Windham, NY Homes

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  /39

  $340,000 Sold Dec 17, 2025

  4 French Park Dr Unit 1 (2a), Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1983

  Last Sold Summary

  • 5% Below List Price
  • $244/SF
  • 88 Days On Market

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  4 French Park Dr Unit 1 (2a), Windham, NY 12496
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  /5

  Not Listed For Sale

  0 Vining Rd Unit 135863, Windham, NY 12496

  0 Vining Rd Unit 135863, Windham, NY 12496
• 

  

  

  /27

  $999,000 Pending

  • 7 Beds
  • 3 Baths
  • 4,281 Sq Ft

  5474 New York 23, Windham, NY 12496

  This large historic home is the original site of Windham's first settler in 1785 and the Reynolds have been entertaining family & friends there since 1959!Located on the west side of town, it is an easy walk to Windham's shops & restaurants.It has a formal living room, (which has been used for an office and playroom), a large dining area and a large, comfortable family room. The kitchen is well

  Jane Reynolds Jane H. Reynolds

  5474 New York 23, Windham, NY 12496
• 

  

  

  /33

  $795,000 Sold Oct 27, 2025

  233 Begley Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 2,542 Sq Ft
  • Built 2001

  Last Sold Summary

  • $313/SF
  • 22 Days On Market

  Current Estimated Value $825,220

  Last Listing Agent Lubomir Hodan Shaw Country Realty, Inc.

  233 Begley Rd, Windham, NY 12496
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  /8

  Not Listed For Sale

  0 Mill St Unit 131275, Windham, NY 12496

  0 Mill St Unit 131275, Windham, NY 12496
• 

  

  /18

  $463,000

  • 3 Beds
  • 2 Baths
  • 1,249 Sq Ft

  111 Brainard Ridge Rd Unit 11B, Windham, NY 12496

  Brainard Ridge Charmer!Ready for 4 season active life style. Charming 3 bedroom, 2 bath plus extra sleeping alcove, Brainard Ridge Townhome. Open and airy floor plan, lots of natural light! Cozy living room with large wood burning fireplace, nice dining area, cheery kitchen, Primary bedroom with ensuite bath, plus extra sleeping alcove. Lower level with bunkroom, and guest bedroom, second

  Patricia Charbonneau Brainard Ridge Management

  111 Brainard Ridge Rd Unit 11B, Windham, NY 12496
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  /54

  Sold Apr 07, 2025

  11 Whisper Creek Dr Unit 601B, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 1,506 Sq Ft
  • Built 2019

  Last Sold Summary

  • 92 Days On Market

  Last Listing Agent Regina Tortorella Past Member

  11 Whisper Creek Dr Unit 601B, Windham, NY 12496
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  /13

  Not Listed For Sale

  0 Club Rd Unit 131268, Windham, NY 12496

  0 Club Rd Unit 131268, Windham, NY 12496
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  /49

  $1,295,000

  • 4 Beds
  • 3.5 Baths
  • 2,900 Sq Ft

  129 Club Rd, Windham, NY 12496

  Gorgeous Windham Mountain Contemporary. An abundance of natural light and impressive landscaping establish the setting as you step into this beautiful 4-bedroom 3.5 bath mountain home. Panoramic, stunning views from every room, spacious living room with cozy, tasteful furnishings, striking stone wood burning fireplace, bright kitchen with granite counters, solid maple cabinetry and Bosch

  Patricia Charbonneau Brainard Ridge Management

  129 Club Rd, Windham, NY 12496
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  /40

  $2,250,000 Sold May 15, 2025

  18 White Way, Windham, NY 12496

  • 6 Beds
  • 6 Baths
  • 4,228 Sq Ft
  • Built 2015

  Last Sold Summary

  • 10% Below List Price
  • $532/SF
  • 82 Days On Market

  Current Estimated Value $2,390,407

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  18 White Way, Windham, NY 12496
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  /57

  Est $1,267,575 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,316 Sq Ft

  38 Galway Rd, Windham, NY 12496

  

  38 Galway Rd, Windham, NY 12496
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  /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
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  /26

  $425,000 Sold Dec 15, 2025

  410 Big Hollow Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1970

  Last Sold Summary

  • $316/SF
  • 28 Days On Market

  Last Listing Agent Diana Polack Compass Greater NY, LLC

  410 Big Hollow Rd, Windham, NY 12496
• 

  

  /19

  Est $692,667 Not Listed For Sale

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

  12 Mount View Estates Rd, Windham, NY 12496

  12 Mount View Estates Rd, Windham, NY 12496
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  /7

  $1,998,500 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,000 Sq Ft

  4 Estate View Dr, Windham, NY 12496

  To be built. Experience unparalleled luxury in this custom-built mountain retreat. Situated on 10.5 private acres in the heart of the Catskills, Windham Luxury Estates offers an extraordinary opportunity to own a meticulously designed 3 level, 5k+ sq ft retreat. Built by Vaughn Construction, this 5 bed, 5.5 bath will showcase an open concept that connects the kitchen, dining & living areas-with

