Windham, NY Homes

• 

  

  

  /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
• 

  

  

  /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.
• 

  

  

  /68

  $1,899,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,723 Sq Ft

  4 Goff Rd, Windham, NY 12496

  Are you sitting down? Because this one will take your breath away! This brand new modern mountain masterpiece with an indoor pool, glass walls & slope views is offered fully furnished & turn-key! It's a show stopping contemporary retreat where every inch has been crafted for ultimate luxury, relaxation, and awe-inspiring views. Enveloped in two-story walls of glass, this brand new residence

  Regina Tortorella Coldwell Banker Village GreenW

  4 Goff Rd, Windham, NY 12496
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /67

  $1,749,000

  • 5 Beds
  • 2.5 Baths
  • 3,893 Sq Ft

  33 Elm Ridge Rd, Windham, NY 12496

  The Mountains Are Calling and I Must Go.'' P.S., I plan to be VERY comfortable when I get there!Welcome to 33 Elm Ridge - the best of the Catskills - the ultimate in mountain opulence. This shingled contemporary makes quite the impression on its incredible setting; 3,900sqft of living space spans over 3 floors which include 5 bds, 3.5 bths & a walk-out basement that's ready to party. It's set on

  Regina Tortorella Coldwell Banker Village GreenW

  33 Elm Ridge Rd, Windham, NY 12496
• 

  

  /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
• 

  

  /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
• 

  

  /68

  $875,000

  • 4 Beds
  • 3.5 Baths
  • 3,075 Sq Ft

  116 Nilson Dr, Windham, NY 12496

  Fall in love with the ease of single-level living wrapped in privacy, beauty, and timeless style. Set on three peaceful acres, this thoughtfully reimagined home feels like a hidden retreat -- close to everything, yet wonderfully your own. From the moment you enter, the home welcomes you with warmth and refinement. Arched openings, crown moldings, and curated details create an elegant flow from

  Lisa Jaeger Coldwell Banker Village GreenW

  116 Nilson Dr, Windham, NY 12496
• 

  

  /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
• 

  

  /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
• 

  

  /34

  $239,500

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

  55 Quads Way, Windham, NY 12496

  Price Reduced -- Major Value in Windham! This charming turnkey condo delivers affordable four-season living close to skiing, golf, hiking, dining, and everything buyers love about Windham. Just minutes from Windham Mountain Club, this fully furnished 2-bedroom, 2-bath retreat offers an easy mountain lifestyle in one of the Catskills' most desirable destinations. Enjoy winter days on the slopes,

  Lisa Jaeger Coldwell Banker Village GreenW

  55 Quads Way, Windham, NY 12496
• 

  

  /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
• 

  

  /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
• 

  

  /41

  $399,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,472 Sq Ft

  317 Mitchell Hollow Rd, Windham, NY 12496

  PRICE REDUCTION! — calling all investors, DIY buyers, and project-minded designers! Prime Windham location, major updates done — now it's your turn to finish and make it shine. This spacious 5-bedroom, 3-bath home offers tremendous potential with many big-ticket updates already completed, including a new roof, wood flooring, updated kitchen with granite counters and newer appliances, fresh

  Lisa Jaeger Coldwell Banker Village GreenW

  317 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /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
• 

  

  /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
• 

  

  /100

  $2,799,000 Pending

  • 6 Beds
  • 4.5 Baths
  • 5,872 Sq Ft

  81 Sundance Dr, Windham, NY 12496

  Secluded Mountain Estate with 20+ Acres, Panoramic Views & Sport Court in Windham, NY. Privately gated at the very end of Sundance Drive, this extraordinary log estate is one of only five luxury homes in this sought-after enclave each on expansive land, but none offering the privacy, scale, or setting of this one. Set on a sweeping tract with panoramic mountain views, this home blends refined

  Regina Tortorella Coldwell Banker Village GreenW

  81 Sundance Dr, Windham, NY 12496
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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.
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

Showing Results 81 - 120, Page 3 of 18