54 C Upton Rd

5,808 Sq. Ft.
$568 / Sq. Ft.
5,808
Sq. Ft.
$568
per Sq. Ft.

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...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.
  1. Listed by T Story Jenks • LandVest, Inc/Woodstock
  2. Listed by Dia Jenks • LandVest, Inc/Woodstock

Property Details for 54 C Upton Road

Zoning
residential
LISTING UPDATED: 03/10/2026 12:25 PM

Property Details for 54 C Upton Road

StatusActive
MLS #5078620
Days on Market12
Taxes$52,612 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built2004
Lot Size91.40 AC / 3,981,384 SF
CountyWindham County

Location

Listing Courtesy of LandVest, Inc/Woodstock
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Building Information for 54 C Upton Road

Stories2Year Built2004Building Size-Lot Size91.40 AC / 3,981,384 SF

Payment Calculator

$20,400 per month

30 year fixed, 6.11% Interest

Principal and Interest

$16,015

Property Taxes

$4,384

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 54 C Upton Road

Summary
Location and General Information
  • City: Dover
  • County: VT-Windham
  • Latitude: 42.981358000001002
  • Longitude: -72.872332000000000
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05356
Taxes and HOA Information
  • SPAN Number: 183-058-12606
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Gravel
Virtual Tour
Property
Lot Information
  • Lot Features: Field/Pasture, Mountain View, Orchards, Sloping, View, Walking Trails, Wooded
  • Lot Size Acres: 91.4
  • Road Frontage Length: 787.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Yes
  • Year Built: 2004
Utilities
  • Electric: On-Site
  • Sewer: Mound, On-Site Septic Exists
  • Water Source: Drilled Well, On-Site Well Exists, Private
  • Utilities: Phone, Satellite, Telephone at Site
  • Internet: Satellite Internet
Interior and Exterior Features
Exterior Features
  • Construction Materials: Post and Beam, Timber Frame, Wood Frame, Stone Exterior, Wood Exterior
  • Roof: Metal
Interior Features
  • Appliances: Propane Water Heater
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Finished
  • Flooring: Hardwood
  • Heating: Propane, Radiant
  • Cooling: None
  • Total Stories: 2

Property History for 54 C Upton Road

DateEvent & SourcePriceAppreciation
Mar 9, 2026

Listed (Active)

New England Real Estate Network #5078620

$3,300,000
Dec 15, 2020

Sold (Public Record)

Public Record #686106480

$2,825,000
Dec 11, 2020

Sold

New England Real Estate Network #4828571

$2,825,000
Nov 20, 2020

Pending

New England Real Estate Network #4828571

Sep 14, 2020

Listed (Active)

New England Real Estate Network #4828571

$2,900,000
DateEvent & SourcePrice
03/09/2026

Listed (Active)

New England Real Estate Network #5078620

$3,300,000
12/15/2020

Sold (Public Record)

Public Record #686106480

$2,825,000
12/11/2020

Sold

New England Real Estate Network #4828571

$2,825,000
11/20/2020

Pending

New England Real Estate Network #4828571

09/14/2020

Listed (Active)

New England Real Estate Network #4828571

$2,900,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 54 C Upton Road

Taxable ValueLand-Additions-Total-
Tax Record2024$51,317 ($4,276 / month)
Home Facts
Beds5Baths5Total Finished SqFt4,432 SqFtAbove Grade Finished SqFt4,432 SqFtUnfinished Basement SqFt720 SqFtStories1Lot Size4,512,816 SqFtStyleSingle Family ResidenceYear Built2004CountyWINDHAMAPN(058) UR001

Schools near 54 C Upton Road

This home is within River Valleys Unified School District #73.
Rating
School
Type
Grades
Distance
Public - PK to 6
Rating
School
Distance
Dover Elementary School
PublicPK to 6

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

54 C Upton Road is a single family home for sale in West Dover, VT 05356. This property was listed for sale on March 9, 2026 by LandVest, Inc/Woodstock, it's currently listed at $3,300,000. It has been on the market for a total of 12 days and was last sold on December 15, 2020. This listing's school district is River Valleys Unified School District #73. Nearby schools include Dover Elementary School. 54 C Upton Road is a 5-bed, 5-bath, 5,808 sqft single family home built in 2004.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of LandVest, Inc/Woodstock

Copyright 2026 PrimeMLS, Inc. 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 03/22/2026 02:10 AM