2069 Upper Hollow Road

Closed 5/7/21
Closed 5/7/21
Gallery Image 1
Sold
Last Sold Price
$800,000
4 beds4,512 sqft
2069 Upper Hollow Rd, Dorset, VT 05251
Single FamilyProperty Type
8.8 acresLot Size
1987Year Built
$177/sq ftPrice per sq ft
2 carsParking Spaces

Description

Nestled within the rolling hills of the enchanting Dorset Upper Hollow and tucked in on 8+ private and serene acres, sits a charming renovated, antique post and beam barn. Revealing a stunning open floor plan, graced with Palladian windows allowing an abundance of light and majestic mountain views. Four ample size bedrooms, and second floor loft which is perfect for home office, three baths with lower level partially finished off bonus room, laundry room and attached two car garage, this lovely home...Nestled within the rolling hills of the enchanting Dorset Upper Hollow and tucked in on 8+ private and serene acres, sits a charming renovated, antique post and beam barn. Revealing a stunning open floor plan, graced with Palladian windows allowing an abundance of light and majestic mountain views. Four ample size bedrooms, and second floor loft which is perfect for home office, three baths with lower level partially finished off bonus room, laundry room and attached two car garage, this lovely home has it all... Waiting for a new family to take Stewardship, lots of walking trails, very accessible to the wonderful amenities that Dorset has to offer.

    Sold By Four Seasons Sotheby's Int'l Realty

    • Listed by: Sunny Breen • Josiah Allen Real Estate, Inc.
    Listing closed: 05/07/2021 12:00 AM • Source: New England Real Estate Network, MLS#: 4848341

    Recent comparable sales

    Median sold price

    $776,000

    Avg days on market

    23

    Sale-to-list ratio

    97.1%

    Dorset, VT

    9 comparable properties found

    $650,000 | 364 Barrows Heights, Dorset, VT 05251
    1/35
    1

    $650,000

    Sold 10/07/24

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    Bedrooms
    4,228
    Square Feet
    3.2
    Acres

    364 Barrows Heights, Dorset, VT 05251

    $776,000 | 267 Eagle Ridge, Dorset, VT 05251
    1/15
    2

    $776,000

    Sold 08/04/26

    4
    Bedrooms
    4,282
    Square Feet
    5.92
    Acres

    267 Eagle Ridge, Dorset, VT 05251

    $875,000 | 81 Windward Hill, Dorset, VT 05251
    1/39
    3

    $875,000

    Sold 12/19/25

    4
    Bedrooms
    4,650
    Square Feet
    5.8
    Acres

    81 Windward Hill, Dorset, VT 05251

    $684,000 | 2744 Danby Mountain Road, Dorset, VT 05251
    1/35
    4

    $684,000

    Sold 06/22/26

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    Bedrooms
    4,683
    Square Feet
    5.9
    Acres

    2744 Danby Mountain Road, Dorset, VT 05251

    $380,000 | 567 Kirby Hollow Road, Dorset, VT 05251
    1/33
    5

    $380,000

    Sold 11/22/24

    4
    Bedrooms
    1,332
    Square Feet
    0.44
    Acres

    567 Kirby Hollow Road, Dorset, VT 05251

    $939,000 | 3478 Highway 30, Dorset, VT 05251
    1/40
    6

    $939,000

    Sold 10/11/24

    5
    Bedrooms
    4,452
    Square Feet
    0.45
    Acres

    3478 Highway 30, Dorset, VT 05251

    $2,600,000 | 198 Church Street, Dorset, VT 05251
    1/46
    7

    $2,600,000

    Sold 07/29/26

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    2,338
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    0.76
    Acres

    198 Church Street, Dorset, VT 05251

    $1,369,000 | 393 Red Tail Lane, Dorset, VT 05251
    1/60
    8

    $1,369,000

    Sold 09/04/25

    3
    Bedrooms
    3,967
    Square Feet
    11.52
    Acres

    393 Red Tail Lane, Dorset, VT 05251

    $670,000 | 1489 Highway 30, Dorset, VT 05251
    1/36
    9

    $670,000

    Sold 12/02/24

    3
    Bedrooms
    2,924
    Square Feet
    3.2
    Acres

    1489 Highway 30, Dorset, VT 05251

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    $5,072 per month

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    Property Information for 2069 Upper Hollow Road