  Patrick Dunn KW Platform

  4 Estate View Dr, Windham, NY 12496
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  /9

  $440,000 Sold Oct 27, 2025

  65 Sundance Dr, Windham, NY 12496

  • Land
  • 15.36 Acres
  • $28,646 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 219 Days On Market

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  65 Sundance Dr, Windham, NY 12496
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  /18

  Est $743,841 Not Listed For Sale

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

  13 Huckleberry Ln, Windham, NY 12496

  13 Huckleberry Ln, Windham, NY 12496
• 

  

  /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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  /16

  $1,900,000 Sold May 02, 2025

  28 - 5D Stonewall Ln, Windham, NY 12496

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

  Last Sold Summary

  • $604/SF
  • 15 Days On Market

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

  28 - 5D Stonewall Ln, Windham, NY 12496
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  /10

  Est $1,292,620 Not Listed For Sale

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

  99 Buckskin Loop, Windham, NY 12496

  99 Buckskin Loop, Windham, NY 12496
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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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  /26

  $695,000 Sold May 16, 2025

  23 Circle Rd, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $348/SF
  • 106 Days On Market

  Current Estimated Value $725,393

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  23 Circle Rd, Windham, NY 12496
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  /16

  Est $274,559 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,407 Sq Ft

  28 Siam Rd, Windham, NY 12496

  28 Siam Rd, Windham, NY 12496
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  /39

  $849,000

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

  407 Mill St, Windham, NY 12496

  Welcome to Round Haus Chalet, a high design retro retreat set on five acres with spectacular 360-degree views, just minutes from Windham Mountain. Built in 1986, this distinctive three-bedroom, two-and-a-half-bath residence pairs playful, postmodern geometrical architecture with mid-century design. From cozy apres-ski gatherings, to chic summer soirees, this home was designed for every season of

  Anthony D'Argenzio Houlihan Lawrence

  407 Mill St, Windham, NY 12496
• 

  

  /29

  Sold Apr 24, 2025

  25 - 4C Stonewall Ln, Windham, NY 12496

  • 4 Beds
  • 3.5 Baths
  • 2,700 Sq Ft

  Last Sold Summary

  • 1 Day On Market

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

  25 - 4C Stonewall Ln, Windham, NY 12496
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  /2

  Est $711,162 Not Listed For Sale

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

  261 Siam Rd, Windham, NY 12496

  261 Siam Rd, Windham, NY 12496
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  /48

  $399,000

  • 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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  /6

  $120,000 Sold Apr 04, 2025

  80 Begley Rd, Windham, NY 12496

  • Land
  • 3.58 Acres
  • $33,520 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 120 Days On Market

  Last Listing Agent Regina Tortorella Past Member

  80 Begley Rd, Windham, NY 12496
• 

  

  /35

  Est $636,329 Not Listed For Sale

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

  861 County Route 10, Windham, NY 12496

  861 County Route 10, Windham, NY 12496
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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
• 

  

  /43

  $927,000 Sold Aug 15, 2025

  92 Northridge Exd, Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 3,104 Sq Ft
  • Built 2003

  Last Sold Summary

  • $299/SF
  • 30 Days On Market

  Last Listing Agent Mark McAlpine Compass Greater New York, LLC

  92 Northridge Exd, Windham, NY 12496
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  /35

  Not Listed For Sale

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

  11 Whisper Unit 105g, Windham, NY 12496

  11 Whisper Unit 105g, Windham, NY 12496
• 

  

  /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
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  /42

  $300,000 Sold Dec 04, 2025

  333 Begley Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Below List Price
  • $191/SF
  • 26 Days On Market

  Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

  333 Begley Rd, Windham, NY 12496
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  /33

  Not Listed For Sale

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

  11 Whisper Unit 405f, Windham, NY 12496

  11 Whisper Unit 405f, Windham, NY 12496
• 

  

  /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
• 

  

  /31

  $550,000 Sold Aug 08, 2025

  89 Siam Rd, Windham, NY 12496

  • 4 Beds
  • 1 Bath
  • 2,270 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $242/SF
  • 119 Days On Market

  Current Estimated Value $590,840

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  89 Siam Rd, Windham, NY 12496
• 

  

  /35

  Not Listed For Sale

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

  11 Whisper Unit 108c, Windham, NY 12496

  11 Whisper Unit 108c, Windham, NY 12496
• 

  

  /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
• 

  

  /22

  $255,000 Sold Apr 07, 2025

  24 Quads Way, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $253/SF
  • 140 Days On Market

  Current Estimated Value $273,329

  Last Listing Agent Lacey Sala Keller Williams Realty HV Nort

  24 Quads Way, Windham, NY 12496

Showing Results 161 - 200, Page 5 of 18