Windham, NY Homes

• 

  

  

  /41

  $155,000

  • Land
  • 5.99 Acres
  • $25,876 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
• 

  

  

  /35

  Est $1,685,907

  Not Listed For Sale

  128 Mounty Pisgah Rd, Windham, NY 12496

  • 5 Beds
  • 5 Baths
  • 4,233 Sq Ft
  • Built 2008

  128 Mounty Pisgah Rd, Windham, NY 12496

  Last Sold Summary

  • 478 Days On Market
• 

  

  

  /33

  $439,000

  $10K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  274 County Route 65 Unit 29, Windham, NY 12496

  A proven rental property with exceptional 5-star Airbnb reviews and guaranteed rental income well into 2027, this fully furnished and completely turnkey Catskills retreat offers a rare opportunity to own a luxury mountain getaway with immediate revenue potential. Perched on a desirable corner location at one of the highest points within the community, this exceptional 2-bedroom, 2-bath

  Derek Henriksen Dugo Realty

  274 County Route 65 Unit 29, Windham, NY 12496
• 

  

  

  /10

  Est $1,096,349

  Not Listed For Sale

  20 Oliver Rd, Windham, NY 12496

  • 4 Beds
  • 3.5 Baths
  • 2,326 Sq Ft
  • Built 2014

  20 Oliver Rd, Windham, NY 12496

  Last Sold Summary

  • 198 Days On Market
• 

  

  

  /18

  $3,195,000

  $405K PRICE DROP Pending

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

  209 Club Rd, Windham, NY 12496

  This is the mountain house everyone else wishes they'd found first. Set on one of Windham's most coveted lots, this 6-bedroom, 5-bath home combines true slope-side access with panoramic views that stretch across the Catskills. It's a genuine ski-in, ski-out property with easy access to Wonderama and Lower Wipeout. In the mornings, clip in and go. At day's end, you can choose your own finale, take

  Patricia Charbonneau Brainard Ridge Management

  209 Club Rd, Windham, NY 12496
• 

  

  /10

  Not Listed For Sale

  880 Rt 296, Jewett, NY 12444

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • Built 1960

  880 Rt 296, Jewett, NY 12444

  Last Sold Summary

  • 226 Days On Market
• 

  

  /77

  $2,250,000

  • 5 Beds
  • 4.5 Baths
  • 3,600 Sq Ft

  90 Club Rd, Windham, NY 12496

  Spectacular mountain views and steps away from the trails, this chalet is a Windham Mountain classic! One of the original homes on the mountain, it combines rustic charm with modern amenities. The heart of this home is its expansive great room perfect for relaxing after a day on the slopes or entertaining friends and family. Soaring cathedral ceilings with exposed wood beams add a sense of

  Sharri Cunningham Bunce Realty

  90 Club Rd, Windham, NY 12496
• 

  

  /10

  Est $1,141,564

  Not Listed For Sale

  98 Sky Hill Rd, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 2,044 Sq Ft
  • Built 2014

  98 Sky Hill Rd, Windham, NY 12496

  Last Sold Summary

  • 22 Days On Market
• 

  

  /41

  $1,700,000

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft

  23 Stonewall Ln, Windham, NY 12496

  Set within the natural beauty of the Windham Mountain Club, Stonewall Glen is a private mountain enclave defined by thoughtful design, understated luxury, and a deep connection to its surroundings. Conceived as a retreat for those who value privacy, craftsmanship, and a slower rhythm of living, the community offers a refined setting for gathering, entertaining, or quiet escape amid the Catskills’

  John Oliveira Douglas Elliman Real Estate

  23 Stonewall Ln, Windham, NY 12496
• 

  

  /10

  Est $744,329

  Not Listed For Sale

  3 Dusty Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,578 Sq Ft
  • Built 2014

  3 Dusty Rd, Windham, NY 12496

  Last Sold Summary

  • 42 Days On Market
• 

  

  /4

  $799,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,118 Sq Ft

  69 County Road 32c, Windham, NY 12496

  • Escape NYC• Catskills Mountain Retreat• New Construction in Windham Area The proposed 2,118-square-foot home is designed for modern Catskill living, featuring soaring vaulted ceilings with exposed beams and dramatic trapezoid windows that capture natural light and panoramic views of the surrounding mountains.The open-concept layout connects the great room, kitchen, and dining area,

  John Pumilia Shaw Country Realty, Inc.

