Windham, NY Homes

/33
$799,000
- 6 Beds
- 3 Baths
- 2,468 Sq Ft
5429 New York 23, Windham, NY 12496

In the Heart of Windham Village Perfectly positioned in the center of it all, this beautifully restored Village home offers effortless access to Windham's vibrant lifestyle--restaurants, pubs, brewery, weekend Farmers Market, and seasonal events all just moments away. The NYC bus route is nearby, making this an ideal getaway with no car required, and popular wedding venues are close at hand.

Carol Shaw

SHAW COUNTRY REALTY INC

5429 New York 23, Windham, NY 12496
/14
$2,150 Per Month
- 2 Beds
- 2 Baths
- 1,062 Sq Ft
- House for Rent
18 Brockett Rd, Windham, NY 12496

Charming 2 bed, 2 bath house, very close to town. Beautifully renovated, clean, light and bright, with hardwood and cork flooring, dishwasher, gas fireplace, and heated bathroom floors! Full basement with washer and dryer, and detached garage. Front porch, back patio and yard for outdoor enjoyment. Available fully, partially or unfurnished. Rent includes internet, landscaping/plowing and use of

Jessica Surbeck Windstar Realty Group, LLC

18 Brockett Rd, Windham, NY 12496
/60
$575,000

Sold Nov 07, 2025

36 Mount Greenery Rd, Windham, NY 12496
- 3 Beds
- 2 Baths
- 1,376 Sq Ft
- Built 1986
Last Sold Summary
- 4% Below List Price
- $418/SF
- 72 Days On Market
Current Estimated Value $604,736

Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

36 Mount Greenery Rd, Windham, NY 12496

/25
Not Listed For Sale

0 Route 10, Windham, NY 12496
- 3 Beds
- Built 2016
0 Route 10, Windham, NY 12496

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

/22
$269,000

$20K PRICE DROP
- 2 Beds
- 2 Baths
- 838 Sq Ft
5359 Main St Unit 2h., Windham, NY 12496

Prime Windham Village Location - Step out your door and wander to restaurants, the farmers market, local brewery, miniature golf, movies, and year-round town events. Convenient NYC bus access just moments away makes this the perfect easy escape. Only minutes to Windham Mountain skiing and nearby golf courses, this desirable 2-bedroom, 2-bath condo with slope views offers both lifestyle and

Carol Shaw

SHAW COUNTRY REALTY INC

5359 Main St Unit 2h., Windham, NY 12496
/36
$8,495 Per Month
- 5 Beds
- 4 Baths
- 3,000 Sq Ft
- House for Rent
170 Maplecrest Rd, Hensonville, NY 12439

WELCOME TO THE MID-CENTURY WINDHAM ART HOUSE WITH LUXURIOUS YEAR-ROUND HOT TUB, OUTDOOR SEASONAL SWIMMING POOL, WALL-TO-WALL FIREPLACE, CUSTOM BAR, 2.7 ACRES LAND WITH PRIVATE CREEK AND MORE! This gorgeous 5 bedroom 2.5 bath home of nearly 3,000 sq ft offers so much: NATURE and PRIVACY, beautiful lawns, a creek, huge trees; RELAX and ENTERTAINMENT, swimming pool, hot tub, fireplace, bar, grill,

Martina Dechevska Find Real Estate LLC

170 Maplecrest Rd, Hensonville, NY 12439
/63
$2,260,000

Sold Jul 06, 2026

110 Old Rd, Windham, NY 12496
- 7 Beds
- 5.5 Baths
- 5,569 Sq Ft
- Built 2023
Last Sold Summary
- 16% Below List Price
- $406/SF
- 100 Days On Market
Current Estimated Value $2,406,993

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

110 Old Rd, Windham, NY 12496

/34
Est $1,777,406

Not Listed For Sale

21 Sundance Dr, Windham, NY 12496
- 4 Beds
- 4.5 Baths
- 4,359 Sq Ft
- Built 2005
21 Sundance Dr, Windham, NY 12496

Last Sold Summary
- 58 Days On Market
Last Listing Agent Josie Reo MLS 4 Less Realty

/35
$684,000

$15K PRICE DROP
- 5 Beds
- 3 Baths
- 2,640 Sq Ft
134 Magda Ln, Windham, NY 12496

Charming Country Retreat Just Minutes to Windham Nestled on a private dead-end road just minutes from Windham's slopes, golf courses, and vibrant village, this beautifully renovated 5-bedroom, 3-bath home sits on 5.5 acres of peaceful country setting. Blending timeless country charm with modern style, the home features warm wood floors, an inviting open kitchen and dining area, and multiple

