Windham, NY Houses for Sale

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  /40

  $899,500

  • 5 Beds
  • 4.5 Baths
  • 4,220 Sq Ft

  8 Evans Rd, Windham, NY 12496

  Experience the charm and comfort of this meticulously maintained property located in the heart of Windham. Nestled in a private setting, this home offers serene living while being just moments away from the village, ski mountain, golf courses, and hiking trails, fabulous restaurants, making it a perfect four-seasons community.This expansive home is perfect for a large family and guests, featuring

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 684-5981

  8 Evans Rd, Windham, NY 12496
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  /35

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  16 Hickory Hill Rd, Windham, NY 12496

  This gem has direct views of Windham slopes, proximity to golf courses, Windham Village, restaurants, and walking paths, makes it a captivating endeavor. Renovated in 2022 with new roof, skylights and custom kitchen, This property boasts a prime location in a vibrant 4-season community. Offering 3 bedrooms and 2 baths, it includes a sunroom, a fully equipped kitchen featuring a 6-burner

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 667-9038

  16 Hickory Hill Rd, Windham, NY 12496
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  /29

  $599,500

  • 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) 674-9897

  215 Siam Rd, Windham, NY 12496
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  /40

  $935,000

  • 5 Beds
  • 4.5 Baths
  • 4,117 Sq Ft

  24 Windham View Rd, Windham, NY 12496

  A warm abundance of natural light greets as you enter this beautiful 5-bedroom 4.5 bath Contemporary Home. Situated on a quiet road with outstanding views of Windham Mountain. This home offers you a perfect getaway to enjoy 4 season country living at its best.The commanding entrance gives way to a wonderful, spacious living room with a second bright, cozy living area with welcoming gas fireplace.

  

  Patricia Charbonneau

  Brainard Ridge Management

  (518) 413-1348

  24 Windham View Rd, Windham, NY 12496
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  /68

  $1,170,000

  • 4 Beds
  • 5 Baths
  • 2,140 Sq Ft

  149 Magda Ln, Windham, NY 12496

  Serene Country and Ski Living at its Finest! Discover the ultimate in luxury and sophistication with this impeccably renovated 4-bedroom, 5 bath estate. Every detail has been thoughtfully designed to combine timeless elegance with modern convenience. The heart of the home is a breathtaking open concept kitchen, featuring white French oak engineered hardwood floors, Caesarstone countertops and

  

  Patricia Charbonneau

  Brainard Ridge Management

  (518) 684-7136

  149 Magda Ln, Windham, NY 12496
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  /17

  $339,000

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  504 Rt 40, Windham, NY 12454

  Nestled in the quaint hamlet of Maplecrest, this inviting 2-bedroom home offers the perfect blend of tranquility and convenience. Ideally located between Windham and Hunter Mountains, it's just minutes from world-class skiing, hiking, golf, and other outdoor adventures. Enjoy easy access to nearby CD Lane Park, Colgate Lake, and the iconic Kaaterskill Falls.This home boasts a semi-finished

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 333-3680

  504 Rt 40, Windham, NY 12454
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  /30

  $1,199,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,287 Sq Ft

  20 Brookhollow Ln, Windham, NY 12496

  Welcome to this stunning new construction home in the sought-after town of Windham, NY! This contemporary, sun-drenched home features 3 spacious bedrooms and 3.5 baths, with an expansive layout perfect for modern living.On the Main floor, Enjoy a large, beautiful primary bedroom with an en-suite bath, providing a luxurious and private retreat. Vaulted ceilings throughout the main level enhance

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 809-7724

  20 Brookhollow Ln, Windham, NY 12496
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  /96

  $1,699,000

  • 5 Beds
  • 4.5 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, 4

  Regina Tortorella Coldwell Banker Village Green

  102 Thunderbird Terrace, Windham, NY 12496
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  /50

  $1,495,000

  • 3 Beds
  • 3 Baths
  • 2,554 Sq Ft

  342 Old Rd, Windham, NY 12496

  Experience modern mountain living in this brand-new, architecturally designed A-frame, just 5 minutes from Windham Mountain. This 3-bedroom, 3-bathroom with a loft retreat offers high-end finishes, an open-concept layout, and exceptional indoor-outdoor spaces, perfect for all-season enjoyment.Step inside to find soaring cathedral ceilings, floor-to-ceiling windows, and a cozy yet

