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  • $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
    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.
    92 days
    on Zillow
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    304
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    16
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    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#: 156438MLS Logo
    Travel times

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 150 Trailside Road.

    Next available tour time:Tomorrow at 11am

    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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