Windham, NY Homes

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  /11

  Not Listed For Sale

  0 N Ridge Extension Lot 25 Unit 145406, Windham, NY 12496

  0 N Ridge Extension Lot 25 Unit 145406, Windham, NY 12496

  Last Sold Summary

  • 263 Days On Market
• 

  

  

  /15

  $439,000

  • Land
  • 3.46 Acres
  • $126,879 per Acre

  2 Windham Farms Rd, Windham, NY 12496

  Welcome to Windham Farms in Windham, NY, where two premium building lots offer an exceptional opportunity for custom homes that blend eco-friendly design with aesthetic appeal, complementing the year-round environment just minutes from Windham Mountain Club. Lot 2 is prepared for immediate construction, featuring an installed driveway to the designated house site, 200 amp underground electric

  Laurie Hanenberg Hunter Windham Real Estate

  2 Windham Farms Rd, Windham, NY 12496
• 

  

  

  /43

  $1,200,000

  Sold Jun 08, 2026

  7 Meadow Ln, Windham, NY 12496

  • 5 Beds
  • 5.5 Baths
  • 3,752 Sq Ft
  • Built 1979

  Last Sold Summary

  • 14% Below List Price
  • $320/SF
  • 243 Days On Market

  Current Estimated Value $1,328,280

  Last Listing Agent Joseph Satto Compass Greater NY, LLC

  7 Meadow Ln, Windham, NY 12496
• 

  

  

  /5

  Est $1,336,244

  Not Listed For Sale

  127 Brainard Ridge Rd, Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 2020

  127 Brainard Ridge Rd, Windham, NY 12496

  Last Sold Summary

  • 97 Days On Market
• 

  

  

  /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
• 

  

  /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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  /46

  Est $353,776

  Not Listed For Sale

  66 Loo Bridge Ln Unit 12G, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,211 Sq Ft
  • Built 1987

  66 Loo Bridge Ln Unit 12G, Windham, NY 12496

  Last Sold Summary

  • 173 Days On Market
• 

  

  /18

  $427,000

  $36K PRICE DROP

  • 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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  /36

  $310,000

  Sold Feb 11, 2026

  73 Windham Ridge Rd Unit 16-H, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,058 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $293/SF
  • 161 Days On Market

  Current Estimated Value $310,161

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  73 Windham Ridge Rd Unit 16-H, Windham, NY 12496
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  /72

  Est $928,676

  Not Listed For Sale

  39 Trail View Ln, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 3,914 Sq Ft
  • Built 2022

  39 Trail View Ln, Windham, NY 12496

  Last Sold Summary

  • 508 Days On Market
• 

  

  /55

  $599,000

  Pending

  • 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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  /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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  /25

  Not Listed For Sale

  5344 Main St, Windham, NY 12496

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

  5344 Main St, Windham, NY 12496

  Last Sold Summary
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  /29

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 1,227 Sq Ft

  5044 State Route 23, Windham, NY 12496

  Walk to the Windham Path from this newly renovated two story home. Offered fully furnished, stocked with everything you need to greet your next guest, this active Airbnb is ready for the next owner. Two first floor bedrooms each with their own beautifully new tiled bath. New kitchen with butcher block counter tops, new appliances with induction stove. Upstairs 2 more bedroom with its own half

  Cynthia Welch Welch Realty Inc.

  5044 State Route 23, Windham, NY 12496
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  /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 $594,846

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  89 Siam Rd, Windham, NY 12496
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  /2

  Est $1,934,892

  Not Listed For Sale

  502 County Route 10, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 4,300 Sq Ft
  • Built 2023

  502 County Route 10, Windham, NY 12496

  Last Sold Summary

  • 108 Days On Market
• 

  

  /7

  $1,998,500

  New Construction Pending

  • 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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  /19

  $485,000

  Sold Dec 18, 2025

  804 Mitchell Hollow Rd, Windham, NY 12496

  • 7 Beds
  • 2.5 Baths
  • 3,114 Sq Ft
  • Built 1852

  Last Sold Summary

  • 91% Below List Price
  • $156/SF
  • 55 Days On Market

  Current Estimated Value $506,941

  Last Listing Agent Chris Tripsas Reliant Property Services

  804 Mitchell Hollow Rd, Windham, NY 12496
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  /10

  Not Listed For Sale

  0 Mount Pisgah Rd, Windham, NY 12496

  • 3 Beds
  • Built 2008

  0 Mount Pisgah Rd, Windham, NY 12496

  Last Sold Summary

  • 70 Days On Market
• 

  

  /31

  $525,000

  $64K PRICE DROP Pending

  • 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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  /103

  $3,100,000

  Sold May 05, 2026

  219 Club Rd, Windham, NY 12496

  • 6 Beds
  • 5 Baths
  • 5,021 Sq Ft
  • Built 2023

  Last Sold Summary

  • 17% Below List Price
  • $617/SF
  • 254 Days On Market

  Current Estimated Value $2,962,989

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  219 Club Rd, Windham, NY 12496
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  /65

