Windham, NY Homes

/35
Not Listed For Sale
- 3 Beds
- 4 Baths
- 1,856 Sq Ft
11 Whisper Unit 305f, Windham, NY 12496

11 Whisper Unit 305f, Windham, NY 12496

/49
$149,000
- Land
- 5.25 Acres
- $28,381 per Acre
TBD Boulder Brook Rd Unit Lot 13, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Kyla Thomas Howard Hanna Rand Realty

TBD Boulder Brook Rd Unit Lot 13, Windham, NY 12496
/19
$485,000 Sold Dec 18, 2025

804 Mitchell Hollow Rd, Windham, NY 12496
- 7 Beds
- 2.5 Baths
- 3,114 Sq Ft
- Built 1852
Last Sold Summary
- 91% Below List Price
- $156/SF
- 55 Days On Market
Last Listing Agent Chris Tripsas Reliant Property Services

804 Mitchell Hollow Rd, Windham, NY 12496

/35
Est $1,694,968 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,276 Sq Ft
10 Enclave Dr W, Windham, NY 12496

10 Enclave Dr W, Windham, NY 12496

/38
$2,495,000
- 8 Beds
- 3.5 Baths
- 3,350 Sq Ft
3 Leon MacGlashan Rd, Windham, NY 12454

Experience Rustic Elegance and Timeless Wonder at 3 Leon Macglashan RoadNestled on over 210 acres of pristine Catskill landscapes, this extraordinary estate offers an unparalleled opportunity to embrace the serenity, privacy, and natural beauty of Windham, NY. From the moment you arrive, the property captivates with its historic charm, panoramic mountain views, and endless possibilities.

Cameron Ashkarkhizani Serhant LLC

3 Leon MacGlashan Rd, Windham, NY 12454
/26
$700,000 Sold Apr 02, 2025

22 Brook Hollow Ln, Windham, NY 12496
- 4 Beds
- 2 Baths
- 2,842 Sq Ft
- Built 2007
Last Sold Summary
- 2% Below List Price
- $246/SF
- 42 Days On Market
Current Estimated Value $753,792

Last Listing Agent Wyatt Dusenbury Corcoran Country Living

22 Brook Hollow Ln, Windham, NY 12496

/15
Not Listed For Sale
0 Vining & Goff Rd Unit 20214430, Windham, NY 12496

0 Vining & Goff Rd Unit 20214430, Windham, NY 12496

/47
$169,900
- Land
- 6.17 Acres
- $27,536 per Acre
TBD Lot 8 Boulder Brook Rd, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Kyla Thomas Howard Hanna Rand Realty

TBD Lot 8 Boulder Brook Rd, Windham, NY 12496
/74
$1,535,000 Sold Nov 19, 2025

869 County Route 10 Rd, Windham, NY 12496
- 5 Beds
- 4.5 Baths
- 3,812 Sq Ft
- Built 2023
Last Sold Summary
- 1% Below List Price
- $403/SF
- 40 Days On Market
Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

869 County Route 10 Rd, Windham, NY 12496

/41
Est $414,099 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,142 Sq Ft
53 Shock St, Windham, NY 12496

53 Shock St, Windham, NY 12496

/14
$75,000
- Land
- 1 Acre
- $75,000 per Acre
0 Mountain View Rd, Windham, NY 12496

Your 1 Acre in Windham Awaits! For everyone who's ever called us and said, "I just want a small piece of land to hold onto, "maybe build on it someday." This one is for you! This 1-acre wooded lot on a private country road offers the ideal setting for your next project. Whether you're planning to build a cozy cabin, dream home, or vacation rental, this mostly level property is ready for you to

Regina Tortorella Coldwell Banker Village GreenW

0 Mountain View Rd, Windham, NY 12496
/72
$1,311,000 Sold Dec 30, 2025

61 Cambridge Heights Rd, Windham, NY 12496
- 5 Beds
- 3.5 Baths
- 4,214 Sq Ft
- Built 1970
Last Sold Summary
- 9% Above List Price
- $311/SF
- 30 Days On Market
Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

61 Cambridge Heights Rd, Windham, NY 12496

/26
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,192 Sq Ft
15 W Wind Dr, Windham, NY 12439

15 W Wind Dr, Windham, NY 12439

/20
$479,000
- 4 Beds
- 3 Baths
- 2,058 Sq Ft
274 N Brooksburg Rd Unit 35, Windham, NY 12496

Charming 4-Bedroom Townhome Just Minutes from Windham Slopes!Discover this beautifully designed townhome in a vibrant four-season community, just five minutes from Windham's premier ski slopes, golf courses, scenic walking paths, top-rated restaurants, and stunning hiking trails. This thoughtfully crafted three-level home offers:4 Spacious Bedrooms - Plenty of space for family and guestsCozy up

John Pumilia Shaw Country Realty, Inc.

