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Courtesy of T Story Jenks of LandVest, Inc/Woodstock: .

54 Upton Road

Dover, VT 05356
  • $3,150,000
  • STATUS: Closed
  • ON SITE: 62 Days
  • MLS #: 5078620
Sold - 05/08/2026
$3,150,000
SOLD - 05/08/2026
  • 5
    BEDS
  • 91.4
    ACRES
  • 5
    BATHS
  • 0
    1/2 BATHS
  • 5,808
    SQFT
  • $542
    $/SQFT
Type:
Single-Family Home
Built:
2004
County:
Area:

School Ratings & Info

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.

Sold by Southern Vermont Realty Group.

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© Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is 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. Data last updated 2026-05-11T08:05:32.067.
www.mcguirkproperties.com/homes/173853498
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54 Upton Road Dover, VT 05356

  • Price: $3,300,000
  • Status: Closed
  • On Site: 62 Days
  • Updated: 21 min ago
  • MLS #: 5078620
5
Beds
5
Baths
0
½ Baths
91.4
Acres
5,808
SQFT
$542
$/SQFT
2004
Built
County:
Windham
Area:
Dover
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.
Exterior Features

Architectural Style Post and Beam Construction Materials Post and BeamTimber FrameWood FrameStone ExteriorWood Exterior Driveway Gravel Has Garage Yes Lot Features Field/PastureMountain ViewOrchardsSlopingViewWalking TrailsWooded Parking Attached Road Frontage Yes Road Frontage Length 787 Roof Metal

Interior Features

Appliances Propane Water Heater Basement Access Type Interior Basement Description Finished Cooling None Flooring Hardwood Foundation Concrete Has Basement Yes Heating PropaneRadiant Interior Features Cathedral CeilingWood Fireplace1 FireplaceKitchen/DiningPrimary BR w/ BANatural WoodworkSoaking Tub Quarter Baths 0 Rooms Total 9 Sq Ft Approx Fin Above Grade 3776 Sq Ft Approx Fin Below Grade 2032

Property Features

Auction No Construction Status Existing Covenants Unknown Electric On-Site Flood Zone No Foreclosed / Bank Owned / REO No Pre Construction No Property Type Single Family Road Frontage Type Other Seasonal No Sewer MoundOn-Site Septic Exists Span Number 183-058-12606 Surveyed Yes Tax Gross Amount 52612.32 Tax Year 2025 Taxes Tbd No Timeshare Fractional Own No Utilities PhoneSatelliteTelephone at Site Water Source Drilled WellOn-Site Well ExistsPrivate Zoning residential

Courtesy of T Story Jenks of LandVest, Inc/Woodstock: .


© Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is 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. Data last updated 2026-05-11T08:05:32.067.
 
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