Windham, NY Homes for Sale with Garage

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  /28

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  215 Siam Rd, Windham, NY 12496

  Nestled in the scenic beauty of Windham, NY, this unique octagon house offers a truly one-of-a-kind retreat close to skiing, golf, and hiking adventures. Set on over 5 acres of parklike surroundings, this property provides plenty of space for relaxation and exploration. The main home features 3 bedrooms and 2.5 baths, offering comfort and charm with stunning mountain views. The perfect country

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  (518) 351-7588

  215 Siam Rd, Windham, NY 12496
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  /54

  $850,000

  • 8 Beds
  • 8 Baths
  • 3,712 Sq Ft

  5320 New York 23, Windham, NY 12496

  In the heart of Windham, ''the place to be,'' this rare multi-use property offers endless possibilities for residential, commercial, or mixed-use ventures. Formerly a thriving B&B, it features two buildings with a total of 8 bedrooms and 8 bathrooms, a large open kitchen plus accessory kitchen, and expansive spaces perfect for a restaurant, cafe, art studio, gallery, retail shop, or rental income

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 261-9298

  5320 New York 23, Windham, NY 12496
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  /35

  $699,000

  • 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

  (518) 413-0731

  134 Magda Ln, Windham, NY 12496
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  /28

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft

  215 Siam Rd, Windham, NY 12496

  Nestled in the scenic beauty of Windham, NY, this unique octagon house offers a truly one-of-a-kind retreat close to skiing, golf, and hiking adventures. Set on over 5 acres of parklike surroundings, this property provides plenty of space for relaxation and exploration. The main home features 3 bedrooms and 2.5 baths, offering comfort and charm with stunning mountain views with surround windows

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 757-0479

  215 Siam Rd, Windham, NY 12496
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  /42

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 2,004 Sq Ft

  442 Mitchell Hollow Rd, Windham, NY 12496

  Nestled just 2.9 miles away from the breathtaking slopes of Windham Mountain and across the street from 89 acres of protected land sits this stunning 3 bed, 2.5 bath ranch. The home offers a captivating blend of modern touches and natural beauty. As you step into this picturesque retreat, panoramic views of the surrounding landscape greet you from every window, with the Windham slopes on display

  

  Mark McAlpine

  Compass Greater New York, LLC

  (518) 327-4735

  442 Mitchell Hollow Rd, Windham, NY 12496
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  /45

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,069 Sq Ft

  28 Sutton Hollow Rd, Windham, NY 12496

  Welcome to this charming, freshly painted Cape-style farmhouse, where comfort and character meet. Inside, a warm and inviting living room with a wood-burning fireplace offers the perfect place to relax after a day of adventure. Step outside onto the back deck and soak in the tranquil wooded setting—ideal for morning coffee, evening sunsets, or simply enjoying nature's beauty. Perfectly situated

  

  Jamie Mazuryk

  Venture Fox Realty Group LLC

  (518) 749-3527

  28 Sutton Hollow Rd, Windham, NY 12496
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  /31

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  436 Big Hollow Rd, Maplecrest, NY 12454

  Up the road from thousands of acres of state hiking trails and from CD Lane Park with swimming, kayaking, and family fun, this location is a true four-season retreat. Minutes to Windham and Hunter ski resorts, golf courses, and local venues, the setting offers year-round recreation at your doorstep.Set back from a quiet country road on nearly 4 acres, this property is all about the outdoors.

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 667-5960

  436 Big Hollow Rd, Maplecrest, NY 12454
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  /42

  $1,949,000

  • 5 Beds
  • 2.5 Baths
  • 3,893 Sq Ft

  33 Elm Ridge Rd, Windham, NY 12496

  The Mountains Are Calling and I Must Go.'' P.S., I plan to be VERY comfortable when I get there!Welcome to 33 Elm Ridge - the best of the Catskills - the ultimate in mountain opulence. This shingled contemporary makes quite the impression on its incredible setting; 3,900sqft of living space spans over 3 floors which include 5 bds, 3.5 bths & a walk-out basement that's ready to party. It's set on

  Regina Tortorella Coldwell Banker Village GreenW

  33 Elm Ridge Rd, Windham, NY 12496
• 

  

  /105

  $3,750,000 New Construction

  • 6 Beds
  • 5 Baths
  • 2,870 Sq Ft

  219 Club Rd, Windham, NY 12496

  Welcome to the ultimate ski-in/ski-out escape at Windham Mountain Club, where modern design, four-season mountain living, and front-row slope access come together in a way that feels both luxurious and totally effortless. This brand-new, custom-built home is perched just steps from the chairlift, making it one of the most desirable on-mountain properties available at WMC today. Designed to bring

