Windham, NY Homes

/54
$1,495,000 Pending
- 6 Beds
- 5.5 Baths
- 5,500 Sq Ft
12 Jacob Strasse Rd, Windham, NY 12496

Welcome to High Peak, an exquisite modern retreat perched high above Windham with uninterrupted views of Windham's High Peak mountain, and the surrounding mountains. Custom-built and thoughtfully designed across three expansive levels, this one-of-a-kind home is a rare blend of architectural precision, natural light, and breathtaking landscape. Sited on over 3 acres, the setting is as exceptional

Catherine Quintard

Compass Greater NY, LLC

(518) 667-5945

12 Jacob Strasse Rd, Windham, NY 12496
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/26
$66,000 Sold Jun 04, 2025
- Land
- 5.00 Acres
- $13,200 per Acre
- 330 Days On Market
0 Hayden Rd, Windham, NY 12496

The perfect canvas to build your dream home in a picturesque setting close to the village of Windham. Expansive 5-acre parcel of vacant land is a unique property that presents a rare opportunity to build in a location where such options are becoming increasingly scarce. Tucked away on a private road, just off the main route as you enter the village, this wooded lot promises an ideal blend of

Lisa Jaeger Coldwell Banker Village Green

0 Hayden 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

/54
$850,000
- 8 Beds
- 8 Baths
- 3,712 Sq Ft
5320 New York 23, Windham, NY 12496

In the heart of Windham, ''the place to be,'' this rare multi-use property offers endless possibilities for residential, commercial, or mixed-use ventures. Formerly a thriving B&B, it features two buildings with a total of 8 bedrooms and 8 bathrooms, a large open kitchen plus accessory kitchen, and expansive spaces perfect for a restaurant, cafe, art studio, gallery, retail shop, or rental income

Carol Shaw

Shaw Country Realty, Inc.

(518) 261-9298

5320 New York 23, Windham, NY 12496
/29
$1,900,000 Sold Jun 02, 2025
- 3,148 Sq Ft
- $604/SF
- 1 Day On Market
- 5 Beds
- 4.5 Baths
22 - 5A Stonewall Ln, Windham, NY 12496

Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers a perfect blend of modern mountain living and serene country life. Whether it's for family, friends, or your own getaway, this community surrounds you with year-round recreational opportunities.Our 3, 4, and 5-bedroom custom townhomes feature spacious, thoughtfully designed floor plans, ranging from 2,356

Pamela King-Belfor Four Seasons Sotheby's Int.

22 - 5A Stonewall Ln, Windham, NY 12496

/45
Est $1,203,667 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

/19
$334,900
- 3 Beds
- 2 Baths
- 1,040 Sq Ft
504 Route 40, Maplecrest, NY 12454

Nestled in the quaint hamlet of Maplecrest, this inviting 2-bedroom home offers the perfect blend of tranquility and convenience. Ideally located between Windham and Hunter Mountains, it's just minutes from world-class skiing, hiking, golf, and other outdoor adventures. Enjoy easy access to nearby CD Lane Park, Colgate Lake, and the iconic Kaaterskill Falls.This home boasts a semi-finished

Carol Shaw

SHAW COUNTRY REALTY INC

(518) 759-6904

504 Route 40, Maplecrest, NY 12454
/34
$450,000 Sold May 23, 2025
- 1,867 Sq Ft
- $241/SF
- 66 Days On Market
- 3 Beds
- 2 Baths
- Built 2021
116 Galway Rd, Windham, NY 12496

Discover this stunningly renovated 3 bed 2 bath traditional 2 story home. Designed with an open concept layout, this residence features high end finishes throughout, including sleek quartz countertops and a matching backsplash. 1st floor bed and full bath offer convenience for guests or single-level living. Enjoy peace of mind with brand new everything—roof, HVAC, electrical, siding, and

Patrick Dunn KW Platform

116 Galway Rd, Windham, NY 12496

/30
Est $303,682 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

/24
$334,900
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
504 Rt 40, Windham, NY 12454

Nestled in the quaint hamlet of Maplecrest, this inviting 2-bedroom home offers the perfect blend of tranquility and convenience. Ideally located between Windham and Hunter Mountains, it's just minutes from world-class skiing, hiking, golf, and other outdoor adventures. Enjoy easy access to nearby CD Lane Park, Colgate Lake, and the iconic Kaaterskill Falls.This home boasts a semi-finished

Carol Shaw

Shaw Country Realty, Inc.

