Windham, NY Homes

/12
Not Listed For Sale

5220 New York 23, Windham, NY 12496
- 2 Beds
- 2 Baths
- 900 Sq Ft
- Built 1960
5220 New York 23, Windham, NY 12496

Last Sold Summary
- 60 Days On Market
Last Listing Agent Claudia Zucker Living Structures

/27
$565,000
- 5 Beds
- 2 Baths
96 56, Windham, NY 12496

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

96 56, Windham, NY 12496
/76
$1,350,000

Sold May 02, 2026

11 Whisper Creek Dr Unit 504, Windham, NY 12496
- 4 Beds
- 4 Baths
- 1,856 Sq Ft
- Built 2016
Last Sold Summary
- $727/SF
- 100 Days On Market
Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

11 Whisper Creek Dr Unit 504, Windham, NY 12496

/35
Not Listed For Sale

18 Evergreen Ln, Maplecrest, NY 12454
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
- Built 1991
18 Evergreen Ln, Maplecrest, NY 12454

Last Sold Summary
- 126 Days On Market
Last Listing Agent Doina Dewell Past Member

/77
$599,900

Under Contract
- 3 Beds
- 3 Baths
- 1,870 Sq Ft
513 County Road 10, Windham, NY 12496

Mountain Majesty Meets Everyday Luxury on 2.8 Serene Acres! Escape to the perfect blend of rustic warmth and contemporary functionality. Nestled against the spectacular backdrop of Windham Mountain, this exceptional log home effortlessly serves as an active full-time residence or the ultimate four-season mountain getaway. The main level features a bright, open-concept floor plan designed for both

Ted Banta RVW Select Properties

513 County Road 10, Windham, NY 12496
/55
$600,000

Sold May 22, 2026

57 Brainard Ridge Rd Unit 3-E, Windham, NY 12496
- 4 Beds
- 3.5 Baths
- 2,100 Sq Ft
- Built 1986
Last Sold Summary
- 7% Below List Price
- $286/SF
- 161 Days On Market
Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

57 Brainard Ridge Rd Unit 3-E, Windham, NY 12496

/12
Not Listed For Sale

5576 State Route 23, Windham, NY 12496
- 6 Beds
- 2 Baths
- 2,164 Sq Ft
- Built 1908
5576 State Route 23, Windham, NY 12496

Last Sold Summary
- 40 Days On Market
Last Listing Agent Mary King Past Member

/15
$239,000

$40K PRICE DROP
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
5359 New York 23 Unit 2E, Windham, NY 12496

Experience easy mountain living in Windham! This charming 2-bedroom, 2-bath condo features a welcoming living room, dedicated dining space, and the convenience of in-unit laundry. Includes assigned parking and is just moments from Windham Mountain—perfect for those seeking relaxation and recreation.

Simran Bajaj Realty Connect USA LLC

5359 New York 23 Unit 2E, Windham, NY 12496
/64
$780,000

Sold Mar 19, 2026

78 Mitchell Hollow Rd, Windham, NY 12496
- 3 Beds
- 3.5 Baths
- 2,324 Sq Ft
- Built 2019
Last Sold Summary
- 1% Below List Price
- $336/SF
- 44 Days On Market
Current Estimated Value $821,649

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

78 Mitchell Hollow Rd, Windham, NY 12496

/35
Est $1,511,397

Not Listed For Sale

50 Larsen Rd, Windham, NY 12496
- 4 Beds
- 3.5 Baths
- 2,625 Sq Ft
- Built 2017
50 Larsen Rd, Windham, NY 12496

Last Sold Summary
- 125 Days On Market
Last Listing Agent Laurie Hanenberg Past Member

/48
$449,000

$50K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,287 Sq Ft
18 Maplewood Ave, Windham, NY 12496

Charming 4-Bedroom Ranch on 1.6 Acres in Windham, NY Discover your dream retreat in the heart of the Catskills! Nestled in the picturesque village of Windham, just minutes from vibrant downtown and the renowned Windham Mountain Resort with its array of restaurants and shops, this spacious 4-bedroom, 2-bathroom ranch offers the perfect blend of comfort and charm. Situated on a generous 1.6-acre

Fred Mazza Bunce Realty

18 Maplewood Ave, Windham, NY 12496
/33
$730,000

Sold Jul 17, 2026

415 Old Rd, Windham, NY 12496
- 3 Beds
- 3.5 Baths
- 3,279 Sq Ft
- Built 1988
Last Sold Summary
- 9% Below List Price
- $223/SF
- 265 Days On Market
Current Estimated Value $779,419

