Windham, NY Houses for Sale

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  /40

  $599,000

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

  16 Hickory Hill Rd, Windham, NY 12496

  Discover the perfect mountain lifestyle in this beautifully renovated, fully furnished, 3-bedroom, 2-bath home with direct slope views and seamless access to world-class recreation. Completely renovated in 2022 with a new roof, skylights, and custom kitchen featuring a professional 6-burner Vulcan stove, this property blends modern comfort with outdoor living. Inside, you'll find stainless steel

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 855-9686

  16 Hickory Hill Rd, Windham, NY 12496
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  /47

  $1,595,000

  • 5 Beds
  • 4 Baths
  • 4,056 Sq Ft

  5433 New York 23, Windham, NY 12496

  Set right in the heart of the town of Windham, this exceptional brand new construction offers the rare combination of village proximity, mountain views, and income producing potential. Thoughtfully designed as a two-story residence with a private backyard and a separate barn with utilities already in place, the property presents a turnkey opportunity for an accessory dwelling unit, guest house,

  

  Catherine Quintard

  Compass Greater NY, LLC

  (518) 400-5046

  5433 New York 23, Windham, NY 12496
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  /59

  $685,000

  • 5 Beds
  • 3 Baths
  • 3,184 Sq Ft

  523 Mitchell Hollow Rd, Windham, NY 12496

  Catskills living with standout appeal in Windham—the ultimate four-season destination for skiing, golf, hiking, breweries, and live music venues. This sprawling, rambling layout was designed for memorable gatherings, offering 5 generous bedrooms and 3 full baths, ideal for hosting family, friends, or guests in style. Warm up by the fireplace after a day on the mountain, then step outside to your

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 777-2454

  523 Mitchell Hollow Rd, Windham, NY 12496
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  /40

  $684,000

  • 5 Beds
  • 3.5 Baths
  • 2,640 Sq Ft

  134 Magda Ln, Windham, NY 12496

  Charming Country Retreat Just Minutes to WindhamNestled on a private dead-end road just minutes from Windham's slopes, golf courses, and vibrant village, this beautiful recently 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

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 413-0731

  134 Magda Ln, Windham, NY 12496
• 

  

  

  /23

  $349,000

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

  315 Begley Rd, Windham, NY 12496

  Just minutes from the village of Windham, skiing, and golf, this meticulously maintained ranch is set on a beautiful country road in a true four-season community. The easy, flowing floor plan features a bright eat-in kitchen that opens directly to a spacious rear deck—perfect for outdoor dining and entertaining. Inside, you'll find three comfortable bedrooms, 1.5 baths, and a welcoming living

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 735-6784

  315 Begley Rd, Windham, NY 12496
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  /26

  $399,000

  • 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. Owners are in the process of installing a new

  

  Jack Yao

  Realmart Realty, LLC

  (518) 897-3596

  2914 Route 10, 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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  /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

  (518) 627-5170

  5134 New York 23, Windham, NY 12496
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  /49

  $499,000

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

  215 Siam Rd, Windham, NY 12496

  Incredible buy at this new price! The Windham Round House, one of most distinctive and architecturally unique homes in the area. Lovingly designed and built by the original owners, this octagon-style residence sits on 5 private acres with open lawns, a charming stone wall, evergreen woods beyond, multiple outbuildings including a two-car garage—offers a remarkable setting that must be seen to be

  Lisa Jaeger Coldwell Banker Village GreenW

  215 Siam Rd, Windham, NY 12496
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  /64

  $1,899,000

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

  22 The Loop, Windham, NY 12496

  A short 1-2 minute walk to the trail access (870 ft)!! 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

  Regina Tortorella Coldwell Banker Village GreenW

  22 The Loop, Windham, NY 12496
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  /68

  $875,000

  • 4 Beds
  • 3.5 Baths
  • 3,075 Sq Ft

  116 Nilson Dr, Windham, NY 12496

  Fall in love with the ease of single-level living wrapped in privacy, beauty, and timeless style. Set on three peaceful acres, this thoughtfully reimagined home feels like a hidden retreat -- close to everything, yet wonderfully your own. From the moment you enter, the home welcomes you with warmth and refinement. Arched openings, crown moldings, and curated details create an elegant flow from

  Lisa Jaeger Coldwell Banker Village GreenW

  116 Nilson Dr, Windham, NY 12496
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  /109

  $2,175,000

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

  19 Twin Maples, Windham, NY 12496

  Experience mountain luxury at its finest in this stunning post-and-beam home at Windham Mountain Club's exclusive Village East community just a little over two hours from New York City. Designed for those who love the outdoors but don't want to sacrifice comfort, this 6-bedroom, 3.5-bath retreat spans more than 4,100 sq ft and combines timeless craftsmanship with breathtaking views of the

