Windham, NY Homes

/38
Est $576,271

Not Listed For Sale

153 Slater Rd, Maplecrest, NY 12454
- 3 Beds
- 2 Baths
- 1,215 Sq Ft
- Built 1983
153 Slater Rd, Maplecrest, NY 12454

Last Sold Summary
- 19 Days On Market

/28
$234,500

$234K PRICE INCREASE
- Land
- 2.3 Acres
- $101,957 per Acre
0 N Ridge Extension Unit 20255019, Windham, NY 12496

Welcome to North Ridge Estates - Build Your Catskills Dream Getaway Here's your chance to own the last remaining building lot in North Ridge Estates, an exclusive, private enclave known for its high-end vacation homes and newly built million-dollar properties. Set on 2.30 acres, this prime parcel has already been surveyed and features a driveway leading into the heart of the property with a

Lisa Jaeger

Coldwell Banker Village GreenW

0 N Ridge Extension Unit 20255019, Windham, NY 12496
/50
$885,000

Sold Dec 15, 2025

30 The Loop, Windham, NY 12496
- 5 Beds
- 4 Baths
- 3,100 Sq Ft
- Built 1970
Last Sold Summary
- 11% Below List Price
- $285/SF
- 291 Days On Market
Current Estimated Value $905,443

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

30 The Loop, Windham, NY 12496

/15
Not Listed For Sale

0 Ruland Rd Unit 155000, Windham, NY 12454
0 Ruland Rd Unit 155000, Windham, NY 12454

Last Sold Summary
- 57 Days On Market

/22
$289,000
- 2 Beds
- 2 Baths
- 838 Sq Ft
5359 Main St, Windham, NY 12496

Prime Windham Village Location: Just outside your door, wander to restaurants, movies, breweries, pubs, miniature golf, seasonal farmers market and year round town events.Convenient NYC bus access just outside your door for easy escape for the weekend. Only minutes to the Windham Mt. Club for skiing and nearby golf courses makes this a desirable location for this 2 bedroom, 2 bath condo with

Carol Shaw

SHAW COUNTRY REALTY INC

5359 Main St, Windham, NY 12496
/35
$815,000

Sold Dec 24, 2025

2 Biff Andrus Rd, Windham, NY 12496
- 4 Beds
- 3 Baths
- 3,500 Sq Ft
- Built 2002
Last Sold Summary
- 18% Below List Price
- $233/SF
- 346 Days On Market
Current Estimated Value $924,543

Last Listing Agent Richard Vizzini Corcoran Country Living

2 Biff Andrus Rd, Windham, NY 12496

/6
Not Listed For Sale

80 Begley Rd, Windham, NY 12496
80 Begley Rd, Windham, NY 12496

Last Sold Summary
- 120 Days On Market

/31
$349,000

$50K PRICE DROP
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
436 Big Hollow Rd, Maplecrest, NY 12454

Up the road from thousands of acres of state hiking trails and from CD Lane Park with swimming, kayaking, and family fun, this location is a true four-season retreat. Minutes to Windham and Hunter ski resorts, golf courses, and local venues, the setting offers year-round recreation at your doorstep.Set back from a quiet country road on nearly 4 acres, this property is all about the outdoors.

Carol Shaw

Shaw Country Realty, Inc.

436 Big Hollow Rd, Maplecrest, NY 12454
/15
$81,500

Sold Aug 13, 2025

1 - 886 Mill St, Windham, NY 12496
- Land
- 1.2 Acres
- $67,917 per Acre
Last Sold Summary
- 14% Below List Price
- 268 Days On Market
Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

1 - 886 Mill St, Windham, NY 12496

/28
Est $446,484

Not Listed For Sale

904 N Settlement Rd, Windham, NY 12496
- 2 Beds
- 2 Baths
- 1,024 Sq Ft
- Built 2003
904 N Settlement Rd, Windham, NY 12496

Last Sold Summary
- 139 Days On Market

/13
$99,000
- Land
- 8.24 Acres
- $12,015 per Acre
539 Route 40, Maplecrest, NY 12454

Centrally located between Windham and Hunter, minutes to CD Lane Park, State hiking trails, Colgate Lake and everything this area has to offer. This 8 + acre parcel has a septic design in place designed by Kaaterskill Engineering and submitted to DEP and approved but would need to be updated with the town. This makes this lot desirable with no soil testing and design which could usually take

Carol Shaw

Shaw Country Realty, Inc.