Carol Shaw

SHAW COUNTRY REALTY INC

134 Magda Ln, Windham, NY 12496
/14
$3,500 Per Month
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
- Townhouse for Rent
24 Quads Way, Windham, NY 12496

This newly updated ski season rental is the perfect base for your winter adventures! Minutes from Windham Mountain, the unit is available December 1- March 31, Fully furnished and outfitted, the condo offers 2 full baths and 2 bedrooms with room for 5. Enjoy hearty breakfasts in the eat-in kitchen and cozy evenings around the wood burning fireplace. The outdoor deck features a propane grill for

Jessica Surbeck WINDSTAR REALTY GROUP LLC

24 Quads Way, Windham, NY 12496
$269,000

Sold Sep 19, 2025

79 Windham Ridge Rd Unit 17A, Windham, NY 12496
- 2 Beds
- 2.5 Baths
- 1,211 Sq Ft
- Built 1983
Last Sold Summary
- $222/SF
- 14 Days On Market
Current Estimated Value $292,994

Last Listing Agent FRANK GOMEZ Real Broker NY LLC

79 Windham Ridge Rd Unit 17A, Windham, NY 12496

/29
Not Listed For Sale

12 - 2C Stonewall Ln, Windham, NY 12496
- 4 Beds
- 3.5 Baths
- 2,700 Sq Ft
12 - 2C Stonewall Ln, Windham, NY 12496

Last Sold Summary
- 0 Days On Market
Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

/36
$649,000
- 4 Beds
- 2.5 Baths
- 2,150 Sq Ft
1100 County Route 10, Windham, NY 12496

Windham Gem - Timeless Catskill Living. Discover a beautifully updated farmhouse where classic country character meets refined modern comfort, privately nestled on 2.3 beautifully landscaped acres in one of Windham's most desirable four-season destinations. Lovingly maintained and truly move-in ready, this distinctive home showcases beautiful wide-plank wood floors, exposed wood-beamed ceilings,

Carol Shaw

Shaw Country Realty, Inc.

1100 County Route 10, Windham, NY 12496
/26
$13,000 Per Month
- 2 Beds
- 2 Baths
- 295 Sq Ft
- Townhouse for Rent
274 County Road 65 Unit 40, Windham, NY 12496

Seasonal Rental, development has shuttle bus to and from Windham Mt. Club, great location. Lovely 2 bedroom, 2 baths with laundry. Open living area, stone wood burning fireplace, sliding doors to deck. Upper level has 2 bedrooms, living room has pull out couch, Unit sleeps 7 persons. Don't miss out on this lovely rental. ** AVAILABLE for entire 26/27 ski season 13000 or 3,900 per month.

Mary Donovan Gallagher & Company

274 County Road 65 Unit 40, Windham, NY 12496
/33
$639,000

Sold Jan 30, 2026

19 Brook Hollow Ln, Windham, NY 12496
- 4 Beds
- 2 Baths
- 2,240 Sq Ft
- Built 1983
Last Sold Summary
- $285/SF
- 51 Days On Market
Current Estimated Value $673,075

Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

19 Brook Hollow Ln, Windham, NY 12496

/6
Not Listed For Sale

0 Larsen Dr Unit 152095, Windham, NY 12496
0 Larsen Dr Unit 152095, Windham, NY 12496

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

/27
$799,000
- 3 Beds
- 3 Baths
- 1,528 Sq Ft
71 Windham Mount Village Unit 71, Windham, NY 12496

Windham Mt. Village . This Beautiful Townhouse is located at the base of Windham slopes . Just steps from skiing and directly across from the clubhouse and indoor pool, this beautifully updated residence offers exceptional four-season appeal and strong rental demand. The flexible layout is easily adaptable to a 2-bedroom plus sleeping loft, with a separate lockout bedroom/studio-ideal for

Carol Shaw

SHAW COUNTRY REALTY INC

71 Windham Mount Village Unit 71, Windham, NY 12496
/3
$2,100 Per Month
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
- Condo for Rent
5359 State Route 231, 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 State Route 231, Windham, NY 12496
/14
$76,000

Sold Dec 30, 2025

0 County Route 40, Windham, NY 12454
- Land
- 4.9 Acres
- $15,510 per Acre
Last Sold Summary
- 45% Below List Price
- 204 Days On Market
Last Listing Agent Anne Jakubowski Bunce Realty

