Windham, NY Homes for Sale

/15
$1,395,000
- 6 Beds
- 4 Baths
- 3,800 Sq Ft
5628 New York 23, Windham, NY 12496

"Best of Windham" - Exceptional Development Opportunity in the Heart of Windham, NY Discover a rare 5-acre property on the best location in Windham. Offering a unique blend of proximity to Main Street, Skiing within minutes, legacy vacation rentals and prime development potential all while having privacy located high off the main road with beautiful mountain views. This property is more

Agnieszka Wdziekowska Taufield CORE REAL ESTATE TEAM

5628 New York 23, Windham, NY 12496
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/85
$1,749,999
- 6 Beds
- 4.5 Baths
- 4,855 Sq Ft
12 Lauren Ln, Windham, NY 12496

The Ultimate Catskills Retreat — Just Minutes from Windham Resort Nestled on 12 private wooded acres less than seven minutes from Windham Resort, this 5,400 sq. ft. luxury log cabin embodies the best of mountain living — where timeless craftsmanship meets modern comfort. Designed across three levels, the home features six bedrooms, four and a half bathrooms, and radiant heat throughout. Natural

Regina Tortorella Coldwell Banker Village GreenW

12 Lauren Ln, Windham, NY 12496
/32
$799,000
- 3 Beds
- 3.5 Baths
- 2,434 Sq Ft
415 Old Rd, Windham, NY 12496

Don't miss this unique opportunity to establish a year-round retreat in the Catskill Mountains, ideal for hosting family and friends on two separate lots. The grounds offer apple picking, fishing in the pond, and swimming, while children can enjoy outdoor activities and grandparents relax on the upper deck with scenic mountain views—all accessible from your own front yard. In winter, prepare for

Laurie Hanenberg Hunter Windham Real Estate

415 Old Rd, Windham, NY 12496
/49
$1,295,000
- 4 Beds
- 3.5 Baths
- 1,353 Sq Ft
129 Club Rd, Windham, NY 12496

Gorgeous Windham Mountain Contemporary. An abundance of natural light and impressive landscaping establish the setting as you step into this beautiful 4-bedroom 3.5 bath mountain home. Panoramic, stunning views from every room, spacious living room with cozy, tasteful furnishings, striking stone wood burning fireplace, bright kitchen with granite counters, solid maple cabinetry and Bosch

Patricia Charbonneau Brainard Ridge Management

129 Club Rd, Windham, NY 12496
/39
$849,000
- 3 Beds
- 2.5 Baths
- 2,864 Sq Ft
407 Mill St, Windham, NY 12496

Welcome to Round Haus Chalet, a high design retro retreat set on five acres with spectacular 360-degree views, just minutes from Windham Mountain. Built in 1986, this distinctive three-bedroom, two-and-a-half-bath residence pairs playful, postmodern geometrical architecture with mid-century design. From cozy apres-ski gatherings, to chic summer soirees, this home was designed for every season of

Anthony D'Argenzio Houlihan Lawrence

407 Mill St, Windham, NY 12496
/44
$979,000
- 5 Beds
- 3 Baths
- 2,400 Sq Ft
81 Barnum Rd, Maplecrest, NY 12454

Turn-key opportunity for business or private use, this successful Guest Favorite short term rental is perfectly located between Hunter and Windham Mountains, secluded yet close to everything you need! Completely renovated, this post-and-beam style log home home has been fully restored and outfitted to embrace modern-rustic design choices. The sunny ground floor entry features ceramic tile floors

Jessica Surbeck WINDSTAR REALTY GROUP LLC

81 Barnum Rd, Maplecrest, NY 12454
/37
$1,175,000 New Construction
- 3 Beds
- 3.5 Baths
- 3,284 Sq Ft
20 Brookhollow Ln, Windham, NY 12496

Experience contemporary mountain living at its finest in this exceptional new-construction residence, perfectly positioned just one mile from the Village of Windham. Thoughtfully designed and impeccably built, this light-filled retreat captures the essence of refined modern living in the heart of the Catskills. The home's sophisticated open layout features three spacious bedrooms and three and a

Pamela King-Belfor Four Seasons Sotheby's Int.