  Artan Volaj Metro Scape Realty LLC

  342 Old Rd, Windham, NY 12496
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  /45

  $1,495,000

  • 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 Fresh Air Realty

  7 Meadow Ln, Windham, NY 12496
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  /56

  $999,000

  • 5 Beds
  • 4 Baths
  • 3,100 Sq Ft

  30 The Loop, Windham, NY 12496

  Walk to the Slopes! Escape to Luxury in the Catskill Mountains - Your Dream Ski Chalet Awaits! Step into the extraordinary at this stunning ski chalet a short distance from the slopes at the Windham Mountain Resort! Perfect for city escapes or quality time with loved ones, this luxurious retreat is designed to help you unwind, reconnect, and create unforgettable memories. Unmatched Mountain

  Regina Tortorella Coldwell Banker Village Green

  30 The Loop, Windham, NY 12496
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  /35

  $949,000

  • 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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  /64

  $1,975,000

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft

  22 The Loop, Windham, NY 12496

  Walk to the Slopes! Nestled on the scenic slopes of Windham Mountain and just over two hours from NYC, this mountain haven beautifully marries opulence with rustic allure. The home's exterior, featuring cedar shakes and stone, harmonizes with its lush, landscaped surroundings, creating impeccable curb appeal. Inside, a grand two-story great room welcomes you with a magnificent wall of glass

  Regina Tortorella Coldwell Banker Village Green

  22 The Loop, Windham, NY 12496
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  /27

  $999,000

  • 7 Beds
  • 3 Baths
  • 4,281 Sq Ft

  5474 New York 23, Windham, NY 12496

  This large historic home is the original site of Windham's first settler in 1785 and the Reynolds have been entertaining family & friends there since 1959!Located on the west side of town, it is an easy walk to Windham's shops & restaurants.It has a formal living room, (which has been used for an office and playroom), a large dining area and a large, comfortable family room. The kitchen is well

  Jane Reynolds Jane H. Reynolds

  5474 New York 23, Windham, NY 12496
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  /29

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

  • 4 Beds
  • 3.5 Baths
  • 2,700 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 2,356

  Pamela King-Belfor Four Seasons Sotheby's Int.

  13 Stonewall Ln, Windham, NY 12496
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  /44

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,294 Sq Ft

  429 Mill St, Windham, NY 12496

  Discover serenity in this exquisite cedar contemporary home with seasonal slope views nestled in a private wooded setting, just 5 minutes from the charming resort town of Windham and a mere 2.5 hours outside of New York City. This stunning property offers a harmonious blend of rustic charm and modern amenities. Step inside to find a home that radiates warmth and sophistication. Hardwood floors

  Regina Tortorella Coldwell Banker Village Green

  429 Mill St, Windham, NY 12496
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  /34

  $439,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 1 Bath
  • 1,486 Sq Ft

  296 Mitchell Hollow Rd, Windham, NY 12496

  Hemlock Cabin | 296 Mitchell Hollow Road | Windham, NY - Tucked away on a coveted country road just three minutes from the Windham Mountain Club, the Hemlock Cabin blends rustic character with modern comfort in one of the Catskills' most sought-after year-round destinations. Sided with durable hemlock with copper detailing, this charming cape sits on 1.1 acres with a large yard perfect for

  Leslie Foti Coldwell Banker Village Green

  296 Mitchell Hollow Rd, Windham, NY 12496
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  /72

  $699,000

  • 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 Green

  25 Vets Rd, Windham, NY 12496
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  /33

  $345,000

  • 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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  /22

  $545,000

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

  15 Route 79, Windham, NY 12496

  Welcome to Windham! This one-of-a-kind village retreat blends modern luxury with country charm, offering the perfect escape in the heart of it all. Nestled along the Batavia creek, this home invites you to relax and enjoy the soothing sounds of the water, all while being just steps from restaurants, pubs, a wine bar, Windham's famous ski slopes, the world-class golf club, and the NYC bus

  Melissa Mayes 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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  /68

  $2,250,000

  • 9 Beds
  • 7 Baths
  • 6,859 Sq Ft

  150 Trailside Rd, Windham, NY 12496

  Luxury Slopeside Living at Windham Mountain Club- This is a rare opportunity to own the most competitively priced slopeside home at Windham Mountain Club, close to the lodge and lifts. With 6,859 sq. ft. of high-end living space and direct access to the slopes, this home is a dream for anyone looking for adventure and a smart move for investors seeking strong rental potential in the Catskills.

