150 Trailside Road
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 914.466.0329 secondhomeguru@gmail.com • Coldwell Banker Village GreenW
- Listed by: Aaron Perer 518.734.4200 aaronperer.realestate@gmail.com • Coldwell Banker Village GreenW
Recent comparable sales
Median sold price
$1,843,750
Avg days on market
79
Sale-to-list ratio
87.2%
Windham, NY
9 comparable properties found
$1,500,000
Sold 12/24/24
- 7
- Bedrooms
- 8
- Bathrooms
- 7,761
- Square Feet
- 2.74
- Acres
$1,998,500
Sold 06/26/26
- 5
- Bedrooms
- 6
- Bathrooms
- 5,000
- Square Feet
- 10.35
- Acres
$1,200,000
Sold 05/01/25
- 3
- Bedrooms
- 3
- Bathrooms
- 6,400
- Square Feet
- 0.18
- Acres
$1,900,000
Sold 05/02/25
- 5
- Bedrooms
- 5
- Bathrooms
- 3,148
- Square Feet
- 0.07
- Acres
Location
Sold By Coldwell Banker Village GreenW
Payment Calculator
$10,995 per month
30 year fixed, 6.71% Interest
$9,353
$1,642
$0
Know your buying power with a preapproval and custom rate in minutes
1Property Information for 150 Trailside Road
- MLS Type: Residential / Single Family Residence
- County: Greene County
- Zoning: 01
- Basement YN: Yes
- Year Built: 2001
- Lot Size: 0.62 AC / 27,007 SF
- 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
Property History for 150 Trailside Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Feb 27, 2026 | Sold (Public Record) Public Record #1932077279 | $1,810,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 02/27/2026 | Sold (Public Record) Public Record #1932077279 | $1,810,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
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.
Similar Homes
New listings in 12496
$1,458,000
- 4
- Bedrooms
- 3
- Bathrooms
- 1,948
- Square Feet
- 0.06
- Acres
Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 150 Trailside Road, Windham, NY 12496 | $1,810,000 | 9 | 7 | 6,859 | 27,007 |
$1,750,000 | 5 | 4 | 4,364 | 38,768 | |
$600,000 | 4 | 4 | 2,296 | 13,068 | |
$350,000 | 5 | 5 | 2,450 | 32,234 | |
– | 4 | 5 | 2,688 | 23,958 | |
$2,300,000 | 5 | 5 | 5,548 | 17,860 | |
$1,780,000 | 6 | 6 | 5,150 | 18,731 | |
– | 5 | 4 | 2,620 | 13,504 | |
$1,700,000 | 7 | 4 | 4,300 | 19,602 | |
– | – | – | – | 24,829 | |
– | 5 | 6 | 4,998 | 17,860 | |
– | – | – | – | 66,211 | |
$2,900,000 | 4 | 3 | 3,588 | 12,632 | |
$975,000 | 4 | 4 | 3,588 | 12,632 | |
– | – | – | – | 65,776 | |
– | – | – | 8,049 | 107,158 |
Explore Nearby Homes
- Conesville Homes for Sale
- Windham Hamlet Homes for Sale
- Lexington Homes for Sale
- Prattsville Hamlet Homes for Sale
- Preston-Potter Hollow Homes for Sale
- Hunter Village Homes for Sale
- Broome Homes for Sale
- Halcott Homes for Sale
- Cairo Hamlet Homes for Sale
- Blenheim Homes for Sale
- Greenville Hamlet Homes for Sale
- Fulton Homes for Sale
- Middletown Town Homes for Sale
- Middleburgh Town Homes for Sale
- Stamford Village Homes for Sale
- Durham Homes for Sale
- Prattsville Homes for Sale
- Jewett Homes for Sale
- Cornwallville Homes for Sale
- Ashland Homes for Sale
- Windham Homes for Sale
- Cairo Homes for Sale
- Maplecrest Homes for Sale
- Rensselaerville Homes for Sale
- Hensonville Homes for Sale
- Oak Hill Homes for Sale
- Acra Homes for Sale
- East Durham Homes for Sale
- Preston Hollow Homes for Sale
- Hunter Homes for Sale
- 12076 Homes for Sale
- 12407 Homes for Sale
- 12468 Homes for Sale
- 12444 Homes for Sale
- 12439 Homes for Sale
- 12422 Homes for Sale
- 12418 Homes for Sale
- 12405 Homes for Sale
- 12454 Homes for Sale
- 12442 Homes for Sale
- 12424 Homes for Sale
- 12469 Homes for Sale
- 12423 Homes for Sale
- 12413 Homes for Sale
- 12460 Homes for Sale
No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
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 2026, OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. All rights reserved. Data last updated: 05/08/2026 09:54 PM