20 Brookhollow Ln, Windham, NY 12496
/18
$463,000
- 3 Beds
- 2 Baths
- 1,249 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

Patricia Charbonneau Brainard Ridge Management

111 Brainard Ridge Rd Unit 11B, Windham, NY 12496
/26
$215,000
- 3 Beds
- 1.5 Baths
- 1,200 Sq Ft
384 New York 296, Hensonville, NY 12439

Handyman special in the heart of the Catskills! This 3-bedroom, 2-bath, 1.5-story home is ready for your finishing touch. Great location just minutes to Windham Mountain, hiking trails, golf, and year-round outdoor fun. Perfect for renovation, investment, or a mountain getaway—bring your vision and make it shine! Perfect for second home, Rental or AirBnB!

Brian Kozloski Century 21 New West

384 New York 296, Hensonville, NY 12439
/28
$234,500
- 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 GetawayHere'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

Lisa Jaeger Coldwell Banker Village GreenW

0 N Ridge Extension Unit 20255019, Windham, NY 12496
/42
$425,000
- 5 Beds
- 3 Baths
- 2,472 Sq Ft
317 Mitchell Hollow Rd, Windham, NY 12496

Breathe New Life Into This Mid-Century Split Ranch Full of Potential! Opportunity is knocking with this spacious 5-bedroom, 3-bath home — ready for someone to bring their vision and creativity. Many of the big-ticket updates are already complete, including a new roof, wood flooring, kitchen and appliances, fresh paint, closed circuit security system, whole-house generator, black top circular

Lisa Jaeger Coldwell Banker Village GreenW

317 Mitchell Hollow Rd, Windham, NY 12496
/19
$550,000
- 7 Beds
- 2.5 Baths
- 3,114 Sq Ft
804 Mitchell Hollow Rd, Windham, NY 12496

Huge price reduction. For the first time on the market in almost 50 years we are offering this unique home and property for sale.The Greek style home has seven bedrooms, two and half baths. a large living room, a large dining room with wainscotingwalls, cabinets and ceiling, old style kitchen, large workshop or spare room and a large front porch to enjoy the views.All this on 18 acres with

Chris Tripsas Reliant Property Services

804 Mitchell Hollow Rd, Windham, NY 12496
/27
$170,000
- 1 Bed
- 1 Bath
- 423 Sq Ft
5220 New York 23 Unit 126, Windham, NY 12496

Dreaming of a vacation home? This one pays for itself! A turnkey investment opportunity awaits with this one-bedroom, low maintenance condo. Enjoy modern comforts and the benefit of being close to dining, shopping, and the ski slopes. The amenities include a seasonal pool, restaurant& bar, game room, fitness center, movie theater and an on-site coin operated laundry facility. A shuttle bus is

Savannah Delaney Weichert Realtors Fontaine

5220 New York 23 Unit 126, Windham, NY 12496
/19
$399,000
- Land
- 0.46 Acre
- $867,391 per Acre
2 Twin Maples Ln, Windham, NY 12496

Premier Building Lot at Windham Mountain Club - Ready for Your Dream Home. Bring your vision to life on this shovel-ready homesite located in Village East, an exclusive enclave within the prestigious Windham Mountain Club. Whether you're a builder, investor, or avid skier dreaming of a luxury mountain retreat, this property offers the perfect foundation for your next project. Turnkey Build-Ready:

Regina Tortorella Coldwell Banker Village GreenW

2 Twin Maples Ln, Windham, NY 12496
/38
$2,495,000
- 8 Beds
- 3.5 Baths
- 5,500 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
/59
$1,599,000
- 4 Beds
- 4.5 Baths
- 2,083 Sq Ft
3 the Enclave, Windham, NY 12496

Luxury Ski Townhouse in the Heart of Windham Mountain Club's Premier Enclave CommunityDiscover the ultimate ski lifestyle in this luxurious tri-level townhouse, ideally located in the exclusive Enclave at Windham Mountain Club. Just steps from the slopes, base lodge, pool, fitness center, and restaurants, this home offers unmatched convenience—no car needed. Simply step outside and

