Windham, NY Homes

• 

  

  

  /77

  $930,000

  Sold Nov 14, 2025

  68 Hilltop Dr, Maplecrest, NY 12454

  • 4 Beds
  • 4.5 Baths
  • 3,500 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $266/SF
  • 112 Days On Market

  Current Estimated Value $949,120

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  68 Hilltop Dr, Maplecrest, NY 12454
• 

  

  

  /56

  Est $1,366,131

  Not Listed For Sale

  86 Timber Trail, Windham, NY 12496

  • 5 Beds
  • 4 Baths
  • 3,887 Sq Ft
  • Built 2019

  86 Timber Trail, Windham, NY 12496

  Last Sold Summary

  • 98 Days On Market
• 

  

  

  /103

  $2,300,000

  • 5 Beds
  • 4.5 Baths
  • 4,069 Sq Ft

  16 White Way, Windham, NY 12496

  There are ski homes, and then there are homes that truly define what ski-in/ski-out living is meant to be. Positioned directly on Windham Mountain Club's coveted White Way trail, this extraordinary timber-frame residence offers what is arguably the most desirable slope-side location on the mountain. No shuttles. No parking lots. No loading gear into the car. Simply step into your heated ski room,

  Regina Tortorella Coldwell Banker Village GreenW

  16 White Way, Windham, NY 12496
• 

  

  

  /58

  $690,000

  Sold Oct 24, 2025

  73 Cross Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 2,792 Sq Ft
  • Built 2005

  Last Sold Summary

  • $247/SF
  • 124 Days On Market

  Current Estimated Value $705,530

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  73 Cross Rd, Windham, NY 12496
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  /45

  Not Listed For Sale

  4 French Park Dr Unit C-8, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1983

  4 French Park Dr Unit C-8, Windham, NY 12496

  Last Sold Summary

  • 75 Days On Market
• 

  

  /48

  $749,000

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,088 Sq Ft

  93 Maplewood Ave, Windham, NY 12496

  Nestled at the end of a tranquil cul -de-sac, this spacious 3+1 bedroom perched on a hill just a short distance to downtown Windham has breathtaking views of the slopes at Windham Mountain.On the main level, floor-to-ceiling glass sliding doors showcase expansive mountain views. An open-concept layout with vaulted ceilings unites the living room, dining room, and kitchen—all oriented toward

  Doina Dewell Coldwell Banker Village GreenW

  93 Maplewood Ave, Windham, NY 12496
• 

  

  /54

  $1,350,000

  Sold Aug 08, 2025

  12 Jacob Strasse Rd, Windham, NY 12496

  • 6 Beds
  • 5.5 Baths
  • 5,500 Sq Ft
  • Built 1988

  Last Sold Summary

  • 10% Below List Price
  • $245/SF
  • 41 Days On Market

  Current Estimated Value $1,396,654

  Last Listing Agent Catherine Quintard Compass Greater NY, LLC

  12 Jacob Strasse Rd, Windham, NY 12496
• 

  

  /39

  Not Listed For Sale

  4 French Park Dr Unit 4B, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1983

  4 French Park Dr Unit 4B, Windham, NY 12496

  Last Sold Summary

  • 278 Days On Market
• 

  

  /97

  $1,349,000

  • 4 Beds
  • 3.5 Baths
  • 3,977 Sq Ft

  78 Buckskin Loop, Windham, NY 12496

  Welcome to Windmont--Windham's most exclusive gated community--where luxury living meets the serenity of a private, thousand-acre natural preserve. Opportunities to own here are few and far between, making this a truly rare offering. Enter through secured gates and follow a scenic road to a paved, winding driveway that leads to this beautifully updated contemporary home, privately sited on 5

  Regina Tortorella Coldwell Banker Village GreenW

  78 Buckskin Loop, Windham, NY 12496
• 

  

  /57

  $169,900

  Sold Jun 22, 2026

  Tbd Boulder Brook Lot 8 Rd, Windham, NY 12496

  • Land
  • 6.17 Acres
  • $27,536 per Acre

  Last Sold Summary

  • 341 Days On Market

  Last Listing Agent Kyla Thomas Howard Hanna Rand Realty

  Tbd Boulder Brook Lot 8 Rd, Windham, NY 12496
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  /51

  Not Listed For Sale

  31 French Park Ct, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1986

  31 French Park Ct, Windham, NY 12496

  Last Sold Summary

  • 54 Days On Market
• 

  

  /8

  $325,000

  $100K PRICE INCREASE

  • Land
  • 1.2 Acres
  • $270,833 per Acre

  L37 Panarama Ln, Windham, NY 12496

  Destination Windham! This 1.2 acre parcel is the perfect location to build your primary residence, ski home,weekend getaway, or log cabin. Stunning views of both the town and the mountain!Enjoy the traffic-free,peaceful setting off the mountain. Minutes to the slopes. Walking distance to the golf course and country club.Minutes to Main Street to enjoy the shops and restaurants. The lot has been