539 Route 40, Maplecrest, NY 12454
/73
$1,810,000

Sold Mar 05, 2026

150 Trailside Rd, Windham, NY 12496
- 9 Beds
- 7 Baths
- 6,859 Sq Ft
- Built 2001
Last Sold Summary
- 20% Below List Price
- $264/SF
- 304 Days On Market
Current Estimated Value $1,808,856

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

150 Trailside Rd, Windham, NY 12496

/26
Est $767,548

Not Listed For Sale

22 Brook Hollow Ln, Windham, NY 12496
- 4 Beds
- 2 Baths
- 2,842 Sq Ft
- Built 2007
22 Brook Hollow Ln, Windham, NY 12496

Last Sold Summary
- 42 Days On Market

/42
$315,000
- 2 Beds
- 2 Baths
- 1,542 Sq Ft
689 Old Rd, Hensonville, NY 12439

Step into the charm of this 1930s 2-bedroom, 2-bath ranch, just minutes from the Village of Windham and Windham Mountain. Nestled on a full acre and bordered by 25.5 acres of protected NYC watershed land, the property offers rare privacy and a seamless connection to nature. Wake up to the gentle sounds of a seasonal creek and lush surrounding greenery, a true mountain escape.Outside, a

Mark McAlpine

Compass Greater New York, LLC

689 Old Rd, Hensonville, NY 12439
/73
$715,000

Sold Nov 24, 2025

122 Old Rd, Windham, NY 12496
- 4 Beds
- 2.5 Baths
- 1,823 Sq Ft
- Built 1982
Last Sold Summary
- 5% Below List Price
- $392/SF
- 42 Days On Market
Current Estimated Value $725,285

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

122 Old Rd, Windham, NY 12496

/31
Est $248,032

Not Listed For Sale

60 Quads Way, Windham, NY 12496
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
- Built 1986
60 Quads Way, Windham, NY 12496

Last Sold Summary
- 350 Days On Market

/33
$789,000

$11K PRICE DROP
- 6 Beds
- 3.5 Baths
- 4,368 Sq Ft
559 Case Rd, Windham, NY 12496

AT 559, ITS TIME! TO MAKE YOUR CASE FOR WINDHAM. Welcome to 559 Case Road in Ashland-Windham, a spacious Colonial set on almost 8 private acres, surrounded by the natural beauty of the Catskills in the Upper Hudson Valley. Offering 6 bedrooms and 3.5 bathrooms, this property is a great full-time residence, weekend retreat, or investment property. A sun-filled entryway with soaring ceilings and

Al Iaquinta

Iaquinta Premier Properties

559 Case Rd, Windham, NY 12496
/41
$640,000

Sold Nov 21, 2025

212 South St, Windham, NY 12496
- 3 Beds
- 2 Baths
- 2,240 Sq Ft
- Built 1970
Last Sold Summary
- 4% Below List Price
- $286/SF
- 69 Days On Market
Last Listing Agent Mary Donovan Gallagher & Company

212 South St, Windham, NY 12496

/22
Est $255,639

Not Listed For Sale

24 Quads Way, Windham, NY 12496
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
- Built 1986
24 Quads Way, Windham, NY 12496

Last Sold Summary
- 140 Days On Market

/4
$115,000
- Land
- 1.6 Acres
- $71,875 per Acre
0 County Road 65 Unit 20261215, Windham, NY 12496

Windham Townhship (Hensonville) these 2 adjoining lots are set back behind House #225 each lot is .8 acre with total of 1.6 acresPotential sewer hook up to be brought up from road . Sewer goes to first house. There is one .8 acre lot between house and lots for sale. Property starts apprx 351' in from road. Great place for small houses, RV wooded and fairly level

Carol Shaw

Shaw Country Realty, Inc.

