3-5 Hickory Hill Road, Windham

$1,590,000

5 Beds
3 Baths
2,974 Sqft
2¾ Acres
2 Garages

Experience an exceptional mountain retreat in one of Windham's most desirable locations. Set on 2.7 private acres and just a short walk to the heart of the village, this remarkable estate offers breathtaking panoramic views of the Windham Mountain Club, the ski slopes, and the surrounding Catskill Mountains. The main residence features 5 spacious bedrooms and 3 full bathrooms, designed for comfortable everyday living and effortless entertaining.The spectacular mountain scenery, filling the home with natural light and creating a seamless connection to the outdoors. Step outside to your own private oasis featuring an outdoor swimming pool, generous entertaining space, and unforgettable views that can be enjoyed year-round. Adding incredible versatility is a charming A-frame guest house complete with 1 bedroom and 1 full bathroom-perfect for hosting family and friends, creating a private workspace, or generating additional rental income. Whether you're searching for a full-time residence, a luxury weekend escape, or an investment opportunity in the heart of the Catskills, this unique property delivers an unmatched combination of privacy, convenience, and iconic mountain views. Just minutes from skiing, golf, hiking, restaurants, and all that Windham has to offer, this is a rare opportunity to own one of the area's most captivating properties.

Essential Information
MLS® #20263929
Price$1,590,000
Bedrooms5
Bathrooms3.00
Full Baths3
Square Footage2,974
Acres2.75
Year Built2007
TypeResidential
Sub-TypeSingle Family Residence
StyleChalet
StatusActive
Community Information
Address3-5 Hickory Hill Road
AreaWindham
CityWindham
CountyGreene
StateNY
Zip Code12496
Amenities
# of Garages2
ViewMountain(s)
Has PoolYes
PoolIn Ground
Parking

Garage Faces Front, Paved, Driveway

Interior
HeatingBaseboard, Propane, Wood Stove
StoriesBi-Level
Appliances

Washer/Dryer, Refrigerator, Microwave, Gas Oven, Gas Cooktop, Dishwasher

Cooling

Ductless, Heat Pump, Multi Units, Zoned

Exterior
ExteriorWood Siding
Lot DescriptionLandscaped, Views
RoofAsphalt, Shingle
ConstructionWood Siding
School Information
DistrictWind-Ash-Jewett
Additional Information
Zoning01
Listing Details
AgentAaron Siegel
Listing Courtesy of Venture Fox Realty Group
LISTING MAP

Get directions to this property:

Properties for Sale Similar to 3-5 Hickory Hill Road, Windham, NY

Photo of Listing #20263447

33 Elm Ridge Road, Windham

$1,749,000 - 5 Beds, 4 Baths, 3,893 Sf

MLS® # 20263447

Ulster County Board of Realtors Logo
Photo of Listing #20262533

37 The Loop, Windham

$1,850,000 - 5 Beds, 3 Baths, 3,740 Sf

MLS® # 20262533

Ulster County Board of Realtors Logo
Photo of Listing #20261997

78 Buckskin Loop, Windham

$1,349,000 - 4 Beds, 4 Baths, 3,977 Sf

MLS® # 20261997

Ulster County Board of Realtors Logo

Ulster County Board of Realtors Logo The 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 Flemming 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.