'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.
Active
Listed by: Josiah Allen Real Estate, Inc.
$5,600,000
1060 Upper Hollow Road, Dorset, VT 05251
5beds
4,674sqft
Est.:
Single Family Residence
Built in 1965
66.6 Acres Lot
$-- Zestimate®
$1,198/sqft
$-- HOA
What's special
Dramatic stone fireplaceContemporary open layout
- 85 days |
- 684 |
- 17 |
Zillow last checked:
Listing updated:
Listed by:
Sunny Breen,
Josiah Allen Real Estate, Inc. 802-867-5555
Source: PrimeMLS,MLS#: 5075285
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 1
- 3/4 bathrooms: 4
- 1/2 bathrooms: 1
Heating
- Propane, Radiant
Cooling
- Central Air
Appliances
- Included: Electric Cooktop, Dishwasher, Dryer, Microwave, Double Oven, Refrigerator, Washer, Induction Cooktop, Wine Cooler
- Laundry: In Basement
Features
- Cathedral Ceiling(s), Ceiling Fan(s), Kitchen Island, Living/Dining, Walk-In Closet(s)
- Flooring: Carpet, Tile, Wood
- Basement: Climate Controlled,Finished,Walkout,Interior Entry
- Number of fireplaces: 1
- Fireplace features: 1 Fireplace
Interior area
- Total structure area: 4,800
- Total interior livable area: 4,674 sqft
- Finished area above ground: 2,650
- Finished area below ground: 2,024
Property
Parking
- Total spaces: 7
- Parking features: Gravel
- Garage spaces: 7
Features
- Levels: One
- Stories: 1
- Patio & porch: Patio, Covered Porch
- Exterior features: Deck, Storage
- Has view: Yes
- View description: Mountain(s), Water
- Water view: Water
- Waterfront features: Pond, River
- Frontage length: Road frontage: 700
Lot
- Size: 66.6 Acres
- Features: Country Setting, Rolling Slope, Near Paths
Details
- Additional structures: Outbuilding
- Parcel number: 18005710019
- Zoning description: RR
- Other equipment: Standby Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Wood Frame
- Foundation: Concrete
- Roof: Asphalt Shingle,Slate
Condition
- New construction: No
- Year built: 1965
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: On-Site Septic Exists
- Utilities for property: Phone, Cable
Community & HOA
Community
- Security: Security, Carbon Monoxide Detector(s), Smoke Detector(s)
Location
- Region: Dorset
Financial & listing details
- Price per square foot: $1,198/sqft
- Tax assessed value: $1,289,300
- Annual tax amount: $30,070
- Date on market: 1/30/2026
- Road surface type: Dirt
Estimated market value
Not available
Estimated sales range
Not available
$5,143/mo
Price history
| Date | Event | Price |
|---|---|---|
| 1/30/2026 | Listed for sale | $5,600,000+330.8%$1,198/sqft |
Source:  PrimeMLS #5075285 Report a problem | ||
| 5/7/2013 | Sold | $1,300,000$278/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $1,289,300 |
| 2023 | -- | $1,289,300 |
| 2022 | -- | $1,289,300 +4.9% |
| 2021 | -- | $1,228,800 |
| 2020 | -- | $1,228,800 -1% |
| 2019 | -- | $1,240,800 +0.7% |
| 2018 | -- | $1,232,370 +2.8% |
| 2017 | -- | $1,198,510 +0% |
| 2016 | -- | $1,198,500 +9900% |
| 2015 | -- | $11,985 +11.1% |
| 2014 | -- | $10,790 |
| 2013 | -- | $10,790 |
| 2012 | -- | $10,790 |
| 2011 | -- | $10,790 |
| 2010 | -- | $10,790 |
| 2009 | -- | $10,790 |
| 2008 | -- | $10,790 |
| 2007 | -- | $10,790 |
Find assessor info on the county website
Monthly payment
Est. payment
$35,839/mo
Principal & interest
$27859
Property taxes
$7980
More affordability tools
Climate risks
Neighborhood: 05251
Getting around
0 / 100
Car-DependentNearby schools
GreatSchools rating
- 6/10Dorset Elementary SchoolGrades: PK-8Distance: 2.9 mi
- NABurr & Burton AcademyGrades: 9-12Distance: 7 mi
Schools provided by the listing agent
- High: Burr and Burton Academy
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Vermont
- Bennington County
- Dorset
- 05251
- 1060 Upper Hollow Road
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