Listed by Sunny Breen • Josiah Allen Real Estate, Inc.
For sale
$5,600,000
Est. $32,823/mo —
5
bd
•
5.5 ba
•
4,674
sq ft
1060 Upper Hollow Rd, Dorset, VT 05251
About this home
'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.
Single-familyProperty Type
1965Year Built
66.6 acresLot Size
$1,198Price/Sq.Ft.
7 car garageParking
Listed by Sunny Breen• Josiah Allen Real Estate, Inc.
Wow Factor in Spades Prestigious Dorset Upper Hollow, privacy, panoramic mountain views, large upper and lower ponds with swimming dock, 67 acres with incredible trails, 1,200 feet of frontage on the Mettowee river. Tri-level colonial that was renovated in 2001 adding spectacular viewing deck, new windows, siding, cathedral ceiling living room with fireplace, kitchen with island, cozy guest cottage and detached two car garage. There are 5+ secluded lots with 4 having septic permits that could be developed (family compound potential ?) are perked for septic; access if from Paddock Road with 50 foot right away along stone wall. This is a must see, if looking for the best of best settings and best of best unobstructed panoramic views.
Year
Property tax
Land + Additions
Assessment*
2025
$28,186 (+11.5%)
$1,100,300 + $1,463,700
$2,564,000
2024
$25,274 (+14.3%)
$658,600 + $630,700
$1,289,300
2023
$22,102 (−11.7%)
$658,600 + $630,700
$1,289,300
2022
$25,032 (+7.8%)
$658,600 + $630,700
$1,289,300
2021
$23,212 (+1.6%)
$658,600 + $570,170
$1,228,770
2020
$22,842 (+4.6%)
$658,600 + $570,170
$1,228,770
2019
$21,839 (+1.3%)
$658,600 + $582,240
$1,240,840
2018
$21,562 (+4.0%)
$658,600 + $573,770
$1,232,370
2017
$20,724 (+1.7%)
$658,600 + $539,910
$1,198,510
2016
$20,382 (+3.3%)
$658,600 + $539,910
$1,198,510
2015
$19,730
$658,600 + $539,910
$1,198,510
2013
Public record
Beds
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Lot size
67 Acres
Year renovated
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Finished Sq. Ft.
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Unfinished Sq. Ft.
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Total Sq. Ft.
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Year built
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Style
Other
County
Bennington County
APN
18005710019
Parking Spaces
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Accessible
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Last updated by owner on Jul 15, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
1/10 Heat Factor
7 days above 88° expected this year, 16 days in 30 years
3/10 Wind Factor
5% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Dorset, VT • 05251
Average low and high temperatures (°F)
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46
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76
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72
49
59
39
44
30
31
16
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Sun exposure
Try the sun simulator tool to see how light moves across the property at different times of day and year.
Provided by Shadowmap
Redfin Estimate for 1060 Upper Hollow Rd
$4,998,098
$602K under list price of $5.60M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $725K to $2.6M.