54 Upton Road, West Dover, VT 05356
SOLD
MAY 8, 2026
Listed by T Story Jenks, LandVest, Inc/Woodstock, (802) 457-4977 . Bought with Southern Vermont Realty Group

54 Upton Road
West Dover, VT 05356

  • 5 Beds
  • 5 Baths
  • 5,808 sqft (on 91.40 acres)

$3,150,000

Last Sold: May 8, 2026
5% below list $3.3M
$542/sqft

$3,150,000

Last Sold: May 8, 2026
5% below list $3.3M
$542/sqft
5 Beds
5 Baths
5,808 sqft
(on 91.40 acres)

Homes for sale near 54 Upton Road

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination
Last check for updates: about 7 hours ago
Listed by T Story Jenks
LandVest, Inc/Woodstock, (802) 457-4977
Dia Jenks
LandVest, Inc/Woodstock, (802) 457-4977
Bought with: Erica Reynolds, Southern Vermont Realty Group, (802) 464-2585
Source: PrimeMLS, MLS#5078620

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from May 08, 2026

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
$542/sqft
Listed
61 days ago

Home Details for 54 Upton Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Finished,Interior EntryNumber of Rooms: 9
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 5808 Square Feet
Appliances & Utilities
Utilities: Phone, Satellite, Telephone at Site, Satellite InternetAppliances: Propane Water Heater
Heating & Cooling
Heating: Propane,RadiantNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Propane
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood Burning, 1 FireplaceHas a Fireplace
Gas & Electric
Electric: On-SiteHas Electric on Property
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Hardwood
View
Has a ViewView: Mountain(s)

Exterior Features

Exterior Home Features
Roof: MetalFoundation: Concrete
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageParking Spaces: 2Parking: Gravel,Attached
Frontage
Road Frontage: Other
Water & Sewer
Sewer: Mound Septic, On-Site Septic Exists
Farm & Range
Frontage Length: Road frontage: 787
Finished Area
Finished Area (above surface): 3776 Square FeetFinished Area (below surface): 2032 Square Feet

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Post and BeamArchitecture: Post and Beam
Building
Construction Materials: Post and Beam, Timber Frame, Wood Frame, Stone Exterior, Wood ExteriorNot a New Construction

Price & Status

Price
List Price: $3,300,000Price Per Sqft: $542/sqft

Media

Location

Direction & Address
City: Dover

Building

Building Area
Building Area: 5808 Square Feet

Lot Information

Lot Area: 91.4 Acres

Miscellaneous

BasementMls Number: 5078620Above Grade Unfinished Area: 3776Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square Feet

Price History for 54 Upton Road

DatePriceEventSource
05/08/2026$3,150,000Sold
PrimeMLS #5078620
03/09/2026$3,300,000Listed For SalePrimeMLS #5078620
12/11/2020$2,825,000Sold
PrimeMLS #4828571
09/14/2020$2,900,000Listed For SaleAgent Provided
12/18/2000$30,000Sold
N/A
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Property Tax and Assessment

Year2024
Tax
Assessment$2,078,470
Home facts updated by county records

Comparable Sales for 54 Upton Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
15 View Point Road, West Dover, VT
0.37
Single-Family Home
$20,000
01/09/26
5
5
3,644
233 Blue Brook Road, West Dover, VT
0.39
Single-Family Home
$170,000
07/25/25
6
4
2,764
204 Blue Brook Road, West Dover, VT
0.54
Single-Family Home
$270,000
09/19/25
3
1.5
1,386
592 RT 100, Stratton, VT
1.10
Single-Family Home
$510,000
07/30/25
6
3.5
2,352
55 Joans Ridge Road, West Dover, VT
1.76
Single-Family Home
$829,000
08/15/25
5
4
5,599
1 Sundance Village Loop, West Dover, VT
2.09
Single-Family Home
$2,700,000
11/19/25
5
5.5
5,413
8 Challenger Hill Extension, West Dover, VT
1.65
Single-Family Home
$975,000
06/12/25
4
3
4,500
261 Handle Road, West Dover, VT
1.69
Single-Family Home
$780,000
04/29/26
6
3
2,900

Assigned Schools

These are the assigned schools for 54 Upton Road.
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What Locals Say about Dover

At least 7 Trulia users voted on each feature.

  • 100 % Say parking is easy

  • 92 % Say it's quiet

  • 92 % Say people would walk alone at night

  • 89 % Say it's dog friendly

  • 88 % Say car is needed

  • 73 % Say there's wildlife

  • 44 % Say streets are well-lit

  • 43 % Say kids play outside

  • 43 % Say yards are well-kept

  • 42 % Say they plan to stay for at least 5 years

  • 40 % Say neighbors are friendly

  • 38 % Say it's walkable to grocery stores

  • 38 % Say there's holiday spirit

  • 33 % Say it's walkable to restaurants

  • 33 % Say there are sidewalks

  • 33 % Say there are community events

Learn more about our methodology.
  • Darva K.
    "I have a residence here, love to come whenever possible. Great people, great place. "
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LGBTQ Local Legal Protections

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display 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 2026-05-09 15:46:26 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

Homes for rent near 54 Upton Road

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Off Market Homes Near 54 Upton Road

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Explore by feature

54 Upton Road, West Dover, VT 05356 is a 5 bedroom, 5 bathroom, 5,808 sqft single-family home built in 2004. This property is not currently available for sale. 54 Upton Road was last sold on May 8, 2026 for $3,150,000 (5% lower than the asking price of $3,300,000). The current Trulia Estimate for 54 Upton Road is $3,118,000.