  69 County Road 32c, Windham, NY 12496
• 

  

  /11

  Not Listed For Sale

  0 Sky Hill Rd Unit 20143695, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 2,044 Sq Ft
  • Built 2014

  0 Sky Hill Rd Unit 20143695, Windham, NY 12496

  Last Sold Summary

  • 115 Days On Market
• 

  

  /42

  $1,040,000

  • 3 Beds
  • 2.5 Baths
  • 2,342 Sq Ft

  216 New York 296, Windham, NY 12496

  Nestled in the Northern Catskills, Maple Terrace is a cedar shake Cape that has quietly stood in these mountains since the early 1900s. Once a beloved inn welcoming city dwellers escaping for cool mountain air and slower summer days, it is now a private residence and one of the most storied homes in all of Greene County. That history is still deeply felt here. Nearly three acres of protected

  Alexandra Demetrakis Upstate Down

  216 New York 296, Windham, NY 12496
• 

  

  /27

  Not Listed For Sale

  333 State Route 296, Windham, NY 12496

  • 5 Beds
  • 4.5 Baths
  • 3,135 Sq Ft
  • Built 1880

  333 State Route 296, Windham, NY 12496

  Last Sold Summary

  • 368 Days On Market
• 

  

  /29

  $429,777

  • 4 Beds
  • 3 Baths
  • 2,058 Sq Ft

  274 N Brooksburg Rd Unit 35, Windham, NY 12496

  Welcome to Crystal Pond at Windham! This wonderful townhome is perfect for that weekend getaway, Winter resort home, or year round living, and has great potential for a short term rental. It comes ''fully furnished'' and ready to use! Offering Three sprawling floors of living space, 4-5 bedrooms and 3 Full baths! This beautiful town home has a great working kitchen w/ granite counters & large

  Douglas Schenk RE/MAX Capital

  274 N Brooksburg Rd Unit 35, Windham, NY 12496
• 

  

  /15

  Not Listed For Sale

  2942 County Route 10, Windham, NY 12496

  • 4 Beds
  • 1 Bath
  • 2,320 Sq Ft
  • Built 1790

  2942 County Route 10, Windham, NY 12496

  Last Sold Summary

  • 394 Days On Market
• 

  

  /30

  $489,000

  • 4 Beds
  • 3.5 Baths
  • 2,058 Sq Ft

  274 Brooksburgh Rd Unit 48, Windham, NY 12496

  Ine of just a few larger units in Crystal Pond. First floor has mud-room, half bath with laundry, Kitchen as well ad a dining room, large living room with sliding doors to large deck, lovely stone wood burning fireplace. Lots of light in this unit. Second floor has two main bedrooms each with a full bath.as well as a separate area for home office or TV. Third level has two well sized bedrooms,

  Mary Donovan Gallagher & Company

  274 Brooksburgh Rd Unit 48, Windham, NY 12496
• 

  

  /22

  Est $412,892

  Not Listed For Sale

  278 Big Hollow Rd, Maplecrest, NY 12454

  • 3 Beds
  • 2 Baths
  • 1,908 Sq Ft
  • Built 1979

  278 Big Hollow Rd, Maplecrest, NY 12454

  Last Sold Summary

  • 19 Days On Market
• 

  

  /22

  $285,000

  $15K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,446 Sq Ft

  542 Mitchell Hollow Rd, Windham, NY 12496

  Welcome to 542 Mitchell Hollow Road, Windham, NY, a charming home set on a beautifully maintained property in the heart of the Catskills. This inviting residence offers a wonderful combination of comfort, space, and natural surroundings, making it ideal as a full-time home, weekend retreat, or investment opportunity. Expansive decking provides excellent outdoor living space for relaxing,

