Windham NY Real Estate & Homes for Sale

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Beds:
5
Baths:
3.00
Sq.Ft.:
2,268
Status:
NEW LISTING
MLS#:
20266660
Type:
Single Family
Lot size:
0.55 Acres
Year built:
1989
A broker reciprocity listing Courtesy: Shaw Country Realty, Inc. 518-734-3500
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ADDITIONAL INFORMATION

WINDHAM - BEAUTIFULLY MAINTAINED DUPLEX WITH INCOME POTENTIAL! A fantastic opportunity to own a versatile two-family property in the heart of Windham's four-season playground! Both apartments are completely above grade, offering bright, comfortable living spaces with separate outdoor decks. The spacious upper-level apartment features 3 bedrooms, 2 full baths, a flex room (3rd bedroom)vaulted ceilings, and an inviting open-concept kitchen and living area with a cozy fireplace. Sliding glass doors lead to a deck with lovely country views. The lower-level apartment offers 2 bedrooms, 1 full bath, an additional flex room perfect for a home office or flexible use, and its own deck. Situated on a manageable, low-maintenance parcel, leaving more time to enjoy everything Windham has to offer! The upper apartment is currently being used as an Airbnb, offering an attractive opportunity for rental income. Live in one and rent the other, enjoy the entire property with extended family, or explore the potential for two income-producing units. Just minutes to Windham Mountain Club, golf, restaurants, hiking, walking paths, and year-round activities. A smart investment, weekend getaway, or full-time residence with income potential in one of the Catskills' most desirable four-season destinations!

Beds:
5
Baths:
5.00
Sq.Ft.:
4,117
Status:
NEW LISTING
MLS#:
20266662
Type:
Single Family
Lot size:
1.2 Acres
Year built:
2003
A broker reciprocity listing Courtesy: Shaw Country Realty, Inc. 518-734-3500
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ADDITIONAL INFORMATION

Impressive Windham Center Hall Colonial - 5 Bedrooms, 4.5 Baths, Mountain Views! Space, elegance, comfort, and incredible entertaining potential! This impressive Center Hall Colonial offers 5 spacious bedrooms, 4.5 baths, hardwood floors throughout, soaring ceilings, and beautiful views of the Windham Mountain slopes. With multiple living areas and a versatile floor plan, this home is ideal for large family gatherings, a four-season mountain retreat, or an Airbnb investment property with excellent rental potential! Enter through the grand center hallway, where high ceilings create a wonderful first impression. To the left, a spacious room with French doors offers flexibility as a bedroom, additional family room, or home office. To the right, a cozy living room flows into the generous dining area and large, sun-filled kitchen featuring stainless steel appliances, double ovens, a wine cooler, and oversized windows framing the mountain views. Just beyond the kitchen is another inviting family room with a fireplace, perfect for relaxing after a day on the slopes. A convenient half bath completes this level. Upstairs, you'll find three spacious bedroom suites, each with its own private bath, large windows, and plenty of natural light. The finished lower level offers even more room to spread out, featuring an additional ensuite bedroom, a comfortable family room, and a large utility/recreation area. Plenty of space for guests, game nights, or simply enjoying time together! Step outside to the expansive rear deck with hot tub, ideal for entertaining or unwinding in the fresh mountain air. Additional features include oil heat and central air conditioning. and a 2 car attached garage. Location, location, location! Less than one mile to charming Windham Village and just minutes to Windham Mountain Club, golf, restaurants, shops, and year-round activities. So much house, so many possibilities! Whether you're looking for a spacious family getaway, a full-time residence, or an income-producing investment, this property offers it all. Ideal for Airbnb or vacation rental income, subject to local regulations, with five bedrooms, multiple gathering spaces, private bedroom suites, and a fantastic location near Windham's year-round attractions. Enjoy it yourself, rent it out, or do both! A must-see Windham investment opportunity!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,276
Status:
NEW LISTING
MLS#:
20266626
Type:
Condo
Lot size:
0.01 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

DIRECT SKI-IN/SKI-OUT LIVING WITH RESORT-STYLE AMENITIES AT WINDHAM MOUNTAIN CLUB! Wake up to mountain views, step into your gear and ski directly from one of Windham Mountain Club's most desirable buildings. Enclave Unit 307 presents a rare opportunity to own in a premier slopeside setting where residences seldom come to market. Direct ski-in access, a heated pool, hot tubs, fitness room, heated garage and private ski locker make every stay effortless, whether you are arriving for first tracks, a summer mountain escape or a relaxing weekend away. Originally showcased as the building's model residence, this impeccably maintained two-bedroom, two-bath condominium features a collection of upgraded finishes. Gleaming hardwood floors flow through the great room, where a fireplace, custom built-in shelving and cabinetry, and access to a spacious balcony create an inviting place to gather against a backdrop of picturesque mountain views. The custom kitchen is appointed with granite countertops, a breakfast bar and stainless-steel appliances. The en-suite primary bedroom enjoys private balcony access and a luxurious bath with double vanities, a tiled glass-enclosed shower and jetted tub. A custom barn door opens to the second bedroom and adjacent full bath. Every room offers a view, while in-unit laundry adds everyday convenience. Tastefully decorated and offered furnished with high-end pieces from Restoration Hardware and Ralph Lauren, Unit 307 is ready to enjoy from day one. From mornings on the slopes to evenings by the fire, this is more than a mountain residence - it is the Windham lifestyle at its most effortless. Opportunities to purchase in the Enclave are few and far between, making this a rare chance to own in the heart of the resort. A 3D Walkthrough Tour is available by request.