(518) 741-2720

504 Rt 40, Windham, NY 12454
/26
$695,000 Sold May 16, 2025
- 2,000 Sq Ft
- $348/SF
- 106 Days On Market
- 3 Beds
- 3 Baths
- Built 2024
23 Circle Rd, Windham, NY 12496

Nestled in the heart of Windham, NY, this newly constructed contemporary ranch is the perfect blend of style and convenience. Located just minutes from the ski slopes and the charming village, this home offers breathtaking southern-exposure views of the ski slopes from every window.Thoughtfully designed, the layout features a spacious primary suite on one side and additional bedrooms on the

Carol Shaw Shaw Country Realty, Inc.

23 Circle Rd, Windham, NY 12496

/9
Est $503,788 Not Listed For Sale
248 Club Rd, Windham, NY 12496

248 Club Rd, Windham, NY 12496

/30
$999,000
- 4 Beds
- 3.5 Baths
- 3,245 Sq Ft
5 Jacob Strasse Rd, Windham, NY 12496

Modern Mountain Retreat just minutes from Windham Village! Looking for that perfect mix of modern style and cozy mountain living? Welcome to your dream home! This beautifully updated 4-bedroom, 3.5-bathroom escape offers over 3,000 square feet of space, set on five peaceful acres and it's just a few minutes from Windham's village shops, restaurants, and world-class ski slopes.Enter through a

Christine Hinz

Coldwell Banker Village Green

(518) 576-1632

5 Jacob Strasse Rd, Windham, NY 12496
/40
$2,250,000 Sold May 15, 2025
- 4,228 Sq Ft
- $532/SF
- 82 Days On Market
- 6 Beds
- 6 Baths
- Built 2015
18 White Way, Windham, NY 12496

LOCATION!!!Welcome to the ultimate mountain retreat! This exceptional home offers the rare opportunity to ski right out your back door onto the slopes of Windham Mountain. With 6 spacious bedrooms and 6 well-appointed bathrooms, this home is perfect for large family gatherings or hosting friends and guests.The open-concept kitchen, living, and dining area flows seamlessly, providing the ideal

Carol Shaw Shaw Country Realty, Inc.

18 White Way, Windham, NY 12496

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

TBD Mill St, Windham, NY 12496

/60
$1,199,000 New Construction
- 3 Beds
- 3.5 Baths
- 3,287 Sq Ft
20 Brookhollow Ln, Windham, NY 12496

Welcome to this stunning new construction home in the sought-after town of Windham, NY! This contemporary, sun-drenched home features 3 spacious bedrooms and 3.5 baths, with an expansive layout perfect for modern living.On the Main floor, Enjoy a large, beautiful primary bedroom with an en-suite bath, providing a luxurious and private retreat. Vaulted ceilings throughout the main level enhance

Carol Shaw

Shaw Country Realty, Inc.

(518) 757-9788

20 Brookhollow Ln, Windham, NY 12496
/29
$1,675,000 Sold May 12, 2025
- 3,148 Sq Ft
- $532/SF
- 0 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2024
21 - 4A Stonewall Ln, Windham, NY 12496

Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers a perfect blend of modern mountain living and serene country life. Whether it's for family, friends, or your own getaway, this community surrounds you with year-round recreational opportunities.Our 3, 4, and 5-bedroom custom townhomes feature spacious, thoughtfully designed floor plans, ranging from 2,356

Pamela King-Belfor Four Seasons Sotheby's Int.

21 - 4A Stonewall Ln, Windham, NY 12496

/31
Est $435,963 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

/35
$899,000
- 4 Beds
- 3 Baths
- 2,720 Sq Ft
2 Biff Andrus Rd, Windham, NY 12496

Windham Mountain Retreat - situated in a prime location just minutes to town and Windham Mountain Club. Designed with comfort and relaxation in mind, this space is also ideal for entertaining guests. Enjoy breathtaking mountain views from nearly every vantage point. Enter the home into the spacious mudroom, ideal for ski gear storage. The open concept living space, accentuated by a the grandeur

Richard Vizzini Corcoran Country Living

2 Biff Andrus Rd, Windham, NY 12496
/29
$1,650,000 Sold May 09, 2025
- 2,700 Sq Ft
- $611/SF
- 0 Days On Market
- 4 Beds
- 3.5 Baths
12 - 2C Stonewall Ln, Windham, NY 12496

Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers a perfect blend of modern mountain living and serene country life. Whether it's for family, friends, or your own getaway, this community surrounds you with year-round recreational opportunities.Our 3, 4, and 5-bedroom custom townhomes feature spacious, thoughtfully designed floor plans, ranging from 2,356

Pamela King-Belfor Four Seasons Sotheby's Int.

