150 Trailside Rd
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...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, 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. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.
- Listed by Regina Tortorella • Coldwell Banker Village GreenWP: (914)-466-0329 C: (914)-466-0329 secondhomeguru@gmail.com
- Listed by Aaron Perer • Coldwell Banker Village GreenWP: (518)-734-4200 aaronperer.realestate@gmail.com
Property Details for 150 Trailside Road
Property Details for 150 Trailside Road
| Status | Active |
|---|---|
| MLS # | 156438 |
| Days on Market | 272 |
| Taxes | - |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Single Family |
| MLS Type | Residential / Single Family Residence |
| Year Built | 2001 |
| Lot Size | 0.62 AC / 27,007 SF |
| County | Greene County |
Location
Virtual Tour
Building Information for 150 Trailside Road
Payment Calculator
$12,688 per month
30 year fixed, 6.28% Interest
$11,118
$1,570
$0
Property Information for 150 Trailside Road
- Directions: South Street Windham to Trailside Rd (Village East), follow to the T intersection and bear Right, follow to the end-house is on the Right of the cul-de-sac
- Township: Windham
- MLS Area Major: Windham
- County: Greene
- Latitude: 42.297412
- Longitude: -74.254177
- MLS Area Major: Windham
- Sign On Property YN: No
- Entry Level: 2007
- Mountain(s): Yes
- Rural: Yes
- Association YN: Yes
- Association Fee: $.00
- Association Fee Frequency: Monthly
- Parcel Number: 95.10-3-21
- Tax Block: 3
- Tax Legal Description: 95.10-3-21
- Tax Annual Amount: $.00
- Association YN: Yes
- Association Fee: $.00
- Association Fee Frequency: Monthly
- Garage YN: No
- Garage YN: No
- Virtual Tour URLUnbranded: https://my.matterport.com/show/?m=seYdhCRsSMZ
- New Construction YN: No
- Lot Size Acres: 0.62
- Above Grade Finished Area: 4572.0
- Below Grade Finished Area: 2286.0
- Living Area: 6859.0
- Lot Size Area: 0.62
- Lot Size Units: Acres
- Lot Size Square Feet: 27007.2
- Above Grade Finished Area: 4572.0
- Below Grade Finished Area: 2286.0
- Lot Size Acres: 0.62
- Contemporary: Yes
- Cedar: Yes
- Frame: Yes
- Shake Siding: Yes
- Wood Siding: Yes
- Owner Name: Winter Time LLC
- Total Floor Plans Count: 3
- Property Type: Residential,Single Family Residence
- Year Built: 2001
- Property Sub Type: Single Family Residence
- New Construction YN: No
- Page: 213
- Section: 95.10
- Tax Assessed Value: 113160.0
- Tax Lot: 21
- Electric Water Heater: Yes
- Public Sewer: Yes
- Public: Yes
- Porch: Yes
- Shingle: Yes
- Security System: Yes
- Basement YN: Yes
- Room Total: 14
- Entry Level: 2007
- Bathrooms Total (Integer): 7
- Bathrooms Total (Decimal): 7.0
- Bathrooms Total (Notational): 7.0
- Heating: Yes
- Bedrooms Total: 9
- Bathrooms Full: 7
- Bathrooms Half: 0
- Rooms Total: 14.0
- Bathrooms Half: 0.0
- Dishwasher: Yes
- Dryer: Yes
- Range: Yes
- Refrigerator: Yes
- Washer: Yes
- Water Heater: Yes
- Exterior Entry: Yes
- Finished: Yes
- Walk-Out Access: Yes
- Walk-Up Access: Yes
- Carpet: Yes
- Ceramic Tile: Yes
- Hardwood: Yes
- Slab: Yes
- Baseboard: Yes
- Oil: Yes
- Radiant: Yes
- High Speed Internet: Yes
- Tri-Level: Yes
- Casement Window(s): Yes
- Bathroom: Yes
- Bathroom Level: Second
- Dining Room Level: First
- Great Room Level: First
- Other Room: Yes
- Other Room Level: Second
- Sign On Property YN: No
- Occupant Type: Owner
- Occupant Type: Owner
Public Records for 150 Trailside Road
Schools near 150 Trailside Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 12 |
Rating | School | Distance |
|---|---|---|
Windham Ashland Central School PublicPK to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Listing Courtesy of Coldwell Banker Village GreenW
The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale or lease on this webpage comes from the the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. Real estate listings held by brokerage firms other than Compass are marked with a OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS or Ulster County Board of REALTORS Logo. Use of these search facilities other than by a consumer seeking to purchase or lease real estate is prohibited. The accuracy of all information is deemed reliable but not guaranteed and should be verified through personal inspection by and/or with appropriate professionals. The data contained herein is copyrighted by the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Information Copyright 2025, OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. All rights reserved. Data last updated: 12/08/2025 04:26 PM