1284 Upper Hollow Road

Closed 11/16/20
Closed 11/16/20
Gallery Image 1
Sold
Last Sold Price
$1,000,000
4 beds3,938 sqft
1284 Upper Hollow Rd, Dorset, VT 05251
Single FamilyProperty Type
25 acresLot Size
1855Year Built
$254/sq ftPrice per sq ft
4 carsParking Spaces

Description

Offered for the first time in 65 years take the park like drive on Upper Hollow to 1284 at its pinnacle, this historic Vermont hill farm is ideally situated to provide 360 degree views of the mountains forming the Dorset Hollow. Mature plantings shield the property from the road with open rolling meadows all around. Originally built in 1855, total rebuild in 1955 and there's a circa 2000 addition creating a main level vaulted & beamed ceiling primary suite, two walk-in closets, south west facing...Offered for the first time in 65 years take the park like drive on Upper Hollow to 1284 at its pinnacle, this historic Vermont hill farm is ideally situated to provide 360 degree views of the mountains forming the Dorset Hollow. Mature plantings shield the property from the road with open rolling meadows all around. Originally built in 1855, total rebuild in 1955 and there's a circa 2000 addition creating a main level vaulted & beamed ceiling primary suite, two walk-in closets, south west facing morning room, walk out substantial guest quarters or in-law space below. The L-shaped living / dining room has numerous windows providing views and light, wood floors, exposed beams and a central wood burning fireplace. The corner eat-in kitchen is open and light-filled with plentiful cabinetry and access to all living areas, a sunny deck and fenced in side yard. Exposed ceiling beams, two walk-in closets, wood floor and a white tile bath comprise the master. Upstairs there are two additional spacious bedrooms, one with wood burning fireplace and loaded with architectural detail. Antique wide pine floor, light, views and a third tile bath complete this floor. 1020 sqft detached garage. 25 pastoral acres that shall service agriculture, equine or the animals desired! Private Retreat, family compound or develop as the property offers long road frontage of tremendous quality open land! A sanctuary that self sustains!

    Sold By Josiah Allen Real Estate, Inc.

    • Listed by: Laura Beckwith • Josiah Allen Real Estate, Manchester Branch Office
    Listing closed: 11/16/2020 12:00 AM • Source: New England Real Estate Network, MLS#: 4806732

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    Recent comparable sales

    Median sold price

    $1,075,000

    Avg days on market

    26

    Sale-to-list ratio

    95.0%

    Dorset, VT

    9 comparable properties found

    $1,075,000 | 5173 Highway 30, Dorset, VT 05251
    1/45
    1

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    Bedrooms
    3,584
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    0.85
    Acres

    5173 Highway 30, Dorset, VT 05251

    $875,000 | 81 Windward Hill, Dorset, VT 05251
    1/39
    2

    $875,000

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    4
    Bedrooms
    4,650
    Square Feet
    5.8
    Acres

    81 Windward Hill, Dorset, VT 05251

    $650,000 | 364 Barrows Heights, Dorset, VT 05251
    1/35
    3

    $650,000

    Sold 10/07/24

    4
    Bedrooms
    4,228
    Square Feet
    3.2
    Acres

    364 Barrows Heights, Dorset, VT 05251

    $939,000 | 3478 Highway 30, Dorset, VT 05251
    1/40
    4

    $939,000

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    Bedrooms
    4,452
    Square Feet
    0.45
    Acres

    3478 Highway 30, Dorset, VT 05251

    $776,000 | 267 Eagle Ridge, Dorset, VT 05251
    1/15
    5

    $776,000

    Sold 08/04/26

    4
    Bedrooms
    4,282
    Square Feet
    5.92
    Acres

    267 Eagle Ridge, Dorset, VT 05251

    $1,369,000 | 393 Red Tail Lane, Dorset, VT 05251
    1/60
    6

    $1,369,000

    Sold 09/04/25

    3
    Bedrooms
    3,967
    Square Feet
    11.52
    Acres

    393 Red Tail Lane, Dorset, VT 05251

    $1,275,000 | 3360 Dorset West Road, Dorset, VT 05251
    1/51
    7

    $1,275,000

    Sold 09/05/25

    4
    Bedrooms
    3,610
    Square Feet
    1.86
    Acres

    3360 Dorset West Road, Dorset, VT 05251

    $1,250,000 | 7 Timberbrook North, Dorset, VT 05251
    1/38
    8

    $1,250,000

    Sold 11/21/25

    5
    Bedrooms
    4,686
    Square Feet
    4.7
    Acres

    7 Timberbrook North, Dorset, VT 05251

    $1,390,000 | 92 Barrows Heights, Dorset, VT 05251
    1/46
    9

    $1,390,000

    Sold 08/20/25

    5
    Bedrooms
    3,165
    Square Feet
    3.89
    Acres

    92 Barrows Heights, Dorset, VT 05251

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    Property Information for 1284 Upper Hollow Road

