When was property at 1060 Upper Hollow Road built and last sold?

The property at 1060 Upper Hollow Road was built in and last sold on May 3, 2013 for $1,300,000.

How much is this home worth?

The estimated value of the home located at 1060 Upper Hollow Road is $5,656,000.

What are some comparable homes to 1060 Upper Hollow Road?

There are currently no comparable homes to 1060 Upper Hollow Road.

Bennington

05251

1060 Upper Hollow

Map

Listed by: Sunny Breen, Josiah Allen Real Estate, Inc., 802-867-5555, Listing Courtesy of Prime MLS

$5,600,000

● House - For Sale

1060 Upper Hollow

Dorset, VT 05251

5 Beds

1 Bath, 1 Half Bath

4,800 Ft²

$30,003

Est. Monthly

About This Property

'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.

Unit Size

4,800 Ft²

Days on Market

Land Size

66.60 acres

Price per sqft

$1,167

Property Type

House

Property Taxes

$2,506

HOA Dues

Year Built

Listed By

Sunny Breen

[email protected]

Josiah Allen Real Estate, Inc.

Payment Calculator (Computations Provided by RealtyHop)

Cap Rate Calculator

Last updated: 5 months ago (Prime MLS #5075285)

Price History

Date / Event	Date	Event	Price
Jan 30, 2026	Listed by Josiah Allen Real Estate, Inc.	$5,600,000
Listed by Josiah Allen Real Estate, Inc.

Property Highlights

Fireplace

Parking Details

Has Garage

Garage Spaces: 7

Interior Details

Half Bathrooms: 1

Full Bathrooms: 1

Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Kitchen Island, Walk-In Closet(s), 1 Fireplace, Living/Dining, Security, Basement Laundry

Appliances: Electric Cooktop, Dishwasher, Dryer, Microwave, Double Oven, Refrigerator, Washer, Induction Cooktop, Wine Cooler

Flooring Type: Carpet, Tile, Wood

Rooms: 9

Basement: Yes

Exterior Details

Square Footage: 4800

Architectural Style: Contemporary

Year Built: 1965

Construction Materials: Wood Siding

Lot Features: Country Setting, Mountain View, Pond, River, Rolling, Water View, Near Paths

Lot Size Area: 2901096

Lot Size Units: Square Feet

Lot Size Acres: 66.6

Lot Size Square Feet: 2901096

Water Source: Spring

Financial Details

Tax Annual Amount: $30,070

Utilities Details

Cooling Type: Central AC

Heating Type: Propane, Radiant, Boiler

Sewer : On-Site Septic Exists

Building Info

Overview

General

Bedroom Count: 0

Building Condition: 0
Building Quality: 0
Construction Type: 0
Building Style: 0
Exterior Walls Type: 0
Interior Walls Type: 0
Roof Shape Type: 0
Roof Cover Type: 0
Floor Cover: 0
Basement Type: 0
Basement Area: 0
Garage Type: 0
Parking Space Count: 0
Patio Type: 0
Porch Type: 0
Pool Type: 0

Dimensions

Lot Size Square Feet: 2,918,520

Total Building Area: 0
Building Area: 0

Heating and Cooling

Air Conditioning: 0

Heating: 0
Heating Fuel Type: 0

Utilities

Sewer System: 0

Water Service: 0

Building

Building Type: 0

Property Class: R
Land Acres: 0000067000
Standard Land Use Code: 1000
County Land Use Code: R2
Legal Description 1: REAL VALUE: 1198500

Neighborhood

School District Name: Bennington Rutland Supervisory Union

Census Tract: 971400

Geography

Parcel: (057)001152

Municipality: DORSET
Latitude: 43.2617
Longitude: -73.0664

Address

Full Address: 1060 Upper Hollow Rd

Address - House Number: 1060
Address - Street Name: Upper Hollow
Address - Suffix Type: Rd
State: VT
City Name: Dorset
Carrier Code: R022
4-Digit Zip Code: 9731
Zip Code: 05251

Valuation

Tax

Tax Year: 2022

Tax Amount: $1,251,588
Tax Rate Code Area: 057

Appraisal Valuation

Standard Deviation: 0.2746

Valuation Date: Apr 19, 2023
Confidence Score: 60
Final Value: 1,981,083
High Value: 2,525,154
Low Value: 1,437,013

Assessments Valuation

Assessed Year: 2022

Assessed Total Value: $1,289,300
Assessed Land Value: $658,600
Assessed Improvements Value: $630,700

Sales

Current Sale Contract Date: May 03, 2013

Current Sale Recording Date: May 07, 2013
Current Sale Price:

Premium
Current Sale Document Type: 27
Current Sale Input Document Number: 201305141118431045

Data used for valuation calculations is provided by RealtyHop, and other third party sources

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Comparables

About Bennington

Stats & Trends

Median Asking:

$410,000

Sale Price/ft²

$173

Below Asking

0.02%

Average Days on Market

Average Home Size

3761 ft²

Average Home Age

68.3 years

Currently For Sale

201 Listings

Based on RH Advisors, Inc. calculations of home data from MLS and/or public records.

Similar Homes for Sale

Currently no similar homes around

Nearby Rentals

Unit for rent at 3093 Route 30, Dorset, VT, 05251

$7,500 /mo

3 Beds
1 Bath
2,850 ft²

3093 Route 30, Dorset, VT, 05251 Listing by Elizabeth Romano

Unit for rent at 133 Kent Hill, Dorset, 05251

$9,000 /mo

4 Beds
1 Bath
2,078 ft²

133 Kent Hill, Dorset, 05251 Listing by Elizabeth Romano

Rentals Near You

Click here to view more rentals in the neighborhood.

Listed by: Sunny Breen, Josiah Allen Real Estate, Inc.
Last Updated Date: 2026-06-17
Last Checked: 3 hours ago
Data Source: Prime MLS, MLS# 5075285

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 The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.