274 N Brooksburg Rd Unit 35, Windham, NY 12496
/29
$1,900,000 Sold Feb 20, 2025

14 - 2D Stonewall Ln, Windham, NY 12496
- 5 Beds
- 4.5 Baths
- 3,148 Sq Ft
Last Sold Summary
- $604/SF
- 0 Days On Market
Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

14 - 2D Stonewall Ln, Windham, NY 12496

/11
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,596 Sq Ft
11366 New York 23, Windham, NY 12496

11366 New York 23, Windham, NY 12496

/13
$120,000
- Land
- 1 Acre
- $120,000 per Acre
L19.11 South St, Windham, NY 12496

Build your Catskills getaway on this 1acre unimproved lot located on South Street in Windham, NY. Offering a peaceful setting with convenient access to Windham Mountain Club, village amenities, dining, and year-round recreation. Adjoining 1.2 acre lot for sale separately. A great opportunity for a custom home, weekend retreat, or long-term investment. Bring your vision and create a home that

Susan Miller WINDSTAR REALTY GROUP LLC

L19.11 South St, Windham, NY 12496
/21
$199,999 Sold Jan 30, 2025

394 State Route 296 Unit 1, Windham, NY 12496
- 2 Beds
- 1.5 Baths
- 750 Sq Ft
- Built 1920
Last Sold Summary
- $267/SF
- 59 Days On Market
Current Estimated Value $216,867

Last Listing Agent Mariana DeLuca Howard Hanna Capital Inc

394 State Route 296 Unit 1, Windham, NY 12496

/5
Not Listed For Sale
0 Old Rd Unit 132994, Windham, NY 12496

0 Old Rd Unit 132994, Windham, NY 12496

/34
$249,000
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
55 Quads Way, Windham, NY 12496

Sweet 2-Bedroom, 2-Bath Condo - Four-Season Windham Living This charming and affordable, easy-to-maintain condo offers the perfect four-season Catskills getaway, just minutes from skiing and winter fun at Windham Mountain Club. From crisp winter ski days to vibrant fall foliage, followed by spring and summer hiking, biking, golf, and outdoor dining, this location delivers year-round enjoyment in

Lisa Jaeger Coldwell Banker Village GreenW

55 Quads Way, Windham, NY 12496
/30
$1,400,000 Sold Sep 18, 2025

4 The Loop, Windham, NY 12496
- 4 Beds
- 3 Baths
- 2,536 Sq Ft
- Built 1974
Last Sold Summary
- 6% Below List Price
- $552/SF
- 121 Days On Market
Current Estimated Value $1,407,971

Last Listing Agent Patricia Charbonneau Brainard Ridge Management

4 The Loop, Windham, NY 12496

/7
Not Listed For Sale
0 Boulder Brook Rd, Windham, NY 12496

0 Boulder Brook Rd, Windham, NY 12496

/44
$1,175,000
- 5 Beds
- 3 Baths
- 4,489 Sq Ft
32 Glennamaddy Rd, Windham, NY 12496

STUNNING LOCATION! Situated above Windham Ridge this Custom designed & built (by one of Windham's top builders) Contemporary style home has direct ski slope views in a special setting. Conveniently just 2 minutes to Windham Village & 5 minutes to Windham Mountain. Extraordinary mountain home. Efficient & economical design. Upon entering, a bit of a WOW, with 25ft. Beamed, vaulted ceilings &

Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

32 Glennamaddy Rd, Windham, NY 12496
/25
$1,200,000 Sold Apr 30, 2025

5344 Main St, Windham, NY 12496
- 3 Beds
- 3 Baths
- 6,400 Sq Ft
- Built 1975
Last Sold Summary
- 7% Below List Price
- $188/SF
Last Listing Agent Phil Uhrik Win Morrison Realty - Catskill

5344 Main St, Windham, NY 12496

/11
Not Listed For Sale
0 Schrader Rd, Windham, NY 12496

0 Schrader Rd, Windham, NY 12496

/44
$159,900
- Land
- 8.72 Acres
- $18,337 per Acre
TBD Boulder Brook Rd Unit Lot 12, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Kyla Thomas Howard Hanna Rand Realty

TBD Boulder Brook Rd Unit Lot 12, Windham, NY 12496
/29
$1,675,000 Sold May 12, 2025

21 - 4A Stonewall Ln, Windham, NY 12496
- 5 Beds
- 4.5 Baths
- 3,148 Sq Ft
- Built 2024
Last Sold Summary
- 12% Below List Price
- $532/SF
- 0 Days On Market
Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

