Windham, NY Homes

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  /43

  $518,000 Sold Aug 21, 2025

  996 County Route 10, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 2020

  Last Sold Summary

  • 5% Below List Price
  • $357/SF
  • 59 Days On Market

  Current Estimated Value $503,215

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  996 County Route 10, Windham, NY 12496
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  /5

  Not Listed For Sale

  Tbd Nauvoo Rd, Windham, NY 12496

  Tbd Nauvoo Rd, Windham, NY 12496

  Last Sold Summary

  • 49 Days On Market

  Last Sold Price $16,000

  Last Listing Agent Arlena Armstrong-petock Country House Realty, Inc.
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  /48

  $749,000

  • 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
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  /29

  $1,650,000 Sold May 09, 2025

  12 - 2C Stonewall Ln, Windham, NY 12496

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

  Last Sold Summary

  • $611/SF
  • 0 Days On Market

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

  12 - 2C Stonewall Ln, Windham, NY 12496
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  /21

  Not Listed For Sale

  0 Off Begley Rd Unit 153152, Windham, NY 12496

  0 Off Begley Rd Unit 153152, Windham, NY 12496

  Last Sold Summary

  • 128 Days On Market

  Last Sold Price $175,000

  Last Listing Agent Regina Tortorella Past Member
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  /61

  $1,125,000

  • 5 Beds
  • 5.5 Baths
  • 3,643 Sq Ft

  3 South St, Windham, NY 12496

  Turn-Key Windham Ski Retreat | Modern End Unit with 4 En-Suites, Full Furnishing Option & High Income Potential Personal Use or Income Ready and hitting the market just in time for peak rental demand, this modern end-unit townhome at 292 South Street offers an unbeatable opportunity for both investors and second-home seekers. Featuring four en-suite bedrooms, panoramic slope views, and a sleek

  Regina Tortorella Coldwell Banker Village GreenW

  3 South St, Windham, NY 12496
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  /35

  $581,250 Sold Dec 01, 2025

  528 New York 296, Hensonville, NY 12439

  • 4 Beds
  • 2.5 Baths
  • 2,194 Sq Ft
  • Built 1895

  Last Sold Summary

  • $265/SF
  • 32 Days On Market

  Last Listing Agent Catherine Quintard Compass Greater NY, LLC

  528 New York 296, Hensonville, NY 12439
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  /14

  Not Listed For Sale

  9 Old State Route 23, Windham, NY 12496

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft
  • Built 1960

  9 Old State Route 23, Windham, NY 12496

  Last Sold Summary

  • $285/SF
  • 33 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Anne Lafferty Anne Lafferty Realty
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  /68

  $769,000

  • 3 Beds
  • 2 Baths
  • 2,049 Sq Ft

  39 Brook Hollow Ln, Windham, NY 12496

  Updated Log Cabin Retreat with Private Fishing Pond & Flowing Stream in the Catskills If you've been dreaming of a place that feels completely tucked away in nature--yet just minutes to town and the slopes--this one delivers in all the right ways. Set at the end of a quiet cul-de-sac, this rustic log home is surrounded by 4 private acres with your own pond and a flowing stream that you can

  Regina Tortorella Coldwell Banker Village GreenW

  39 Brook Hollow Ln, Windham, NY 12496
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  /55

  $355,000 Sold Jan 09, 2026

  23 Townhouse Ln Unit 1, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 1,846 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $192/SF
  • 101 Days On Market

  Current Estimated Value $374,587

  Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

  23 Townhouse Ln Unit 1, Windham, NY 12496
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  /29

  Not Listed For Sale

  18 East Rd Unit 1, Hensonville, NY 12439

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 1981

  18 East Rd Unit 1, Hensonville, NY 12439

  Last Sold Summary

  • $239/SF
  • 91 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Russell Pelham Real Broker, LLC
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  /58

  $715,000

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft

  60 County Route 65 A, Windham, NY 12496

  Price Cut! Windham Creek Lodge is an active, income-producing short-term rental property generating 70K-80K in annual income. The recent price reduction enhances the profit margin while offering additional room to scale and maximize returns. Fully renovated in 2023-2024, this modern multi-family chalet is ideally located just minutes from Windham Mountain Club and Hunter Mountain—positioning it

  Lisa Jaeger Coldwell Banker Village GreenW

  60 County Route 65 A, Windham, NY 12496
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  /46

  $585,000 Sold Aug 29, 2025

  14 - 57 Windham Mountain Village, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 1,510 Sq Ft
  • Built 1986

  Last Sold Summary

  • 11% Below List Price
  • $387/SF
  • 181 Days On Market

  Last Listing Agent Russell Pelham Real Broker, LLC

  14 - 57 Windham Mountain Village, Windham, NY 12496
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  /56