0 County Route 40, Windham, NY 12454

/29
Not Listed For Sale

21 - 4A Stonewall Ln, Windham, NY 12496
- 5 Beds
- 4.5 Baths
- 3,148 Sq Ft
- Built 2024
21 - 4A Stonewall Ln, Windham, NY 12496

Last Sold Summary
- 0 Days On Market
Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

/45
$1,850,000
- 5 Beds
- 3 Baths
- 3,740 Sq Ft
37 The Loop, Windham, NY 12496

VIEWS -LOCATION Spectacular true log home just a short walk to the slopes of Windham Mountain Club offering the perfect four-season retreat in the heart of the Catskills. This meticulously maintained 5-bedroom, 3-bath home blends warm mountain character with comfort and style, all within minutes of Windham Village restaurants, breweries, movies, golf courses, walking trails, and year-round

Carol Shaw

SHAW COUNTRY REALTY INC

37 The Loop, Windham, NY 12496
$520,000

Sold Oct 07, 2025

21 Nauvoo Rd, Windham, NY 12496
- 2 Beds
- 1.5 Baths
- 1,072 Sq Ft
- Built 1956
Last Sold Summary
- 10% Below List Price
- $485/SF
- 173 Days On Market
Current Estimated Value $536,455

Last Listing Agent Joel Craig Coldwell Banker Village Green

21 Nauvoo Rd, Windham, NY 12496

/11
Not Listed For Sale

0 Begley Rd Unit 154599, Windham, NY 12496
0 Begley Rd Unit 154599, Windham, NY 12496

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

/21
$299,000
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
135 Route 40, Windham, NY 12496

Whether you're searching for your first home, a weekend getaway, or a smart investment in the Catskills, this recently renovated ranch in Windham delivers exceptional value. Ideally located just minutes from both Windham Mountain Club and Hunter Mountain, as well as CD Lane Park, hiking, dining, and everything the area has to offer, this move-in-ready home puts four-season recreation right at

Jason Dugo

Dugo Realty

135 Route 40, Windham, NY 12496
/67
$725,000

Sold Sep 09, 2025

8 Evans Rd, Windham, NY 12496
- 5 Beds
- 3.5 Baths
- 3,862 Sq Ft
- Built 2000
Last Sold Summary
- 90,638% Above List Price
- $188/SF
- 22 Days On Market
Current Estimated Value $751,415

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

8 Evans Rd, Windham, NY 12496

/29
Not Listed For Sale

25 - 4C Stonewall Ln, Windham, NY 12496
- 4 Beds
- 3.5 Baths
- 2,700 Sq Ft
25 - 4C Stonewall Ln, Windham, NY 12496

Last Sold Summary
- 1 Day On Market
Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

/37
$599,000
- 3 Beds
- 2 Baths
- 1,125 Sq Ft
16 Hickory Hill Rd, Windham, NY 12496

Windham: ''The place to Be'' for year round outdoor enthusiasts This gem has direct views of Windham slopes, proximity to golf courses, Windham Village, restaurants, walking paths and various venues, makes it a captivating endeavor. Renovated in 2022 with new roof, skylights and custom kitchen, This property boasts a prime location in a vibrant 4-season community. Offering 3 bedrooms and 2 baths,

Carol Shaw

SHAW COUNTRY REALTY INC

16 Hickory Hill Rd, Windham, NY 12496
$158,000

Sold Jan 29, 2026

2 Quads Way, Windham, NY 12496
- 1 Bed
- 1 Bath
- 560 Sq Ft
- Built 1987
Last Sold Summary
- $282/SF
- 50 Days On Market
Current Estimated Value $163,421

Last Listing Agent Gal Ozana Ozana Realty Group

2 Quads Way, Windham, NY 12496

/60
Est $574,414

Not Listed For Sale

162 Ruland Rd, Windham, NY 12496
- 1 Bed
- 1,849 Sq Ft
- Built 2020
162 Ruland Rd, Windham, NY 12496

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

/13
$199,000
- 2 Beds
- 1 Bath
- 893 Sq Ft
394 State Route 296 Unit 3, Hensonville, NY 12439

Charming Condo in the Heart of Hensonville - Town of WindhamPerfectly situated in the heart of Hensonville, this nicely maintained two-story condo offers the ideal Catskills getaway or year-round residence. Just minutes from Windham Mountain, Windham Village, scenic walking paths, golf courses, and only a 10-minute drive to Hunter Mountain, you'll enjoy four seasons of recreation right at

Carol Shaw

Shaw Country Realty, Inc.