    Property Details
    • Taxes: $11,260 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Zoning: Rural residential
    Building Information
    • Stories: 2
    • Year Built: 1987
    • Lot Size: 8.80 AC / 383,328 SF
    Summary
    Location and General Information
    • City: Dorset
    • County: VT-Bennington
    • Directions: Dorset Hollow Road to Upper Hollow Road. Travel approximately 2 miles to 2069 on the left hand side of the road.
    • Latitude: 43.275263377340785
    • Longitude: -73.054103084655765
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip: 05251
    Taxes and HOA Information
    • SPAN Number: 180-057-10157
    • Tax - Gross Amount: $11,260.16
    • Tax Year: 2021
    • Taxes TBD: No
    School Information
    • School - High: Burr and Burton Academy
    • School - Elementary: The Dorset School
    • School - Middle/Jr: The Dorset School
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Gravel
    Virtual Tour
    Property
    Lot Information
    • Lot - Sqft: 383328.0
    • Lot Size Acres: 8.8
    • Road Frontage Length: 550.0
    • Square Feet Apx Finished Above Grade: 2972.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 1540.0
    • Square Feet Apx Finished BG Source: Public Records
    • Square Feet Apx Total: 4512.0
    • Square Feet Apx Total Finished: 4512.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Other
    • Square Feet Apx Unfinished Below Grade: 0.0
    • Square Feet Apx Unfinished BG Source: Other
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete
    • PreConstruction: No
    • Surveyed: Unknown
    • Year Built: 1987
    Utilities
    • Electric Company: GMP
    • Fuel Company: Dorr
    • Electric: Circuit Breaker(s)
    • Sewer: On-Site Septic Exists
    • Utilities: Phone, Gas - At Street, Gas - Underground
    Interior and Exterior Features
    Exterior Features
    • Color: Grey
    • Features - Accessibility: 1st Floor Bedroom, 1st Floor Full Bathroom
    • Features - Exterior: Deck
    • Roads: Dirt
    • Roof: Shingle
    Interior Features
    • Appliances: Dishwasher, Dryer, Freezer, Refrigerator, Washer, Stove - Gas
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Concrete Floor, Finished, Insulated, Stairs - Interior
    • Baths - Total: 3
    • Baths - Full: 3
    • Half Baths: 0
    • One Quarter Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 9
    • Rooms: Level 1: Level 1: Den, Level 1: Dining Room, Level 1: Kitchen, Level 1: Living Room, Level 1: Master Bedroom
    • Rooms: Level 2: Level 2: Bedroom, Level 2: Loft
    • Bedrooms - Total: 4
    • Equipment: Smoke Detector, Stove-Gas
    • Features - Interior: Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace - Gas, Kitchen Island, Master BR w/ BA, Natural Light, Natural Woodwork, Security, Skylight, Wood Stove Hook-up, Laundry - Basement
    • Flooring: Carpet, Tile, Wood
    • Heat Fuel: Gas - LP/Bottle
    • Heating: Baseboard, Hot Air
    • Cooling: None
    • Total Stories: 2
    Room Information
    Room 1
    • Room Dimensions: 14x13
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 16x12
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 23x13
    • Room Level: 1
    • Room Type: Living Room
    Room 4
    • Room Dimensions: 14x13
    • Room Level: 1
    • Room Type: Den
    Room 5
    • Room Dimensions: 13x16
    • Room Level: 1
    • Room Type: Master Bedroom
    Room 6
    • Room Dimensions: 17x14
    • Room Level: 2
    • Room Type: Bedroom
    Room 7
    • Room Dimensions: 14x11
    • Room Level: 2
    • Room Type: Bedroom
    Room 8
    • Room Dimensions: 19x12
    • Room Level: 2
    • Room Type: Bedroom
    Room 9
    • Room Level: 2
    • Room Type: Loft

    Property History for 2069 Upper Hollow Road

    DateEvent & SourcePriceAppreciation
    May 7, 2021

    Sold (Public Record)

    Public Record #1464763657

    		$800,000

    +4.7% / yr

    May 7, 2021

    Sold

    New England Real Estate Network #4848341

    		$800,000—
    Apr 2, 2021

    Pending

    New England Real Estate Network #4848341

    		—
    DateEvent & SourcePrice
    05/07/2021

    Sold (Public Record)

    Public Record #1464763657

    $800,000

    +4.7% / yr

    05/07/2021

    Sold

    New England Real Estate Network #4848341

    $800,000
    04/02/2021

    Pending

    New England Real Estate Network #4848341

    —

    For completeness, we often displays two records for one sale: the MLS record and the public record.

    Public Records for 2069 Upper Hollow Road

    Taxable ValueLand$331,900Additions$669,800Total$1,001,700
    Tax Record2025$11,012 ($918 / month)
    Home Facts
    Beds0Lot Size392,040 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(057)001173

    Schools near 2069 Upper Hollow Road

    This home is within Taconic and Green Regional School District.
    Rating
    School
    Type
    Grades
    Distance
    Dorset Elementary School
    		Public - PK to 8
    Long Trail School
    		Private - 6 to 12
    Rating
    School
    Distance
    Dorset Elementary School
    PublicPK to 8

    Long Trail School
    Private6 to 12

    School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 2069 Upper Hollow Road, Dorset, VT 05251
    $800,000
    4
    4,512
    383,328
    2173 Upper Hollow Road, Dorset, VT 05251
    –
    –
    –
    –
    1,176,120
    2353 Lower Hollow Road, Dorset, VT 05251
    $319,000
    –
    –
    –
    278,784
    2491 Lower Hollow Road, Dorset, VT 05251
    $815,000
    4
    2,280
    200,376
    2430 Lower Hollow Road, Dorset, VT 05251
    –
    –
    –
    –
    225,641
    397 Red Tail Lane, Dorset, VT 05251
    $572,000
    4
    2,838
    2,356,596

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    Listing Courtesy of Josiah Allen Real Estate, Inc.

    Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 09/15/2026 02:35 PM