  Est $1,314,616 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

  • 6% Above List Price
  • $318/SF
  • 98 Days On Market

  Last Sold Price $1,237,500

  Last Listing Agent Regina Tortorella Past Member
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  /106

  $3,250,000 New Construction

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

  219 Club Rd, Windham, NY 12496

  STR Projected Revenue: 161.6K(incl. 13,528 cleaning fee)Occupancy: 42 ADR: 1043 Welcome to the ultimate ski-in/ski-out escape at Windham Mountain Club, where modern design, four-season mountain living, and front-row slope access come together in a way that feels both luxurious and totally effortless. This brand-new, custom-built home is perched just steps from the chairlift, making it one

  Regina Tortorella Coldwell Banker Village GreenW

  219 Club Rd, Windham, NY 12496
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  /24

  $210,000 Sold Jun 11, 2025

  359 Begley Rd, Windham, NY 12496

  • Land
  • 5 Acres
  • $42,000 per Acre

  Last Sold Summary

  • 33% Below List Price
  • 271 Days On Market

  Current Estimated Value $229,479

  Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

  359 Begley 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

  • $242/SF
  • 75 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW
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  /64

  $1,899,000

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft

  22 The Loop, Windham, NY 12496

  A short 1-2 minute walk to the trail access (870 ft)!! Nestled on the scenic slopes of Windham Mountain and just over two hours from NYC, this mountain haven beautifully marries opulence with rustic allure. The home's exterior, featuring cedar shakes and stone, harmonizes with its lush, landscaped surroundings, creating impeccable curb appeal. Inside, a grand two-story great room welcomes you

  Regina Tortorella Coldwell Banker Village GreenW

  22 The Loop, Windham, NY 12496
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  /45

  $521,000 Sold Jul 02, 2025

  13 Boulder Brook Rd, Windham, NY 12496

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $283/SF
  • 39 Days On Market

  Current Estimated Value $533,100

  Last Listing Agent Mary Donovan Gallagher & Company

  13 Boulder Brook 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

  • 3% Below List Price
  • $299/SF
  • 54 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Kevin Novotny Past Member
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  /49

  $599,000

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft

  150 Vining Rd, Windham, NY 12496

  150 Vining Road, Windham, NY Beautifully renovated contemporary mountain retreat set on 1 acre of lush lawn just minutes from the Windham Mountain Club. Blending rustic charm with modern finishes, this inviting home offers 1,394 square feet of above-grade living space plus an additional 788 square feet in the finished lower level--totaling 2,182 square feet of living space designed for

  Regina Tortorella Coldwell Banker Village GreenW

  150 Vining Rd, Windham, NY 12496
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  /50

  $702,000 Sold Dec 22, 2025

  73 Beaver Hill Rd, Windham, NY 12496

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $281/SF
  • 75 Days On Market

  Last Listing Agent Patricia Charbonneau Brainard Ridge Management

  73 Beaver Hill Rd, Windham, NY 12496
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  /21

  Est $205,204 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

  • 3% Above List Price
  • $267/SF
  • 59 Days On Market

  Last Sold Price $199,999

  Last Listing Agent Mariana DeLuca Howard Hanna Capital Inc
• 

  

  /54

  $499,000

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

  215 Siam Rd, Windham, NY 12496

  Incredible buy at this new price! The Windham Round House, one of most distinctive and architecturally unique homes in the area. Lovingly designed and built by the original owners, this octagon-style residence sits on 5 private acres with open lawns, a charming stone wall, evergreen woods beyond, multiple outbuildings including a two-car garage—offers a remarkable setting that must be seen to be

  Lisa Jaeger Coldwell Banker Village GreenW

  215 Siam Rd, Windham, NY 12496
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  /73

  $599,000 Sold Jan 08, 2026

  110 Maplecrest Rd, Windham, NY 12439

  • 8 Beds
  • 4 Baths
  • 3,577 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Below List Price
  • $167/SF
  • 125 Days On Market

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  110 Maplecrest Rd, Windham, NY 12439
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  /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

  • $180/SF
  • 104 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.
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  /109

  $2,175,000

  • 6 Beds
  • 4.5 Baths
  • 4,104 Sq Ft

  19 Twin Maples, Windham, NY 12496

  Experience mountain luxury at its finest in this stunning post-and-beam home at Windham Mountain Club's exclusive Village East community just a little over two hours from New York City. Designed for those who love the outdoors but don't want to sacrifice comfort, this 6-bedroom, 3.5-bath retreat spans more than 4,100 sq ft and combines timeless craftsmanship with breathtaking views of the

