Properties For Sale in Windham

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 luxur...

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 se...

Step into a winter wonderland with this exclusive ski house at The Windham Mountain Club - where luxury meets adventure, right at the doorstep of the slopes. Your dream of a slopeside retreat awaits. Nestled on Windham Mountain's East side, this 6,859 square foot home exudes a perfect blend of ru...

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 fr...

When the powder is fresh and the sun kisses the peaks, your Windham ski retreat awaits with breathtaking views and luxury living minutes from the heart of it all! Designed by a renowned Manhattan architect as his personal residence, this 4,834-square-foot masterpiece combines luxury, comfort, and...

Investor Opportunity: Luxury Slopeside Home at Windham Mountain Club - Airbnb-Ready Income Property Welcome to 150 Trailside Road, the most competitively priced slopeside home at Windham Mountain Club—a rare and lucrative opportunity for savvy property investors targeting the booming sho...

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 ...

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, rela...

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, landscape...

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 an...

Luxury Ski Townhouse in the Heart of Windham Mountain Club's Premier Enclave Community Discover the ultimate ski lifestyle in this luxurious tri-level townhouse, ideally located in the exclusive Enclave at Windham Mountain Club. Just steps from the slopes, base lodge, pool, fitness cente...

Come relax in the cool Mediterranean vibes of this lovingly maintained home with completely separate 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. Shelt...

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-concep...

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 inve...

Welcome to 601 Whisper Creek- a slopeside penthouse with breathtaking views, right at the heart of the slopes. Immerse yourself in a lifestyle defined by luxury and elegance, as you enjoy spectacular views and direct ski access from this exceptional unit. Spanning an impressive 1,506 square feet,...

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 ...

Seize the opportunity to be the inaugural owner of this pristine Windham Mountain Cabin! If you've previously considered this home, it's time for another look. The owners have recently broadened the driveway and selectively cleared a portion of the land. Your personal haven in the Catskill Mount...

Discover the ultimate Catskills mountain retreat with stunning views of the Windham Mountain Club ski slopes in Windham, NY. This beautifully crafted cabin blends timeless rustic character with modern comfort, making it an ideal primary residence, weekend escape, or investment property.

Bright Sparrow Farmhouse - Modern Farmhouse on 8+ Acres with Private Pond, Mountain Views & Proven Rental Income | Windham, NY Welcome to Bright Sparrow Farmhouse—your dream Catskills retreat where modern farmhouse style meets timeless charm on over 8.22 private acres with a spring-fed p...

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-conc...

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 ...

Another Price Improvement — Exceptional Value for a Turn-Key, Four-Season Mountain Retreat in the Catskills This beautifully renovated corner townhouse at Brainard Ridge presents an outstanding opportunity to own a fully furnished, move-in-ready retreat at Windham Mountain Club. With a r...

Nestled in the serene hamlet of Maplecrest, down a long private road, lies a hidden streamside oasis that offers the quintessential setting for your upstate retreat. This charming cabin peacefully situated beside a stream, a cascading waterfall, and year-round breathtaking mountain views. The pro...