  Susan Miller WINDSTAR REALTY GROUP LLC

  L37 Panarama Ln, Windham, NY 12496
• 

  

  /29

  $475,000

  Sold May 21, 2026

  38 Cambridge Heights Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Below List Price
  • $417/SF
  • 122 Days On Market

  Current Estimated Value $475,773

  Last Listing Agent Paul Heintz Anatole House LLC

  38 Cambridge Heights Rd, Windham, NY 12496
• 

  

  /21

  Est $204,600

  Not Listed For Sale

  394 State Route 296 Unit 1, Windham, NY 12496

  • 2 Beds
  • 1.5 Baths
  • 750 Sq Ft
  • Built 1920

  394 State Route 296 Unit 1, Windham, NY 12496

  Last Sold Summary

  • 59 Days On Market
• 

  

  /33

  $335,000

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

  274 County Route 65 Unit 68, Windham, NY 12496

  Step into this well maintained, upgraded unit and fall in love. Beautiful light enters this End Unit. Sliding doors to a patio looking out onto nature. There is an outside ski storage closet. Step into a welcoming mud room. There is a half bath/laundry room, a lovely galley kitchen with granite counters, a lovely large window, all appliances are stainless steel, the closets have pull out shelves.

  Mary Donovan Gallagher & Company

  274 County Route 65 Unit 68, Windham, NY 12496
• 

  

  /22

  $250,000

  Sold Jun 15, 2026

  63 Windham Ridge Rd Unit 16C, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,178 Sq Ft
  • Built 1986

  Last Sold Summary

  • 22% Below List Price
  • $212/SF
  • 59 Days On Market

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  63 Windham Ridge Rd Unit 16C, Windham, NY 12496
• 

  

  /27

  Not Listed For Sale

  5650 New York 23, Windham, NY 12496

  • 5 Beds
  • 3 Baths
  • 2,468 Sq Ft
  • Built 1987

  5650 New York 23, Windham, NY 12496

  Last Sold Summary

  • 104 Days On Market
• 

  

  /5

  $154,000

  • Land
  • 17.15 Acres
  • $8,980 per Acre

  0 High Peak Road Lot 61 & 20, Windham, NY 12496

  Nestled in the heart of the Catskills, this 17-acre parcel of unimproved land on High Peak Road offers a rare opportunity to own a significant piece of Greene County's most sought-after landscape. Surrounded by the natural splendor that has made Windham a beloved four-season destination, this blank canvas invites you to bring your vision -- whether a private retreat, a custom dream home, or a

  Sheila Word Coldwell Banker Village GreenW

  0 High Peak Road Lot 61 & 20, Windham, NY 12496
• 

  /2

  $960,000

  Sold Nov 07, 2025

  149 Magda Ln, Windham, NY 12496

  • 4 Beds
  • 5 Baths
  • 2,140 Sq Ft
  • Built 1988

  Last Sold Summary

  • 4% Below List Price
  • $449/SF

  Last Listing Agent non-member non member NON MLS OFFICE

  149 Magda Ln, Windham, NY 12496
• 

  

  /45

  Est $1,327,578

  Not Listed For Sale

  70 Sky Hill Rd, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 3,595 Sq Ft
  • Built 2016

  70 Sky Hill Rd, Windham, NY 12496

  Last Sold Summary

  • 126 Days On Market
• 

  

  /37

  $399,000

  $26K PRICE DROP

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

  751 Mitchell Hollow Rd, Windham, NY 12496

  Charming 3-bedroom, 2-bath ranch set on over an acre of picturesque property in Windham. Offering the ease of single-level living and sold completely furnished, this move-in-ready home is the perfect mountain retreat, full-time residence, or weekend getaway. The home is in a highly desirable area close to local restaurants, parks, hiking trails and the Windham Mountain Resort. Inside, enjoy

  Kathy Marino Bunce Realty

  751 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /37

  $999,999

  Sold Mar 10, 2026

  20 Brookhollow Ln, Windham, NY 12496

  • 3 Beds
  • 3.5 Baths
  • 3,284 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $305/SF
  • 68 Days On Market

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

  20 Brookhollow Ln, Windham, NY 12496
• 

  

  /22

  Est $486,644

  Not Listed For Sale

  544 N Settlement Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1987

  544 N Settlement Rd, Windham, NY 12496

  Last Sold Summary

  • 42 Days On Market
• 

  

  /11

  $135,000

  • Land
  • 1.2 Acres
  • $112,500 per Acre

  L19.12 South St, Windham, NY 12496

  Build your Catskills getaway on this 1.2-acre unimproved lot located on South Street in Windham, NY. Offering a peaceful setting with convenient access to Windham Mountain Club, village amenities, dining, and year-round recreation. Adjoining 1 acre lot for sale separately. A great opportunity for a custom home, weekend retreat, or long-term investment. Bring your vision and create a home that

