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 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 with built-in BBQ grill to the 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.
Active
$2,250,000
150 Trailside Road, Windham, NY 12496
9beds
6,859sqft
Single Family Residence
Built in 2001
0.62 Acres Lot
$2,148,300 Zestimate®
$328/sqft
$-- HOA
What's special
Wood-burning fireplacesBuilt-in bbq grillBreathtaking trail viewsBackup generatorExpansive wraparound deckDual walk-in closetsSlopeside home
- 92 days
- on Zillow |
- 304 |
- 16 |
Zillow last checked: 7 hours ago
Listing updated: August 07, 2025 at 05:32am
Listing by:
Coldwell Banker Village GreenW 518-734-4200,
Regina Tortorella 914-466-0329,
Aaron Perer,
Coldwell Banker Village Green
Source: HVCRMLS,MLS#: 156438

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 9
- Bathrooms: 7
- Full bathrooms: 7
Bedroom
- Level: Second
Bedroom
- Level: Second
Bedroom
- Level: First
Bedroom
- Level: Second
Bedroom
- Level: Second
Bathroom
- Level: Second
Bathroom
- Level: First
Dining room
- Level: First
Great room
- Level: First
Kitchen
- Level: First
Other
- Level: First
Other
- Level: Second
Heating
- Baseboard, Oil, Radiant
Appliances
- Included: Water Heater, Washer, Refrigerator, Range, Electric Water Heater, Dryer, Dishwasher
Features
- High Speed Internet
- Flooring: Carpet, Ceramic Tile, Hardwood, Other
- Basement: Exterior Entry,Finished,Walk-Out Access,Walk-Up Access
Interior area
- Total structure area: 6,859
- Total interior livable area: 6,859 sqft
- Finished area above ground: 4,572
- Finished area below ground: 2,286
Video & virtual tour
Property
Features
- Levels: Tri-Level
- Patio & porch: Deck, Porch
- Has view: Yes
- View description: Mountain(s), Neighborhood, Rural, Other
Lot
- Size: 0.62 Acres
Details
- Parcel number: 95.10321
- Zoning: 01
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Cedar, Frame, Shake Siding, Wood Siding, Other
- Foundation: Slab
- Roof: Asphalt,Shingle
Condition
- New construction: No
- Year built: 2001
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Security: Security System
HOA
- Has HOA: Yes
Location
- Region: Windham
Financial & listing details
- Price per square foot: $328/sqft
- Tax assessed value: $113,160
- Date on market: 3/28/2025
- Road surface type: Paved
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