12 - 2C Stonewall Ln, 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

/42
$700,000
- 3 Beds
- 2.5 Baths
- 2,004 Sq Ft
442 Mitchell Hollow Rd, Windham, NY 12496

Nestled just 2.9 miles away from the breathtaking slopes of Windham Mountain and across the street from 89 acres of protected land sits this stunning 3 bed, 2.5 bath ranch. The home offers a captivating blend of modern touches and natural beauty. As you step into this picturesque retreat, panoramic views of the surrounding landscape greet you from every window, with the Windham slopes on display

Mark McAlpine Compass Greater New York, LLC

442 Mitchell Hollow Rd, Windham, NY 12496
/16
$1,900,000 Sold May 02, 2025
- 3,148 Sq Ft
- $604/SF
- 15 Days On Market
- 5 Beds
- 4.5 Baths
28 - 5D Stonewall Ln, Windham, NY 12496

Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers a perfect blend of modern mountain living and serene country life. Whether it's for family, friends, or your own getaway, this community surrounds you with year-round recreational opportunities.Our 3, 4, and 5-bedroom custom townhomes feature spacious, thoughtfully designed floor plans, ranging from 2,356

Pamela King-Belfor Four Seasons Sotheby's Int.

28 - 5D Stonewall Ln, Windham, NY 12496

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

79 Old Rd, Windham, NY 12496

/57
$815,000
- 4 Beds
- 4.5 Baths
- 1,904 Sq Ft
122 Brainard Ridge Rd Unit 14f, Windham, NY 12496

Three Levels consisting of a spacious 2896 square feet of living space. is a Well-maintained custom double-size town home in Brainard Ridge, one of a kind!These 4 bedrooms, 3 are ensuite - plus a sleeping alcove, 4.5 baths, 3 full floors, 3 fireplaces: stone wrapped wood burning in the central living room, gas fireplace in main level tv/game room as well as in the primary suite. Hardwood

Irene Pinto Brainard Ridge Management

122 Brainard Ridge Rd Unit 14f, Windham, NY 12496
/25
$1,200,000 Sold Apr 30, 2025
- 6,400 Sq Ft
- $188/SF
- 3 Beds
- 3 Baths
- Built 1975
5344 Main St, Windham, NY 12496

One of the most iconic pieces of Real Estate in Windham, New York is Back on the Market!! Seller Financing Available! Nestled in the Heart of Windham on bustling Main Street, this unique mixed-use property offers a blend of commercial & retail opportunity plus income generating apartments. The perfect investment that is fully rented and generating great returns that could easily carry a

Phil Uhrik Win Morrison Realty - Catskill

5344 Main St, Windham, NY 12496

/5
Est $1,121,388 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,200 Sq Ft
127 Brainard Ridge Rd, Windham, NY 12496

127 Brainard Ridge Rd, Windham, NY 12496

/67
$769,000
- 5 Beds
- 3.5 Baths
- 2,315 Sq Ft
8 Evans Rd, Windham, NY 12496

Stunning 3,862 Sq Ft Windham Retreat with Ski Slope Views, Pool, A/C, Masonry Patios, Lush Landscaping, Dual 2-Car Garages & Paved Driveway. Pride of ownership radiates throughout this meticulously maintained Windham property, offering 3,862 square feet of finished living space—including a beautifully appointed lower level—in a serene, park-like setting just two minutes from the heart of

Regina Tortorella Coldwell Banker Village GreenW

8 Evans Rd, Windham, NY 12496
/28
$280,000 Sold Apr 24, 2025
- 1,211 Sq Ft
- $231/SF
- 118 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1987
36 Loo Bridge Ln, Windham, NY 12496

Windham Ridge Townhouse:Nestled in the heart of Windham's sought-after 4-seasons community, this beautifully renovated townhouse offers the perfect blend of comfort, style, and convenience. With views of the slopes and a prime location just a short stroll to the village, this property is ideal for year-round enjoyment or as a lucrative investment opportunity2 spacious bedrooms with a bonus room

Carol Shaw Shaw Country Realty, Inc.