394 State Route 296 Unit 3, Hensonville, NY 12439
/47
$169,900

Sold Jun 22, 2026

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

8 Boulder Brook Rd, Windham, NY 12496

/39
Est $345,097

Not Listed For Sale

51 Carrington Rd, Windham, NY 12496
- 1 Bed
- 1 Bath
- 1,144 Sq Ft
- Built 1984
51 Carrington Rd, Windham, NY 12496

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

/35
$460,000

$25K PRICE DROP
- 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 so

Jason Dugo

Dugo Realty

5134 New York 23, Windham, NY 12496
/33
$283,500

Sold Aug 26, 2025

71 County Road 65 Unit 4, Hensonville, NY 12439
- 2 Beds
- 2 Baths
- 1,290 Sq Ft
- Built 2020
Last Sold Summary
- 4% Below List Price
- $220/SF
- 47 Days On Market
Current Estimated Value $340,703

Last Listing Agent Susanna Scott-Mitchell Compass Greater NY, LLC

71 County Road 65 Unit 4, Hensonville, NY 12439

/54
Not Listed For Sale

11 Whisper Creek Dr Unit 601B, Windham, NY 12496
- 3 Beds
- 3 Baths
- 1,506 Sq Ft
- Built 2019
11 Whisper Creek Dr Unit 601B, Windham, NY 12496

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

/7
$689,000
- 5 Beds
- 5 Baths
- 2,500 Sq Ft
5355 New York 23, Windham, NY 12496

CALLING INVESTORS - PRIME WINDHAM VILLAGE OPPORTUNITY Rare opportunity in the heart of Windham Village with exceptional commercial and residential development potential. Positioned in one of the Catskills' most desirable four-season destinations, this property offers investors the chance to capitalize on the continued growth and popularity of Windham.Windham is truly ''the place to be,''

Carol Shaw

Shaw Country Realty, Inc.

5355 New York 23, Windham, NY 12496
/75
$1,450,000

Sold Sep 05, 2025

16 High Rd W, Windham, NY 12496
- 5 Beds
- 4.5 Baths
- 4,140 Sq Ft
- Built 2017
Last Sold Summary
- 3% Below List Price
- $350/SF
- 55 Days On Market
Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

16 High Rd W, Windham, NY 12496

/27
Est $363,380

Not Listed For Sale

24 Vets Rd, Windham, NY 12496
- 3 Beds
- 1.5 Baths
- 1,588 Sq Ft
- Built 1947
24 Vets Rd, Windham, NY 12496

Last Sold Summary
- 36 Days On Market
Last Listing Agent Megan Morse Romeo Team Realty

/25
$415,000

$19K PRICE INCREASE
- 3 Beds
- 3.5 Baths
- 3,683 Sq Ft
2914 Route 10, Windham, NY 12496

Escape to the Catskills and enjoy the privacy, space, and year-round lifestyle you've been looking for. Set on more than 5 private acres, this move-in-ready home offers over 2,600 square feet of living space with 3 bedrooms and 3.5 bathrooms, creating the perfect retreat for weekend getaways, full-time living, or a vacation home with income potential. Inside, you'll find spacious living areas

Jack Yao

Realmart Realty, LLC

2914 Route 10, Windham, NY 12496
/27
$950,000

Sold Jun 30, 2026

5474 New York 23, Windham, NY 12496
- 7 Beds
- 3 Baths
- 4,281 Sq Ft
- Built 1840
Last Sold Summary
- 5% Below List Price
- $222/SF
- 861 Days On Market
Last Listing Agent Jane Reynolds Jane H. Reynolds

5474 New York 23, Windham, NY 12496

Showing Results 1 - 40, Page 1 of 18

New York Greene County

Home Prices in Windham, NY

The median home sale price in Windham, NY is $708,500, up 54% year-over-year. Homes in Windham sell in 125 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $708,500	Median Single Family Sale Price $684,000
Median Townhouse Sale Price $425,000	Median 2 Bedroom Sale Price $319,000
Median 1 Bedroom Sale Price $158,000	Average Price Per Sq Ft $342
Number of Homes for Sale 79	Last 12 months Home Sales 92
Months of Supply 10.30	Median List Price $694,500
Median Change From 1st List Price 6%	Median Home Sale Price YoY Change 54%

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Windham, NY Homes

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