274 Upper Hollow Road

Closed 11/13/20
Closed 11/13/20
Gallery Image 1
Sold
Last Sold Price
$975,000
5 beds3,808 sqft
274 Upper Hollow Rd, Dorset, VT 05251
Single FamilyProperty Type
4.72 acresLot Size
1930Year Built
$256/sq ftPrice per sq ft
3 carsParking Spaces

Description

Never before listed - stunning antique vintage gem located in the Dorset Upper Hollow. Hand painted cabinetry throughout. Gracious, elegant living with a most dramatic view of the Dorset Mountains. Perfect in every way.Never before listed - stunning antique vintage gem located in the Dorset Upper Hollow. Hand painted cabinetry throughout. Gracious, elegant living with a most dramatic view of the Dorset Mountains. Perfect in every way.

    Sold By Josiah Allen Real Estate, Manchester Branch Office

    • Listed by: Sunny Breen • Josiah Allen Real Estate, Inc.
    Listing closed: 11/13/2020 12:00 AM • Source: New England Real Estate Network, MLS#: 4824394

    Recent comparable sales

    Median sold price

    $1,275,000

    Avg days on market

    36

    Sale-to-list ratio

    93.8%

    Dorset, VT

    9 comparable properties found

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

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    Sold 10/11/24

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    Bedrooms
    4,452
    Square Feet
    0.45
    Acres

    3478 Highway 30, Dorset, VT 05251

    $1,500,000 | 59 Church Street, Dorset, VT 05251
    1/41
    2

    $1,500,000

    Sold 10/01/25

    5
    Bedrooms
    3,436
    Square Feet
    0.45
    Acres

    59 Church Street, Dorset, VT 05251

    $1,075,000 | 5173 Highway 30, Dorset, VT 05251
    1/45
    3

    $1,075,000

    Sold 07/17/26

    4
    Bedrooms
    3,584
    Square Feet
    0.85
    Acres

    5173 Highway 30, Dorset, VT 05251

    $1,390,000 | 92 Barrows Heights, Dorset, VT 05251
    1/46
    4

    $1,390,000

    Sold 08/20/25

    5
    Bedrooms
    3,165
    Square Feet
    3.89
    Acres

    92 Barrows Heights, Dorset, VT 05251

    $1,275,000 | 3360 Dorset West Road, Dorset, VT 05251
    1/51
    5

    $1,275,000

    Sold 09/05/25

    4
    Bedrooms
    3,610
    Square Feet
    1.86
    Acres

    3360 Dorset West Road, Dorset, VT 05251

    $1,672,500 | 75 Church Street, Dorset, VT 05251
    1/59
    6

    $1,672,500

    Sold 08/25/25

    5
    Bedrooms
    6,165
    Square Feet
    0.46
    Acres

    75 Church Street, Dorset, VT 05251

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

    $1,250,000

    Sold 11/21/25

    5
    Bedrooms
    4,686
    Square Feet
    4.7
    Acres

    7 Timberbrook North, Dorset, VT 05251

    $650,000 | 364 Barrows Heights, Dorset, VT 05251
    1/35
    8

    $650,000

    Sold 10/07/24

    4
    Bedrooms
    4,228
    Square Feet
    3.2
    Acres

    364 Barrows Heights, Dorset, VT 05251

    $1,369,000 | 393 Red Tail Lane, Dorset, VT 05251
    1/60
    9

    $1,369,000

    Sold 09/04/25

    3
    Bedrooms
    3,967
    Square Feet
    11.52
    Acres

    393 Red Tail Lane, Dorset, VT 05251

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    $6,304 per month

    30 year fixed, 6.71% Interest

    Principal and Interest

    $5,038

    Property Taxes

    $1,266

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    Property Information for 274 Upper Hollow Road

