54 Upton Road Dover, VT $ 3,300,000
54 Upton Road
$ 3,300,000
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54 Upton Road

Dover, VT, 05356
$ 3,300,000
Bedrooms5 Baths5.0 Sq 5,808

Monthly Estimate*

$ 20,319

Listed by T Story Jenks, LandVest, Inc/Woodstock, sjenks@landvest.com
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Single Family Home for sale in Dover, VT for $3,300,000 with 5 bedrooms and 5 full baths. This 5,808 square foot home was built in 2004 on a lot size of 91.4.

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.

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Single Family Contingent

Price

$ 3,300,000

Bedrooms

5

Full Bath

5

Property Type

Single Family

Taxes

$ 0

Style

Post and Beam

Lot Size

91.4

Year Built

2004

Town/City

Dover

County/Region

WINDHAM

MLS | Web ID

5078620

Features
Interior
Basement Description Finished
Interior Amenities Cathedral Ceiling Wood Fireplace 1 Fireplace Kitchen/Dining Primary BR w/ BA Natural Woodwork Soaking Tub
Basement Yes
Flooring Hardwood
Beds 5
Total Rooms 9
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General
Road Frontage Yes
Sewer Mound On-Site Septic Exists
Heating Propane Radiant
Cooling None
Utilities Phone Satellite Telephone at Site
Roof Metal
Appliances Propane Water Heater
Garage Yes
Flood Zone No
Zoning residential
3/4 Baths 0
Full Baths 5
Half Baths 0
Bathrooms 5
Year Built 2004
Electric On-Site
Style Post and Beam
Stories Count 2
Construction Status Existing
Type Single Family
Auction No
Tax Year 2025
Status Detail 1
Covenants Unknown
Construction Materials Post and Beam Timber Frame Wood Frame Stone Exterior Wood Exterior
City Dover
Seasonal No
DOM 22
Price Per Sq Ft Total AG 568.18
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Exterior
Lot Features Field/Pasture Mountain View Orchards Sloping View Walking Trails Wooded
Driveway Gravel
Lot Size Area 91.4
Water Source Drilled Well On-Site Well Exists Private
Parking Features Attached
Garage Capacity 2
Foundation Concrete
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* Excluded Features
List By
T Story Jenks

Listing Agent

Landvest, Inc/Woodstock

Broker

sjenks@landvest.com

Email

Affordability Calculator

$20,319
Per Month
100%
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Monthly Principal & Interest
$20,319
Monthly Property Taxes
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Monthly Home Insurance
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
451920 Elementary School
452237 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
3/9/2026$3,300,000 Listed Price

Map


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54 Upton Road, Dover, VT, 05356 is a Single Family Home for sale at $3,300,000 with 5,808 sqft and a lot size of 91.4. 54 Upton Road has 5 bedrooms, 5.0 baths, and was built in 2004. The property's zip code is 05356 which is in Dover, VT