  Regina Tortorella Coldwell Banker Village GreenW

  219 Club Rd, Windham, NY 12496
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  /100

  $2,799,000

  • 6 Beds
  • 5.5 Baths
  • 3,828 Sq Ft

  81 Sundance Dr, Windham, NY 12496

  Secluded Mountain Estate with 20+ Acres, Panoramic Views & Sport Court in Windham, NYPrivately gated at the very end of Sundance Drive, this extraordinary log estate is one of only five luxury homes in this sought-after enclave each on expansive land, but none offering the privacy, scale, or setting of this one. Set on a sweeping tract with panoramic mountain views, this home blends

  Regina Tortorella Coldwell Banker Village GreenW

  81 Sundance Dr, Windham, NY 12496
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  /39

  $484,000

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  7 Karlstadt Rd, Windham, NY 12496

  Charming & Freshly Renovated Cottage in the Heart of Windham — Just 1 mile from skiing at Windham MountainEscape to the mountains and fall in love with this newly renovated Catskill Mountain cottage, ideally situated just minutes from world-class skiing and golfing at Windham Resort. Nestled in a prestigious yet charming community only about two hours from NYC, this property blends cozy

  Regina Tortorella Coldwell Banker Village GreenW

  7 Karlstadt Rd, Windham, NY 12496
• 

  

  /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
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  /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
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  /48

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,088 Sq Ft

  93 Maplewood Ave, Windham, NY 12496

  Nestled at the end of a tranquil cul -de-sac, this spacious 3+1 bedroom perched on a hill just a short distance to downtown Windham has breathtaking views of the slopes at Windham Mountain.On the main level, floor-to-ceiling glass sliding doors showcase expansive mountain views. An open-concept layout with vaulted ceilings unites the living room, dining room, and kitchen—all oriented toward

  Doina Dewell Coldwell Banker Village GreenW

  93 Maplewood Ave, Windham, NY 12496
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  /36

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  315 Begley Rd, Windham, NY 12496

  Located just minutes from the heart of Windham, NY, this inviting 3-bedroom, 1.5-bath ranch is the perfect base for four-season living in the Catskills. Set on a spacious, tree-lined lot with a detached two-car garage and generous backyard, the home offers the ideal balance of privacy, convenience, and potential.Step inside to find a warm and welcoming layout featuring a large living area

  Regina Tortorella Coldwell Banker Village GreenW

  315 Begley Rd, Windham, NY 12496
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  /96

  $1,699,000

  • 5 Beds
  • 3.5 Baths
  • 4,312 Sq Ft

  102 Thunderbird Terrace, Windham, NY 12496

  Custom Log Cabin with Modern Finishes, The Feel of a New Build, and Stunning Mountain Views- Nestled on nearly 2 acres, this breathtaking custom log cabin combines luxury, charm, and nature. Built with meticulous attention to detail, the home shows as if it is new construction, exuding a fresh and pristine feel throughout, making it indistinguishable from a brand-new build. With 5 bedrooms, 3.5

  Regina Tortorella Coldwell Banker Village GreenW

  102 Thunderbird Terrace, Windham, NY 12496
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  /74

  $599,000

  • 4 Beds
  • 4 Baths
  • 2,950 Sq Ft

  25 Vets Rd, Windham, NY 12496

  Peaceful Sanctuary in the Heart of WindhamStep into a unique opportunity to own a stunning property perfectly balancing convenience, tranquility, and potential. Located less than half a mile from Windham Ski Resort and tucked just behind Main Street, this rambling ranch offers the best of both worlds easy access to dining, shopping, bars, skiing, festivals, and concerts, while feeling like a

  Regina Tortorella Coldwell Banker Village GreenW

  25 Vets Rd, Windham, NY 12496
• 

  

  /63

  $1,149,000

  • 5 Beds
  • 5.5 Baths
  • 3,460 Sq Ft

  292 South St Unit 2, Windham, NY 12496

  Incredible Investment Opportunity - Proven Short-Term Rental Income!Welcome to 292 South St, Windham - a luxury townhouse with exceptional income potential, already generating 85,000-110,000 annually while being rented for just a small portion of the year. This high-performing vacation rental has significant upside for buyers active on platforms like Airbnb, Vrbo, and AirDNA. With full-time

