Windham, NY Homes

/14
Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,088 Sq Ft
9 Old State Route 23, Windham, NY 12496

9 Old State Route 23, Windham, NY 12496

/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
/29
$285,000 Sold Feb 19, 2025

18 East Rd Unit 1, Hensonville, NY 12439
- 2 Beds
- 2 Baths
- 1,192 Sq Ft
- Built 1981
Last Sold Summary
- $239/SF
- 91 Days On Market
Last Listing Agent Russell Pelham Real Broker, LLC

18 East Rd Unit 1, Hensonville, NY 12439

/56
Est $1,366,883 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,887 Sq Ft
86 Timber Trail, Windham, NY 12496

86 Timber Trail, Windham, NY 12496

/100
$2,799,000
- 6 Beds
- 5.5 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
/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

/45
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,632 Sq Ft
4 French Park Dr Unit C-8, Windham, NY 12496

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

/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
/60
$550,000 Sold Feb 28, 2025

162 Ruland Rd, Windham, NY 12496
- 1,849 Sq Ft
- Built 2020
Last Sold Summary
- 4% Below List Price
- $297/SF
- 64 Days On Market
Current Estimated Value $614,704

Last Listing Agent Regina Tortorella Past Member

162 Ruland Rd, Windham, NY 12496

/51
Est $372,000 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,288 Sq Ft
31 French Park Ct, Windham, NY 12496

31 French Park Ct, Windham, NY 12496

/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
/22
$210,000 Sold Mar 14, 2025

544 N Settlement Rd, Windham, NY 12496
- 3 Beds
- 2 Baths
- 1,620 Sq Ft
- Built 1987
Last Sold Summary
- 12% Below List Price
- $130/SF
- 42 Days On Market
Current Estimated Value $289,569

Last Listing Agent Jason Dugo Dugo Realty

544 N Settlement Rd, Windham, NY 12496

/28
Est $615,000 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,528 Sq Ft
35 Windham Mount Village, Windham, NY 12496

35 Windham Mount Village, Windham, NY 12496

/36
$329,999 Pending
- 2 Beds
- 2.5 Baths
- 1,058 Sq Ft
73 Windham Ridge Rd Unit 16-H, Windham, NY 12496

Competitively Priced Catskills End Unit Townhouse - Fully Renovated, Furnished & Move-In Ready! This beautifully updated end-unit townhouse combines modern elegance with mountain charm, offering comfort, style, and unbeatable value. As you enter, you'll be welcomed by a stunning, fully remodeled kitchen outfitted with rich granite surfaces and a convenient breakfast bar, The kitchen flows

Regina Tortorella Coldwell Banker Village GreenW

73 Windham Ridge Rd Unit 16-H, 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

/45
Est $1,322,293 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,595 Sq Ft
70 Sky Hill Rd, Windham, NY 12496

70 Sky Hill Rd, Windham, NY 12496

/59
$715,000
- 4 Beds
- 2 Baths
- 2,240 Sq Ft
60 County Route 65 A, Windham, NY 12496

Price Cut! Windham Creek Lodge is a proven, income-producing short-term rental generating approximately 70K-80K in annual GCI. 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
/72
$810,000 Sold Mar 11, 2025

39 Trail View Ln, Windham, NY 12496
- 3 Beds
- 3 Baths
- 3,914 Sq Ft
- Built 2022
Last Sold Summary
- 10% Below List Price
- $207/SF
- 508 Days On Market
Current Estimated Value $920,633

Last Listing Agent Regina Tortorella Past Member

39 Trail View Ln, Windham, NY 12496

/30
Est $330,685 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,295 Sq Ft
274 Route 65 Unit 29, Windham, NY 12496

274 Route 65 Unit 29, Windham, NY 12496

/106
$3,750,000 New Construction
- 6 Beds
- 5 Baths
- 5,005 Sq Ft
219 Club Rd, Windham, NY 12496

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 of the most desirable on-mountain properties available at WMC today. Designed to bring

Regina Tortorella Coldwell Banker Village GreenW

219 Club Rd, 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
Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

23 Townhouse Ln Unit 1, Windham, NY 12496

/9
Est $724,466 Not Listed For Sale
248 Club Rd, Windham, NY 12496

248 Club Rd, Windham, NY 12496

/64
$1,899,000
- 5 Beds
- 3.5 Baths
- 4,044 Sq Ft
22 The Loop, Windham, NY 12496

Walk to the Slopes! 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 with a magnificent wall of glass

Regina Tortorella Coldwell Banker Village GreenW

22 The Loop, 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

/18
Est $257,841 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
14 Martin Ln, Hensonville, NY 12439

14 Martin Ln, Hensonville, NY 12439

/22
$1,950,000
- 5 Beds
- 3.5 Baths
- 4,834 Sq Ft
77 Beaver Hill Rd, Windham, NY 12496

Designed by a renowned Manhattan architect known for 20M dollar Aspen ski homes, this 4,834-square-foot Catskills estate offers world-class design and unparalleled craftsmanship. Built as the architect's personal residence, it's a sanctuary for relaxation, entertaining, and year-round mountain living. Set on over four private acres bordering the protected Bataviakill Watershed, the home

Regina Tortorella Coldwell Banker Village GreenW

77 Beaver Hill 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 $242,853

Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

359 Begley Rd, Windham, NY 12496

/2
Est $568,671 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,622 Sq Ft
770 Mitchell Hollow Rd, Windham, NY 12496

770 Mitchell Hollow Rd, Windham, NY 12496

/65
$515,000
- 3 Beds
- 2.5 Baths
- 1,903 Sq Ft
215 Siam Rd, Windham, NY 12496

Welcome to the Windham Round House, one of the area's most distinctive and architecturally unique round homes. 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 fully appreciated.

Lisa Jaeger Coldwell Banker Village GreenW

215 Siam Rd, 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 $564,852

Last Listing Agent Mary Donovan Gallagher & Company

13 Boulder Brook Rd, Windham, NY 12496

/7
Not Listed For Sale
TBD Mill St, Windham, NY 12496

TBD Mill St, Windham, NY 12496

/109
$2,175,000
- 6 Beds
- 3.5 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
/27
$445,000 Sold Feb 21, 2025

5650 New York 23, Windham, NY 12496
- 5 Beds
- 3 Baths
- 2,468 Sq Ft
- Built 1987
Last Sold Summary
- 11% Below List Price
- $180/SF
- 104 Days On Market
Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

5650 New York 23, Windham, NY 12496

/31
Est $431,392 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,486 Sq Ft
296 Mitchell Hollow Rd, Windham, NY 12496

296 Mitchell Hollow Rd, Windham, NY 12496

/63
$575,000
- 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
/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

/11
Not Listed For Sale
0 N Ridge Extension Lot 25 Unit 145406, Windham, NY 12496

0 N Ridge Extension Lot 25 Unit 145406, Windham, NY 12496

/96
$1,649,000
- 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
/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

/4
Not Listed For Sale
79 Old Rd, Windham, NY 12496

79 Old Rd, Windham, NY 12496

Showing Results 81 - 120, Page 3 of 18

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