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.
Active
Listed by: LandVest, Inc/Woodstock
$3,300,000
54 Upton Road, Dover, VT 05356
5beds
5,808sqft
Est.:
Single Family Residence
Built in 2004
91.4 Acres Lot
$3,006,800 Zestimate®
$568/sqft
$-- HOA
What's special
Huge viewsDining room and kitchen
- 15 hours |
- 747 |
- 58 |
Zillow last checked: 7 hours ago
Listing updated: 19 hours ago
Listed by:
T Story Jenks,
LandVest, Inc/Woodstock 802-457-4977,
Dia Jenks,
LandVest, Inc/Woodstock
Source: PrimeMLS,MLS#: 5078620
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 5
Heating
- Propane, Radiant
Cooling
- None
Appliances
- Included: Propane Water Heater
Features
- Cathedral Ceiling(s), Kitchen/Dining, Primary BR w/ BA, Natural Woodwork, Soaking Tub
- Flooring: Hardwood
- Basement: Finished,Interior Entry
- Number of fireplaces: 1
- Fireplace features: Wood Burning, 1 Fireplace
Interior area
- Total structure area: 5,808
- Total interior livable area: 5,808 sqft
- Finished area above ground: 3,776
- Finished area below ground: 2,032
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Gravel, Attached
- Garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Has view: Yes
- View description: Mountain(s)
- Frontage length: Road frontage: 787
Lot
- Size: 91.4 Acres
- Features: Field/Pasture, Orchard(s), Sloped, Views, Walking Trails, Wooded
Details
- Parcel number: 18305812606
- Zoning description: residential
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Post and Beam, Timber Frame, Wood Frame, Stone Exterior, Wood Exterior
- Foundation: Concrete
- Roof: Metal
Condition
- New construction: No
- Year built: 2004
Utilities & green energy
- Electric: On-Site
- Sewer: Mound Septic, On-Site Septic Exists
- Utilities for property: Phone, Satellite, Telephone at Site, Satellite Internet
Community & HOA
Location
- Region: West Dover
Financial & listing details
- Price per square foot: $568/sqft
- Tax assessed value: $2,078,470
- Annual tax amount: $52,612
- Date on market: 3/9/2026
- Electric utility on property: Yes
Estimated market value
$3,006,800
$2.29M - $3.79M
$5,705/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 3/9/2026 | Listed for sale | $3,300,000+16.8%$568/sqft |
Source: | ||
| 12/11/2020 | Sold | $2,825,000-2.6%$486/sqft |
Source: | ||
| 9/14/2020 | Listed for sale | $2,900,000+9566.7%$499/sqft |
Source: LandVest, Inc/Woodstock #4828571 Report a problem | ||
| 12/18/2000 | Sold | $30,000$5/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $2,078,470 |
| 2023 | -- | $2,078,470 |
| 2022 | -- | $2,078,470 |
| 2021 | -- | $2,078,470 +52.7% |
| 2020 | -- | $1,361,300 |
| 2019 | -- | $1,361,300 |
| 2018 | -- | $1,361,300 |
| 2017 | -- | $1,361,300 +1.3% |
| 2016 | -- | $1,343,180 +10084.9% |
| 2015 | -- | $13,188 |
| 2014 | -- | $13,188 |
| 2013 | -- | $13,188 |
| 2012 | -- | $13,188 |
| 2011 | -- | $13,188 |
| 2010 | -- | $13,188 +28.6% |
| 2009 | -- | $10,259 +1.8% |
| 2008 | -- | $10,074 |
| 2007 | -- | $10,074 |
| 2006 | -- | $10,074 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$22,161/mo
Principal & interest
$17018
Property taxes
$5143
Climate risks
Neighborhood: 05356
Getting around
0 / 100
Car-DependentNearby schools
GreatSchools rating
- NADover Elementary SchoolGrades: PK-6Distance: 4.3 mi
- NAMarlboro Elementary SchoolGrades: PK-8Distance: 11 mi
- 3/10Leland & Gray Uhsd #34Grades: 6-12Distance: 11.3 mi