    Property Details
    • Taxes: $15,189 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Zoning: rural residential
    Building Information
    • Stories: 2
    • Year Built: 1930
    • Lot Size: 4.72 AC / 205,603 SF
    Summary
    Location and General Information
    • City: Dorset
    • County: VT-Bennington
    • Directions: Dorset Hollow road. Bear left onto Upper Hollow Rd. House is 3rd House on the right.
    • Latitude: 43.261877878309612
    • Longitude: -73.079133001327520
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip: 05251
    Taxes and HOA Information
    • SPAN Number: 180-057-10314
    • Tax - Gross Amount: $15,188.58
    • Tax Year: 2020
    • Taxes TBD: No
    Parking
    • Garage: Yes
    • Garage Capacity: 3.00
    • Driveway: Circular, Crushed Stone
    Virtual Tour
    Property
    Lot Information
    • Lot - Sqft: 205603.0
    • Lot Size Acres: 4.72
    • Road Frontage Length: 300.0
    • Square Feet Apx Finished Above Grade: 3808.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Total: 5760.0
    • Square Feet Apx Total Finished: 3808.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished Below Grade: 1952.0
    • 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: No
    • Year Built: 1930
    Utilities
    • Electric: Generator, On-Site
    • Sewer: On-Site Septic Exists
    • Utilities: Telephone At Site
    Interior and Exterior Features
    Exterior Features
    • Roads: Dirt, Public
    • Roof: Shingle
    Interior Features
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Concrete Floor, Full, Stairs - Exterior, Stairs - Interior, Unfinished, Exterior Access, Stairs - Basement
    • Baths - Total: 5
    • Baths - Full: 3
    • Half Baths: 1
    • One Quarter Baths: 0
    • Three Quarter Bath: 1
    • Rooms - Total: 10
    • Rooms: Level 1: Level 1: Breakfast Nook, Level 1: Den, Level 1: Dining Room, Level 1: Kitchen, Level 1: Living Room
    • Rooms: Level 2: Level 2: Bedroom, Level 2: Den, Level 2: Master Bedroom
    • Bedrooms - Total: 5
    • Heat Fuel: Oil
    • Heating: Radiator
    • Cooling: None
    • Total Stories: 2
    Room Information
    Room 1
    • Room Dimensions: 28' 4" x 16' 1"
    • Room Level: 1
    • Room Type: Living Room
    Room 2
    • Room Dimensions: 14' 9" x 16' 3"
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 11' 11" x 17' 9"
    • Room Level: 1
    • Room Type: Den
    Room 4
    • Room Dimensions: 12' x 21'
    • Room Level: 1
    • Room Type: Kitchen
    Room 5
    • Room Dimensions: 10' 1" x 11' 2"
    • Room Level: 1
    • Room Type: Breakfast Nook
    Room 6
    • Room Dimensions: 24' 6" x 12'
    • Room Level: 2
    • Room Type: Master Bedroom
    Room 7
    • Room Dimensions: 10' 2" x 12' 4"
    • Room Level: 2
    • Room Type: Bedroom
    Room 8
    • Room Dimensions: 12' 10" x 15' 9"
    • Room Level: 2
    • Room Type: Bedroom
    Room 9
    • Room Dimensions: 14' 10" x 12' 11"
    • Room Level: 2
    • Room Type: Bedroom
    Room 10
    • Room Dimensions: 12' 1" x 14' 5"
    • Room Level: 2
    • Room Type: Bedroom
    Room 11
    • Room Dimensions: 9' 7" x 11' 3"
    • Room Level: 2
    • Room Type: Den

    Property History for 274 Upper Hollow Road

    DateEvent & SourcePriceAppreciation
    Nov 18, 2020

    Sold (Public Record)

    Public Record #683588736

    		$975,000—
    Nov 13, 2020

    Sold

    New England Real Estate Network #4824394

    		$975,000—
    Nov 13, 2020

    Pending

    New England Real Estate Network #4824394

    		—
    DateEvent & SourcePrice
    11/18/2020

    Sold (Public Record)

    Public Record #683588736

    $975,000
    11/13/2020

    Sold

    New England Real Estate Network #4824394

    $975,000
    11/13/2020

    Pending

    New England Real Estate Network #4824394

    —

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

    Public Records for 274 Upper Hollow Road

    Taxable ValueLand$327,900Additions$662,700Total$990,600
    Tax Record2025$10,890 ($908 / month)
    Home Facts
    Beds0Lot Size205,603 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(057)000874

    Schools near 274 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: 274 Upper Hollow Road, Dorset, VT 05251
    $975,000
    5
    3,808
    205,603
    164 Upper Hollow Road, Dorset, VT 05251
    $1,150,000
    5
    5,200
    439,956
    312 Upper Hollow Road, Dorset, VT 05251
    $945,000
    3
    2,867
    98,010
    345 Upper Hollow Road, Dorset, VT 05251
    –
    –
    –
    –
    69,696
    299205 Upper Hollow Road, Dorset, VT 05251
    $600,000
    1
    1
    616
    1,767,665
    82 Upper Hollow Road, Dorset, VT 05251
    $645,000
    4
    2,676
    239,580

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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 09/20/2026 02:47 PM