Last Listing Agent Laurie Hanenberg Hunter Windham Real Estate

415 Old Rd, Windham, NY 12496

/35
Not Listed For Sale

340 1 High Peak Rd, Hensonville, NY 12439
- 4 Beds
- 2 Baths
- 2,340 Sq Ft
- Built 1976
340 1 High Peak Rd, Hensonville, NY 12439

Last Sold Summary
- 110 Days On Market
Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

/33
$610,000
- 4 Beds
- 2.5 Baths
- 2,227 Sq Ft
49 Brainard Ridge Rd Unit 3A, Windham, NY 12496

Move in ready! Warm and Welcoming describes this beautiful, Brainard Ridge large end unit, 4 bedroom 2.5 bath with a sun drenched extra den/family room. Beautifully renovated kitchen with new Cambria Windermere Quarts countertops, attractive wood cabinets, new electric stove, refrigerator and microwave. Spacious living area with wood burning fireplace to enjoy relaxing moments with family and

Patricia Charbonneau Brainard Ridge Management

49 Brainard Ridge Rd Unit 3A, Windham, NY 12496

/35
Est $1,012,744

Not Listed For Sale

194 Vining Rd, Windham, NY 12496
- 3 Beds
- 3 Baths
- 2,162 Sq Ft
- Built 2018
194 Vining Rd, Windham, NY 12496

Last Sold Summary
- 217 Days On Market
Last Listing Agent Laurie Hanenberg Past Member

/19
$399,000
- Land
- 20,037 Sq Ft
- $867,391 per Acre
2 Twin Maples Ln, Windham, NY 12496

Premier Building Lot at Windham Mountain Club - Ready for Your Dream Home. Bring your vision to life on this shovel-ready homesite located in Village East, an exclusive enclave within the prestigious Windham Mountain Club. Whether you're a builder, investor, or avid skier dreaming of a luxury mountain retreat, this property offers the perfect foundation for your next project. Turnkey Build-Ready:

Regina Tortorella Coldwell Banker Village GreenW

2 Twin Maples Ln, Windham, NY 12496

/30
Est $696,099

Not Listed For Sale

45 Andrea Way, Maplecrest, NY 12454
- 4 Beds
- 2 Baths
- 2,596 Sq Ft
- Built 1989
45 Andrea Way, Maplecrest, NY 12454

Last Sold Summary
- 65 Days On Market
Last Listing Agent Pam Fontaine Weichert Realtors Fontaine

/17
$300,000
- Land
- 7.52 Acres
- $39,894 per Acre
1 Estate View Dr, Windham, NY 12496

Only a select number of lots remain! Welcome to Windham Luxury Estates, where an exceptional opportunity awaits with this fully approved, shovel ready 7.5 acre residential building lot. This premier parcel includes complete engineering, topographical and survey maps, along with a fully approved DEP septic design for an estate sized home, making the building process as seamless as possible.

Patrick Dunn KW Platform

1 Estate View Dr, Windham, NY 12496

/14
Not Listed For Sale

45-1 Blodgett Rd, Windham, NY 12496
45-1 Blodgett Rd, Windham, NY 12496

Last Sold Summary
- 7 Days On Market
Last Listing Agent Kyla Thomas Howard Hanna Rand Realty

/16
$269,000

$11K PRICE DROP
- 2 Beds
- 2.5 Baths
- 1,058 Sq Ft
45 Windham Ridge Rd Unit C, Windham, NY 12496

Nestled in the heart of the Catskills, this beautifully updated 2-bedroom, 2.5-bath townhome offers stunning views of Windham Mountain Club and the perfect blend of comfort, style, and four-season recreation. Featuring approximately 1,300 square feet of living space, this turnkey retreat showcases a newly remodeled kitchen with quartz countertops, new appliances, and modern finishes throughout.