  Regina Tortorella Coldwell Banker Village GreenW

  292 South St Unit 2, Windham, NY 12496
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  /71

  $2,099,000

  • 5 Beds
  • 3.5 Baths
  • 4,834 Sq Ft

  77 Beaver Hill Rd, Windham, NY 12496

  Designed by a renowned Manhattan architect known for $20M Aspen ski homes, this 4,834-square-foot Catskills estate offers world-class design and unparalleled craftsmanship. Built as the architect's personal residence, it's a sanctuary for relaxation, entertaining, and year-round mountain living. Set on over four private acres bordering the protected Bataviakill Watershed, the home seamlessly

  Regina Tortorella Coldwell Banker Village GreenW

  77 Beaver Hill Rd, Windham, NY 12496
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  /35

  $879,000

  • 4 Beds
  • 3 Baths
  • 2,720 Sq Ft

  2 Biff Andrus Rd, Windham, NY 12496

  Windham Mountain Retreat - situated in a prime location just minutes to town and Windham Mountain Club. Designed with comfort and relaxation in mind, this space is also ideal for entertaining guests. Enjoy breathtaking mountain views from nearly every vantage point. Enter the home into the spacious mudroom, ideal for ski gear storage. The open concept living space, accentuated by a the grandeur

  Richard Vizzini Corcoran Country Living

  2 Biff Andrus Rd, Windham, NY 12496
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  /58

  $750,000

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft

  60 County Route 65 A, Windham, NY 12496

  Welcome to Windham Creek Lodge — a modern mountain retreat designed for both luxury living and income potential, where style meets sophistication in the heart of the Catskill Mountains.This beautifully remodeled multi-family chalet offers a rare blend of modern comfort, flexible design, and proven rental performance, located just minutes from Windham Mountain Club and Hunter

  Lisa Jaeger Coldwell Banker Village GreenW

  60 County Route 65 A, Windham, NY 12496
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  /61

  $1,125,000

  • 5 Beds
  • 5.5 Baths
  • 3,643 Sq Ft

  3 South St, Windham, NY 12496

  Turn-Key Windham Ski Retreat | Modern End Unit with 4 En-Suites, Full Furnishing Option & High Income Potential Personal Use or Income Ready and hitting the market just in time for peak rental demand, this modern end-unit townhome at 292 South Street offers an unbeatable opportunity for both investors and second-home seekers. Featuring four en-suite bedrooms, panoramic slope views, and a sleek

  Regina Tortorella Coldwell Banker Village GreenW

  3 South St, Windham, NY 12496
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  /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
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  /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
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  /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
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  /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
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  /42

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  333 Begley Rd, Windham, NY 12496

  What a sweet home only 3 miles from Windham Mountain! Winter, summer or year-round, this one is ready to move right in. Pick your pleasure!Sit on the cozy front porch and have a hot chocolate after skiing or warm up by the lovely stone woodburning fireplace. Wander out back and relax on the new expansive deck and head down to roast marshmallows at the firepit.This home has been totally

  Sharon Knudsen Coldwell Banker Village GreenW

  333 Begley Rd, Windham, NY 12496
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  /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
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  /41

  $654,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  212 South St, Windham, NY 12496

  Location is everything, This home sits on 1.80 acres/ Beautiful views in ever direction. The perfect location of skiing, golfing, walk to town, library, movies, restaurants. Watch the fireworks at /Windham, Mt. Club. Upper level boasts a stone fireplace w/wood insert, wood floors, even a bar, eat in kitchen, plus dining room with a wall of windows, to enjoy the views. Kitchen has been redone

  Mary Donovan Gallagher & Company

  212 South St, Windham, NY 12496
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  /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
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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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  /33

  $340,000

  • 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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  /14

  $1,650,000

  • 3 Beds
  • 3 Baths
  • 1,655 Sq Ft

  10 Enclave Dr N Unit 106, Windham, NY 12496

  Stunning Enclave 3 bedroom, 3 bath, inspired full renovation, impeccably furnished with slopeside views!Enjoy trailside living at its best, natural sunlight abounds in the gorgeous living area with stunning gas fireplace, modern decor, contemporary sleek kitchen with farmhouse sink, elegant cabinetry and counter tops. A separate wonderful dining area with plenty of seating for friends and

  Irene Pinto Brainard Ridge Management

  10 Enclave Dr N Unit 106, 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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  /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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  /33

  $340,000

  • 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

  689 Old Rd, Hensonville, NY 12439
• 

  

  /33

  $340,000

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

  689 Old Farm Rd, East Windham, 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 Farm Rd, East Windham, NY 12439
• 

  

  /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
• 

  

  /27

  $628,000

  • 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
• 

  

  /61

  $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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