Windham, NY Houses for Sale

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  $1,775,000 Open Sun 12:30PM - 2PM

  • 5 Beds
  • 4.5 Baths
  • 3,218 Sq Ft

  31 Windham Farms Rd, Windham, NY 12496

  Modern Mountain Luxury | Windham, New YorkExperience 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

  Pamela King-Belfor Four Seasons Sotheby's Int.

  31 Windham Farms Rd, Windham, NY 12496
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  /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
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  $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
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  $565,000

  • 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
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  $294,000

  • 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 relaxation.

  Susanna Scott-Mitchell Compass Greater NY, LLC

  71 County Road 65 Unit 6, Hensonville, NY 12439
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  /40

  $1,900,000

  • 5 Beds
  • 4.5 Baths
  • 3,150 Sq Ft

  19 Stonewall Ln, Windham, NY 12496

  Set within the natural beauty of the Windham Mountain Club, Stonewall Glen is a private mountain enclave defined by thoughtful design, understated luxury, and a deep connection to its surroundings. Conceived as a retreat for those who value privacy, craftsmanship, and a slower rhythm of living, the community offers a refined setting for gathering, entertaining, or quiet escape amid the Catskills’

  John Oliveira Douglas Elliman Real Estate

  19 Stonewall Ln, Windham, NY 12496
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  $375,000

  • 3 Beds
  • 1 Bath
  • 1,739 Sq Ft

  477 Campbell Rd, Windham, NY 12496

  Skiers and Hunters! 7 glorious acres 8 minutes to Windham Mountain! Charming Updated Home with mature trees, beautiful plantings and landscapes. Welcome to this inviting 3-bedroom, 1-bath home set on 7 beautiful acres offering privacy, space, and stunning natural surroundings. Located only 8 minutes from the local ski area, it's the perfect retreat for outdoor enthusiasts or anyone seeking a

  Robyn Tricinelli Century 21 Alliance

  477 Campbell Rd, Windham, NY 12496
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  $735,000

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft

  730 Mill St, Windham, NY 12496

  Wonderful Windham Cape Cod on picturesque 6.8 acres, gazebo, and private pond! Welcome to this country gem! Many renovations in 2016: with a one car garage, breezeway, well equipped kitchen with granite counters, island and lovely, sun filled first floor ensuite bedroom with beautiful views out to the deck and gorgeous grounds. The main floor offers a second full bath, dining area and

  Patricia Charbonneau Brainard Ridge Management

  730 Mill St, Windham, NY 12496
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  /34

  $299,777

  • 4 Beds
  • 1.5 Baths
  • 1,457 Sq Ft

  28 Sutton Hollow Rd, Windham, NY 12496

  Want to be close to Windham Mountain? Looking for an affordable country home? A money making Air B&B? Look no further! Welcome to 28 Sutton Hollow Road. This single-family home located only 5 minutes to Windam Main Street, and only 10 miles to Hunter! Offering nice sized rooms with plenty of closet and storage space, partial basement and oversized garage for additional storage! On the first floor

  Douglas Schenk RE/MAX Capital

  28 Sutton Hollow Rd, Windham, NY 12496
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  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,287 Sq Ft

  18 Maplewood Ave, Windham, NY 12496

  Charming 4-Bedroom Ranch on 1.6 Acres in Windham, NY Discover your dream retreat in the heart of the Catskills! Nestled in the picturesque village of Windham, just minutes from vibrant downtown and the renowned Windham Mountain Resort with its array of restaurants and shops, this spacious 4-bedroom, 2-bathroom ranch offers the perfect blend of comfort and charm. Situated on a generous 1.6-acre

  Fred Mazza Bunce Realty

  18 Maplewood Ave, Windham, NY 12496
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  $449,000

  • 4 Beds
  • 2 Baths
  • 2,457 Sq Ft

  20 Slater Rd, Maplecrest, NY 12454

  Discover the perfect blend of charm, space, and convenience in this beautiful 4-bedroom, 2-bathroom countryside home, ideally located less than 3 hours from NYC. Set on scenic land in historic Windham NY. This vibrant small town is surrounded by renowned ski resorts; this is the ideal getaway or year-round residence.An exceptionally inviting home that is perfect for guests or extended family,

  Brian Cohen RHR Realty Group

  20 Slater Rd, Maplecrest, NY 12454
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  $1,375,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,280 Sq Ft

  305 Mitchell Hollow Rd, Windham, NY 12496

  Modern Mountain Luxury | Windham, New York. 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

  Pamela King-Belfor Four Seasons Sotheby's Int.

