1060 Upper Hollow RoadDorset, VT 05251MLS Number 5075285

Price: $5,600,000
Est. Mortgage of $/month
20 Days on Market

'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'... This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplace, perfect for cozy evenings. The main residence captures the landscape from every angle blending modern architecture seamlessly with nature. This is much more than a home, it is truly a legacy property... Prestigious, Private and Profoundly Peaceful and must be seen to be fully appreciated!! Beauty, solitude, quiet luxury!!! Subdivision potential.

More Info

Tax Information

Tax Year2025

Location

Building Number1060
StreetUpper Hollow Road
TownDorset
StateVT
Zip05251
CountyBennington
High SchoolBurr and Burton Academy
Flood Zone Y/NNo
Address1060 Upper Hollow Road

Property

Acreage66.6
Lot DescriptionCountry Setting, Mountain View, Pond, River, Rolling, Water View, Near Paths
AreaVT-Bennington
DrivewayGravel
RoadsDirt, Public Maintained Road
Road Frontage700

Amenities

AmenitiesCO Detector, Smoke Detector, Standby Generator
PricePerSqFt1198.12

Other

SeasonalNo
Page547
Date Listed01/30/2026
View Count5

Parking

Parking Spaces7
GarageYes

Building

Year Built1965
Building ConstructionWood Frame
ConstructionExisting
Property StyleContemporary
Bedrooms5
Bathroom6
Total Baths6
3/4 Baths4
Half Bath1
Total Rooms9
Square Feet4,674
APX Unfin Below Grade126
BasementClimate Controlled, Finished, Walkout
FoundationConcrete

Exterior

Exterior FeaturesDeck, Outbuilding, Patio, Covered Porch, Storage
RoofAsphalt Shingle, Slate

Legal

Taxes$30,070.34
Tax ReductionNo
ZoningRR
Surveyed Y/NYes

Rooms

Full Bath1

Basic Information

MLS Number5075285
MLS StatusActive
Virtual TourView Tour
StatusACT
Property TypeSingle Family
List Price$5,600,000
Listing Agent NameSunny Breen
Broker NameJosiah Allen Real Estate, Inc.

Interior

Interior FeaturesCathedral Ceiling, Ceiling Fan,1 Fireplace, Kitchen Island, Living/Dining, Security, Walk-in Closet, Basement Laundry
FloorsCarpet, Tile, Wood
Stories1

Utilities

Heat SystemPropane, Radiant, Boiler
WaterSpring
SewerOn-Site Septic Exists
ElectricCircuit Breaker(s)
UtilitiesPhone, Cable

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 February 18, 2026 8:08 PM EST

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1060 Upper Hollow RoadDorset, VT 05251MLS Number 5075285

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