Beds:
4
Baths:
4.00
Sq.Ft.:
1,717
Status:
NEW LISTING
MLS#:
20266582
Type:
Townhouse
Lot size:
0.02 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Welcome to Crystal Pond, a beautifully maintained country townhouse community nestled on 20 picturesque acres of rolling lawns, mature trees, ponds, and a meandering creek, surrounded by the Catskill Mountains. With buildings thoughtfully spread throughout the property, there's plenty of breathing room and a wonderful country feel. A place to slow down, enjoy the fresh mountain air, and make the most of every season. This well-appointed 4-bedroom, 3.5-bath townhouse offers three levels of comfortable living with room to gather, relax, and unwind. Cherished by the same owners for the past decade, this inviting retreat has been beautifully maintained and is offered fully furnished and stocked, ready for its next chapter. Just arrive and enjoy! The main level features a mudroom entry, powder room, laundry, and a spacious open-concept floor plan with ceramic tile and wood laminate flooring. Multiple seating areas offer inviting spaces to gather or simply relax. The well-equipped kitchen with granite countertops and breakfast bar flows into the dining area and living room, where a handsome wood-burning fireplace creates a cozy gathering spot to unwind and recount the day's adventures. Glass sliders open to an outdoor patio with BBQ and green lawn, perfect for morning coffee or summer dining. The second floor offers two bedrooms, each with a private ensuite bath. Two additional bedrooms on the third floor include a bunk room with desk area and a guest bedroom sharing a full bath. Plush Berber carpeting, excellent storage, three mini-splits for heating and cooling, and a stairlift to access the second floor. Life at Crystal Pond is about enjoying the surroundings. Stroll the landscaped grounds, cool off in the outdoor swimming pool, and enjoy the welcoming, dog-friendly community. Come winter, take advantage of one of the best perks: door-to-door ski shuttle service to Windham Mountain Club! Leave the car behind and skip the mountain parking hassle. Hunter Mountain, CD Lane Park, golf, hiking trails, and Windham's Main Street restaurants and shops are all close by. Pride of ownership is evident throughout, with attentive management, beautifully maintained grounds, assigned parking, and a roof just five years old. Short-term rentals are permitted, offering flexibility for personal enjoyment and potential rental income. Lock the door and leave your worries behind! Four seasons of Catskills living, without the upkeep. Come for the mountains, stay for the memories!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,824
Status:
NEW LISTING
MLS#:
20266568
Type:
Townhouse
Lot size:
0.03 Acres
Year built:
1983
A broker reciprocity listing Courtesy: Brainard Ridge Management 518-734-5333
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ADDITIONAL INFORMATION

Unique Elm Ridge Townhome Welcome to the distinctive character of this beautiful 3 bedroom, 3 bath Elm Ridge Townhome, Elm Ridge offers a feeling of peaceful tranquility, amongst the surrounding woodlands. This lovely turnkey Townhome exudes pride in ownership, with its bright open kitchen complete with granite counters, Jenn Air convection oven, Jenn-Air cooktop, Bosch dishwasher, Kitchen Aide Refrigerator, and warm classic cabinetry. Plenty of room in the dining area for family and friends to gather over memorable meals. Spacious, well designed living room tastefully furnished with comfortable sofas and chairs for you to relax around the welcoming wood-burned brick fireplace after a day in the great outdoors. The open and airy living area offers large windows and sliding doors to let in an abondance of natural light while giving you access to wonderful warp around decking, complete with an outdoor table, Adirondack chairs, cozy outdoor gas firepit to enjoy stunning sets and take in the sounds of nature. The upper level offers Primary bedroom with ensuite bath with king bed, and two more spacious bedrooms ( one with 2 full beds, one with a single bed) as well a third full bath. Each bedroom also has a balcony that extends the full length of the townhome. The finished lower level has a well-equipped laundry room and custom built in cabinetry for plenty of storage space. Elm Ridge is known for its well-run HOA with low maintenance fees! You can choose to join The High Ridge Club with pool and tennis for summer enjoyment. Come and explore the Catskills in this maintenance free home. Minutes from Windham or Hunter Mountain ski areas, many restaurants, hiking trails, biking, golf courses, day spas, yoga, indie bookstore and shopping.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,448
Status:
Active
MLS#:
20266435
Type:
Single Family
Lot size:
6.8 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