  Not Listed For Sale

  128 Mount Pisgah Rd, Windham, NY 12496

  • 5 Beds
  • 5 Baths
  • 4,233 Sq Ft
  • Built 2007

  128 Mount Pisgah Rd, Windham, NY 12496

  Last Sold Summary

  • 89 Days On Market
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  /48

  $349,000

  $91K PRICE DROP

  • 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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  /14

  $1,525,000

  Sold Feb 12, 2026

  10 Enclave Dr N Unit 106, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 1,655 Sq Ft
  • Built 2005

  Last Sold Summary

  • 8% Below List Price
  • $921/SF
  • 203 Days On Market

  Last Listing Agent Irene Pinto Brainard Ridge Management

  10 Enclave Dr N Unit 106, Windham, NY 12496
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  /26

  Est $445,786

  Not Listed For Sale

  111 Carrington Rd, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 1,526 Sq Ft
  • Built 2008

  111 Carrington Rd, Windham, NY 12496

  Last Sold Summary

  • 119 Days On Market
• 

  

  /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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  /74

  $1,535,000

  Sold Nov 19, 2025

  869 County Route 10 Rd, Windham, NY 12496

  • 5 Beds
  • 4.5 Baths
  • 3,812 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $403/SF
  • 40 Days On Market

  Current Estimated Value $1,535,029

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  869 County Route 10 Rd, Windham, NY 12496
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  /28

  Not Listed For Sale

  11025 New York 23, Windham, NY 12496

  • 3 Beds
  • 1.5 Baths
  • 1,647 Sq Ft
  • Built 1800

  11025 New York 23, Windham, NY 12496

  Last Sold Summary

  • 137 Days On Market
• 

  

  /37

  $179,900

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

  L35 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

  L35 Boulder Brook Rd Unit Lot 11, Windham, NY 12496
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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 $1,100,027

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  61 Cambridge Heights Rd, Windham, NY 12496
• 

  

  /27

  Est $687,150

  Not Listed For Sale

  118 Brainard Ridge Rd Unit 14D, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 1,702 Sq Ft
  • Built 1985

  118 Brainard Ridge Rd Unit 14D, Windham, NY 12496

  Last Sold Summary

  • 396 Days On Market
• 

  

  /32

  $319,000

  $20K PRICE DROP

  • 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, Plus a surprise room and bath to use as needed, bunk room, office, small den. Come and be part of the Windham Family in this sweet year round community. 1st level has Primary ensuite, and 2nd bedroom-ensuite. 2nd level opens up to a spacious great room with open concept, bright and sunny. Fully equipped

  Irene Pinto Brainard Ridge Management

  44 Loo Bridge Ln Unit 14B, Windham, NY 12496
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  /59

  $545,000

  Sold Apr 30, 2026

  274 Route 65 Unit 28, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 3,190 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $171/SF
  • 154 Days On Market

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  274 Route 65 Unit 28, Windham, NY 12496
• 

  

  /28

  Est $307,144

  Not Listed For Sale

  36 Loo Bridge Ln, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,211 Sq Ft
  • Built 1987

  36 Loo Bridge Ln, Windham, NY 12496

  Last Sold Summary

  • 118 Days On Market
• 

  

  /36

  $549,000

  $50K PRICE DROP Under Contract

  • 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
• 

  

  /96

  $1,571,126

  Sold May 12, 2026

  102 Thunderbird Terrace, Windham, NY 12496

  • 5 Beds
  • 3.5 Baths
  • 4,312 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $364/SF
  • 340 Days On Market

  Current Estimated Value $1,501,521

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  102 Thunderbird Terrace, Windham, NY 12496
• 

  

  /30

  Est $701,074

  Not Listed For Sale

  208 South St, Windham, NY 12496

  • 5 Beds
  • 3.5 Baths
  • 2,280 Sq Ft
  • Built 1920

  208 South St, Windham, NY 12496

  Last Sold Summary

  • 171 Days On Market
• 

  

  /46

  $1,750,000

  New Construction $25K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,218 Sq Ft

  31 Windham Farms Rd, Windham, NY 12496

  Modern Mountain Luxury | Windham, New YorkExperience contemporary mountain living at its finest in this exceptional new-construction residence, perfectly positioned just one mile from the Village of Windham. Thoughtfully designed and impeccably built, this light-filled retreat captures the essence of refined modern living in the heart of the Catskills. The home's sophisticated open layout

  Pamela King-Belfor Four Seasons Sotheby's Int.

  31 Windham Farms Rd, Windham, NY 12496
• 

  

  /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 $1,429,860

  Last Listing Agent Patricia Charbonneau Brainard Ridge Management

  4 The Loop, Windham, NY 12496
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  /21

  Not Listed For Sale

  5220 New York 23 Unit 130, Windham, NY 12496

  • 1 Bed
  • 1 Bath
  • 458 Sq Ft
  • Built 1960

  5220 New York 23 Unit 130, Windham, NY 12496

  Last Sold Summary

  • 16 Days On Market

Showing Results 161 - 200, Page 5 of 18