Windham, NY Homes for Sale with Garage

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

Regina Tortorella Coldwell Banker Village GreenW

Luxury Mountain Retreat | 7 Bed • 5.5 Bath • 5 Acres | Direct Windham Mountain Views | Smart Home | No HOA. Experience luxury mountain living in this brand-new custom-built 7-bedroom, 5.5-bath chalet with unobstructed views of Windham Mountain Club, set on 5 private acres just minutes from downtown Windham, NY. Designed with impeccable European craftsmanship, high-end technology, and

Regina Tortorella Coldwell Banker Village GreenW

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

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

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

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

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

Regina Tortorella Coldwell Banker Village GreenW

The Catskills Called -- And This Log Cabin Answered. Privately set among the trees with sweeping mountain views, this beautifully maintained log cabin is minutes to Windham Mountain Club and Main Street. Spanning three levels with five bedrooms and three full baths, it offers open-concept living with a soaring great room, floor-to-ceiling stone fireplace, and a wall of glass framing the views.

Regina Tortorella Coldwell Banker Village GreenW

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

Regina Tortorella Coldwell Banker Village GreenW

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

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

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

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

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

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

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

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.

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

Patrick Dunn KW Platform

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

STUNNING LOCATION! Situated above Windham Ridge this Custom designed & built (by one of Windham's top builders) Contemporary style home has direct ski slope views in a special setting. Conveniently just 2 minutes to Windham Village & 5 minutes to Windham Mountain. Extraordinary mountain home. Efficient & economical design. Upon entering, a bit of a WOW, with 25ft. Beamed, vaulted ceilings &

Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

Take advantage of this meticulously refreshed winter escape in the heart of Windham. Step inside to a bright and inviting layout featuring newly added hardwood floors, fresh paint inside and out, and a brand-new washer and dryer. The main living level is anchored by a charming wood stove that sets a cozy tone for the whole group to enjoy after a day of outdoor activities. Four bedrooms and two

Brandon Oot Core Real Estate Team

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

Skiers and Hunters! 7 glorious acres 8 minutes to Windham Mountain! Charming Updated Home with mature trees, beautiful plantings and landscapes. Welcome to this inviting 3-bedroom, 1-bath home set on 7 beautiful acres offering privacy, space, and stunning natural surroundings. Located only 8 minutes from the local ski area, it's the perfect retreat for outdoor enthusiasts or anyone seeking a

Robyn Tricinelli Century 21 Alliance

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

Want to be close to Windham Mountain? Looking for an affordable country home? A money making Air B&B? Look no further! Welcome to 28 Sutton Hollow Road. This single-family home located only 5 minutes to Windam Main Street, and only 10 miles to Hunter! Offering nice sized rooms with plenty of closet and storage space, partial basement and oversized garage for additional storage! On the first floor

Douglas Schenk RE/MAX Capital

Charming 4-Bedroom Ranch on 1.6 Acres in Windham, NY Discover your dream retreat in the heart of the Catskills! Nestled in the picturesque village of Windham, just minutes from vibrant downtown and the renowned Windham Mountain Resort with its array of restaurants and shops, this spacious 4-bedroom, 2-bathroom ranch offers the perfect blend of comfort and charm. Situated on a generous 1.6-acre

Fred Mazza Bunce Realty

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

This is the mountain house everyone else wishes they'd found first. Set on one of Windham's most coveted lots, this 6-bedroom, 5-bath home combines true slope-side access with panoramic views that stretch across the Catskills. It's a genuine ski-in, ski-out property with easy access to Wonderama and Lower Wipeout. In the mornings, clip in and go. At day's end, you can choose your own finale, take

Patricia Charbonneau Brainard Ridge Management

Classic Timber frame Construction, on Windham Mt., Walk to trails. Enjoy the convenience of location in this 4 bedroom 3.5 bath with attached garage to enter a large ski room with all the storage needed. Large formal entrance gives way to Spacious and Comfy Great room with large stone fireplace, vaulted ceilings and plenty of windows to let in the light and the lovely views, leads to a sizable

Irene Pinto Brainard Ridge Management

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. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Sheila Word Coldwell Banker Village GreenW

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

Don't miss this unique opportunity to establish a year-round retreat in the Catskill Mountains, ideal for hosting family and friends on two separate lots. The grounds offer apple picking, fishing in the pond, and swimming, while children can enjoy outdoor activities and grandparents relax on the upper deck with scenic mountain views—all accessible from your own front yard. In winter, prepare for

Laurie Hanenberg Hunter Windham Real Estate