**Windham's Hidden Gem: Private Pond & Mountain Views** An incredible opportunity awaits on one of Windham's most desirable roads, where nearly seven acres of beautiful countryside, lush lawns, a private pond, and mountain views create an exceptional setting just minutes from Main Street and Windham Mountain Club. Offering character, privacy, and room to grow, this 3-bedroom, 2-bath cottage presents exceptional value in a sought-after Catskills location--whether you're searching for a full-time residence, vacation home, or a property with potential for your future vision. Inside, exposed wood beams bring warmth and character to the main living area, complementing the cottage's country setting. The kitchen features granite countertops, a center island, and an adjoining dining area, while the sun-filled living room opens through French doors to a private patio. A first-floor bedroom with an ensuite bathroom offers views of the surrounding grounds and access to the deck. A second full bathroom completes the main level, while a spiral staircase leads upstairs to two additional bedrooms. A one-car garage adds everyday convenience. Outside, an expansive deck sets the scene for summer dinners, lively gatherings, and quiet evenings overlooking the grounds. Lush lawns stretch toward the private pond, framed by wooded acreage, a gazebo, and walking paths that invite you to explore. There is space here to spread out, reconnect with nature, and enjoy the changing Catskills seasons. Adding to the opportunity, a second beautiful building envelope offers pond and mountain views, and a recent satisfactory perc test has been completed on the property. Enjoy the cottage today while imagining a larger home in the future, with the existing residence potentially serving as a guest house, subject to required approvals. The combination of an inviting home, generous acreage, and future building potential makes this one of Windham's hidden gems. Conveniently located near skiing, golf, hiking, biking, restaurants, and shops, this property brings together the privacy of a country retreat with easy access to the heart of Windham. A remarkable opportunity to enjoy the mountain lifestyle now, with room for your plans to evolve. A 3D Walkthrough Tour is available by request.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,339
Status:
Active
MLS#:
20266268
Type:
Single Family
Lot size:
0.25 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Shaw Country Realty, Inc. 518-734-3500
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ADDITIONAL INFORMATION

INVESTOR OPPORTUNITY IN THE HEART OF HENSONVILLE! Calling all investors, contractors, and creative buyers! Here's your chance to bring new life to a property in the increasingly popular hamlet of Hensonville, Town of Windham! A true handyman special with plenty of potential!** Originally a two-family home, the property has since been combined into one residence, offering possibilities for renovation and reconfiguration. The home is in need of substantial cleanup, repairs, and updating, but for the buyer with vision, the location makes it worth a look! A major plus is the connection to municipal water and sewer, offering added convenience for future improvements. The property is presently occupied. Enjoy the charm of Hensonville, with new eateries, dining options, and an event venue just steps away. Only minutes to Windham Mountain Club and Hunter Mountain, golf courses, scenic walking paths, hiking trails, and all the four-season activities that make the Mountaintop such a desirable destination. Bring your imagination, your tools, and your vision! Whether you're looking for a renovation project, investment opportunity, or a place to create your own mountain retreat, this property offers an opportunity to invest in a growing community. Location, potential, and possibilities -- the rest is up to you!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,872
Status:
Active
MLS#:
20266229
Type:
Single Family
Lot size:
2.6 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Shaw Country Realty, Inc. 518-734-3500
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ADDITIONAL INFORMATION

**WINDHAM RETREAT - TURNKEY, PRIVATE & INVESTMENT READY!** Location, privacy, views, and rental potential. Nestled along a beautiful country road on 2.6 acres and surrounded by NYC Watershed property, this updated and beautifully maintained 4-bedroom, 2-bath home offers a peaceful Catskill escape just minutes from Windham Mountain Club, golf courses, restaurants, and Windham Village. **OUTDOOR LIVING AT ITS BEST!** - Spacious front deck with scenic mountain views - Rear deck perfect for entertaining - Hot tub, grill, and firepit - Peaceful surroundings with NYC Watershed property adjacent. Comfortable interior with - 4 bedrooms and 2 full baths - Lower level with bedroom, full bath, game room, and private sauna - Bright upper-level living area with wood-burning stove and beautiful views - Eat-in kitchen overlooking the living area - Tastefully updated and beautifully maintained throughout **EXTRA CONVENIENCES** - Full-house generator - One-car garage - Fully turnkey and ready to enjoy or rent! A GREAT OPPORTUNITY FOR THE SAVVY INVESTOR! All the comforts and amenities are already in place. Whether you're looking for a weekend getaway, year-round residence, or income-producing investment, this property is ready to go! Four seasons of fun are right at your doorstep! Skiing, golf, hiking, mountain biking, and charming village restaurants are all just minutes away. Move right in, start making memories, or explore the rental potential. Windham is the place to be!**