  Regina Tortorella Coldwell Banker Village Green

  150 Trailside Rd, Windham, NY 12496
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  /58

  $720,000

  • 3 Beds
  • 2 Baths
  • 2,792 Sq Ft

  73 Cross Rd, Windham, NY 12496

  Ideal country getaway with beautiful mountain views located just steps away from premier hiking and biking trails and minutes from the charming Village of Windham, you'll find endless opportunities for outdoor exploration and leisure here. Step inside this cozy log sided Chalet and be captivated by open floor plan, where vaulted pine wood ceilings and a wall of glass fill the space with an

  Lisa Jaeger Coldwell Banker Village Green

  73 Cross Rd, 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 Green

  77 Beaver Hill Rd, Windham, NY 12496
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  /33

  $579,000

  • 4 Beds
  • 2 Baths
  • 2,270 Sq Ft

  89 Siam Rd, Windham, NY 12496

  New Price! Swiss Chalet-inspired home close proximity to Windham's Main Street and Windham Mt Club Resort. This cozy fully furnished 5-bedroom, 2-bath home spans 2,270 sq ft offers an inviting blend of rustic warmth with a touch of modern sophistication. The moment you step inside, you'll be captivated by 2- authentic bluestone fireplaces and wood beamed ceilings that imbue that alpine vibe. The

  Lisa Jaeger Coldwell Banker Village Green

  89 Siam Rd, Windham, NY 12496
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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 Green

  85 Cambridge Heights Rd, Windham, NY 12496
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  /40

  $564,000

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  21 Nauvoo Rd, Windham, NY 12496

  No need to check mountain conditions online - just step out onto the back deck and see for yourself! This two bedroom mid-century ranch is conveniently located within sight of Windham Mountain and just down the road from the bustling Village of Windham. The home features expansive mountain views as well as a large yard surrounded by mature trees. The 3.5 acre property insures privacy year round.

  Joel Craig Coldwell Banker Village Green

  21 Nauvoo Rd, Windham, NY 12496
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  /45

  $775,000

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

  212 South St, Windham, NY 12496

  Location is everything.This home sits on 1.80 acres, The perfect location for skiing, golfing, walk to town, library, movies, restaurants. Sit and watch the fireworks at Windham Mt Club. Views in every direction.Upper level boasts a stone fireplace w/wood burning insert, wood floors even a bar on this level. Large dining room with wonderful light. tranquil views. Main bedroom with 2 large

  Mary Lantry Donovan Gallagher & Company

  212 South St, Windham, NY 12496
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  /95

  $549,000

  • 6 Beds
  • 3.5 Baths
  • 4,014 Sq Ft

  231 County Route 65, Windham, NY 12496

  A Spectacular Home with 6 Bedrooms, 3 1/2 Baths, & 3 Floors with over 4,000 Sq Ft in Windham with Beautiful Mountain Views! The home could be an extraordinary Airbnb, an impressive family destination near Windham Ski Mountain, or a grand primary home. The main floor features a family room with a pellet stove, a living room with a fireplace, a 1/2 bath, & a kitchen with a dining area. The 2nd

  Ted Banta RVW Select Properties

  231 County Route 65, Windham, NY 12496
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  /65

  $2,500,000

  • 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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  /66

  $639,000

  • 8 Beds
  • 4 Baths
  • 3,577 Sq Ft

  110 Maplecrest Rd, Windham, NY 12439

  This charming multi-family farmhouse is centrally located to Windham Mountain Club, Hunter Mountain, CD Lane Park and more. Excellent condition well maintained over the years offers four beautifully appointed rental units. Each unit features remodeled tiled baths and beautiful hardwoods floors throughout. Many windows were replaced and was painted in fall of 2024.The Stoney Creek apartment is a

