Listed by T Story Jenks • LandVest, Inc/Woodstock. Bought with Southern Vermont Realty Group.
Sold on May 2026
$3,150,000
5
bd
•
5 ba
•
5,808
sq ft
54 Upton Rd, West Dover, VT 05356
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About this home
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.
Single-familyProperty Type
2004Year Built
91.4 acresLot Size
$542Price/Sq.Ft.
2 car garageParking
Listed by T Story Jenks• LandVest, Inc/Woodstock
Listed by Dia Jenks• LandVest, Inc/Woodstock
Bought with Erica Reynolds• Southern Vermont Realty Group
Est. $4,827 per month, based on comparable rentals
Sale and tax history for 54 Upton Rd
Sale History
Tax History
Date
Event
Price
PrimeMLS #5078620
May 8, 2026
Sold
$3,150,000
$542/sq ft
Mar 31, 2026
Contingent
—
Mar 9, 2026
Listed
$3,300,000
$568/sq ft
PrimeMLS #4828571
Dec 11, 2020
Sold
$2,825,000
$486/sq ft
Nov 23, 2020
Pending
—
Nov 18, 2020
Contingent
—
Sep 14, 2020
Listed
$2,900,000
$499/sq ft
Rare in Vermont ski country is a large property with great privacy, huge views, and a wonderful house. Located on a very private 100+ 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 with the highest quality appliances. 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. 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. Near Mount Snow, the Hermitage & Stratton. Under 2 hours to CT BDL airport, 3 hours to Boston and 4 hours to NYC.
Year
Property tax
Land + Additions
Assessment*
2025
$41,507 (+1.7%)
2024
$40,819 (+14.8%)
2023
$35,544 (−15.1%)
2022
$41,877 (+1.0%)
2021
$41,470 (+49.3%)
2020
$27,784 (+4.5%)
2019
$26,579 (+0.2%)
2018
$26,524 (+2.6%)
2017
$25,851 (+3.0%)
2016
$25,101 (+1.0%)
2015
$24,843
2013
Public record
Beds
5
Baths
5
Stories
1
Lot width
—
Lot depth
—
Lot size
103.6 Acres
Year renovated
—
Sq. Ft.
5,744
Year built
2004
Style
Single Family Residential
County
Windham County
APN
18305812606
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 8, 2026.
Property details
Parking
Parking & Garage
Garage Capacity: 2
Interior
Virtual Tour
Bathroom Information
# of Baths (full): 5
Basement Information
Basement: Yes
Basement Access: Interior
Finished
Other Interior Features
# of Rooms: 9
Flooring: Hardwood
Equipment & Appliance Information
Water Heater-Gas-LP/Bttle
Exterior
Building Information
Architectural Style: Post and Beam
Construction Status: Existing
Construction Materials: Post and Beam, Timber Frame, Wood Frame, Stone Exterior, Wood Exterior