Beds:
4
Baths:
2.00
Sq.Ft.:
1,668
Status:
Active
MLS#:
1064762
Type:
Single Family
Lot size:
0.28 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
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ADDITIONAL INFORMATION

A four bedroom, two bath home in the village of Hensonville, 1,668 square feet on just over a quarter acre, built in 1900. Public water and public sewer, oil heat, annual taxes of $1,830. Four bedrooms at this size and this address is the part worth noting. The house sits in the village itself, walkable, minutes to Windham Mountain Club and its capital program north of $70 million, and a short drive to Hunter. Weekend house, full time home, or a rental that already has a tenant paying $1,600 a month. Currently tenanted. Showings by appointment with notice to the occupant. All information deemed reliable but should be independently verified.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,113
Status:
Active
MLS#:
1064569
Type:
Single Family
Lot size:
0.39 Acres
Year built:
1895
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
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ADDITIONAL INFORMATION

An 1895 village home on Goshen Road with a separate apartment, 2,113 square feet on 0.39 acres, currently producing $3,100 a month. Public water and public sewer, oil hot water heat, annual taxes $2,080. The location is the story. Goshen Road sits in the heart of the village, directly across from The Henson, and Windham Mountain Club is minutes away, now midway through a capital program north of $70 million. Buy it as a home with income that helps carry it, or as a weekend place with a rental to offset the cost. The second unit is already tenanted. A house of this age in the center of Windham, on municipal water and sewer, is not a thing that comes along often. Rent roll, leases and tax bills available on request. Buyers should verify all information independently.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,270
Status:
Active
MLS#:
20266256
Type:
Single Family
Lot size:
2 Acres
Year built:
1991
A broker reciprocity listing Courtesy: Venture Fox Realty Group 518-290-1070
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ADDITIONAL INFORMATION

Enjoy Catskills living at 125 Vining Road in Windham. Set on 2 acres, this three-bedroom, two-bath home offers approximately 1,718 square feet across two levels. A front porch and rear deck provide inviting spaces to relax and enjoy the wooded surroundings. Inside, the layout includes living and dining areas, while a full finished basement and outdoor shed provide additional rooms. Conveniently located near Windham's skiing, hiking, golf, restaurants, and shops, this property offers an appealing opportunity for short-term rental investors. Its three-bedroom layout and manageable size are well suited for an Airbnb mountain getaway. An inviting option for a year-round residence, vacation retreat, or investment property.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,295
Status:
Active
MLS#:
20266027
Type:
Townhouse
Lot size:
0.02 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Shaw Country Realty, Inc. 518-734-3500
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ADDITIONAL INFORMATION

CRYSTAL POND TOWNHOUSE - PRICED TO SELL! Location, Convenience & Opportunity! Just minutes from Windham Mountain Club, this bright and sunny corner townhouse at Crystal Pond offers a fantastic opportunity to own your own mountain getaway at an affordable price! Being sold ''as is,'' this unit is ready for a little TLC, including fresh paint and minor repairs, to make it your own. The townhouse features plenty of natural light and a convenient walk-in shower designed for accessibility. 2 bedrooms with surround windows, an open kitchen to living room with a stone wood burning fireplace to relax after a day on the slopes. For summer months, enjoy the outdoor pool nestled in a private location. Crystal Pond offers shuttle service to and from Windham Mountain Club, making ski days a breeze! Enjoy four seasons of activities with nearby state hiking trails, the Windham Path, golf, and a wonderful selection of local restaurants. Hunter Mountain is just 15 minutes away! Whether you're looking for a weekend retreat, a year-round escape, or an investment opportunity, this townhouse offers great potential in a desirable Windham location. Bring your vision and make it your own! Priced to sell! HOA is 600 per month. Easy maintenance for the weekend adventurer

Beds:
3
Baths:
2.00
Sq.Ft.:
1,295
Status:
Active
MLS#:
20265990
Type:
Single Family
Lot size:
2.1 Acres
Year built:
1980
A broker reciprocity listing Courtesy: Shaw Country Realty, Inc. 518-734-3500
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ADDITIONAL INFORMATION

Escape to the mountains! Located in the Town of Windham, this cute 3-bedroom, 2-bath cottage is just steps from hundreds of acres of State hiking trails in Maplecrest and just up the road from CD Lane Park. The home could use a little sprucing up, but offers a wonderful opportunity to make it your own. Used for many years as a summer cottage, this home needs updated electric to heat the house better . The wood burning stove is not hooked up and the chimney was closed off when the oil was eliminated. Whether you're looking for a weekend getaway, a year-round home, or a base camp for all your Catskill adventures, this cottage puts you close to hiking, swimming, skiing, golf and everything the Mountain Top's four-season community has to offer. A perfect retreat for the outdoor enthusiast in you! Nestled at the end of a dead end road , just step outside and start hiking. This property is being sold ''as is''

