150 Trailside Road, Windham, NY 12496
SOLD
MAR 5, 2026

150 Trailside Road
Windham, NY 12496

  • 9 Beds
  • 7 Baths
  • 6,859 sqft (on 0.62 acres)

$1,810,000

Last Sold: Mar 5, 2026
20% below list $2.25M
$264/sqft
Est. Refi. Payment $11,419/mo*
Refinance Your Home

$1,810,000

Last Sold: Mar 5, 2026
20% below list $2.25M
$264/sqft
Est. Refi. Payment $11,419/mo*
Refinance Your Home
9 Beds
7 Baths
6,859 sqft
(on 0.62 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from May 09, 2026

Home Highlights

Parking
No Info
Outdoor
Porch, Deck
A/C
Heating only
HOA
None
Price/Sqft
$264/sqft
Listed
180+ days ago

Home Details for 150 Trailside Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Exterior Entry,Finished,Walk-Out Access,Walk-Up AccessNumber of Rooms: 14Types of Rooms: Bedroom, Bathroom, Dining Room, Family Room, Great Room, Kitchen, Other Room
Beds & Baths
Number of Bedrooms: 9Number of Bathrooms: 7Number of Bathrooms (full): 7
Dimensions and Layout
Living Area: 6859 Square Feet
Appliances & Utilities
Appliances: Water Heater, Washer, Refrigerator, Range, Electric Water Heater, Dryer, DishwasherDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Oil,RadiantHas HeatingHeating Fuel: Baseboard
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Flooring: Carpet, Ceramic Tile, Hardwood, Other
Levels, Entrance, & Accessibility
Levels: Tri-LevelFloors: Carpet, Ceramic Tile, Hardwood, Other
View
Has a ViewView: Mountain(s), Neighborhood, Rural, Other
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: Asphalt ShinglePatio / Porch: Deck, PorchFoundation: Slab
Parking & Garage
No Garage
Frontage
Road Surface Type: Paved
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 4572 Square FeetFinished Area (below surface): 2286 Square Feet

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Cedar, Frame, Shake Siding, Wood Siding, OtherNot a New Construction
Property Information
Parcel Number: 95.10321

Price & Status

Price
List Price: $2,250,000Price Per Sqft: $264/sqft
Status Change & Dates
Off Market Date: Mon Jan 26 2026

Location

Direction & Address
City: Windham
School Information
High School District: Wind-Ash-Jewett

Building

Building Area
Building Area: 6859 Square Feet

HOA

Has an HOA

Lot Information

Lot Area: 0.62 acres

Miscellaneous

BasementMls Number: 156438Above Grade Unfinished Area: 4572Showing Attended
Last check for updates: about 1 hour ago
Listed by Regina Tortorella, (914) 466-0329
Coldwell Banker Village GreenW
Aaron Perer
Coldwell Banker Village GreenW
Bought with: Regina Tortorella, (914) 466-0329, Coldwell Banker Village GreenW
Source: HVCRMLS, MLS#156438

Price History for 150 Trailside Road

DatePriceEventSource
03/05/2026$1,810,000Sold
HVCRMLS #156438
01/26/2026$2,250,000PendingHVCRMLS #156438
01/06/2026$2,250,000ContingentHVCRMLS #156438
03/27/2025$2,250,000Listed For SaleColumbia Greene Northern Dutchess MLS #156438
08/19/2024$2,775,000ListingRemovedColumbia Greene Northern Dutchess MLS #152420
05/04/2024$2,775,000Listed For SaleColumbia Greene Northern Dutchess MLS #152420
06/29/2000$107,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$2,161,605
Home facts updated by county records

Comparable Sales for 150 Trailside Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
39 White Way, Windham, NY
0.19
Single-Family Home
$999,999
07/03/25
6
4
3,260
219 Club Road, Windham, NY
0.81
Single-Family Home
$3,100,000
05/05/26
6
5
5,021
4 The Loop, Windham, NY
0.45
Single-Family Home
$1,400,000
09/18/25
4
3
2,536
30 The Loop, Windham, NY
0.57
Single-Family Home
$885,000
12/15/25
5
4
3,100
5287 Route 23, Windham, NY
0.80
Single-Family Home
$680,000
04/28/26
3
2
2,350
212 South Street, Windham, NY
0.59
Single-Family Home
$640,000
11/21/25
3
2
2,240

Assigned Schools

These are the assigned schools for 150 Trailside Road.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windham

At least 14 Trulia users voted on each feature.

  • 95 % Say there's holiday spirit

  • 90 % Say there's wildlife

  • 88 % Say parking is easy

  • 80 % Say yards are well-kept

  • 80 % Say it's quiet

  • 79 % Say car is needed

  • 71 % Say they plan to stay for at least 5 years

  • 68 % Say people would walk alone at night

  • 65 % Say it's dog friendly

  • 62 % Say neighbors are friendly

  • 53 % Say kids play outside

  • 47 % Say it's walkable to grocery stores

  • 47 % Say streets are well-lit

  • 40 % Say there are community events

  • 37 % Say it's walkable to restaurants

  • 37 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Claudia H.
    "School parades the primary grade students mid day. The police are out keeping an eye on the children and the fire department gives away hot chocolate and hot dogs!"
    2
    Flag
  • Dan H.
    "Whether you've lived here all your life or if you're just visiting, the people will welcome you and make you feel at home. I encourage people to visit and maybe stay a while. "
    6
    Flag
  • Julissa K.
    "4th of July I can see the parade passing by my house and even fireworks. Winter we have a lot of visitors here because the ski resort. And the summer is always a lot to do including walking in the Windham Path and all the trails around here are just amazing "
    0
    Flag
  • Steven N.
    "You will see dog owners walking their dogs often. The one thing missing for dogs would be a dog run "
    3
    Flag
  • Steven N.
    "It’s a lovely town to walk in with your dog and rumor has it there is a dog run in the town next door. Great trails for walking with your dog as well."
    1
    Flag
  • howardc1
    "I have a vacation condo here. The location is excellent about 3 miles from Ski Windham, and this is one of the very few properties in the area with a swimming pool and two tennis courts. Property management is excellent. Excellent cultural attractions, chamber music performances right in town, jazz and classical performances during the summer in nearby Hunter and Tannersville. "
    1
    Flag
  • Patti
    "Best Place to live, lots of clean air, beautiful scenery, nice people and lots of places to go"
    5
    Flag

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IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS.
Information is deemed reliable but is not guaranteed accurate by the MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes for rent near 150 Trailside Road

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150 Trailside Road, Windham, NY 12496 is a 9 bedroom, 7 bathroom, 6,859 sqft single-family home built in 2001. This property is not currently available for sale. 150 Trailside Road was last sold on Mar 5, 2026 for $1,810,000 (20% lower than the asking price of $2,250,000). The current Trulia Estimate for 150 Trailside Road is $1,819,600.