Regina Tortorella Coldwell Banker Village GreenW

3 the Enclave, Windham, NY 12496
/25
$415,000
- 3 Beds
- 3.5 Baths
- 3,683 Sq Ft
2914 Route 10, Windham, NY 12496

This large 3 bed, 3.5 bath home sits on 5 peaceful acres and has plenty of space inside and out. Built in 1993, it offers 2,610 sq ft of living space. The home has new tile floors, central A/C, and a 10-year-old roof. We are located just a short drive from popular ski slopes, restaurants and other entertainment. Interior in good livable condition. We are in the process of obtaining interior

Qizhan Yao Realmart Realty, LLC

2914 Route 10, Windham, NY 12496
/51
$399,000
- 3 Beds
- 2 Baths
- 1,876 Sq Ft
370 Begley Rd, Windham, NY 12496

Rare Opportunity Surrounded by 700 Acres of State LandThat's right—700 acres of forever-protected State Land at your doorstep! Step into your own personal oasis where you can hike, hunt, explore, or simply enjoy the peace and quiet with birdsong, wildlife, and the whispering wind through the trees.This spotless 1,800 sq ft modular ranch offers a bright and open floor plan with

Lisa Jaeger Coldwell Banker Village GreenW

370 Begley Rd, Windham, NY 12496
/13
$199,000
- Land
- 5.7 Acres
- $34,912 per Acre
611 Mitchell Hollow Rd, Windham, NY 12496

5.7 Acres with Utilities in Place - Perfect Setting for Your Dream HomeThis 5.7-acre property offers the ideal blend of open fields and wooded areas, creating a beautiful mix of natural landscapes and privacy. While there is an existing single-wide mobile home on site, it has been vacant for some time, is not considered habitable, and has not been given value. The true value here lies in

Regina Tortorella Coldwell Banker Village GreenW

611 Mitchell Hollow Rd, Windham, NY 12496
/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
/5
$253,000
- Land
- 0.59 Acre
- $428,814 per Acre
57 South St, Windham, NY 12496

Unique opportunity - one of the LAST lots on South Street! Flat parcel overlooking the golf course. Walking distance to everything Windham has to offer - ski, golf, biking, movie theater, shops and downtown restaurants. Utilities - This lot is serviced by municipal water, municipal sewer, electric, and cable directly off the road.

Aira Ilao ListWithFreedom.com

57 South St, Windham, NY 12496
/9
$500,000
- Land
- 0.52 Acre
- $961,538 per Acre
220 & 240 Club Rd, Windham, NY 12496

Be captivated by the breathtaking, panoramic views that will mesmerize you from dusk till dawn from either of these 2 building lots, with ski access being offered by Windham Mountain Club. Let your imagine soar with the possibilities of designing your dream home to last for generations on one of the few remaining building lots offered by Windham Mountain Club. Envision waking up in your mountain

Patricia Charbonneau Brainard Ridge Management

220 & 240 Club Rd, Windham, NY 12496
/65
$1,999,999
- 5 Beds
- 4 Baths
- 3,409 Sq Ft
5433 New York 23, Windham, NY 12496

A One-of-a-Kind Masterpiece in the Heart of Windham, NY!Welcome to Main Street Magic—an exceptional, fully reimagined 5-bedroom, 4-bathroom home (2 full, 2 half) located just 2 hours from NYC in the sought-after Catskills town of Windham. This stunning property perfectly blends historic charm with modern luxury and lifestyle-driven design.Step inside to soaring 13' vaulted

Caitlin Cucchiella Hunt Real Estate ERA

5433 New York 23, Windham, NY 12496
/38
$295,000
- 2 Beds
- 2 Baths
- 1,290 Sq Ft
71 County Road 65 Unit 6, Hensonville, NY 12439

Built in 2020 and maintained in like-new condition, this end-unit townhome offers contemporary design, lasting quality, and proven versatility. Whether you're looking for a strong short-term rental investment or your own Catskills escape, this property checks every box.The bright, open-concept living and dining area flows easily to a private deck, ideal for outdoor meals or quiet