Beds:
4
Baths:
3.00
Sq.Ft.:
2,340
Status:
Active
MLS#:
20265888
Type:
Single Family
Lot size:
1 Acres
Year built:
1986
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Morning coffee on the deck, days spent exploring the Catskills, and evenings gathered beside the fire--28 McGovern Road captures the relaxed mountain lifestyle that makes Windham such a special place to call home. Privately sited on one acre surrounded by mountains, this cedar-sided saltbox offers a peaceful setting just approximately five minutes from Main Street. Inside, new hardwood floors, a vaulted ceiling with exposed beams, and an open floor plan create a warm, inviting atmosphere. The great room's fireplace anchors the gathering space, setting the scene for cozy après-ski evenings and leisurely weekends. A spacious kitchen with a breakfast bar makes casual dining and conversation easy, while the adjoining dining and living areas provide room to gather and entertain. Sliding glass doors from both the dining and living rooms open onto the deck, creating an effortless flow between indoor and outdoor living. Enjoy summer dinners outside, quiet mornings in the mountain air, pretty seasonal mountain views, and a welcoming backyard with space to relax, play, or garden. The finished walkout lower level adds flexible living space, including a convenient ski and boot room area--a practical place to organize gear after a day of winter adventure. Life in Windham invites you to enjoy every season: skiing and fireside evenings in winter, hiking and golf in warmer months, and brilliant Catskills foliage in fall. With Main Street's shops and dining just minutes away, you can enjoy both the privacy of a mountain retreat and the pleasures of small-town living. Whether envisioned as a full-time residence or a weekend escape, 28 McGovern Road offers a comfortable home base for making Windham memories. A 3D Walkthrough Tour is available by request.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,115
Status:
Active
MLS#:
20265868
Type:
Townhouse
Lot size:
0.3 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Brainard Ridge Management 518-734-5333
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ADDITIONAL INFORMATION

Timeless Timber Frame Townhome Walk to Trails from this Graceful, Timeless Timber Frame Townhome, warmth and charm exudes from this 3 bedroom plus loft, 3.5 bath Windham Beauty. Lovely entrance with sizable ski and boot room, opening to vaulted ceiling living room with plenty of windows to take in the valley views, tasteful furnishings to relax around the impressive stone wood burning fireplace. Spacious kitchen and dining area to entertain friends and family. Wonderful decking to gaze upon the beautiful valley views. The upper level offers an open loft area leading to a tastefully furnished Primary bedroom with spacious ensuite bath. Gracious stairway leads you to lower level with a family room to enjoy movies, games, a full bath, a 2nd bedroom with 2 singles and a 3rd comfortable guest ensuite bedroom. The convenience of an attached heated garage, laundry room, radiant oil heat and A/C splits add to the amenities. Located on Windham Clubs west side, don't miss this opportunity to make Windham your 4 season getaway, enjoy skiing, boarding, hiking, golf, biking, fresh clear streams and lakes, farmers market, fine restaurants, local shops, indie bookstore, cafes, movies, yoga, day spas and more.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,600
Status:
Active
MLS#:
20265814
Type:
Single Family
Lot size:
0.7 Acres
Year built:
1971
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

This Windham Mountain Club chalet sits on one of the Club's largest lots along the ski slopes. Come home for lunch, shed a layer, and head back out--or settle in for an afternoon watching skiers and snowboarders glide past. Here, every weekend feels like a mountain vacation. The moment you step inside, a large, heated ski and boot room with bluestone flooring welcomes you and your gear--a thoughtful, functional introduction to a home designed around ski life. Upstairs, the entire main floor unfolds into an expansive open plan connecting the great room, game room, kitchen, and dining area, with a convenient half bath. Soaring pine-clad vaulted ceilings, beautiful wood floors, and a wall of glass create a bright, inviting setting drenched in natural sunlight. A dramatic floor-to-ceiling stone wood-burning fireplace anchors the space, bringing warmth and character to every gathering. There is room for everyone to come together while enjoying different activities: play pool in the game area, prepare dinner in the kitchen, or relax beside the fire, all within the connected main floor. Log staircase railings blend European chalet charm with rustic Catskills character, while the updated kitchen--with granite countertops, stainless steel appliances, and a breakfast bar-- brings modern convenience to the mountain setting. Multiple access points open onto the front deck, where views of the ski slopes, and the energy of mountain life become part of your day. Five bedrooms, including two ensuites, and four-and-a-half baths provide comfortable accommodations, complemented by a finished den with a separate entrance. Air conditioning in the great room and primary suite adds comfort for year-round enjoyment. Return from the slopes to your outdoor sauna, soak in the hot tub, and finish the evening beside the wood-burning fireplace. Multiple porches and the recently stained deck extend the living spaces outdoors. The exceptionally large lot is another defining feature, offering room to explore a home addition, an outdoor firepit gathering area, or possibly a pool in the side yard, subject to applicable approvals. Imagine pairing effortless ski access with your own summer retreat. Renovation since 2008 purchase, include converting/upgrading the heating system to propane, running all new electric throughout the house and expanding the size of the primary suite. The exterior was painted in 2025. Most furnishings included. This Windham ski chalet offers an inviting personal escape with potential short-term rental appeal. From first tracks to fireside evenings, this is mountain living worth coming back to. A 3D Walkthrough Tour is available by request.

