Windham, NY Houses for Sale

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  $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
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  /33

  $375,000

  • 2 Beds
  • 3 Baths
  • 2,026 Sq Ft

  61 South St, Windham, NY 12496

  Sold as is.3 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 to do. Property is a useable acre that directly abuts golf course (across the street) and clubhouse. Excellent Airbnb opportunity. Year round and vacation home living. Location, location

  Eric Schatz Schatz Realty Group

  61 South St, Windham, NY 12496
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  /47

  $630,000

  • 4 Beds
  • 2 Baths
  • 1,052 Sq Ft

  31 Koonan Rd, Windham, NY 12496

  Escape to the mountains in this tastefully renovated 4-bedroom, 2-bath home just outside Windham. Designed with open, easy living in mind, the upper level is centered around a wood stove that adds warmth and character. Recent improvements include newly installed hardwood floors, updated interior and exterior paint, upgraded drainage, and a brand-new washer and dryer. Outdoor spaces were made for

  Brandon Oot Core Real Estate Team

  31 Koonan Rd, Windham, NY 12496
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  $343,000

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  689 Old Rd, Windham, NY 12496

  Charming 2-bedroom 2 full bathroom ranch in Windham, New York. Sits on an acre with panoramic views of the Catskills. Relax in the backyard along the seasonal creek listening to the sounds of chirping from the many varieties of wild birds in the area. Entertain friends, family and pets from the back deck under a beautifully constructed gazebo. Enjoy the warmth of a winter fire in your striking

  Kathy Shumway Win Morrison Realty

  689 Old Rd, Windham, NY 12496
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  /41

  $2,200,000

  • 4 Beds
  • 3.5 Baths
  • 2,004 Sq Ft

  22 Club Rd, Windham, NY 12496

  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 table and 8 upholstered

  Irene Pinto Brainard Ridge Management

  22 Club Rd, Windham, NY 12496
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  /12

  $649,000

  • 2 Beds
  • 1 Bath
  • 1,122 Sq Ft

  183 N South St N, Windham, NY 12496

  Exceptional Opportunity in a Prime Windham Location!Transform this property into a true showpiece — take this Chevy and turn it into a Rolls Royce!Situated directly across from the Windham Country Club, enjoy unobstructed views of the golf course. This property also offers potential for subdivision, adding long-term investment oppertunity.Just a short walk (2,500 feet) to Windham

  John Pumilia Shaw Country Realty, Inc.

  183 N South St N, Windham, NY 12496
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  /47

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,942 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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  /48

  $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, NYDiscover 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

  Fred Mazza Bunce Realty

  18 Maplewood Ave, Windham, NY 12496
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  /30

  $545,000

  • 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

  Regina Tortorella Coldwell Banker Village GreenW

  20 Sutton Hollow Rd, Windham, NY 12496
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  /34

  $479,000

  • 3 Beds
  • 2.5 Baths
  • 1,812 Sq Ft

  4992 New York 23, Windham, NY 12496

  Perched above the road on a private and wooded1.50 acres, opposite the Windham Path, sits this thoughtfully renovated 3 bedroom, 2.5 bath . this home is ready for you to enjoy year round! The bright and airy professional kitchen offers GE Cafe appliances 8-9 years old,, striking granite counters and island. The generous dining area affords plenty of room for family and friends. Enjoy lush green

  Irene Pinto Brainard Ridge Management

  4992 New York 23, Windham, NY 12496
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  /34

  $410,000

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  81 Route 65, Windham, NY 12496

  Just a stones throw from the slopes at Windham Mountain, you will find this gem. A 5 bedroom, 3 bathroom village home that has been fully renovated while maintaining much of the original character. The exterior boasts a rocking chair porch, abundant space for entertaining or enjoying, extensive garden area, hot tub, orchard(apples and pears), hiking, bird watching, and so much more! The turn-key

  Jessica Surbeck WINDSTAR REALTY GROUP LLC

  81 Route 65, Windham, NY 12496
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  /48

  $405,000

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  110/2 Highridge Rd, Hensonville, NY 12439