  Shpresa Camaj Real Broker NY LLC

  542 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /10

  Est $550,012

  Not Listed For Sale

  53 Windham Mt Village, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,222 Sq Ft
  • Built 1986

  53 Windham Mt Village, Windham, NY 12496

  Last Sold Summary

  • 143 Days On Market
• 

  

  /11

  $174,999

  $20K PRICE DROP

  • Land
  • 5.6 Acres
  • $31,250 per Acre

  0 Peck Rd, Windham, NY 12454

  If you have always dreamed of building the country home you've always wanted, it all starts with the right location. Let Windham, New York -- known as ''The Gem of the Catskills'' -- be that location.Windham is one of the Catskills' most sought-after destinations, offering year-round recreation including skiing, golf, hiking, trout fishing, mountain biking, and much more. With great

  John Pumilia Shaw Country Realty, Inc.

  0 Peck Rd, Windham, NY 12454
• 

  

  /10

  Est $613,977

  Not Listed For Sale

  225 South St, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1951

  225 South St, Windham, NY 12496

  Last Sold Summary

  • 120 Days On Market
• 

  

  /41

  $1,345,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  2 Watch Hill Ln, Windham, NY 12496

  Classic Timber frame Construction, on Windham Mt., Walk to trails. Enjoy the convenience of location in this 4 bedroom 3.5 bath with attached garage to enter a large ski room with all the storage needed. Large formal entrance gives way to Spacious and Comfy Great room with large stone fireplace, vaulted ceilings and plenty of windows to let in the light and the lovely views, leads to a sizable

  Irene Pinto Brainard Ridge Management

  2 Watch Hill Ln, Windham, NY 12496
• 

  /2

  Est $589,329

  Not Listed For Sale

  79 Windham Mt Village, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,222 Sq Ft
  • Built 1986

  79 Windham Mt Village, Windham, NY 12496

  Last Sold Summary

  • 234 Days On Market
• 

  

  /49

  $149,000

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

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

  

  /28

  Est $2,892,788

  Not Listed For Sale

  200 Club Rd, Windham, NY 12496

  • 4 Beds
  • 5 Baths
  • 4,112 Sq Ft
  • Built 2011

  200 Club Rd, Windham, NY 12496

  Last Sold Summary

  • 304 Days On Market
• 

  

  /40

  $155,000

  • Land
  • 5.99 Acres
  • $25,876 per Acre

  L38 Boulder Brook Rd Unit Lot 14, 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

  L38 Boulder Brook Rd Unit Lot 14, Windham, NY 12496
• 

  

  /10

  Est $363,790

  Not Listed For Sale

  81 Windham Ridge Rd Unit 17B, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 1,211 Sq Ft
  • Built 1986

  81 Windham Ridge Rd Unit 17B, Windham, NY 12496

  Last Sold Summary

  • 601 Days On Market
• 

  

  /49

  $569,900

  $330K PRICE DROP

  • Land
  • 40.02 Acres
  • $14,240 per Acre

  L35-38 Boulder Brook Rd Unit Lots 35-38, Windham, NY 12496

  A Rare Opportunity in the Heart of Windham, NY. Welcome to Boulder Brook, an extraordinary and rare offering in the majestic Catskills. Just minutes from the slopes of Windham Ski Resort, this private subdivision presents a unique chance to own an entire mountain retreat or select from four individually surveyed lots, all nestled along a quiet, established country road. Boulder Brook is a blend

  Kyla Thomas Howard Hanna Rand Realty

  L35-38 Boulder Brook Rd Unit Lots 35-38, Windham, NY 12496
• 

  

  /9

  Not Listed For Sale

  497 County Road 56, Maplecrest, NY 12454

  • 2 Beds
  • 1 Bath
  • 1,015 Sq Ft
  • Built 1942

  497 County Road 56, Maplecrest, NY 12454

  Last Sold Summary

  • 38 Days On Market
• 

  

  /36

  $399,000

  $60K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,717 Sq Ft

  274 Brooksburgh Rd Unit 67, Windham, NY 12496

  This 4 bedroom, 3.5 bath unit is ''Like New''. Half bath/laundry. Kitchen with granite counters, upgraded cabinets, SS appliances, tile flooring. This is open concept. Nice counter in the kitchen with stools, open to the dining and living room area. Living room has a gas fireplace and sliding doors to a patio with a lovely view. Second floor has two main bedrooms with their full baths, third