0 County Road 65 Unit 20261215, Windham, NY 12496
/31
$159,900

Sold Jun 22, 2026

Tbd, Windham, NY 12496
- Land
- 8.33 Acres
- $19,196 per Acre
Last Sold Summary
- 341 Days On Market
Last Listing Agent Kyla Thomas Howard Hanna Rand Realty

Tbd, Windham, NY 12496

/64
Est $598,533

Not Listed For Sale

29 Martin Ln, Hensonville, NY 12439
- 4 Beds
- 2 Baths
- 2,116 Sq Ft
- Built 1994
29 Martin Ln, Hensonville, NY 12439

Last Sold Summary
- 40 Days On Market

/35
$485,000
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
5134 New York 23, Windham, NY 12496

Introducing a treasure in the heart of Windham, where charm and convenience beautifully coalesce. This three-bedroom oasis offers a newly renovated, low maintenance home that encapsulates comfort and serenity.Set amidst the breathtaking mountain views, this property boasts an enchanting creekside grotto. The firepit area is an idyllic spot for tranquil evenings under the stars, a feature

Jason Dugo

Dugo Realty

5134 New York 23, Windham, NY 12496
/41
$999,000

Sold Dec 30, 2025

51 Barnum Rd, Windham, NY 12496
- 6 Beds
- 4.5 Baths
- 2,679 Sq Ft
- Built 1985
Last Sold Summary
- 9% Above List Price
- $373/SF
- 15 Days On Market
Last Listing Agent Catherine Quintard Compass Greater NY, LLC

51 Barnum Rd, Windham, NY 12496

/30
Est $676,829

Not Listed For Sale

67 Clarence D Lane Rd Unit 1, Windham, NY 12496
- 3 Beds
- 2 Baths
- 1,624 Sq Ft
- Built 1973
67 Clarence D Lane Rd Unit 1, Windham, NY 12496

Last Sold Summary
- 54 Days On Market

/30
$525,000

$20K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,335 Sq Ft
20 Sutton Hollow Rd, Windham, NY 12496

Modern Farmhouse Getaway with Streamside Serenity - Fully Renovated & Fully Furnished! This turn-key, completely renovated modern farmhouse is ready to welcome you! Just 12 minutes from the Windham Mountain Club and only a short drive to Hunter and Belleayre, this stylish 3-bedroom plus open sleeping loft retreat delivers four-season Catskill charm with designer finishes and a prime location for

Regina Tortorella Coldwell Banker Village GreenW

20 Sutton Hollow Rd, Windham, NY 12496
/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 $493,434

Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

996 County Route 10, Windham, NY 12496

/17
Est $583,480

Not Listed For Sale

120 Mount Greenery Rd, Windham, NY 12496
- 3 Beds
- 3 Baths
- 2,017 Sq Ft
- Built 1988
120 Mount Greenery Rd, Windham, NY 12496

Last Sold Summary
- 61 Days On Market

/66
$799,000
- 4 Beds
- 3.5 Baths
- 2,878 Sq Ft
5678 New York 23, Windham, NY 12496

Turn-Key Catskills Timber Frame Retreat | Sold Fully Furnished | Mountain Views | Walk to Restaurants | Minutes to Windham Mountain Club This is the kind of authentic Catskills Mountain retreat buyers spend years searching for. Proudly perched on a hill in one of Windham's most charming locations, this true 1900s timber frame home seamlessly blends historic character with the modern finishes and