  Lisa Jaeger Coldwell Banker Village Green

  110 Maplecrest Rd, Windham, NY 12439
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  /37

  $340,000

  • 3 Beds
  • 1 Bath
  • 1,404 Sq Ft

  573 Sutton Hollow Rd, Windham, NY 12496

  Move in ready ranch with lovely mountain views. Come check out this sweet ranch home with plenty of room to grow. This home has 3 nicely sized bedrooms and a spacious kitchen with tons of storage. The large four-lite bow window allows the sunlight to pour into the cozy living room where you can relax and take in the mountain views. Glass sliders take you from the dining area to a small back deck.

  Sharon Knudsen Coldwell Banker Village Green

  573 Sutton Hollow Rd, Windham, NY 12496
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  /98

  $2,100,000

  • 6 Beds
  • 5.5 Baths
  • 4,104 Sq Ft

  19 Twin Maples, Windham, NY 12496

  Welcome to an unparalleled luxury living experience at this exquisite post-and-beam residence, expertly crafted to captivate the most discerning of high-end homebuyers, luxury vacationers, and ski enthusiasts. Spanning over 4,100 square feet, this six-bedroom, six-bathroom marvel is a testament to superior craftsmanship and sophisticated design. Step into the grand great room, where a two-story

  Regina Tortorella Coldwell Banker Village Green

  19 Twin Maples, Windham, NY 12496
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  /49

  $850,000

  • 8 Beds
  • 8 Baths

  5320 New York 23, Windham, NY 12496

  Historic Inn on Main Street in downtown section of the Ski/Resort Community of Windham, NY. 7 Guest Suites plus Owners Apartment and Photo/Music/Art Studio. Well appointed and turn-key. (formerly rated #1 on Trip Advisor) Sale to settle an Estate.

  5320 New York 23, Windham, NY 12496
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  /33

  $1,399,000

  • 5 Beds
  • 3 Baths
  • 2,974 Sq Ft

  3-5 Hickory Hill Rd, Windham, NY 12496

  Experience mountainside living in the ultimate ski house, nestled in the heart of Windham. Situated on just under 3 picturesque acres, boasting mountain views abound and close proximity to Windham Mountain Ski Club. An ideal setting for those seeking an upstate retreat. Upon entering the home, you're greeted by soaring ceilings and an abundance of natural light that floods the space through large

  Richard Vizzini Corcoran Country Living

  3-5 Hickory Hill 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 so

  Jason Dugo Dugo Realty

  5134 New York 23, Windham, NY 12496
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  /30

  $395,000

  • 4 Beds
  • 2 Baths
  • 1,303 Sq Ft

  821 Mitchell Hollow Rd, Windham, NY 12496

  Warm and welcoming old style country farmhouse. Completely renovated inside with some original touches remaining. Sizeable eat-in kitchen, new appliances, new flooring and living area with original fireplace. Convenient mud/laundry room off of kitchen. Sit on the new deck and enjoy beautiful wide open mountain and ski slope views. Large detached 16 x 32 out-building with sliders opening out to a

  Lisa Gambella WINDSTAR REALTY GROUP LLC

  821 Mitchell Hollow Rd, Windham, NY 12496
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  /34

  $730,000

  • 5 Beds
  • 3 Baths
  • 2,318 Sq Ft

  134 Magda Ln, Windham, NY 12496

  Welcome to paradise! This 5-bedroom, 3 full bathroom home is just minutes to Windham Ski Center, Hiking, fishing, and many other outdoor activities. The home has been extensively renovated with the following upgrades: New Kitchen countertops and painted cabinets. Entire house new electric baseboard heaters along with smart thermostats that can be remotely controlled. A new driveway was put in. A

  134 Magda Ln, Windham, NY 12496
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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 Green

  33 Elm Ridge Rd, Windham, NY 12496
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  /9

  $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 Core Real Estate Team

  4 Estate View Dr, Windham, NY 12496

Showing Results 1 - 40, Page 1 of 2