Properties For Sale in Windham

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,...

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...

Walk to the Slopes! Nestled on the scenic slopes of Windham Mountain and just over two hours from NYC, this mountain haven beautifully marries opulence with rustic allure. The home's exterior, featuring cedar shakes and stone, harmonizes with its lush, landscaped surroundings, creating impeccable...

The Ultimate Catskills Retreat — Just Minutes from Windham Resort Nestled on 12 private wooded acres less than seven minutes from Windham Resort, this 5,400 sq. ft. luxury log cabin embodies the best of mountain living — where timeless craftsmanship meets modern comfort. Designed across three lev...

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...

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 renta...

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,...

Price Cut! Don't be fooled by first impressions — this ranch-style home is far more expansive than it appears from the road. Step inside and be truly enthralled by this beautifully expanded and thoughtfully reimagined residence, set in a quiet residential cul-de-sac where peaceful neighborhood li...

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 a proven, income-producing short-term rental and sought-after Catskills retreat, now offered at a new price of 715,000, making this opportunity even more compelling. Fully renovated in 2023-2024, this modern multi-family chalet is ideally located just minutes fr...

Just in time for ski season! Make this your base for winter fun at Windham Mountain Club. Beautifully renovated with comfort and quiet luxury in mind, this gorgeous corner townhouse in the desirable Brainard Ridge development offers a rare expanded floor plan featuring 4-5 bedrooms and 3.5 ba...

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...