Homes in ZIP Code 12496

/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
/12
$2,600 Per Month
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
- Condo 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
/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

/30
Est $1,440,194

Not Listed For Sale

4 The Loop, Windham, NY 12496
- 4 Beds
- 3 Baths
- 2,536 Sq Ft
- Built 1974
4 The Loop, Windham, NY 12496

Last Sold Summary
- 121 Days On Market
Last Listing Agent Patricia Charbonneau Brainard Ridge Management

/33
$925,000
- 5 Beds
- 3.5 Baths
- 3,434 Sq Ft
11 Vining Heights Rd, Windham, NY 12496

Your Windham Mountain Escape--Made for Entertaining!Just 1 mile up the hill from Windham Village, this spacious 5-bedroom, 3.5-bath Catskills retreat combines comfort, versatility and fabulous indoor-outdoor living on approximately 2.5 acres with anexpansive open yard and desirable southern exposure.Step inside to soaring ceilings and a bright, open layout where the living room flows

Carol Shaw

Shaw Country Realty, Inc.

11 Vining Heights Rd, Windham, NY 12496
/8
$1,700 Per Month
- 2 Beds
- 1 Bath
- Condo for Rent
128 South St Unit 2B, Windham, NY 12496

Property Id: 1494611 **IMAGES ARE FOR OUR 1 BED UNIT - LAYOUT WILL BE SLIGHTLY DIFFERENT WITH LARGER KITCHEN - on 2nd floor** Located in the heart of Windham, NY - Apartment for rent - 2 bed/1 bath, central air and heat with private washer and dryer in unit. Garbage, water, and sewer included. If interested, please send an email we will send you a video walkthrough of the unit. In

128 South St Unit 2B, Windham, NY 12496
/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

/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

/45
$1,850,000

Pending
- 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
/29
$5,500 Per Month
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
- House for Rent
63 N Settlement Rd, Windham, NY 12496

WINTER SEASONAL RENTAL IN THE WINDHAM AREA! Enjoy the warmth and character of this inviting log cabin-style home, available for a seasonal rental from December through March 31st. Featuring beautiful natural wood interiors, 3 bedrooms, 2 baths, a cozy living room with a stone fireplace, and a comfortable atmosphere perfect for relaxing after a day outdoors. Step outside onto the spacious deck,

Lisa Gambella

Windstar Realty Group, LLC

63 N Settlement Rd, 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

/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

/39
$549,000
- 3 Beds
- 2 Baths
- 2,250 Sq Ft
16 Hickory Hill Rd, Windham, NY 12496

Discover the perfect mountain lifestyle in this beautifully renovated, fully furnished, 3-bedroom, 2-bath home with direct slope views and seamless access to world-class recreation. Completely renovated in 2022 with a new roof, skylights, and custom kitchen featuring a professional 6-burner Vulcan stove, this property blends modern comfort with outdoor living. Inside, you'll find stainless steel

Carol Shaw

Shaw Country Realty, Inc.

16 Hickory Hill Rd, Windham, NY 12496
/17
$3,500 Per Month
- 2 Beds
- 1 Bath
- 1,496 Sq Ft
- House for Rent
53 Mitchell Hollow Rd, Windham, NY 12496

Winter in Windham Paradise Seasonal Rental - December 2026 through April 2027 - Look out your back window and you see the slopes peeking at you. This beautifully renovated home is ready to pamper you; there is a lovely country kitchen for cooking family meals, with the natural light pouring into the adjacent family room and living rooms which were made for entertaining. perhaps you prefer the hot

Maureen Anshanslin

Windstar Realty Group, LLC

53 Mitchell Hollow Rd, 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

/75
Not Listed For Sale

16 High Rd W, Windham, NY 12496
- 5 Beds
- 4.5 Baths
- 4,140 Sq Ft
- Built 2017
16 High Rd W, Windham, NY 12496

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

/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
/30
$30,000 Per Month
- 3 Beds
- 2 Baths
- 1,748 Sq Ft
- House for Rent
281 Old Rd, Windham, NY 12496

Beautiful Country Home! Enjoy a memorable season in this lovely 3 bedroom, 2 bath Windham home, 5 minutes from the slopes and town. This charming home offers tasteful furnishings, spacious sun filled kitchen with Viking stove, dining room with plenty of room for family and friends. Cozy up in the comfortable living room with welcoming fireplace. Primary bedroom with ensuite bath, 2 more

Patricia Charbonneau Brainard Ridge Management

281 Old 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

/43
Not Listed For Sale

92 Northridge Exd, Windham, NY 12496
- 4 Beds
- 3 Baths
- 3,104 Sq Ft
- Built 2003
92 Northridge Exd, Windham, NY 12496

Last Sold Summary
- 30 Days On Market
Last Listing Agent Mark McAlpine Compass Greater New York, LLC

/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
/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

/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.