  Mary Donovan Gallagher & Company

  274 Brooksburgh Rd Unit 67, Windham, NY 12496
• 

  

  /35

  Est $757,748

  Not Listed For Sale

  5088 State Route 23, Windham, NY 12496

  • 7 Beds
  • 7 Baths
  • 5,000 Sq Ft
  • Built 1960

  5088 State Route 23, Windham, NY 12496

  Last Sold Summary

  • 551 Days On Market
• 

  

  /59

  $935,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,922 Sq Ft

  2074 County Road 10, Windham, NY 12496

  A Private Mountain Escape with Two Homes!Set on 12 breathtaking acres with sweeping views of Windham Mountain and the surrounding ranges, this exceptional 3-bedroom, 2-bath property offers a rare combination of luxury, versatility, and investment opportunity. Offered only due to relocation, this is a truly one-of-a-kind Catskills retreat. The beautifully appointed, recently completed main

  Lisa Gambella Windstar Realty Group, LLC

  2074 County Road 10, Windham, NY 12496
• 

  

  /33

  Not Listed For Sale

  2101 Siam Rd, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,100 Sq Ft
  • Built 1988

  2101 Siam Rd, Windham, NY 12496

  Last Sold Summary

  • 30 Days On Market
• 

  

  /53

  $579,000

  • 6 Beds
  • 3 Baths
  • 1,680 Sq Ft

  49 Chase Dr, Hensonville, NY 12439

  A rare income-generating property nestled in the heart of the Catskills -- fully positioned to capitalize on year-round ski and outdoor tourism.This turnkey investment property features two self-contained apartments, each ideally suited for short-term rental on Airbnb. With ski season drawing visitors from across the region, the property's proximity to both Windham Mountain Club and Hunter

  Sheila Word Coldwell Banker Village GreenW

  49 Chase Dr, Hensonville, NY 12439
• 

  

  /17

  Not Listed For Sale

  0 Slater Rd Unit 20161584, Maplecrest, NY 12454

  0 Slater Rd Unit 20161584, Maplecrest, NY 12454

  Last Sold Summary

  • 67 Days On Market
• 

  

  /32

  $325,000

  • 2 Beds
  • 2.5 Baths
  • 1,295 Sq Ft

  274 County Route 65 Unit 55, Windham, NY 12496

  Step into this immaculate, well furnished home! Unit being sold ''as is'', fully furnished. This Is a well maintained unit, move right in and be comfortable. There is an outside storage closet, Mud room, half bath and laundry on first level along with a lovely kitchen, granite counters, SS appliances. Lovely living room with propane fireplace, sliding doors to a patio and a bay window, Plenty of

  Mary Donovan Gallagher & Company

  274 County Route 65 Unit 55, Windham, NY 12496
• 

  

  /8

  Not Listed For Sale

  0 Trailside Rd Unit 20162071, Windham, NY 12496

  0 Trailside Rd Unit 20162071, Windham, NY 12496

  Last Sold Summary

  • 178 Days On Market
• 

  

  /8

  $99,900

  • Land
  • 1.1 Acres
  • $90,818 per Acre

  L46.111 Panarama Ln, Windham, NY 12496

  Build your dream mountain getaway on this 1.1 acre unimproved lot just minutes from the Windham Mountain Club expansion. Surrounded by natural beauty, this property offers privacy, fresh air, and easy access to skiing, hiking, biking, golf, and charming village amenities. A perfect canvas for a custom Catskills home.A great opportunity in a rapidly evolving Catskills destination.

  Susan Miller WINDSTAR REALTY GROUP LLC

  L46.111 Panarama Ln, Windham, NY 12496
• 

  

  /32

  Est $1,329,041

  Not Listed For Sale

  2831 County Road 10, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 4,574 Sq Ft
  • Built 2007

  2831 County Road 10, Windham, NY 12496

  Last Sold Summary

  • 326 Days On Market

Showing Results 321 - 360, Page 9 of 18