  Regina Tortorella Coldwell Banker Village GreenW

  19 Twin Maples, Windham, NY 12496
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  /58

  $715,000

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

  60 County Route 65 A, Windham, NY 12496

  Price Cut! Windham Creek Lodge is an active, income-producing short-term rental property generating 70K-80K in annual income. The recent price reduction enhances the profit margin while offering additional room to scale and maximize returns. Fully renovated in 2023-2024, this modern multi-family chalet is ideally located just minutes from Windham Mountain Club and Hunter Mountain—positioning it

  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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  /48

  $749,000

  • 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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  /110

  $1,450,000

  • 6 Beds
  • 6 Baths
  • 4,284 Sq Ft

  93 & 99 Nauvoo Rd, Windham, NY 12496

  Come relax in the cool Mediterranean vibes of this lovingly maintained home with gorgeous GUEST HOUSE. The huge wrap around deck is perfect for your alfresco dining while you enjoy the stunning view of Windham Mtn and your enchanting back yard with cozy pond. Sheltered on two sides by state land, this property is a private oasis yet conveniently located close to town. You will appreciate the

  Sharon Knudsen Coldwell Banker Village GreenW

  93 & 99 Nauvoo Rd, Windham, NY 12496
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  /59

  $759,000

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft

  769 Mitchell Hollow Rd, Windham, NY 12496

  Bright Sparrow Farmhouse - Modern Catskills Farmhouse with Solar Power Backup, Private Pond, Mountain Views & Proven Airbnb Income | Windham, NY Welcome to Bright Sparrow Farmhouse--where modern farmhouse style meets smart, energy-efficient living on over 8.22 private acres with a pond, unobstructed Catskill Mountain views, and a turnkey short-term rental / Airbnb investment property with proven

  Regina Tortorella Coldwell Banker Village GreenW

  769 Mitchell Hollow Rd, Windham, NY 12496
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  /30

  $535,000

  • 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 location for

  Regina Tortorella Coldwell Banker Village GreenW

  20 Sutton Hollow Rd, Windham, NY 12496
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  /74

  $449,000

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

  25 Vets Rd, Windham, NY 12496

  Welcome to your peaceful sanctuary in the heart of Windham, a rare blend of convenience, natural beauty, and endless potential. Just a short stroll from Main Street and less than half a mile from the slopes, this rambling ranch sits in the perfect spot to enjoy everything Windham has to offer while feeling miles away from it all. Surrounded by lush Macintosh apple and pear trees, grape arbors,

  Regina Tortorella Coldwell Banker Village GreenW

  25 Vets Rd, Windham, NY 12496
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  /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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  /67

  $1,749,000

  • 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
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  /106

  $3,250,000 New Construction

  • 6 Beds
  • 5 Baths
  • 5,021 Sq Ft

  219 Club Rd, Windham, NY 12496

  STR Projected Revenue: 161.6K(incl. 13,528 cleaning fee)Occupancy: 42 ADR: 1043 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

  Regina Tortorella Coldwell Banker Village GreenW

  219 Club Rd, Windham, NY 12496
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  /68

  $1,899,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,723 Sq Ft

  4 Goff Rd, Windham, NY 12496

  Are you sitting down? Because this one will take your breath away! This brand new modern mountain masterpiece with an indoor pool, glass walls & slope views is offered fully furnished & turn-key! It's a show stopping contemporary retreat where every inch has been crafted for ultimate luxury, relaxation, and awe-inspiring views. Enveloped in two-story walls of glass, this brand new residence

  Regina Tortorella Coldwell Banker Village GreenW

  4 Goff Rd, Windham, NY 12496
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  /68

  $769,000

  • 3 Beds
  • 2 Baths
  • 2,049 Sq Ft

  39 Brook Hollow Ln, Windham, NY 12496

  Updated Log Cabin Retreat with Private Fishing Pond & Flowing Stream in the Catskills If you've been dreaming of a place that feels completely tucked away in nature--yet just minutes to town and the slopes--this one delivers in all the right ways. Set at the end of a quiet cul-de-sac, this rustic log home is surrounded by 4 private acres with your own pond and a flowing stream that you can

  Regina Tortorella Coldwell Banker Village GreenW

  39 Brook Hollow Ln, Windham, NY 12496
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  /44

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  97 Carrington Rd, Windham, NY 12496

