Windham, NY Homes

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  /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
• 

  

  

  /18

  $3,000,000

  Sold Aug 07, 2026

  209 Club Rd, Windham, NY 12496

  • 6 Beds
  • 5 Baths
  • 5,000 Sq Ft
  • Built 2016

  Last Sold Summary

  • 17% Below List Price
  • $600/SF
  • 195 Days On Market

  Current Estimated Value $3,084,730

  Last Listing Agent Patricia Charbonneau Brainard Ridge Management

  209 Club Rd, Windham, NY 12496
• 

  

  

  /34

  Est $475,265

  Not Listed For Sale

  116 Galway Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 2021

  116 Galway Rd, Windham, NY 12496

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Patrick Dunn Core Real Estate Team
• 

  

  

  /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
• 

  

  

  /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
• 

  /2

  Est $658,748

  Not Listed For Sale

  108 Begley Rd, Windham, NY 12496

  • 3 Beds
  • Built 2025

  108 Begley Rd, Windham, NY 12496

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Mark McAlpine Past Member
• 

  

  /28

  $559,000

  • 5 Beds
  • 2 Baths
  • 1,900 Sq Ft

  96 Route 56, Maplecrest, NY 12454

  An amazing opportunity to own the perfect mountain retreat! This legal two-family home offers incredible flexibility as a two-unit investment property or an owner-occupied home with income-producing potential. The main house features a living room and formal dining room with beautifully refinished hardwood floors, an updated kitchen with granite countertops and brand-new stainless steel

  Doris Kennedy KENNEDY L I REALTY INC

  96 Route 56, Maplecrest, NY 12454
• 

  

  /57

  $445,000

  Sold Jul 23, 2026

  215 Siam Rd, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft
  • Built 1998

  Last Sold Summary

  • 14% Below List Price
  • $234/SF
  • 169 Days On Market

  Current Estimated Value $546,369

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  215 Siam Rd, Windham, NY 12496
• 

  

  /16

  Not Listed For Sale

  605 Old Rd, Windham, NY 12496

  • 2 Beds
  • 1 Bath
  • 889 Sq Ft
  • Built 1900

  605 Old Rd, Windham, NY 12496

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Breia Hunter Darby Real Estate of New York Inc
• 

  

  /38

  $2,495,000

  $2M PRICE INCREASE

  • 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
• 

  

  /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 $1,583,819

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  869 County Route 10 Rd, Windham, NY 12496
• 

  

  /35

  Est $1,498,807

  Not Listed For Sale

  241 Campbell Rd, Windham, NY 12496

  • 5 Beds
  • 3.5 Baths
  • 5,580 Sq Ft
  • Built 2005

  241 Campbell Rd, Windham, NY 12496

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW
• 

  

  /34

  $319,000

  • 2 Beds
  • 2.5 Baths
  • 1,238 Sq Ft

  55 Windham Ridge Rd Unit 15H, Windham, NY 12496

  Competitively Priced Catskills End Unit Townhouse - Renovated and furnishings are optional adding potential for practically turnkey property! This beautifully updated end-unit townhouse blends modern comfort with mountain charm, offering style, warmth, and exceptional value. As you step inside, you're welcomed by a tastefully renovated kitchen that flows effortlessly into the inviting main living

  Regina Tortorella Coldwell Banker Village GreenW

  55 Windham Ridge Rd Unit 15H, 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 $1,111,837

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  61 Cambridge Heights 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

  Last Sold Summary

  • 618 Days On Market

  Last Listing Agent Gregory Kardos Kardos & Co Real Estate, LLC
• 

  

  /14

  $75,000

  • Land
  • 1 Acre
  • $75,000 per Acre

  0 Mountain View Rd, Windham, NY 12496

  Your 1 Acre in Windham Awaits! For everyone who's ever called us and said, "I just want a small piece of land to hold onto, "maybe build on it someday." This one is for you! This 1-acre wooded lot on a private country road offers the ideal setting for your next project. Whether you're planning to build a cozy cabin, dream home, or vacation rental, this mostly level property is ready for you to

  Regina Tortorella Coldwell Banker Village GreenW

  0 Mountain View Rd, Windham, NY 12496
• 

  

  /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
• 

  

  /13

  Not Listed For Sale

  0 Club Rd Unit 131268, Windham, NY 12496

  0 Club Rd Unit 131268, Windham, NY 12496

  Last Sold Summary

  • 516 Days On Market

  Last Listing Agent Regina Tortorella Past Member
• 

  

  /14

  $120,000

  • Land
  • 1 Acre
  • $120,000 per Acre

  L19.11 South St, Windham, NY 12496

  Build your Catskills getaway on this 1acre 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 1.2 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

  L19.11 South St, Windham, NY 12496
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  /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 $1,543,740

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  102 Thunderbird Terrace, Windham, NY 12496
• 

  

  /48

  Est $588,253

  Not Listed For Sale

  50 County Rd Unit 65, Windham, NY 12496

  • 5 Beds
  • 4.5 Baths
  • 2,404 Sq Ft
  • Built 1875

  50 County Rd Unit 65, Windham, NY 12496

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Patrick Dunn Core Real Estate Team
• 

  

  /42

  $1,330,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,280 Sq Ft

  305 Mitchell Hollow Rd, Windham, NY 12496

  Modern Mountain Luxury | Windham, New York. Experience 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.