Beds:
13
Baths:
12.00
Sq.Ft.:
10,900
Status:
Active
MLS#:
20265730
Type:
Single Family
Lot size:
2.5 Acres
Year built:
1835
A broker reciprocity listing Courtesy: Win Morrison Realty - W 845-679-9444
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ADDITIONAL INFORMATION

WINDHAMERE 1835 · Catskills Greene County Historical Register Historic Inn Windham, NY. Some properties are bought. This one is claimed. For nearly 190 years, Windhamere has had only two private owners. Built in 1835 and listed on the Greene County Historical Register, it was rebuilt from 1998 to 2001 as a modern compound: landmark bones, contemporary systems, and town-approved multi-unit use -- steps from the Windham Mountain ski lifts. From the wraparound porch, Windham Mountain is the view. The house faces the slopes and borders Windham Country Club. 2.5 open, usable acres at the seam of village and mountain. South Street is Windham's ski-and-village spine: lifts, golf, tubing, and trails on one side and Main Street a short stroll on the other. Nearly 11,000 sq ft finished. Main residence sits at 7,000 sq ft: 8 bedrooms (6 ensuite), 6.5 baths. A 1,200 sq ft great room opens to the golf course. Three private, town-approved accessory apartments -- a 1BR, a 2BR, and a 2BR -- each with its own entry. Use them for family, staff, or income. The units are currently income-producing and season-tested. A landmark that can host a crowd and help pay its own way year-round. Windham Mountain Club's owners have invested tens of millions into lifts, snowmaking, dining, golf, and year-round amenities, with more still to come. Plenty of room to expand and grow with access to municipal water and sewer.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,572
Status:
Active
MLS#:
20265733
Type:
Single Family
Lot size:
5 Acres
Year built:
1981
A broker reciprocity listing Courtesy: Keller Williams Realty HV Nort 845-481-2700
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ADDITIONAL INFORMATION

Just minutes from the slopes of Windham and Hunter Mountains, this contemporary Catskills retreat sits tucked away on five secluded acres, offering privacy, space and that true mountain getaway feeling, all about 2½ hours from New York City. Step inside to an open floor plan with a sunken living room, soaring ceilings and a freestanding wood stove at the heart of the home. Two sets of sliding glass doors, one from the living room and another from the dining room, connect the living spaces to the outdoors and bring the surrounding woods into view. Three bedrooms and two full baths provide plenty of room for company. The extensive decking, while in need of repair, offers plenty of outdoor space to dine, gather and unwind among the trees. A full unfinished basement provides generous storage and additional possibilities, while a newer roof adds an important update. There's an authenticity to this home that's increasingly hard to find in Windham. It has been enjoyed as a mountain retreat for years and is ready for its next owner to bring a fresh perspective and make it their own. Offered with its current character and future possibilities in mind, the price creates an opportunity to own five private acres this close to the mountain and add value along the way. Whether you envision a ski house, weekend escape or full-time Catskills home, 50 Mount Greenery puts you close to hiking, golf, farm-to-table restaurants, antique shops, wineries and breweries, with Catskill, Hudson and Woodstock all within reach. Come for the mountains, stay for everything else the Catskills have to offer.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,702
Status:
Active
MLS#:
20265654
Type:
Townhouse
Lot size:
0.21 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Brainard Ridge Management 518-734-5333
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ADDITIONAL INFORMATION

Turnkey! Brainard Ridge Large 3 bedroom 2.5 bath plus sleeping alcove, end unit with room to expand if needed on large property foot print, see map. Lovely renovation, Enter to Ski entrance with radiant heated floor, gorgeous hardwood floors, freshly painted and quality carpet. Open and airy floor plan, upgraded appliances, and wine bar. Great room has extra windows to bring in the natural light, cathedral ceilings, striking gas fireplace, with barn beam mantle. Roomy dining area, with sliding doors to private extended deck. Large primary ensuite complete with cathedral ceilings, large loft with large built-in desk and glass privacy wall. Lower level offers 2 spacious bedrooms, one having private door amazing second deck complete with hot tub, classic red Windham triple chair, fenced in dog run, hot-cold water spigot, dual heat/AC, hunter Douglas window treatments and much more. This is a must see. Being sold with all basic furnishings. Also, possibly available for season rental