Susanna Scott-Mitchell Compass Greater NY, LLC

71 County Road 65 Unit 6, Hensonville, NY 12439
/11
$295,000
- 2 Beds
- 2.5 Baths
- 1,211 Sq Ft
76 Loo Bridge Ln, Windham, NY 12496

Cozy Mountain Condo in Windham - Perfect for Family Retreats or Investment Discover this inviting 2-bedroom, 2.5-bath condo with a loft (C of O included), just 10 minutes from Windham Mountain Ski Resort. The open living room with kitchen creates a warm, social space, while large windows bring in natural light and serene views. Surrounded by woods and mountains, this home offers peace and

Agnieszka Wdziekowska Taufield CORE REAL ESTATE TEAM

76 Loo Bridge Ln, Windham, NY 12496
/11
$275,000
- Land
- 0.32 Acre
- $859,375 per Acre
0 Twin Maples Ln Unit 20254325, Windham, NY 12496

Great Opportunity! Priced to sell!Escape to the Catskills, build your home away from home on this desirable building lot located on Windham Mountain's Private and Tranquil Community of Trailside East. This parcel has gentle sloping grade, will have access to far reaching mountain and valley views with clearing. Parcel has access to water, sewer, underground electric, high speed cable-fiber,

Irene Pinto Brainard Ridge Management

0 Twin Maples Ln Unit 20254325, Windham, NY 12496
/29
$500,000
- 3 Beds
- 2 Baths
- 1,140 Sq Ft
38 Cambridge Heights Rd, Windham, NY 12496

Welcome to Alpine Cabin, your dream mountain getaway! Nestled just steps away from the slopes, this charming cabin combines rustic elegance with modern comforts perfect for a cozy winter retreat or an adventurous alpine escape. Situated at the base of the Windham Mountain Club with views of the slopes beyond, and just 130 miles from New York City. The fireplace in the living area is perfect for

Paul Heintz Anatole House LLC

38 Cambridge Heights Rd, Windham, NY 12496
/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
/42
$1,245,000
- 3 Beds
- 3.5 Baths
- 2,225 Sq Ft
6 Watch Hill Ln, Windham, NY 12496

Timeless Timber Frame Townhome!Walk to the trails from this 3bedroom, plus loft 3.5 bath with attached garage, Windham beauty! Enjoy the elegance of a true timber frame home, with all its warmth and charm. Lovely entrance with sizable ski and boot room, opening to vaulted ceiling living room with plenty of windows to take in the beautiful natural surroundings. Tasteful furnishings to relax

Patricia Charbonneau Brainard Ridge Management

6 Watch Hill Ln, Windham, NY 12496
/30
$489,000
- 4 Beds
- 3.5 Baths
- 2,058 Sq Ft
274 Brooksburgh Rd Unit 48, Windham, NY 12496

Ine of just a few larger units in ?Crystal Pond. First floor has mud-room, half bath with laundry, Kitchen as well ad a dining room, large living room with sliding doors to large deck, lovely stone wood burning fireplace. Lots of light in this unit. Second floor has two main bedrooms each with a full bath.as well as a separate area for home office or TV. Third level has two well sized

Mary Donovan Gallagher & Company

274 Brooksburgh Rd Unit 48, Windham, NY 12496
/15
$439,000
- Land
- 3.46 Acres
- $126,879 per Acre
2 Windham Farms Rd, Windham, NY 12496

Welcome to Windham Farms in Windham, NY, where two premium building lots offer an exceptional opportunity for custom homes that blend eco-friendly design with aesthetic appeal, complementing the year-round environment just minutes from Windham Mountain Club. Lot 2 is prepared for immediate construction, featuring an installed driveway to the designated house site, 200 amp underground electric

Laurie Hanenberg Hunter Windham Real Estate

2 Windham Farms Rd, Windham, NY 12496
/16
$289,000
- Land
- 4.33 Acres
- $66,744 per Acre
4 Windham Farms Rd, Windham, NY 12496

Welcome to ''Windham Farms'' in Windham, NY, where two premium building lots offer an exceptional opportunity for custom homes that blend eco-friendly design with aesthetic appeal, complementing the year-round environment just minutes from Windham Mountain Club. Lot 4 features an installed gravel parking area directly off Windham Farms Road, available 200 amp underground electric service at

