5 Beds
5½ Baths
3,643 Sqft
0.06 Acres
1 Garages

Luxury STR Investment Opportunity Across from Windham Mountain Club -- turnkey option, income-producing, and Owner Financing available with as little as 20 pct down- perfectly positioned in one of the Catskills' most desirable four-season destinations. Located within walking distance to Windham's restaurants, shops, nightlife, and ''The Valley,'' Windham Mountain Club's exciting new expansion featuring pools, tennis, pickleball, spa amenities, golf, and more, this luxury townhouse delivers the ultimate combination of lifestyle and investment potential. This proven Airbnb/Vrbo-friendly property offers the option to be sold fully furnished and can include transferable future bookings already secured for upcoming ski seasons--allowing the new owner to generate immediate rental income from day one. A rare opportunity for investors seeking a high-demand short-term rental in a prime resort location with exceptional year-round appeal. Inside, the home features an open-concept design ideal for entertaining, a chef's kitchen with granite countertops and stainless-steel appliances, a spacious great room with fireplace, central air conditioning, heated garage, multiple en-suite bedrooms, and a large deck with beautiful mountain and ski slope views. Just steps from shuttle access and minutes to skiing, hiking, golf, spas, and dining, this is the perfect Catskills getaway, second home, or high-performing investment property only 2.5 hours from NYC. Option to purchase furnished. Future bookings may be transferred at closing if the purchaser wishes. Immediate ROI potential in the heart of Windham. Schedule an in-person viewing today!

 

The Upstate Lifestyle at 292 South Street #3, Windham, NY

 

The location puts you within minutes of Windham Mountain Club's slopes for winter skiing and Windham Country Club's 18-hole course for summer rounds, making it easy to build your day around the season's best activities. Downtown Windham's Main Street is a short walk away, where farm-to-table restaurants like Windham Local Public House and cozy spots like The Day June offer everything from morning coffee to dinner out. The Mountain Top Arboretum provides a peaceful retreat for hiking and botanical exploration when you're looking for something quieter, while Hunter Mountain expands your options for both skiing and warm-weather adventures. Whether you're the type to hit the trails at sunrise or prefer a leisurely brunch followed by an afternoon browse through local shops, the surrounding area supports whatever pace suits your weekend—or your everyday life if you're working remotely from the mountains.

Facts & Features
MLS® # 20254832
Price $1,149,000
Bedrooms 5
Bathrooms 5.50
Full Baths 5
Half Baths 1
Square Footage 3,643
Acres 0.06
Year Built 2021
Type Residential
Sub-Type Single Family Residence
Style Other
Status Active
MLS ucbr
Community Information
Address 292 #3 South Street
Area Windham
City Windham
County Greene
State NY
Zip Code 12496
Amenities
Utilities Cable Available, Electricity Connected, Propane, Sewer Available, Sewer Connected
Parking On Site
# of Garages 1
View Mountain(s), Other
Is Waterfront No
Pool None
Interior
Interior Features Cathedral Ceiling(s), Chandelier, Entrance Foyer, High Speed Internet, Open Floorplan
Appliances Dryer, Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Water Heater
Heating Forced Air, Propane, Radiant
Cooling Central Air
Has Basement No
Fireplace Yes
# of Fireplaces 1
Fireplaces Gas Log, Great Room
Stories Three Or More, Tri-Level
Exterior
Exterior Board & Batten Siding, Frame, Other, Stone
Exterior Features Balcony, Misting System
Roof Asphalt
Construction Board & Batten Siding, Frame, Other, Stone
Foundation Slab
School Information
District Wind-Ash-Jewett
Additional Information
Date Listed October 3rd, 2025
Days on Market 371
Zoning 01
Short Sale No
RE / Bank Owned No
Listing Details
Listing Courtesy of Coldwell Banker Village GreenW
Mortgage Calculator

This mortgage calculator can be used to figure out monthly payments of a home mortgage loan, based on the home's sale price, the term of the loan desired, buyer's down payment percentage, and the loan's interest rate.

Purchase & Financing Information

Photo of Regina Tortorella

Regina Tortorella

Office: 518-734-4200 ext. 103
Cell: 914-466-0329
Photo of Aaron Joseph Perer

Aaron Joseph Perer

Office: 518-734-4200
Cell: 845-514-0186

Yes, I would like more information from Coldwell Banker Village Green Realty. Please use and/or share my information with a Coldwell Banker Village Green representative to contact me about my real estate needs.

By clicking Inquire I agree a Coldwell Banker Village Green Realty representative may contact me by phone or text message including by automated means about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the privacy policy 

Ulster County Board of Realtors LogoTHE DATA RELATING TO REAL ESTATE ON THIS WEBSITE COMES IN PART FROM THE IDX OF THE MULTIPLE LISTING SERVICE OF ULSTER COUNTY, INC. REAL ESTATE LISTINGS HELD BY BROKERAGE FIRMS OTHER THAN Coldwell Banker Village Green Realty ARE MARKED WITH IDX LOGO AND THE DETAILED INFORMATION ABOUT THEM INCLUDES THE NAME OF THE LISTING BROKER.

COPYRIGHT © 2026 BY THE MULTIPLE LISTING SERVICE OF ULSTER COUNTY, INC. ALL RIGHTS RESERVED.

ALL INFORMATION PROVIDED IS DEEMED RELIABLE BUT IS NOT GUARANTEED AND SHOULD BE INDEPENDENTLY VERIFIED. 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.