21 - 4A Stonewall Ln, Windham, NY 12496

/3
Not Listed For Sale
421 County Route 56, Windham, NY 12496

421 County Route 56, Windham, NY 12496

/48
$590,000
- 4 Beds
- 2 Baths
- 1,052 Sq Ft
31 Koonan Rd, Windham, NY 12496

Take advantage of this meticulously refreshed winter escape in the heart of Windham. Step inside to a bright and inviting layout featuring newly added hardwood floors, fresh paint inside and out, and a brand-new washer and dryer. The main living level is anchored by a charming wood stove that sets a cozy tone for the whole group to enjoy after a day of outdoor activities. Four bedrooms and two

Brandon Oot Core Real Estate Team

31 Koonan Rd, Windham, NY 12496
/42
$655,000 Sold Dec 23, 2025

442 Mitchell Hollow Rd, Windham, NY 12496
- 3 Beds
- 2.5 Baths
- 2,868 Sq Ft
- Built 1969
Last Sold Summary
- 6% Below List Price
- $228/SF
- 146 Days On Market
Last Listing Agent Mark McAlpine Compass Greater New York, LLC

442 Mitchell Hollow Rd, Windham, NY 12496

/34
Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,948 Sq Ft
256 County Road 65, Hensonville, NY 12439

256 County Road 65, Hensonville, NY 12439

/28
$339,000
- 2 Beds
- 2.5 Baths
- 1,295 Sq Ft
274 Route 65 Unit 41, Windham, NY 12496

Enter this lovely Townhome and feel right at home. This is an end unit, lovely setting. There is a storage shed for skis and bikes outside, enter the unit into a mud room, The first floor has a half bath/laundry room, lovely galley kitchen with a window, plenty of light. This is open to the living an dining areas. Living room has a large bay window, sliding doors to a patio, plenty of privacy, as

Mary Donovan Gallagher & Company

274 Route 65 Unit 41, Windham, NY 12496
/34
$420,000 Sold Jul 14, 2025

296 Mitchell Hollow Rd, Windham, NY 12496
- 3 Beds
- 1 Bath
- 1,486 Sq Ft
- Built 1847
Last Sold Summary
- 4% Below List Price
- $283/SF
- 33 Days On Market
Current Estimated Value $431,392

Last Listing Agent Allison Morelle Coldwell Banker Village GreenK

296 Mitchell Hollow Rd, Windham, NY 12496

/27
Est $711,179 Not Listed For Sale
- 6 Beds
- 6 Baths
- 3,600 Sq Ft
310 Mill St, Windham, NY 12496

310 Mill St, Windham, NY 12496

/11
$300,000
- Land
- 7.52 Acres
- $39,894 per Acre
1 Galway Rd, Windham, NY 12496

Welcome to Windham Luxury Estates, where an exceptional opportunity awaits you with a fully approved, SHOVEL-ready 7.5 acre residential building lot. This prime parcel includes comprehensive engineering, topographical & survey maps, and a fully approved DEP septic design suitable for an estate-like home, ensuring compliance with environmental regulations for a streamlined building process.

Patrick Dunn KW Platform

1 Galway Rd, Windham, NY 12496
/72
$630,000 Sold Feb 13, 2025

23 Manor Dr, Windham, NY 12496
- 3 Beds
- 3 Baths
- 2,485 Sq Ft
Last Sold Summary
- 3% Below List Price
- $254/SF
- 56 Days On Market
Current Estimated Value $684,474

Last Listing Agent Corey Marikovics Four Seasons Sotheby's Int'l R

23 Manor Dr, Windham, NY 12496

/2
Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,544 Sq Ft
516 Route 40, Windham, NY 12454

516 Route 40, Windham, NY 12454

/9
$450,000
- Land
- 10 Acres
- $45,000 per Acre
000 New York 296, Windham, NY 12496

10 Acres of Prime Forested Land | Windham, NY | Development or Dream Compound PotentialAn extraordinary opportunity awaits on Route 296 in Windham, NY - two adjacent 5-acre parcels totaling 10 acres of pristine Catskills forest, ideally situated for those with vision. Slightly sloped and elevated just enough to offer potential eastern-facing views with selective clearing, this land offers

Jason Dugo Dugo Realty

000 New York 296, Windham, NY 12496
/30
$397,500 Sold Nov 25, 2025

1020 Maplecrest Rd, Windham, NY 12439
- 4 Beds
- 2 Baths
- 2,267 Sq Ft
- Built 1980
Last Sold Summary
- 1% Below List Price
- $175/SF
- 54 Days On Market
Last Listing Agent Mary Donovan Gallagher & Company

1020 Maplecrest Rd, Windham, NY 12439

/35
Not Listed For Sale
Lot 2 New York 23, Windham, NY 12496

Lot 2 New York 23, Windham, NY 12496

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