  Charming 3-Bedroom Retreat in Serene Wooded SettingNestled on a private road in a tranquil wooded haven, this newly renovated 3-bedroom, 2-bath retreat seamlessly blends modern comforts with cozy charm. Perfect as a primary residence, vacation home, or income-generating AirB&B, this property offers exceptional versatility and appeal.Key Features:Upper Level: Spacious

  Fred Mazza Bunce Realty

  110/2 Highridge Rd, Hensonville, NY 12439
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  /33

  $530,000

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft

  15 Route 79, Windham, NY 12496

  Exceptional Village Investment with Airbnb Track Record & Expansion PotentialWelcome to Windham, where modern luxury meets country charm—just steps from ski slopes, golf, restaurants, wine bars, and the NYC bus line. Set along the tranquil Batavia Creek, this beautifully renovated home is both a proven short-term rental success and an incredible four-season getaway.Currently

  Baris Demirel Serhant LLC

  15 Route 79, Windham, NY 12496
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  /54

  $439,000

  • 4 Beds
  • 3 Baths
  • 1,814 Sq Ft

  17 Mitchell Hollow Rd, Windham, NY 12496

  Whether your search is for personal use or investment property, this Windham Farmhouse, just steps from the center of town, offers versatility and plenty of room for the whole family. A unique three floor layout allows for everyone to have their own space. The first and lowest level is the main living area: Kitchen, Dining, Living Room as well as a bedroom and full bath. The sunroom is an added

  Sharri Cunningham Bunce Realty

  17 Mitchell Hollow Rd, Windham, NY 12496
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  /33

  $343,000

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  689 Old Rd, Hensonville, NY 12439

  Charming 2-bedroom 2 full bathroom ranch in Windham, New York. Sits on an acre with panoramic views of the Catskills. Relax in the backyard along the seasonal creek listening to the sounds of chirping from the many varieties of wild birds in the area. Entertain friends, family and pets from the back deck under a beautifully constructed gazebo. Enjoy the warmth of a winter fire in your striking

  Kathy Shumway Win Morrison Realty-K

  689 Old Rd, Hensonville, NY 12439
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  /15

  $215,000

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  384 New York 296, Hensonville, NY 12439

  A Prime Investment Opportunity Fixer-Upper in the Heart of Windham, NY! Unlock the potential of this charming 3-bedroom, 2-bath fixer-upper nestled in the picturesque Hamlet of Hensonville, NYa hidden gem in the Catskill Mountains. Perfect for investors or visionary homeowners, this property offers a solid foundation and endless possibilities to create the perfect retreat or a lucrative rental.

  Phil Uhrik Win Morrison Realty - Catskill

  384 New York 296, Hensonville, NY 12439
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  /41

  $585,000

  • 5 Beds
  • 3 Baths
  • 2,644 Sq Ft

  183 County Road 65, Hensonville, NY 12439

  Fully Renovated Mountain Retreat with Two Fireplaces and Stunning Views Just 3 Miles from the Slopes! Welcome to your dream getaway in Windham! This fully renovated 5-bedroom, 3-bath home combines modern luxury with mountain charm, just 2.5 hours from NYC. Whether you crave adventure or relaxation, this 2,700 sq. ft. retreat has it all. Unwind in a private hot tub under a canopy of stars or hit

  Regina Tortorella Coldwell Banker Village GreenW

  183 County Road 65, Hensonville, NY 12439
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  /27

  $669,000

  • 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.

  Sheila Word Coldwell Banker Village GreenW

  85 Cambridge Heights Rd, Windham, NY 12496
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  /65

  $2,350,000

  • 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

  Kathy Marino Bunce Realty

  90 Club Rd, Windham, NY 12496
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  /18

  $470,000

  • 5 Beds
  • 2.5 Baths
  • 2,460 Sq Ft

  57 Chase Dr, Hensonville, NY 12439

  Great opportunity to own a vacation home in Windham! Lots of room for loved ones & guests.Featuring 5 bedrooms, 2 1/2 baths, open floor plan, and wood burning fireplace. Property has a pond.Conveniently located to Elm Ridge Club which has tennis courts, swimming pool & recreation room.Windham Mountain Club is minutes away.

