Price
  • $175/SF
  • 54 Days On Market

  Last Listing Agent Mary Donovan Gallagher & Company

  1020 Maplecrest Rd, Windham, NY 12439
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  /33

  Not Listed For Sale

  11 Whisper Unit 405f, Windham, NY 12496

  • 4 Beds
  • 4 Baths
  • 1,856 Sq Ft
  • Built 2016

  11 Whisper Unit 405f, Windham, NY 12496

  Last Sold Summary

  • $498/SF
  • 96 Days On Market

  Last Sold Price $925,000

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW
• 

  

  /32

  $319,000

  • 2 Beds
  • 2.5 Baths
  • 1,211 Sq Ft

  44 Loo Bridge Ln Unit 14B, Windham, NY 12496

  NEW PRICE! Turn Key! Pride of Ownership shows in this Windham Ridge 2 bedroom 2.5 bath, come and be part of the Windham Family in this sweet year round community. 1st level has Primary ensuite, and guest room with its own bath. 2nd level opens up to a spacious great room with open concept, bright and sunny. Fully equipped kitchen, A wood burning fireplace for those chilly days, vaulted ceilings

  Irene Pinto Brainard Ridge Management

  44 Loo Bridge Ln Unit 14B, Windham, NY 12496
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  /44

  $840,000 Sold Jun 20, 2025

  429 Mill St, Windham, NY 12496

  • 4 Beds
  • 3.5 Baths
  • 2,294 Sq Ft
  • Built 2003

  Last Sold Summary

  • 1% Below List Price
  • $366/SF
  • 31 Days On Market

  Current Estimated Value $890,339

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  429 Mill St, Windham, NY 12496
• 

  

  /35

  Not Listed For Sale

  11 Whisper Unit 108c, Windham, NY 12496

  • 2 Beds
  • 3 Baths
  • 1,727 Sq Ft
  • Built 2016

  11 Whisper Unit 108c, Windham, NY 12496

  Last Sold Summary

  • $420/SF
  • 72 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW
• 

  

  /36

  $549,000

  • 7 Beds
  • 6 Baths
  • 4,800 Sq Ft

  41 County Road 40, Hensonville, NY 12439

  A Great Investment Opportunity with a 5 Unit Multi-family & a Large Barn in Windham - in the Charming Hamlet of Hensonville! The annual rent roll is 62,700. There are 4 units with 2 bedrooms and 1 bath and 1 unit with 3 bedrooms and 2 baths. There's ample parking, a front covered patio, a 2nd floor covered deck, yard space, a huge barn, and 3 driveway entrances. It has great proximity to the

  Ted Banta RVW Select Properties

  41 County Road 40, Hensonville, NY 12439
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  /52

  $685,000 Sold Dec 15, 2025

  128 Mount Greenery Rd, Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 2,759 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $248/SF
  • 44 Days On Market

  Current Estimated Value $689,401

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  128 Mount Greenery Rd, Windham, NY 12496
• 

  

  /35

  Not Listed For Sale

  11 Whisper Unit 305f, Windham, NY 12496

  • 3 Beds
  • 4 Baths
  • 1,856 Sq Ft
  • Built 2016

  11 Whisper Unit 305f, Windham, NY 12496

  Last Sold Summary

  • $466/SF
  • 7 Days On Market

  Last Sold Price $865,000

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW
• 

  

  /17

  $152,000

  • 1 Bath
  • 560 Sq Ft

  7 Quads Way, Windham, NY 12496

  Welcome to this cozy and beautifully maintained corner unit ground floor condo located at 7 Quads Way in the sought after Quads Condominium in Windham NY. From the moment you step inside you can feel how thoughtfully cared for this inviting space is making it easy to relax and feel right at home! The living area centers around a charming fireplace updated with stone creating the perfect spot to

  Emelisa Mendoza RE/MAX Town & Country

  7 Quads Way, Windham, NY 12496
• 

  

