Properties For Sale in Windham

Welcome to Boulder Brook Estates! A new and exclusive six-home community tucked away on 37 acres in the highly sought-after resort town of Windham, NY. The Lancaster is the first of six homes to be built in this custom home subdivision surrounded by mature trees and abundant wildlife. An exquisit...

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...

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...

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 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,...

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...

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...

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...

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 Mounta...

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...

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...

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...

The Last True Ski-On/Ski-Off Lot at Windham Mountain—Step Out & Ski! This is the one and only true ski-on/ski-off lot available at Windham Mountain Club! Imagine waking up to breathtaking mountain views, stepping outside, putting on your skis, and gliding directly onto the slopes—no walking, ...

Two-Lot Mountain Retreat in Windham - 4-Bedroom Home on 2 Acres + Contiguous 1.5-Acre Buildable Lot | Endless Possibilities for Your Dream Escape or Investment Just two miles from the conveniences of Windham's charming Main Street—and only minutes from year-round recreation—this rare two-lot offe...

Two-Lot Mountain Retreat in Windham - 4-Bedroom Home on 2 Acres + Contiguous 1.5-Acre Buildable Lot | Endless Possibilities for Your Dream Escape or Investment Just two miles from the conveniences of Windham's charming Main Street—and only minutes from year-round recreation—this rare two-lot offe...

Cozy Up in This Fully Renovated Mountain Home- Just in Time for Fall Colors and Winter Skiing! Welcome to your serene mountain retreat—fully renovated, turnkey, and ready for you to enjoy this fall's vibrant foliage and hit the slopes at Windham or Hunter Mountain this winter. Whether yo...

Cozy Up in This Fully Renovated Mountain Home- Just in Time for Fall Colors and Winter Skiing! Welcome to your serene mountain retreat—fully renovated, turnkey, and ready for you to enjoy this fall's vibrant foliage and hit the slopes at Windham or Hunter Mountain this winter. Whether yo...

Ideal country getaway with beautiful mountain views located just steps away from premier hiking and biking trails and minutes from the charming Village of Windham, you'll find endless opportunities for outdoor exploration and leisure here. Step inside this cozy log sided Chalet and be captivated ...

Ideal country getaway with beautiful mountain views located just steps away from premier hiking and biking trails and minutes from the charming Village of Windham, you'll find endless opportunities for outdoor exploration and leisure here. Step inside this cozy log sided Chalet and be captivated ...

Once-in-a-Lifetime Land Offering in Windham, NY - 60 Acres Bordering Forever Wild Mountain PreserveWelcome to a truly rare opportunity in the heart of the Catskills. 60 pristine acres in Windham, NY, a town where large tracts of land are no longer available, especially not ones of this caliber. T...

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.