  Susan Miller WINDSTAR REALTY GROUP LLC

  L19.12 South St, Windham, NY 12496
• 

  

  /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
• 

  

  /30

  Est $305,779

  Not Listed For Sale

  274 Route 65 Unit 29, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Built 1992

  274 Route 65 Unit 29, Windham, NY 12496

  Last Sold Summary

  • 132 Days On Market
• 

  

  /44

  $159,900

  • Land
  • 3.23 Acres
  • $49,505 per Acre

  Tbd Boulder Brook Rd Lot B12, 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 Lot B12, 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 $816,084

  Last Listing Agent Lubomir Hodan Shaw Country Realty, Inc.

  233 Begley Rd, Windham, NY 12496
• 

  

  /9

  Est $893,215

  Not Listed For Sale

  248 Club Rd, Windham, NY 12496

  • 1 Bed
  • Built 2025

  248 Club Rd, Windham, NY 12496

  Last Sold Summary

  • 92 Days On Market
• 

  

  /49

  $149,000

  • Land
  • 5.33 Acres
  • $27,955 per Acre

  Tbd Boulder Brook Rd Lot B13, 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 Lot B13, Windham, NY 12496
• 

  

  /44

  $1,400,000

  Sold Feb 06, 2026

  2 the Enclave Unit W10, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 2,600 Sq Ft
  • Built 1999

  Last Sold Summary

  • 18% Below List Price
  • $538/SF
  • 117 Days On Market

  Last Listing Agent Patricia Charbonneau Brainard Ridge Management

  2 the Enclave Unit W10, Windham, NY 12496
• 

  

  /18

  Est $271,245

  Not Listed For Sale

  14 Martin Ln, Hensonville, NY 12439

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1985

  14 Martin Ln, Hensonville, NY 12439

  Last Sold Summary

  • 157 Days On Market
• 

  

  /12

  $550,000

  • 2 Beds
  • 1 Bath
  • 1,122 Sq Ft

  183 N South St N, Windham, NY 12496

  Exceptional Opportunity in a Prime Windham Location! property is sub- dividable. Owner is motivated bring offers!!!Transform this property into a true showpiece — take this Chevy and turn it into a Rolls Royce! Situated directly across from the Windham Country Club, enjoy unobstructed views of the golf course. This property also offers potential for subdivision, adding long-term investment

  John Pumilia Shaw Country Realty, Inc.

  183 N South St N, Windham, NY 12496
• 

  

  /85

  $1,709,999

  Sold Feb 09, 2026

  12 Lauren Ln, Windham, NY 12496

  • 6 Beds
  • 4.5 Baths
  • 4,855 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Below List Price
  • $352/SF
  • 97 Days On Market

  Current Estimated Value $1,666,929

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  12 Lauren Ln, Windham, NY 12496
• 

  

  /7

  Not Listed For Sale

  TBD Mill St, Windham, NY 12496

  TBD Mill St, Windham, NY 12496

  Last Sold Summary

  • 135 Days On Market
• 

  

  /12

  $359,900

  • Land
  • 4.2 Acres
  • $85,690 per Acre

  L44.10 Panarama Ln, Windham, NY 12496

  Build your Catskills vision on this 4.2-acre vacant parcel ideally located near the Windham Mountain Club expansion. This unimproved lot offers a peaceful, wooded setting with excellent proximity to skiing, golf, dining, and year-round resort amenities. A prime opportunity for a private retreat, vacation home, or future investment in one of the area's most sought-after mountain communities.

  Susan Miller WINDSTAR REALTY GROUP LLC

  L44.10 Panarama Ln, Windham, NY 12496
• 

  

  /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
• 

  

  /31

  Est $438,167

  Not Listed For Sale

  296 Mitchell Hollow Rd, Windham, NY 12496

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

  296 Mitchell Hollow Rd, Windham, NY 12496

  Last Sold Summary

  • 183 Days On Market
• 

  

  /9

  $500,000

  • Land
  • 22,651 Sq Ft
  • $961,538 per Acre

  220 & 240 Club Rd, Windham, NY 12496

  Be captivated by the breathtaking, panoramic views that will mesmerize you from dusk till dawn from either of these 2 building lots, with ski access being offered by Windham Mountain Club. Let your imagine soar with the possibilities of designing your dream home to last for generations on one of the few remaining building lots offered by Windham Mountain Club. Envision waking up in your mountain

  Patricia Charbonneau Brainard Ridge Management

  220 & 240 Club Rd, Windham, NY 12496
• 

  

  /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

Showing Results 121 - 160, Page 4 of 18