  Regina Tortorella Coldwell Banker Village GreenW

  19 Twin Maples, Windham, NY 12496
• 

  

  /34

  $400,000 Sold Dec 30, 2025

  4992 New York 23, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 1,812 Sq Ft
  • Built 1986

  Last Sold Summary

  • 18% Below List Price
  • $221/SF
  • 146 Days On Market

  Last Listing Agent Irene Pinto Brainard Ridge Management

  4992 New York 23, Windham, NY 12496
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  /28

  Not Listed For Sale

  35 Windham Mount Village, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 1,528 Sq Ft
  • Built 1986

  

  35 Windham Mount Village, Windham, NY 12496

  Last Sold Summary

  • 4% Above List Price
  • $385/SF
  • 0 Days On Market

  Last Sold Price $589,000

  Last Listing Agent Susan Miller Listing by Windstar Realty Group LLC
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  /59

  $575,000 Under Contract

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

  274 Route 65 Unit 28, Windham, NY 12496

  Not your ordinary townhouse—this Crystal Pond ''builder's special'' is one of only a few that were ever built with this expanded three-level, 3,190 sq ft floor plan. Designed for comfort, space, and easy living, this corner unit is a true standout in the development. From the covered entry, step into a welcoming heated mudroom with built-in cubbies, hooks, and bench seating—ideal for ski gear and

  Lisa Jaeger Coldwell Banker Village GreenW

  274 Route 65 Unit 28, Windham, NY 12496
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  /17

  $65,000 Sold Aug 14, 2025

  Tbd Hollow View Rd, Windham, NY 12496

  • Land
  • 5.01 Acres
  • $12,974 per Acre

  Last Sold Summary

  • 56% Below List Price
  • 291 Days On Market

  Last Listing Agent Arlena Armstrong Anatole House LLC

  Tbd Hollow View Rd, Windham, NY 12496
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  /45

  Est $1,166,896 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

  • 1% Above List Price
  • $320/SF
  • 126 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Laurie Hanenberg Hunter Windham Real Estate
• 

  

  /96

  $1,649,000 Pending

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

  102 Thunderbird Terrace, Windham, NY 12496

  Custom Log Cabin with Modern Finishes, The Feel of a New Build, and Stunning Mountain Views- Nestled on nearly 2 acres, this breathtaking custom log cabin combines luxury, charm, and nature. Built with meticulous attention to detail, the home shows as if it is new construction, exuding a fresh and pristine feel throughout, making it indistinguishable from a brand-new build. With 5 bedrooms, 3.5

  Regina Tortorella Coldwell Banker Village GreenW

  102 Thunderbird Terrace, Windham, NY 12496
• 

  

  /16

  $225,000 Sold Oct 27, 2025

  40 Quads Way, Windham, NY 12496

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

  Last Sold Summary

  • 10% Below List Price
  • $223/SF
  • 115 Days On Market

  Current Estimated Value $238,540

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  40 Quads Way, Windham, NY 12496
• 

  

  /22

  Est $336,840 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

  • 60% Above List Price
  • $130/SF
  • 42 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Jason Dugo Dugo Realty
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  /43

  $259,000

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

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

  NEW PRICE 259,000 - MOTIVATED SELLERS | BUY NOW!This cozy country townhouse-style condo offers an affordable four-season retreat in the heart of Windham, NY--ideal as a ski getaway, low-maintenance second home, or income-producing rental. Located in a quiet, private section of Windham Ridge, just minutes to Windham Mountain, village shops, restaurants, and golf, and only 2.5 hours from

  Lisa Jaeger Coldwell Banker Village GreenW

  76 Loo Bridge Ln Unit 12B, Windham, NY 12496
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  /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 $980,698

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  68 Hilltop Dr, Maplecrest, NY 12454
• 

  

  /30

  Est $295,083 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

  • 11% Above List Price
  • $205/SF
  • 132 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Kelly Sharifipour Darby Real Estate of New York Inc
• 

  

  /30

  $535,000

  • 3 Beds
  • 2.5 Baths
  • 1,335 Sq Ft

  20 Sutton Hollow Rd, Windham, NY 12496

  Modern Farmhouse Getaway with Streamside Serenity - Fully Renovated & Fully Furnished! This turn-key, completely renovated modern farmhouse is ready to welcome you! Just 12 minutes from the Windham Mountain Club and only a short drive to Hunter and Belleayre, this stylish 3-bedroom plus open sleeping loft retreat delivers four-season Catskill charm with designer finishes and a prime location for

  Regina Tortorella Coldwell Banker Village GreenW

  20 Sutton Hollow Rd, 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 $712,220

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  73 Cross Rd, Windham, NY 12496

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