/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
/11
$107,500

Sold Jun 02, 2026

497 Campbell Rd, Ashland, NY 12496
- Land
- 2.5 Acres
- $43,000 per Acre
Last Sold Summary
- 28% Below List Price
- 180 Days On Market
Last Listing Agent Laurie Hanenberg Hunter Windham Real Estate

497 Campbell Rd, Ashland, 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

/22
$325,000
- 3 Beds
- 1.5 Baths
- 1,152 Sq Ft
315 Begley Rd, Windham, NY 12496

Just minutes from the village of Windham, skiing, and golf, this meticulously maintained ranch is set on a beautiful country road in a true four-season community. The easy, flowing floor plan features a bright eat-in kitchen that opens directly to a spacious rear deck-perfect for outdoor dining and entertaining. Inside, you'll find three comfortable bedrooms, 1.5 baths, and a welcoming living

Carol Shaw

SHAW COUNTRY REALTY INC

315 Begley Rd, 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

/15
Not Listed For Sale

1 - 886 Mill St, Windham, NY 12496
1 - 886 Mill St, Windham, NY 12496

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

/22
$399,000
- 4 Beds
- 3 Baths
- 2,000 Sq Ft
321 Begley Rd, Windham, NY 12496

Turn-Key, Fully Furnished & Ready to Enjoy in Windham!Just bring your bags! This beautifully maintained Windham ranch is being offered fully furnished, making it an ideal primary residence, weekend getaway or four-season Catskills retreat.The inviting main level features charming beamed ceilings and a beautiful stone fireplace in the living room, creating that warm mountain-home feel. The

Carol Shaw

Shaw Country Realty, Inc.

321 Begley Rd, Windham, NY 12496
/55
$540,000

Sold Jun 29, 2026

5376 State Route 23, Windham, NY 12496
- 3 Beds
- 2.5 Baths
- 2,448 Sq Ft
- Built 1900
Last Sold Summary
- 10% Below List Price
- $221/SF
- 47 Days On Market
Current Estimated Value $583,755

Last Listing Agent Sharri Cunningham Bunce Realty

5376 State Route 23, Windham, NY 12496

/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.

/50
$1,599,000
- 5 Beds
- 4 Baths
- 4,056 Sq Ft
5433 New York 23, Windham, NY 12496

Contemporary design blends with historic character in this thoughtfully renovated single-family classic colonial home located on charming Main Street in Windham. Originally built in 1930 and fully redesigned in 2024, this turnkey home creates the perfect environment for hosting lavish get-togethers and unforgettable family memories. Gaze into the skies to celebrate summer fireworks from your

Doug Blum

Windstar Realty Group, LLC

5433 New York 23, 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 $954,417

Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

30 The Loop, 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

/51
$899,000
- 6 Beds
- 5 Baths
- 3,104 Sq Ft
5628 State Route 23, Windham, NY 12496

Welcome to your private Catskills sanctuary. Perfectly positioned on Main Street in Windham, this unique property offers the ultimate flexible layout that lends itself to multiple situations: a multi-generational family compound, a premium vacation escape where friends and family can gather-while still enjoying their own private spaces, a pass through income property with excellent ROI and very

Susan Miller

WINDSTAR REALTY GROUP LLC

5628 State Route 23, Windham, NY 12496
/7
$1,998,500

Sold Jun 26, 2026

4 Estate View Dr, Windham, NY 12496
- 5 Beds
- 5.5 Baths
- 5,000 Sq Ft
Last Sold Summary
- $400/SF
- 301 Days On Market
Last Listing Agent Patrick Dunn KW Platform

4 Estate View Dr, 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.

/39
$649,000
- 4 Beds
- 3.5 Baths
- 3,360 Sq Ft
4 Loretta Ln, Windham, NY 12496

Welcome to this beautifully maintained Colonial, perfectly situated in a quiet dead-end neighborhood just minutes from Windham's slopes, golf courses, wedding venues, hiking trails, walking paths, and all the year-round recreation the area has to offer.A welcoming covered front porch, nicely landscaped grounds, blacktop driveway, and attached 2-car garage create wonderful curb appeal and set

Carol Shaw

Shaw Country Realty, Inc.

4 Loretta Ln, 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 $890,303

Last Listing Agent Richard Vizzini Corcoran Country Living

2 Biff Andrus Rd, Windham, NY 12496

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