    Property Details
    • Taxes: $16,848 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Zoning: residential
    Building Information
    • Stories: 2
    • Year Built: 1855
    • Lot Size: 25.00 AC / 1,089,000 SF
    Summary
    Location and General Information
    • Area Description: In Town, Near Paths, Near Shopping
    • City: Dorset
    • County: VT-Bennington
    • Directions: RT 30 to Dorset Hollow Rd bearing Right meander out toward the Dorset Hollow bearing Left onto Upper Hollow at the height of the road the farm is on your Right.
    • Latitude: 43.265748003647040
    • Longitude: -73.060931187835692
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Map: 06
    • Zip: 05251
    Taxes and HOA Information
    • SPAN Number: 180-057-11297
    • Tax - Gross Amount: $16,848.00
    • Tax Year: 19
    • Taxes TBD: No
    School Information
    • School - High: Burr and Burton Academy
    • School - District: Bennington/Rutland
    • School - Elementary: Dorset Elementary School
    • School - Middle/Jr: Dorset Elementary School
    Parking
    • Garage: Yes
    • Garage Capacity: 4.00
    • Driveway: Paved
    Property
    Lot Information
    • Block: 00
    • Lot: 48.0
    • Lot - Sqft: 1089000.0
    • Lot Size Acres: 25.0
    • Road Frontage Length: 1560.0
    • Square Feet Apx Finished Above Grade: 3938.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Finished BG Source: Public Records
    • Square Feet Apx Total: 5023.0
    • Square Feet Apx Total Finished: 3938.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Public Records
    • Square Feet Apx Unfinished Below Grade: 1085.0
    • Square Feet Apx Unfinished BG Source: Public Records
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete, Stone
    • PreConstruction: No
    • Surveyed: Unknown
    • Year Built: 1855
    Utilities
    • Electric: 200 Amp
    • Sewer: Private, Septic
    • Utilities: Other
    Interior and Exterior Features
    Exterior Features
    • Color: Red
    • Features - Exterior: Barn, Deck
    • Roads: Gravel, Public
    • Roof: Slate
    Interior Features
    • Appliances: Dishwasher, Dryer, Range - Gas, Refrigerator, Washer
    • Basement: Yes
    • Basement Access Type: Walkout
    • Basement Description: Concrete Floor, Stairs - Interior, Storage Space, Walkout
    • Baths - Total: 4
    • Baths - Full: 3
    • Half Baths: 1
    • One Quarter Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 9
    • Rooms: Level 1: Level 1: Dining Room, Level 1: Family Room, Level 1: Foyer, Level 1: Kitchen - Eat-in, Level 1: Living Room, Level 1: Master Bedroom
    • Rooms: Level 2: Level 2: Bedroom
    • Rooms: Level B: Level B: Bedroom, Level B: Family Room
    • Bedrooms - Total: 4
    • Features - Interior: Dining Area, Fireplaces - 2, Hearth, Kitchen/Dining, Living/Dining, Master BR w/ BA, Vaulted Ceiling, Walk-in Closet
    • Flooring: Carpet, Ceramic Tile, Hardwood, Softwood
    • Heat Fuel: Gas - LP/Bottle, Wood
    • Heating: Baseboard, Forced Air, Hot Water
    • Cooling: None
    • Total Stories: 2
    Room Information
    Room 1
    • Room Dimensions: 20.6 X 12
    • Room Level: 1
    • Room Type: Kitchen - Eat-in
    Room 2
    • Room Dimensions: 14.7 X 12.4
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 25.7 X 14.4
    • Room Level: 1
    • Room Type: Living Room
    Room 4
    • Room Dimensions: 24.5 X 12
    • Room Level: 1
    • Room Type: Family Room
    Room 5
    • Room Dimensions: 23 X 14
    • Room Level: 1
    • Room Type: Master Bedroom
    Room 6
    • Room Dimensions: 10.7 X 7.6
    • Room Level: 1
    • Room Type: Foyer
    Room 7
    • Room Dimensions: 23 X 14.4
    • Room Level: Basement
    • Room Type: Family Room
    Room 8
    • Room Dimensions: 23 X 14
    • Room Level: Basement
    • Room Type: Bedroom
    Room 9
    • Room Dimensions: 24.7 X 16.3
    • Room Level: 2
    • Room Type: Bedroom
    Room 10
    • Room Dimensions: 25 X 11.5
    • Room Level: 2
    • Room Type: Bedroom

    Property History for 1284 Upper Hollow Road

    DateEvent & SourcePriceAppreciation
    Nov 19, 2020

    Sold (Public Record)

    Public Record #683588768

    		$1,000,000

    +13.2% / yr

    Nov 16, 2020

    Sold

    New England Real Estate Network #4806732

    		$1,000,000—
    Sep 26, 2020

    Pending

    New England Real Estate Network #4806732

    		—
    DateEvent & SourcePrice
    11/19/2020

    Sold (Public Record)

    Public Record #683588768

    $1,000,000

    +13.2% / yr

    11/16/2020

    Sold

    New England Real Estate Network #4806732

    $1,000,000
    09/26/2020

    Pending

    New England Real Estate Network #4806732

    —

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

    Public Records for 1284 Upper Hollow Road

    Taxable ValueLand$648,800Additions$615,300Total$1,264,100
    Tax Record2025$13,896 ($1,158 / month)
    Home Facts
    Beds2Baths1Total Finished SqFt1,085 SqFtAbove Grade Finished SqFt1,085 SqFtUnfinished Basement SqFt869 SqFtLot Size1,089,000 SqFtStyleSingle Family ResidenceYear Built1805Year Renovated1805CountyBENNINGTONAPN(057)000286

    Schools near 1284 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: 1284 Upper Hollow Road, Dorset, VT 05251
    $1,000,000
    4
    3,938
    1,089,000
    0 Upper Hollow Road, Dorset, VT 05251
    $600,000
    –
    –
    –
    419,047
    886 Upper Hollow Road, Dorset, VT 05251
    $955,000
    5
    3,632
    477,417
    135 Paddock Farm Lane, Dorset, VT 05251
    $4,850,000
    6
    12,126
    814,572
    26 Paddock Farm Lane, Dorset, VT 05251
    –
    –
    –
    –
    411,206
    61 Dunn Lane, Dorset, VT 05251
    $1,150,000
    4
    6,238
    740,520

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    Listing Courtesy of Josiah Allen Real Estate, Manchester Branch Office

    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 09/22/2026 08:10 AM