Mary Jo Warner Listing by Howard Hanna

45 Windham Ridge Rd Unit C, Windham, NY 12496

/7
Est $199,691

Not Listed For Sale

139 Windham Ridge Rd, Windham, NY 12496
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Built 1986
139 Windham Ridge Rd, Windham, NY 12496

Last Sold Summary
- 396 Days On Market
Last Listing Agent Mary King Past Member

/47
$449,000

$51K PRICE DROP
- 4 Beds
- 2 Baths
- 2,457 Sq Ft
20 Slater Rd, Maplecrest, NY 12454

Discover the perfect blend of charm, space, and convenience in this beautiful 4-bedroom, 2-bathroom countryside home, ideally located less than 3 hours from NYC. Set on scenic land in historic Windham NY. This vibrant small town is surrounded by renowned ski resorts; this is the ideal getaway or year-round residence.An exceptionally inviting home that is perfect for guests or extended family,

Brian Cohen RHR Realty Group

20 Slater Rd, Maplecrest, NY 12454

/10
Not Listed For Sale

16 Lower Loop, Windham, NY 12496
- 7 Beds
- 2 Baths
- 4,200 Sq Ft
- Built 1970
16 Lower Loop, Windham, NY 12496

Last Sold Summary
- 388 Days On Market
Last Listing Agent Mary King Past Member

/37
$285,000

$10K PRICE DROP
- 2 Beds
- 2 Baths
- 1,290 Sq Ft
71 County Road 65 Unit 6, Hensonville, NY 12439

Built in 2020 and maintained in like-new condition, this end-unit townhome offers contemporary design, lasting quality, and proven versatility. Whether you're looking for a strong short-term rental investment or your own Catskills escape/ski home, this property checks every box. The bright, open-concept living and dining area flows easily to a private deck, ideal for outdoor meals or quiet

Susanna Scott-Mitchell Compass Greater NY, LLC

71 County Road 65 Unit 6, Hensonville, NY 12439

/8
Not Listed For Sale

Unlisted Address
- 3 Beds
- 1 Bath
- 1,141 Sq Ft
- Built 1932
Unlisted Address

Last Sold Summary
- 78 Days On Market
Last Listing Agent Claudia Zucker Living Structures

/43
$479,000
- 3 Beds
- 2 Baths
- 1,652 Sq Ft
177 Mill St, Windham, NY 12496

Welcome to 177 Mill Street: Spectacular views, terrific location and a house ready for new owners and its next chapter! A classic chalet, this cozy home is just the right size - not too big, not too small. The main living area is as one might expect; tall ceilings accented by wood beams and an open floor plan combining living, dining and kitchen areas. Two sets of sliding doors open to the deck.

Sharri Cunningham Bunce Realty

177 Mill St, Windham, NY 12496

/10
Est $987,270

Not Listed For Sale

29 Club Rd, Windham, NY 12496
- 4 Beds
- 3 Baths
- 1,928 Sq Ft
- Built 1970
29 Club Rd, Windham, NY 12496

Last Sold Summary
- 49 Days On Market
Last Listing Agent Sheila Word Coldwell Banker Village GreenW

/55
$575,000

$124K PRICE DROP
- 7 Beds
- 3 Baths
- 3,485 Sq Ft
200 & 212 Co Rd 40, Windham, NY 12496

UNIQUE REDEVELOPMENT & RESTORATION OPPORTUNITY on 7.2 scenic acres along the Batavia Kill Creek, featuring open meadows, sweeping hillside views, and a peaceful Catskills setting. LOCATED just 3.5 miles to Windham Mountain and under 10 miles to Hunter Mountain.FORMERLY the site of an inn, the original inn building has been removed, creating a blank canvas for a hospitality destination,

Susan Lennon Coldwell Banker Timberland

200 & 212 Co Rd 40, Windham, NY 12496

/2
Not Listed For Sale

68 Chase Dr, Hensonville, NY 12439
- 3 Beds
- 2 Baths
- 1,432 Sq Ft
- Built 1972
68 Chase Dr, Hensonville, NY 12439

Last Sold Summary
- 118 Days On Market
Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

/56
$464,000
- 6 Beds
- 2.5 Baths
- 2,251 Sq Ft
10 Vets Rd, Windham, NY 12496

Location, Location, Location!!! Rarely is this characterization more appropriate than for 10 Vets Road. This charming village home is truly in the heart of Windham - a terrific location just steps away from the bustling activity. Full-time home? Weekend or vacation getaway? Investment? No matter what your need or wish might be, this well-maintained home with a deceptively spacious interior can

Sharri Cunningham Bunce Realty

10 Vets Rd, Windham, NY 12496

/10
Est $264,902

Not Listed For Sale

36 Mill St, Windham, NY 12496
- 3 Beds
- 1 Bath
- 956 Sq Ft
- Built 1900
36 Mill St, Windham, NY 12496

Last Sold Summary
- 207 Days On Market
Last Listing Agent Mary King Past Member

/105
$1,999,000

Under Contract
- 4 Beds
- 3.5 Baths
- 4,247 Sq Ft
37 White Way, Windham, NY 12496