Beds:
9
Baths:
8.00
Sq.Ft.:
10,611
Status:
Active
MLS#:
1044804
Type:
Single Family
Lot size:
5.52 Acres
Year built:
2009
A broker reciprocity listing Courtesy: Keller Williams Village Sq Rlt 201-445-4300
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ADDITIONAL INFORMATION

Set on 5.52 private acres amid the mountains of Windham, this extraordinary nine-bedroom estate offers a rare combination of architectural character, impressive scale, and resort-style living. Dramatic timber framing, soaring ceilings, expansive windows, and seven interior fireplaces create a warm yet grand atmosphere throughout. The open-concept kitchen and generous gathering spaces are designed for effortless entertaining, while multiple levels provide exceptional flexibility for guests and extended stays. At the heart of the home is an indoor in-ground pool, complemented by a private theater, separate recreation room, dedicated gym, and highly efficient mechanical systems designed to support the home’s substantial scale. Expansive wraparound decks extend the living experience outdoors with a hot tub, outdoor fireplace, and firepit surrounded by a wooded mountain setting. Located just five minutes - approximately 1.7 miles from Windham Mountain Club and Windham Mountain, the estate is ideally positioned for year-round recreation. Whether envisioned as a private mountain retreat, multigenerational residence, or income-producing luxury rental, this is a truly distinctive Catskills offering.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,276
Status:
Active
MLS#:
20265510
Type:
Single Family
Lot size:
5.2 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Bunce Realty 518-734-4461
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ADDITIONAL INFORMATION

Contemporary Mountain Retreat Near Windham Mountain Welcome to this charming contemporary mountain-style ski home, ideally located just minutes from Windham Mountain. Built in 1987 and lovingly maintained by its original owners, this three-bedroom, two-bath home offers a peaceful and private setting bordering state land and surrounded by the natural beauty of the Catskills. The light-filled interior features a spacious kitchen and dining area that flows into an open living room with vaulted ceilings and a beautiful stone, wood-burning fireplace--creating a warm and inviting space for relaxing after a day on the slopes or enjoying time with family and friends. The home offers three comfortable bedrooms and two full baths, including one with a sauna and another with a jacuzzi for the ultimate in relaxation. Step outside onto the private deck, perfect for morning coffee, outdoor dining, entertaining, or simply enjoying the tranquil surroundings. An oversized attached garage provides excellent space for vehicles, recreational equipment, and storage. The property is being offered fully furnished and move-in ready, providing an easy opportunity to enjoy the Windham lifestyle from day one. Just minutes from everything Windham has to offer, including skiing, fine dining, hiking, golf, and year-round outdoor recreation, this inviting mountain getaway is ready to become your Catskill retreat.

Beds:
1
Baths:
1.00
Sq.Ft.:
458
Status:
Active
MLS#:
20265434
Type:
Condo
Year built:
1960
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 838-877-8283
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ADDITIONAL INFORMATION

This is your mountain getaway that offers ease, amenities, and an affordable price - a second-floor condo with views of Windham ski mountain and a rental option allowing you to bring in income when you aren't there. The unit is part of the updated Winwood complex at the Windham Mountain Club. Easily accessible to the village of Windham's many shops and restaurants, it is also just a few minutes away from the slopes with free shuttle service provided during ski season. In the summer, you can enjoy the large saltwater pool or venture to some of the Catskills finest hiking and mountain biking trails or golf courses. The condo comes fully turn-key - all furniture and effects are included. Efficiently using space, there is a kitchenette with ample cabinetry, microwave, dishwasher and a cooktop. The cozy living room also has space for a dining table and connects to the balcony where you can take in the mountain views. The separate bedroom and full bath are all you need to rest and recharge for another day out on the mountain. Amenities - in addition to what was already mentioned - include guaranteed access to lift tickets for Windham Mountain, on-site parking with EV charger, as well as an on-site fitness center, game room, movie theater, and laundry area. Let this be your Catskills homebase so you can use your time away for what it's meant for - time to explore and recharge.