  305 Mitchell Hollow 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 $1,459,636

  Last Listing Agent Patricia Charbonneau Brainard Ridge Management

  4 The Loop, Windham, NY 12496
• 

  

  /7

  Est $200,288

  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

  • 7 Days On Market

  Last Listing Agent Kathy Marino Bunce Realty
• 

  

  /26

  $599,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  406 Campbell Rd, Windham, NY 12496

  Welcome to 406 Campbell Road, a peaceful Catskills retreat tucked among mature trees just minutes from the heart of Windham. This inviting home offers the perfect blend of privacy, comfort, and year-round recreation. Relax on the spacious covered front porch overlooking beautifully crafted bluestone walkways and landscaped grounds. The setting creates a true mountain-lodge atmosphere while

  Agnieszka Wdziekowska Taufield VENTURE FOX REALTY GROUP LLC

  406 Campbell Rd, Windham, NY 12496
• 

  

  /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 $708,643

  Last Listing Agent Mark McAlpine Compass Greater New York, LLC

  442 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /19

  Est $897,333

  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

  • 5 Days On Market

  Last Listing Agent Brandon Oot Core Real Estate Team
• 

  

  /60

  $399,000

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

  274 County Route 65 Unit 89, Windham, NY 12496

  Looking for a move-in ready vacation home away from the hustle and bustle of everyday life? Maybe you want a full-time home but appreciate the ease of a professionally managed community. Look no further than this terrific Crystal Pond Townhouse. Whether you want to spend your summer in the Catskills or enjoy winter in one of the region's premier ski destinations, this may be the opportunity you

  Sharri Cunningham Bunce Realty

  274 County Route 65 Unit 89, Windham, NY 12496
• 

  

  /39

  $232,500

  Sold Jul 16, 2026

  76 Loo Bridge Ln Unit 12B, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,411 Sq Ft
  • Built 1987

  Last Sold Summary

  • 18% Below List Price
  • $165/SF
  • 173 Days On Market

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  76 Loo Bridge Ln Unit 12B, Windham, NY 12496
• 

  

  /10

  Est $1,339,627

  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

  • 68 Days On Market

  Last Listing Agent Jacqueline Coyle Coldwell Banker Village GreenW
• 

  

  /6

  $257,000

  • Land
  • 25,700 Sq Ft
  • $435,593 per Acre

  57 South St, Windham, NY 12496

  Unique opportunity - one of the LAST lots on South Street! Flat parcel overlooking the golf course. Close access to everything Windham has to offer: ski, golf, biking, movie theater, shops and downtown restaurants. Utilities access on site: water (town), sewer (town), electric (NYSEG).

  Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

  57 South St, Windham, NY 12496
• 

  

  /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
• 

  

  /35

  Est $674,066

  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

  • 5 Days On Market

  Last Listing Agent Joseph Satto Compass Greater NY, LLC
• 

  

  /26

  $350,000

  $30K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  69 Windham Ridge Rd Unit 16F, Windham, NY 12496

  Welcome to Windham Ridge with views of Windham Mountain! This 3 Bedroom, 2.5 Bath townhome which offers large spacious rooms, great storage and closet space, the 1st floor offers wonderful open floorplan with Dining room, Kitchen, Living room (with wood fireplace) front and rear decks. Windham Ridge is affordable with low taxes and association fees. It's located just a couple of minutes to

  Douglas Schenk RE/MAX Capital

  69 Windham Ridge Rd Unit 16F, 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
• 

  Est $596,242

  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

  • 40 Days On Market

  Last Listing Agent Jennifer Woods Daniel Gale Sothebys Intl Rlty
• 

  

  /56

  $899,000

  Open House 8/22

  • 6 Beds
  • 5 Baths
  • 3,104 Sq Ft

  5628 State Route 23, Windham, NY 12496

  Welcome to your private Catskills sanctuary. Perfectly positioned on Main Street in Windham, this unique property offers the ultimate flexible layout that lends itself to multiple situations: a multi-generational family compound, a premium vacation escape where friends and family can gather-while still enjoying their own private spaces, a pass through income property with excellent ROI and very

  Susan Miller WINDSTAR REALTY GROUP LLC

  5628 State Route 23, Windham, NY 12496
• 

  

  /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 $730,901

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  128 Mount Greenery Rd, Windham, NY 12496
• 

  

  /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

  • 24 Days On Market

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW
• 

  

  /37

  $179,900

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

  Tbd Boulder Brook Rd 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. On this specific lot, an area has been cleared and

  Philip Kelly Howard Hanna Rand Realty

  Tbd Boulder Brook Rd Lot 11, Windham, NY 12496

Showing Results 201 - 240, Page 6 of 18