  /54

  $398,000 Sold Mar 23, 2026

  17 Mitchell Hollow Rd, Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 1,914 Sq Ft
  • Built 1900

  Last Sold Summary

  • 9% Below List Price
  • $208/SF
  • 98 Days On Market

  Last Listing Agent Sharri Cunningham Bunce Realty

  17 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /35

  Est $1,569,134 Not Listed For Sale

  10 Enclave Dr W, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Built 2005

  10 Enclave Dr W, Windham, NY 12496

  Last Sold Summary

  • 238% Above List Price
  • $364/SF
  • 218 Days On Market

  Last Sold Price $464,000

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW
• 

  

  /13

  $335,000

  • Land
  • 15.67 Acres
  • $21,378 per Acre

  10 Galway Rd, Windham, NY 12496

  Welcome to Windham Luxury Estates, where an exceptional opportunity awaits you with a fully approved, SHOVEL-ready 15.67 acre residential building lot. This prime parcel includes comprehensive engineering, topographical & survey maps, and a fully approved DEP septic design suitable for an estate-like home, ensuring compliance with environmental regulations for a streamlined building process.

  Patrick Dunn KW Platform

  10 Galway Rd, Windham, NY 12496
• 

  

  /31

  $850,000 Sold Oct 03, 2025

  205 Nauvoo Rd, Windham, NY 12496

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Above List Price
  • $386/SF
  • 21 Days On Market

  Current Estimated Value $808,321

  Last Listing Agent Kathy Marino Bunce Realty

  205 Nauvoo Rd, Windham, NY 12496
• 

  

  /15

  Not Listed For Sale

  0 Vining & Goff Rd Unit 20214430, Windham, NY 12496

  0 Vining & Goff Rd Unit 20214430, Windham, NY 12496

  Last Sold Summary

  • 20 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW
• 

  

  /49

  $149,000

  • Land
  • 5.25 Acres
  • $28,381 per Acre

  TBD Boulder Brook Rd Unit Lot 13, Windham, NY 12496

  Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

  Kyla Thomas Howard Hanna Rand Realty

  TBD Boulder Brook Rd Unit Lot 13, Windham, NY 12496
• 

  

  /39

  $835,000 Sold Mar 04, 2026

  407 Mill St, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 2,864 Sq Ft
  • Built 1986

  Last Sold Summary

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

  Current Estimated Value $837,905

  Last Listing Agent Brittany Craig Houlihan Lawrence Inc.

  407 Mill St, Windham, NY 12496
• 

  

  /41

  Est $412,096 Not Listed For Sale

  53 Shock St, Windham, NY 12496

  • 2 Beds
  • 1 Bath
  • 1,142 Sq Ft
  • Built 1984

  53 Shock St, Windham, NY 12496

  Last Sold Summary

  • 25% Above List Price
  • $289/SF
  • 9 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Matthew Loder Country Boy Realty
• 

  

  /38

  $2,495,000

  • 8 Beds
  • 3.5 Baths
  • 3,350 Sq Ft

  3 Leon MacGlashan Rd, Windham, NY 12454

  Experience Rustic Elegance and Timeless Wonder at 3 Leon Macglashan RoadNestled on over 210 acres of pristine Catskill landscapes, this extraordinary estate offers an unparalleled opportunity to embrace the serenity, privacy, and natural beauty of Windham, NY. From the moment you arrive, the property captivates with its historic charm, panoramic mountain views, and endless possibilities.

  Jake Garay Serhant LLC

  3 Leon MacGlashan Rd, Windham, NY 12454
• 

  

  /30

  $220,000 Sold Oct 24, 2025

  91 Windham Ridge Rd Unit 18B, Windham, NY 12496

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $235/SF
  • 199 Days On Market

  Last Listing Agent Wayne Bunce Bunce Realty

  91 Windham Ridge Rd Unit 18B, Windham, NY 12496

Showing Results 201 - 240, Page 6 of 18