  305 Mitchell Hollow Rd, Windham, NY 12496
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  $1,299,000

  • 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
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  /38

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 2,953 Sq Ft

  61 Mount View Estates Rd, Windham, NY 12496

  This beautiful Windham Mountain home is the perfect year-round retreat. Tucked away on 5.5 private acres, the fully renovated property is just minutes from skiing, hiking, golf, restaurants, spas, and shops. Blending classic mountain charm with modern comforts, the home is spacious yet cozy — the ideal place to unwind after a long day, enjoy a getaway, or entertain friends. With two family rooms

  Jennifer Woods Daniel Gale Sothebys Intl Rlty

  61 Mount View Estates Rd, Windham, NY 12496
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  $1,999,000

  • 4 Beds
  • 3.5 Baths
  • 4,247 Sq Ft

  37 White Way, Windham, NY 12496

  Winter in Windham is here and with the ski season in full swing, it's time to find the ski house of your dreams! 37 White Way is being offered for the first time. INCLUDED IS A SECOND, ADJOINING VACANT PARCEL, offering flexibility and opportunity. Build a second home or guest house; sell the lot or, simply keep it as is to ensure privacy! Located on Windham Mountain Club's east side, and just

  Sharri Cunningham Bunce Realty

  37 White Way, Windham, NY 12496
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  $1,400,000

  • 3 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  17 Stonewall Ln, Windham, NY 12496

  Set within the natural beauty of the Windham Mountain Club, Stonewall Glen is a private mountain enclave defined by thoughtful design, understated luxury, and a deep connection to its surroundings. Conceived as a retreat for those who value privacy, craftsmanship, and a slower rhythm of living, the community offers a refined setting for gathering, entertaining, or quiet escape amid the Catskills’

  John Oliveira Douglas Elliman Real Estate

  17 Stonewall Ln, Windham, NY 12496
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  $3,600,000

  • 6 Beds
  • 5 Baths
  • 5,000 Sq Ft

  209 Club Rd, Windham, NY 12496

  This is the mountain house everyone else wishes they'd found first. Set on one of Windham's most coveted lots, this 6-bedroom, 5-bath home combines true slope-side access with panoramic views that stretch across the Catskills. It's a genuine ski-in, ski-out property with easy access to Wonderama and Lower Wipeout. In the mornings, clip in and go. At day's end, you can choose your own finale, take

  Patricia Charbonneau Brainard Ridge Management

  209 Club Rd, Windham, NY 12496
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  $2,250,000

  • 5 Beds
  • 4.5 Baths
  • 3,600 Sq Ft

  90 Club Rd, Windham, NY 12496

  Spectacular mountain views and steps away from the trails, this chalet is a Windham Mountain classic! One of the original homes on the mountain, it combines rustic charm with modern amenities. The heart of this home is its expansive great room perfect for relaxing after a day on the slopes or entertaining friends and family. Soaring cathedral ceilings with exposed wood beams add a sense of

  Sharri Cunningham Bunce Realty

  90 Club Rd, Windham, NY 12496
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  /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
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  $2,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  22 Club Rd, Windham, NY 12496

  New Attractive Price! On Windham Mountain. This Stunning and Immaculate, Contemporary, Log and Stone, shows Pride of Ownership in this 4 bedroom, 3.5 bath Spacious living area with wonderful views and lovely stone fireplace. Spacious working kitchen with granite counters, Stainless-Viking appliances, raised bar counter with 3 stools for that quick cup of coffee in and morning. Large wood dining

  Irene Pinto Brainard Ridge Management

  22 Club Rd, Windham, NY 12496
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  $1,345,000

  • 4 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  2 Watch Hill Ln, Windham, NY 12496

  Classic Timber frame Construction, on Windham Mt., Walk to trails. Enjoy the convenience of location in this 4 bedroom 3.5 bath with attached garage to enter a large ski room with all the storage needed. Large formal entrance gives way to Spacious and Comfy Great room with large stone fireplace, vaulted ceilings and plenty of windows to let in the light and the lovely views, leads to a sizable

  Irene Pinto Brainard Ridge Management

  2 Watch Hill Ln, Windham, NY 12496
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  /27

  $650,000

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  85 Cambridge Heights Rd, Windham, NY 12496

  Enjoy the summer months taking in the beautiful views from the large Trex decking. Warm up in front of the woodburning fireplace in the winter months. Close to Windham Mountain. A great property to enjoy all four seasons. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

  Sheila Word Coldwell Banker Village GreenW

  85 Cambridge Heights Rd, Windham, NY 12496
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  /22

  $289,900

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  107 Route 40 Rd, Windham, NY 12496

  Charming 2 bed home near Windham Mountain. Close to 3 additional ski hills within 35 min. Endless outdoor adverntures await.Welcome to this beautiful 2 bd 1 ba home tucked away in the small hamlet of Hensonville NY. Located minutes from local restaurants and activities. This inviting property offers the ideal blend of comfort and location. Wheather you are looking for a full time residence,

  Brian Cohen RHR Realty Group

  107 Route 40 Rd, Windham, NY 12496
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  $2,750,000

  • 6 Beds
  • 5 Baths
  • 4,730 Sq Ft

  208 Mill St, Windham, NY 12496

  Welcome to 208 Mill Street, Windham—a newer, contemporary Catskills ski home designed for easy mountain weekends and high-performing short-term rental ownership. Set on approximately 2.13 acres with mountain views, this spacious retreat offers roughly 4,795 sq ft of finished living space with 6 bedrooms and 4.5 baths, making it ideal for larger groups, multi-family getaways, or hosting-driven

  Twinkle Barot Iconic Pros

  208 Mill St, Windham, NY 12496
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  $799,000

  • 3 Beds
  • 3.5 Baths
  • 3,729 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

Showing Results 41 - 65, Page 2 of 2