Winter in Windham is here and with the ski season in full swing, it's time to find the ski house of your dreams! 37 White Way is being offered for the first time. INCLUDED IS A SECOND, ADJOINING VACANT PARCEL, offering flexibility and opportunity. Build a second home or guest house; sell the lot or, simply keep it as is to ensure privacy! Located on Windham Mountain Club's east side, and just

Sharri Cunningham Bunce Realty

37 White Way, Windham, NY 12496

/10
Est $1,125,816

Not Listed For Sale

389 Mill St, Windham, NY 12496
- 4 Beds
- 3.5 Baths
- 2,475 Sq Ft
- Built 2013
389 Mill St, Windham, NY 12496

Last Sold Summary
- 98 Days On Market
Last Listing Agent Regina Tortorella Past Member

/29
$227,900

$7K PRICE DROP
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
41 Quads Way, Windham, NY 12496

Perfect Condo Getaway Beautiful 2bd, 2bth with a woodburning fireplace condo located minutes to Windham Mountain skiing and 15 minutes to hunter Mountain. This well priced home is a blink away from the town of Windham with all the restaurant's, night life and local brewery's to enjoy and be home in minutes. There is porch that backs up to a wooded area. Enjoy resort-style amenities including a

Brian Cohen RHR Realty Group

41 Quads Way, Windham, NY 12496

/10
Est $1,295,731

Not Listed For Sale

658 Mill St, Windham, NY 12496
- 4 Beds
- 5 Baths
- 3,750 Sq Ft
- Built 2013
658 Mill St, Windham, NY 12496

Last Sold Summary
- 136 Days On Market
Last Listing Agent Regina Tortorella Past Member

/29
$1,350,000
- Land
- 11.74 Acres
- $114,991 per Acre
0 South St, Windham, NY 12496

Prime Windham Mountain Club Development Opportunity: Nearly 12 Acres Across from the Slopes, Bordering ''The Valley'': Windham Mountain Club's new amenities complex. Underground Electric & Municipal Sewer Access available. Calling all developers, builders, and investors--this is one of Windham's most strategic opportunities. This offering includes two combined lots totaling nearly 12 acres in a

Regina Tortorella Coldwell Banker Village GreenW

0 South St, Windham, NY 12496

/10
Est $1,234,858

Not Listed For Sale

746 Mill St, Windham, NY 12496
- 4 Beds
- 3 Baths
- 3,400 Sq Ft
- Built 2007
746 Mill St, Windham, NY 12496

Last Sold Summary
- 249 Days On Market
Last Listing Agent Mary King Past Member

/9
$179,900
- Land
- 2.1 Acres
- $85,667 per Acre
L45.11 Panarama Ln, Windham, NY 12496

Prime 2.1-acre vacant parcel ideally located near the Windham Mountain Club expansion. This unimproved lot offers an excellent opportunity for future development or a private Catskills retreat. Enjoy close proximity to world-class skiing, golf, dining, and year-round recreation while maintaining a peaceful mountain setting. A rare chance to secure land in one of Windham's fastest-growing areas.

Susan Miller WINDSTAR REALTY GROUP LLC

L45.11 Panarama Ln, Windham, NY 12496

/10
Est $702,340

Not Listed For Sale

58 Mitchell Hollow Rd, Windham, NY 12496
- 3 Beds
- 3 Baths
- 2,120 Sq Ft
- Built 2006
58 Mitchell Hollow Rd, Windham, NY 12496

Last Sold Summary
- 369 Days On Market
Last Listing Agent Jacqueline Coyle Coldwell Banker Village GreenW

/16
$750,000
- Land
- 25,264 Sq Ft
- $1,293,103 per Acre
247 Club Rd, Windham, NY 12496

The Last True Ski-On/Ski-Off Lot at Windham Mountain—Step Out & Ski!This is the one and only true ski-on/ski-off lot available at Windham Mountain Club! Imagine waking up to breathtaking mountain views, stepping outside, putting on your skis, and gliding directly onto the slopes—no walking, no hassle, just pure ski-in/ski-out convenience. Located at the end of a no-outlet road, this prime

Regina Tortorella Coldwell Banker Village GreenW

247 Club Rd, Windham, NY 12496

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