150 Trailside Road Windham, NY 12496
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Key Details
Property Type Single Family Home
Sub Type Single Family Residence
Listing Status Active
Purchase Type For Sale
Square Footage 6,859 sqft
Price per Sqft $328
MLS Listing ID 156438
Style Contemporary
Bedrooms 9
Full Baths 7
HOA Y/N Yes
Year Built 2001
Lot Size 0.620 Acres
Acres 0.62
Property Sub-Type Single Family Residence
Source Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS®)
Property Description
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 short-term rental market in the Catskills. With direct access to the slopes, a sprawling 6,859 sq. ft. layout, and accommodations for over 20 guests, this luxury residence is fully equipped for high-yield Airbnb income in one of the Northeast's premier four-season resort destinations.
This property is not just investment-ready—it's already producing. With over several bookings currently on the calendar, the home offers immediate cash flow for investors looking to step into a turnkey operation with rental momentum already in place.
Designed with upscale mountain living in mind, the home's soaring 20-foot pine ceilings and dramatic wall of windows in the great room deliver breathtaking trail views that set the tone for an unforgettable guest experience. The chef's kitchen is equally impressive, featuring granite countertops, a Viking range, dual dishwashers, and seamless flow into two expansive dining areas—tailor-made for entertaining large groups and corporate retreats.
Guests will love the seamless blend of indoor and outdoor spaces, from the expansive wraparound deck, cozy game room and high-end home theater—easily convertible back to a garage, depending on your rental model. Four wood-burning fireplaces add warmth and charm throughout, while the radiant-heated gear room, central A/C, and backup generator ensure year-round comfort and security.
The private primary suite offers luxury and seclusion, with its own wing on the second floor, dual walk-in closets, a fireplace, and a balcony with panoramic views of the slopes—ideal for owner stays or VIP guests. With nine bedrooms and seven bathrooms spread across 14 rooms, this turnkey property is optimized for large-party bookings and high occupancy rates, a rare find in a slopeside location.
Offered fully furnished, this home enables investors to hit the ground running with immediate rental income and minimal setup. Whether you're seeking premium cash flow or a hybrid use of personal enjoyment and income generation, 150 Trailside Road combines location, scale, and luxury—delivering unmatched value in Windham's most desirable setting. Schedule your private showing today and secure your foothold in one of the Catskills' most dynamic and profitable short-term rental markets.
Location
State NY
County Greene
Area Windham
Zoning 01
Rooms
Basement Exterior Entry, Finished, Walk-Out Access, Walk-Up Access
Interior
Interior Features High Speed Internet
Heating Baseboard, Oil, Radiant
Flooring Carpet, Ceramic Tile, Hardwood, Other
Exterior
View Mountain(s), Neighborhood, Rural, Other
Roof Type Asphalt,Shingle
Porch Deck, Porch
Garage No
Building
Foundation Slab
Sewer Public Sewer
Water Public
Architectural Style Contemporary
Level or Stories Tri-Level
Schools
High Schools Wind-Ash-Jewett
School District Wind-Ash-Jewett
Others
Tax ID 95.10-3-21
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