  Sheila Word Coldwell Banker Village GreenW

  57 Chase Dr, Hensonville, NY 12439
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  /33

  $1,650,000 Open Fri 11AM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 3,148 Sq Ft

  13 Stonewall Ln, Windham, NY 12496

  Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers a perfect blend of modern mountain living and serene country life. Whether it’s for family, friends, or your own getaway, this community surrounds you with year-round recreational opportunities.Our 3, 4, and 5-bedroom custom townhomes feature spacious, thoughtfully designed floor plans, ranging from

  Pamela King-Belfor Four Seasons Sothebys Intl

  13 Stonewall Ln, Windham, NY 12496
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  /7

  $1,900,000 Open Fri 11AM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 3,148 Sq Ft

  15 Stonewall Ln, Windham, NY 12496

  Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers a perfect blend of modern mountain living and serene country life. Whether it’s for family, friends, or your own getaway, this community surrounds you with year-round recreational opportunities.Our 3, 4, and 5-bedroom custom townhomes feature spacious, thoughtfully designed floor plans, ranging from

  Pamela King-Belfor Four Seasons Sothebys Intl

  15 Stonewall Ln, Windham, NY 12496
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  /7

  $1,400,000 Open Fri 11AM - 3PM

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

  17 Stonewall Ln, Windham, NY 12496

  Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers a perfect blend of modern mountain living and serene country life. Whether it’s for family, friends, or your own getaway, this community surrounds you with year-round recreational opportunities.Our 3, 4, and 5-bedroom custom townhomes feature spacious, thoughtfully designed floor plans, ranging from

  Pamela King-Belfor Four Seasons Sothebys Intl

  17 Stonewall Ln, Windham, NY 12496
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  /27

  $638,000

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  9 Pinekill Ln, Windham, NY 12496

  Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and

  Serena Shi Sany Realty Group LLC

  9 Pinekill Ln, Windham, NY 12496
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  $2,900,000 New Construction

  • 7 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  110 Old Rd, Windham, NY 12496

  Presenting direct Windham Mountain views only 2 miles from Windham Mountain Club and minutes from town. This newly built 5,550 Square Foot, 7BR, 5.5BA, 2 Laundry Room, 2 Garage Cabin on 5 Acres is the perfect luxury ski and year-round home! The cabin is stunning, modern, and high-end. No detail overlooked. It is in a very private yet convenient setting. Luxury Finishes throughout- Vermont

  Josie Reo MLS 4 Less Realty

  110 Old Rd, Windham, NY 12496
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  /7

  $1,998,500 New Construction

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

  4 Estate View Dr, Windham, NY 12496

  To be built. Experience unparalleled luxury in this custom-built mountain retreat. Situated on 10.5 private acres in the heart of the Catskills, Windham Luxury Estates offers an extraordinary opportunity to own a meticulously designed 3 level, 5k+ sq ft retreat. Built by Vaughn Construction, this 5 bed, 5.5 bath will showcase an open concept that connects the kitchen, dining & living areas-with

  Patrick Dunn KW Platform

  4 Estate View Dr, Windham, NY 12496
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  /83

  $1,890,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 1,609 Sq Ft

  31 Windham Farms Rd, Windham, NY 12496

  Brand new luxury modern mountain chalet sited at serene Windham Farms subdivision. Now fully furnished, turnkey ready for occupancy. This exquisite new home is set on a private 4.8-acre lot, featuring a modern mountain design complemented by clear blue skies and a pine forest backdrop and a rushing mountain seasonal stream. The property boasts a sleek black standing seam roof and panoramic views

  Laurie Hanenberg Hunter Windham Real Estate

  31 Windham Farms Rd, Windham, NY 12496
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  /90

  $3,895,000 Pre-Foreclosure

  • 5 Beds
  • 7 Baths
  • 4,795 Sq Ft

  6 White Way, Windham, NY 12496

  Welcome to 6 White Way, striking the perfect balance of Mountain Elegance and Rustic Splendor. Enjoy effortless ski in, ski out access from this rare superior trailside home. This impeccably built, 6,207 Sq. Ft. home offers 5 bedrooms and 7 full bathrooms. From the moment you enter the grand entry way with its beautiful log stairway opening to the impressive sun filled elegantly furnished formal

  Patricia Charbonneau Brainard Ridge Management

  6 White Way, Windham, NY 12496

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