54 Upton Road, Dover, VT 05356

• 5 beds |
• 5 baths

Property Description

Rare in Vermont ski country is a large property with great privacy, huge views, and a wonderful house. Located on a very private 91.4 acres close to Mount Snow, Stratton and the Hermitage, Sleepy Bear Farm is sited on one of the highest built elevations in Vermont. The custom Wadsworth timber frame home is designed to take advantage of the unparalleled views of Mount Snow and the Hermitage and is ideal for gathering of friends and family and outdoor recreation. The great room’s expanse of windows frame the view and sunsets to the Southwest. A double-sided stone fireplace, rises up 2 ½ stories, warms the interior, while doors open to a stone patio for summer suppers. On the other side of the fireplace is the dining room and kitchen. The kitchen is equipped to easily handle a hungry crowd. A guest bedroom, bathroom and mudroom round out the first floor. Upstairs are two primary suites, a bedroom with a loft and three bathrooms. On the lower level, a media/game room and wine room complete the apres-ski amenities and an additional six double beds in the bunk room are ready for sleepy bears. The patina of a copper roof, 100% radiant heat, custom iron work and reclaimed wood exude understated quality throughout. Hike, bike, ski, snowshoe, and cross-country ski from the house via glades, wilderness trails and the VAST Trail. In the summer, cool off in the brook with a waterfall and swimming hole and pick fruit for breakfast or pies from the apple trees and blueberry bushes. Attached garage with 2 bays. 1.5 miles to Mount Snow (Epic pass), 5 miles to the Hermitage, 14 miles to Stratton (Ikon pass). Under 2 hours to Bradley International Airport, less than 3 hours to Boston and just over 4 hours to New York.

Listing Status:

Active

Date Added:

March 9, 2026

Data Last Updated:

March 14, 2026 at 8:00AM

Listing Office:

LandVest, Inc/Woodstock : 802-457-4977

Listing Agent:

T Story Jenks :

MLS ID:

5078620

Interior

• General: Cathedral CeilingWood Fireplace1 FireplaceKitchen/DiningPrimary BR w/ BANatural WoodworkSoaking Tub
• Appliances: Propane Water Heater
• Basement: Finished
• Flooring: Hardwood
• A/C: None
• Heating: PropaneRadiant

Exterior

• Style: Post and Beam
• Parking: Attached

Construction

• Roofing: Metal
• General: Post and BeamTimber FrameWood FrameStone ExteriorWood ExteriorConcrete

Location

• Road/Access: Other
• County: Windham

Lot

• Driveway: Gravel
• Zoning: residential

Utilities

• Utilities: Telephone at SitePhoneSatellite
• Water: Drilled WellOn-Site Well ExistsPrivate
• Sewer: MoundOn-Site Septic Exists