Beds:
5
Baths:
2.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
20265408
Type:
Single Family
Lot size:
0.76 Acres
Year built:
1957
A broker reciprocity listing Courtesy: Shaw Country Realty, Inc. 518-734-3500
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ADDITIONAL INFORMATION

Beautifully Renovated Two-Family Ranch - Income Potential & Flexible Living! Located in the charming Village of Maplecrest, Township of Windham, this completely renovated side-by-side two-family ranch offers a wonderful combination of location, versatility and income potential. One side features 3 bedrooms while the adjoining unit offers 2 bedrooms, making it ideal for rental income, a mother-daughter setup, extended family, home office, or the opportunity to live in one side and rent the other. Tastefully renovated throughout and move-in ready. Enjoy four seasons of outdoor recreation right outside your door, with Windham and Hunter ski areas both within 10 minutes, CD Lane Park just up the road, and hundreds of acres of state land and hiking trails nearby. Lakes, golf courses, wedding and entertainment venues, skiing, hiking and year-round recreation surround you. With ski season right around the corner, now is the time to buy and enjoy your own Mountain Top retreat instead of renting! Become part of the wonderful Maplecrest community and enjoy everything the Windham area has to offer. Whether you're looking for a primary home, weekend escape, extended-family property or income-producing investment, this beautifully renovated and versatile property is ready to enjoy.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,457
Status:
Active
MLS#:
20265361
Type:
Single Family
Lot size:
0.36 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Dugo Realty 518-719-5926
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ADDITIONAL INFORMATION

Welcome to this inviting 3-bedroom, 2-bathroom home offering a spacious and comfortable layout with plenty of room to make it your own. Set on approximately 0.36 acres, the property offers outdoor space to enjoy along with ample off-street parking for multiple vehicles. Inside, you'll find versatile living spaces suited for everyday living, entertaining, or relaxing at home. Whether you're looking for a full-time residence or a Catskills getaway, this home offers a great opportunity to enjoy all that the area has to offer. Schedule your private showing and come see it for yourself!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
20265368
Type:
Townhouse
Lot size:
0.03 Acres
Year built:
1979
A broker reciprocity listing Courtesy: RHR Realty Group 518-610-1281
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ADDITIONAL INFORMATION

Interesting & captivating, this triplex mountain escape is special! Discover the perfect blend of alpine adventure and easy living in this incredible 2 bd 2 ba triplex townhouse condominium. Minutes to the slopes, snowmobiling, incredible fly-fishing, biking and some of the greatest hiking trails a short distance away. Wheather you are seeking a lucrative short term rental, a peaceful weekend escape or a place to lay down permanent roots, this home delivers! A multi level layout centers around a stunning wood burning fireplace, the ultimate center piece for warming up and sharing stories after a trilling day on the slopes. There are multiple private decks to enjoy your morning coffee or enjoy the stress free life style. Low common charges 244 per month, with swimming and tennis courts available on the premises. A quick 2.5 hr drive from NYC.

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS. Real estate listings held by brokerage firms other than Xome are marked with IDX logo and the detailed information about them includes the name of the listing broker. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026 by the Hudson Valley Catskill Region MLS and Ulster County Board of Realtors, Inc. All Rights Reserved.

Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, OneKey MLS, Inc. All Rights Reserved.



Windham Real Estate

Windham is located in New York. Windham, New York has a population of 1,553. Windham is less family-centric than the surrounding county with 23.28% of the households containing married families with children. The county average for households married with children is 26.95%.

The median household income in Windham, New York is $55,781. The median household income for the surrounding county is $62,810 compared to the national median of $69,021. The median age of people living in Windham is 49.6 years.

Windham Weather

The average high temperature in July is 78.4 degrees, with an average low temperature in January of 10.7 degrees. The average rainfall is approximately 48 inches per year, with 45 inches of snow per year.

Windham Map

Windham Real Estate Market Conditions

  • Median sales price

    $892,000
    24.5%
    change since last quarter
  • # Active listings

    212
    30-day change

Windham Schools and Demographics

Education near Windham, NY

City County
High School Graduates 84.53 87.93
College Degree - 2 year 9.37 11.42
College Degree - 4 year 26.25 25.62
Graduate Degree 8.53 9.07
Expenditures per Student 29,481 29,481
Students per Teacher 9.9 9.9

Elementary Schools near Windham, NY

Grades Students P/T Ratio ZIP
Hunter Elementary School PK - 06 190 8.6 12442

Middle Schools near Windham, NY

Grades Students P/T Ratio ZIP
Cairo-Durham Elementary School KG - 02 136 13.8 12422

High Schools near Windham, NY

Grades Students P/T Ratio ZIP
Hunter-Tannersville Middle School High School 07 - 12 155 7.2 12485

Ungraded Schools near Windham, NY

Grades Students P/T Ratio ZIP
Gilboa-Conesville Central School PK - 12 339 10 12076
Windham Ashland Central School KG - 12 316 8.8 12496

Demographics near Windham, NY

City County
Neighborhood Type Small Town
Population 1,553 48,026
Population Density 34 74
Median Age 49.6 46.6
People per Household 2.7 2.6
Median Household Income 55,781 62,810
Average Income per Capita 35,661 33,894

Real estate near Windham