  Streamfront Serenity Meets Mountain Views -- Bordering Protected NYC DEP Lands Bordered by 160 acres of DEP land and the pristine Batavia Kill Creek, this beautifully updated split-level retreat delivers the kind of setting buyers come to the Catskills for--wide open meadows, mountain views, and the calming sound of water just steps from your back deck. This is where privacy, nature, and

  Regina Tortorella Coldwell Banker Village GreenW

  97 Carrington Rd, Windham, NY 12496
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  /49

  $599,000

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft

  150 Vining Rd, Windham, NY 12496

  150 Vining Road, Windham, NY Beautifully renovated contemporary mountain retreat set on 1 acre of lush lawn just minutes from the Windham Mountain Club. Blending rustic charm with modern finishes, this inviting home offers 1,394 square feet of above-grade living space plus an additional 788 square feet in the finished lower level--totaling 2,182 square feet of living space designed for

  Regina Tortorella Coldwell Banker Village GreenW

  150 Vining Rd, Windham, NY 12496
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  /44

  $499,000

  • 3 Beds
  • 3 Baths
  • 1,566 Sq Ft

  13 Brainard Ridge Rd, Windham, NY 12496

  5 Years New! Stylishly Renovated Townhome in the Heart of Windham Mountain Club. Renovated approximately five years ago and move-in ready, this beautifully updated 3-bedroom, 3-bath townhome offers exceptional value in the heart of the growing Windham Mountain Club community. With 1,566 square feet of living space across three thoughtfully designed levels (includes the finished basement), the

  Regina Tortorella Coldwell Banker Village GreenW

  13 Brainard Ridge Rd, Windham, NY 12496
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  /77

  $599,900

  • 3 Beds
  • 3 Baths
  • 1,870 Sq Ft

  513 County Road 10, Windham, NY 12496

  Mountain Majesty Meets Everyday Luxury on 2.8 Serene Acres! Escape to the perfect blend of rustic warmth and contemporary functionality. Nestled against the spectacular backdrop of Windham Mountain, this exceptional log home effortlessly serves as an active full-time residence or the ultimate four-season mountain getaway. The main level features a bright, open-concept floor plan designed for both

  Ted Banta RVW Select Properties

  513 County Road 10, Windham, NY 12496
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  /43

  $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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  /54

  $699,000

  • 7 Beds
  • 3 Baths
  • 3,485 Sq Ft

  200 & 212 Co Rd 40, Windham, NY 12496

  HISTORIC Batavia Kill Property - 7.2 Acres with Redevelopment Potential.A rare multi-use setting along the scenic Batavia Kill, featuring open meadows, sweeping hill views, and a peaceful natural backdrop. Land directly across the road is owned by New York City, helping preserve the quiet surroundings and open character of the area. The location is prime only 3.5 miles to Windham Ski Resort

  Susan Lennon Coldwell Banker Timberland

  200 & 212 Co Rd 40, Windham, NY 12496
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  /55

  $599,000

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

  5376 State Route 23, Windham, NY 12496

  Prime location and versatility make this Main Street Windham offering an outstanding opportunity. High visibility at one of the town's busiest intersections is not only great exposure but a rare find. For decades, this building was the home and shop of the local barber. In recent years the street level space served as the main office for a local builder. Currently vacant, this property has great

  Sharri Cunningham Bunce Realty

  5376 State Route 23, 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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  /47

  $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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  /34

  $695,000

  • 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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  /31

  $525,000

  • 3 Beds
  • 1.5 Baths
  • 2,084 Sq Ft

  34 Old Rd, Windham, NY 12496

  Discover an exceptional Windham, NY mountain retreat just ~2 miles from Windham Mountain, offering both lifestyle appeal and income potential. This spacious, rustic 3-bedroom, 1.5-bath home features two separate living rooms—one on the first floor and one on the second floor—providing flexible space for entertaining, relaxing, or multi-group living. A cozy fireplace, open living areas, modern

  Michael Mariani Patricia Forgione's Realty

  34 Old Rd, Windham, NY 12496
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  /12

  $550,000

  • 2 Beds
  • 1 Bath
  • 1,122 Sq Ft

  183 N South St N, Windham, NY 12496

  Exceptional Opportunity in a Prime Windham Location! property is sub- dividable. Owner is motivated bring offers!!!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

  John Pumilia Shaw Country Realty, Inc.

  183 N South St N, Windham, NY 12496
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  /41

  $1,650,000

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft

  10 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

  10 Stonewall Ln, Windham, NY 12496
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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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  /41

  $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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  /77

  $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

Showing Results 1 - 40, Page 1 of 2