Laurie Hanenberg Hunter Windham Real Estate

4 Windham Farms Rd, Windham, NY 12496
/36
$459,000
- 4 Beds
- 3.5 Baths
- 1,717 Sq Ft
274 Brooksburgh Rd Unit 67, Windham, NY 12496

This 4 bedroom, 3.5 bath unit is ''like New''. Halfbath/laudry, kitchen with granite counters, upgraded cabinets, SS appliances, tile flooring. This is open concept. Nice counter in the kitchen with stool, open to the dining and living room area. Living room has a gas fireplace and sliding doors to a patio with a lovely view. Second floor has two main bedrooms with their full baths, third

Mary Donovan Gallagher & Company

274 Brooksburgh Rd Unit 67, Windham, NY 12496
/44
$1,699,000
- 4 Beds
- 4.5 Baths
- 1,990 Sq Ft
2 the Enclave Unit W10, Windham, NY 12496

Premier Trailside Location at Windham Mountain Club! Rarely does the opportunity to experience an Enclave Townhome come along. The Enclave Townhomes located at the base of Windham Mountain Club offers Slopeside living at its best. Timeless elegance awaits you in this distinctive 4 bedroom, 4.5-bath large end unit with double car heated garage. The open and airy kitchen affords you plenty of

Patricia Charbonneau Brainard Ridge Management

2 the Enclave Unit W10, Windham, NY 12496
/45
$1,399,000
- 5 Beds
- 5.5 Baths
- 3,752 Sq Ft
7 Meadow Ln, Windham, NY 12496

At the top of Windham ski mountain and just steps from ski-on, ski-off access sits this uniquely designed, contemporary gem. Significantly further up the mountain than any available property, it's ideal for ski enthusiasts and luxury buyers that want a mountainside retreat with near direct access to the slopes. Rather than fighting traffic, crowds and trudging across parking lots in ski boots,

Joseph Satto Compass Greater NY, LLC

7 Meadow Ln, Windham, NY 12496
/38
$300,000
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
5359 New York 23, Windham, NY 12496

Opportunity awaits as this beautifully designed 2 bedroom 2 bath Windham Condo a minute drive to Windham Mountain hits the market! You get the best of everything here as this property is located right on Main street where you can find everything but also so close to the ski resort! Features include large cozy great room with dining/living room combo with 2 large windows, recessed lighting and

Wayne Newcomb Newcomb Realty Group LLC

5359 New York 23, Windham, NY 12496
/70
$1,999,000
- 4 Beds
- 3.5 Baths
- 2,648 Sq Ft
37 White Way, Windham, NY 12496

Winter in Windham is fast approaching and with ski season just around the corner it's time to find the ski house of your dreams! 37 White Way is being offered for the first time and includes the added value of a second, adjoining lot. Located on Windham Mountain Club's east side, and just steps from the trails, this home overlooks the valley and town below, with far-reaching views that

Sharri Cunningham Bunce Realty

37 White Way, Windham, NY 12496
/14
$599,000
- Land
- 1.23 Acres
- $486,992 per Acre
137-1 South St, Windham, NY 12496

Attention Builders, Developers & Visionaries!Prime 1.23-acre parcel along Windham's sought-after South Street corridor — a high-traffic, high-growth area in the heart of town. Surrounded by established businesses, the local Little League field, new townhouse developments, and close proximity to Windham Mountain Club entrance and Main Street. Offering 138 feet of road frontage and mostly

Lisa Jaeger Coldwell Banker Village GreenW

137-1 South St, Windham, NY 12496
/33
$449,999
- 2 Beds
- 3 Baths
- 2,026 Sq Ft
61 South St, Windham, NY 12496

Sold as is. $100,000 YES - $100,000 DISCOUNT FOR A CASH TRANSACTION ! THIS PROPERTY IS ON THE 5TH AVE OF WINDHAM! minutes to the ski slopes and across the street from the golf course and clubhouse! Mid-century modern ski house, needs considerable maintenance & modernization, but oh so worth it. This is a financial home run! Property is a useable acre that directly abuts golf course (across the

Eric Schatz Schatz Realty Group

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

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