Regina Tortorella Coldwell Banker Village GreenW

5678 New York 23, Windham, NY 12496
$169,900

Sold Jun 22, 2026

TBD Lot 8 Boulder Brook Rd, Windham, NY 12496
- Land
- 6.17 Acres
- $27,536 per Acre
Last Sold Summary
- 287 Days On Market
Last Listing Agent Kyla Thomas Howard Hanna Rand Realty

TBD Lot 8 Boulder Brook Rd, Windham, NY 12496

/18
Est $183,241

Not Listed For Sale

26 Mill St, Windham, NY 12496
- 3 Beds
- 1 Bath
- 824 Sq Ft
- Built 1940
26 Mill St, Windham, NY 12496

Last Sold Summary
- 31 Days On Market

/44
$449,000
- 4 Beds
- 2 Baths
- 1,808 Sq Ft
97 Carrington Rd, Windham, NY 12496

Streamfront Serenity Meets Mountain Views -- Bordering Protected NYC DEP Lands Bordered by 160 acres of DEP land and the pristine Batavia Kill Creek, this beautifully updated split-level retreat delivers the kind of setting buyers come to the Catskills for--wide open meadows, mountain views, and the calming sound of water just steps from your back deck. This is where privacy, nature, and

Regina Tortorella Coldwell Banker Village GreenW

97 Carrington 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

/30
Est $658,677

Not Listed For Sale

121 Thunderbird Terrace, Windham, NY 12496
- 3 Beds
- 2.5 Baths
- 2,020 Sq Ft
- Built 1941
121 Thunderbird Terrace, Windham, NY 12496

Last Sold Summary
- 30 Days On Market

/52
$575,000
- 3 Beds
- 2 Baths
- 1,376 Sq Ft
591 & 587 Co Rd 56, Windham, NY 12496

Looking for a charming home set perfectly on a country road with privacy, mountain views, adjacent to thousands of acres of state land, AND close to Catskill Park trailheads, CD Lane Park and Windham Mtn Club? Come visit 591 County Route 56 - you won't be disappointed! Enter the warm and welcoming living room where the cathedral ceiling and sky lights allow the sun to stream in to brighten your

Sharon Knudsen Coldwell Banker Village GreenW

591 & 587 Co Rd 56, Windham, NY 12496
/48
$560,000

Sold May 25, 2026

31 Koonan Rd, Windham, NY 12496
- 4 Beds
- 2 Baths
- 1,052 Sq Ft
- Built 1987
Last Sold Summary
- 11% Below List Price
- $532/SF
- 232 Days On Market
Current Estimated Value $583,141

Last Listing Agent Brandon Oot Core Real Estate Team

31 Koonan Rd, Windham, NY 12496

/72
Est $768,698

Not Listed For Sale

23 Manor Dr, Windham, NY 12496
- 3 Beds
- 3 Baths
- 2,485 Sq Ft
- Built 2024
23 Manor Dr, Windham, NY 12496

Last Sold Summary
- 56 Days On Market

/40
$545,000
- 2 Beds
- 2 Baths
- 1,390 Sq Ft
53 Windham Mount Village, Windham, NY 12496

Renovated Windham Mountain Village Townhouse - Steps to Slopes & Lodge, Walk to Lift, Season Tenant in Place, Income from Day One, Pool & Tennis Access-Located at the Windham Mountain Club, this beautifully updated 2-bedroom, (plus a flex room that is used as a third bedroom), 2-bathroom townhouse in Windham Mountain Village offers the perfect blend of a peaceful Catskills retreat and a smart

Regina Tortorella Coldwell Banker Village GreenW

53 Windham Mount Village, 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 $375,690

Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

23 Townhouse Ln Unit 1, Windham, NY 12496

/30
Est $379,000

Not Listed For Sale

3 Begley Rd, Windham, NY 12496
- 4 Beds
- 2 Baths
- 1,916 Sq Ft
- Built 1922
3 Begley Rd, Windham, NY 12496

Last Sold Summary
- 96 Days On Market

Showing Results 41 - 80, Page 2 of 18

New York Greene County Windham

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Windham, NY Homes

Real Estate & Homes