36 Loo Bridge Ln, Windham, NY 12496

/2
Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,016 Sq Ft
33 High Ridge Rd, Windham, NY 12439

33 High Ridge Rd, Windham, NY 12439

/44
$820,000
- 4 Beds
- 2 Baths
- 2,442 Sq Ft
720 Mill St, Windham, NY 12496

Back on Market! Due to buyer's financing. Now is the time to grab this incredible property. Situated on a private 5-acres in the heart of Windham, you'll find this extraordinary residence. A masterful blend of history and modern craftsmanship. Huge barn beams and trusses sourced from a1840 New England barn, the structure was meticulously dismantled, transported, and reassembled to create a

Lisa Jaeger Coldwell Banker Village Green

720 Mill St, Windham, NY 12496
/29
Sold Apr 24, 2025
- 2,700 Sq Ft
- 1 Day On Market
- 4 Beds
- 3.5 Baths
25 - 4C Stonewall Ln, Windham, NY 12496

Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers a perfect blend of modern mountain living and serene country life. Whether it's for family, friends, or your own getaway, this community surrounds you with year-round recreational opportunities.Our 3, 4, and 5-bedroom custom townhomes feature spacious, thoughtfully designed floor plans, ranging from 2,356

Pamela King-Belfor Four Seasons Sotheby's Int.

25 - 4C Stonewall Ln, Windham, NY 12496

/2
Est $1,774,520 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,300 Sq Ft
502 County Route 10, Windham, NY 12496

502 County Route 10, Windham, NY 12496

/59
$799,000
- 4 Beds
- 3.5 Baths
- 2,100 Sq Ft
769 Mitchell Hollow Rd, Windham, NY 12496

Bright Sparrow Farmhouse - Modern Farmhouse on 8+ Acres with Private Pond, Mountain Views & Proven Rental Income | Windham, NYWelcome to Bright Sparrow Farmhouse—your dream Catskills retreat where modern farmhouse style meets timeless charm on over 8.22 private acres with a spring-fed pond, unobstructed mountain views, and a turnkey short-term rental setup with proven income. Located just 10

Regina Tortorella Coldwell Banker Village GreenW

769 Mitchell Hollow Rd, Windham, NY 12496
/17
Sold Apr 22, 2025
- Land
- 7 Acres
- 189 Days On Market
70 Begley Rd, Windham, NY 12496

Welcome to Lot 70 at Windham Vista Six-your gateway to peaceful living and breathtaking views. This surveyed 7.2-acre lot boasts approximately 1,239 feet of road frontage on Begley Road and an additional 226 feet of road frontage on a private road off Begley Road, providing multiple access options into the lot.(Carving a driveway off of the private road will maximize the privacy of the building

Regina Tortorella Past Member

70 Begley Rd, Windham, NY 12496

/27
Est $635,026 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,702 Sq Ft
118 Brainard Ridge Rd Unit 14D, Windham, NY 12496

118 Brainard Ridge Rd Unit 14D, Windham, NY 12496

/27
$468,000
- 3 Beds
- 2 Baths
- 1,080 Sq Ft
111 Brainard Ridge Rd Unit 11B, Windham, NY 12496

Brainard Ridge Charmer!Ready for 4 season active life style. Charming 3 bedroom, 2 bath plus extra sleeping alcove, Brainard Ridge Townhome. Open and airy floor plan, lots of natural light! Cozy living room with large wood burning fireplace, nice dining area, cheery kitchen, Primary bedroom with ensuite bath, plus extra sleeping alcove. Lower level with bunkroom, and guest bedroom, second full

Patricia Charbonneau Brainard Ridge Management

111 Brainard Ridge Rd Unit 11B, Windham, NY 12496
/39
$314,500 Sold Apr 09, 2025
- 1,536 Sq Ft
- $205/SF
- 278 Days On Market
- 2 Beds
- 2 Baths
- Built 1983
4 French Park Dr Unit 4B, Windham, NY 12496

Priced to sell, this Windham Ridge townhome is the best value on the market. Located in a highly desirable development overlooking the village of Windham and the ski slope beyond, this home can turn your dream of owning a vacation getaway into a reality.Vaulted ceilings, a wood burning fireplace and abundant windows and skylights flood the open kitchen, dining and living areas with natural light.

Sharri Cunningham Bunce Realty

4 French Park Dr Unit 4B, Windham, NY 12496

/30
Est $859,977 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,280 Sq Ft
208 South St, Windham, NY 12496

208 South St, Windham, NY 12496

/77
$999,000
- 4 Beds
- 4.5 Baths
- 2,168 Sq Ft
68 Hilltop Dr, Maplecrest, NY 12454

Welcome to The Hill, a private enclave of high-end homes tucked away in the scenic hamlet of Maplecrest, just minutes from Windham Mountain Club and CD Lane Park. Perched on 6 peaceful acres at the end of a quiet cul-de-sac, this 3,500+ sq ft custom contemporary blends crisp architectural design with warm rustic touches for the ultimate Catskills retreat.Built by renowned Hitchcock Builders, this

Lisa Jaeger Coldwell Banker Village Green

68 Hilltop Dr, Maplecrest, NY 12454

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