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...

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...

Mountain Luxury Meets Ski-Inspired Living at Windham! Just a little over two hours from New York City, this stunning post-and-beam residence blends mountain charm with upscale comfort, making it the perfect ski getaway or second home. Located in the exclusive Village East community at Windham Mou...

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...

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...

Showing by Appointment Only Saturday 8/16. Please RSVP today! Stunning Contemporary Mountain Retreat with Panoramic Views in Windham, NY Welcome to your dream mountain getaway! Perched above it all and offering breathtaking panoramic views of the Catskill Mountains and Windham's renowned ski slop...

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 Are Calling — Your Private Four-Season Escape With Spectacular Views Awaits! Nestled on two private acres, including an additional lot with road frontage and panoramic views, this contemporary mountain retreat offers the perfect balance of modern amenities and rustic charm....

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 The Hill, a private enclave of high-end homes tucked away in the scenic hamlet of Maplecrest, just minutes from Windham Mountain Club and CD Lane Park. Perched on 6 peaceful acres at the end of a quiet cul-de-sac, this 3,500+ sq ft custom contemporary blends crisp architectural design ...

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,...

Walk to the Slopes in the Winter and Listen to the Soothing Sounds of the Cascading Waterfall from the Primary Ensuite in The Spring & Summer! Escape to Luxury in the Catskill Mountains - Your Dream Ski Chalet Awaits! Step into the extraordinary at this stunning ski chalet a short distance from t...

Tucked away in a quiet residential cul-de-sac, 116 Nilson Drive offers the best of both worlds — peaceful neighborhood living surrounded by nature, yet just minutes from Main Street, Windham Mountain Club, and Christman's Golf Course. A rare find for the area, this welcoming residential enclave a...

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...

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...

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...

Privately nestled down a long driveway off one of Windham's most sought-after roads, this custom 2003 Timberframe home offers rustic elegance, modern updates, and exceptional privacy. Less than 4 miles from both town and the renowned Windham Mountain Club/Ski Resort, the property is the perfect b...

Welcome to Windham Creek Lodge — a modern mountain retreat designed for both luxury living and income potential, where style meets sophistication in the heart of the Catskill Mountains. This beautifully remodeled multi-family chalet offers a rare blend of modern comfort, flexible design,...