415 Old Road, Windham

$799,000

3 Beds
3½ Baths
3,729 Sqft
4 Acres
1 Garage

Don't miss this unique opportunity to establish a year-round retreat in the Catskill Mountains, ideal for hosting family and friends on two separate lots. The grounds offer apple picking, fishing in the pond, and swimming, while children can enjoy outdoor activities and grandparents relax on the upper deck with scenic mountain views—all accessible from your own front yard. In winter, prepare for days on nearby Windham Ski slopes and return to a spacious chalet featuring an open great room with a warm fireplace in the sunken living area. The property includes ample space for holiday gatherings or casual meals at the kitchen island. The main floor consists of two large bedrooms, a full bathroom, laundry facilities, and a half bath adjacent to the kitchen. Upstairs, a primary suite and loft provide additional privacy and comfort.
The sought-after family room is equipped with a supplementary kitchen, wood-burning stove, quality ski furnishings, pool table, dart games, extra office/sleeping space, and another full bathroom. A convenient one-car garage ensures secure late-night arrivals and easy access. The home boasts a new heating system, full-house air conditioning, and high-quality finishes including marble, hardwood and carpet flooring, wood doors and trim, skylights, and vaulted ceilings—creating a true mountain chalet ambiance. Offered furnished and turnkey, this custom-built home has never before been on the market and is ready for its next owners. Located just minutes from Windham Club, it offers access to year-round activities and the potential to become your dream mountain residence.

Essential Information
MLS® #20254472
Price$799,000
Bedrooms3
Bathrooms3.50
Full Baths3
Half Baths1
Square Footage3,729
Acres4.00
Year Built1988
TypeResidential
Sub-TypeSingle Family Residence
StyleChalet
StatusActive
Community Information
Address415 Old Road
AreaWindham
CityWindham
CountyGreene
StateNY
Zip Code12496
Amenities
ParkingGarage Faces Side, Driveway
# of Garages1
ViewMountain(s), Pond
Utilities

Cable Available, Electricity Connected, Phone Available, Water Connected, Underground Utilities

Interior
HeatingBaseboard, Hot Water, Oil
CoolingCeiling Fan(s), Central Air
FireplaceYes
# of Fireplaces1
StoriesThree Or More
Interior Features

Ceiling Fan(s), Double Vanity, Eat-in Kitchen, High Ceilings, High Speed Internet, Kitchen Island, Open Floorplan, Recessed Lighting, Recreation Room

Appliances

Washer/Dryer, Microwave, Exhaust Fan, Electric Range, Dishwasher

Fireplaces

Living Room, Masonry, Wood Burning Stove

Exterior
Exterior FeaturesPrivate Yard
RoofAsphalt
FoundationConcrete Perimeter
Exterior

Batts Insulation, Concrete, Frame, Vinyl Siding

Lot Description

Pond on Lot, Corner Lot, Front Yard, Paved, Private, Rectangular Lot

Construction

Batts Insulation, Concrete, Frame, Vinyl Siding

School Information
DistrictWind-Ash-Jewett
Additional Information
ZoningR
Listing Details
AgentLaurie Hanenberg
Listing Courtesy of Hunter Windham Real Estate
LISTING MAP

Get directions to this property:

Properties for Sale Similar to 415 Old Road, Windham, NY

Photo of Listing #20255369
New Listing

116 Nilson Drive, Windham

$915,000 - 4 Beds, 4 Baths, 3,075 Sf

MLS® # 20255369

Ulster County Board of Realtors Logo
Photo of Listing #20254949

60 County Route 65 A, Windham

$750,000 - 4 Beds, 2 Baths, 2,240 Sf

MLS® # 20254949

Ulster County Board of Realtors Logo
Photo of Listing #20254919

57 Brainard Ridge 3-e, Windham

$645,000 - 4 Beds, 4 Baths, 2,100 Sf

MLS® # 20254919

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 © 2025 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.