444 Upper Hollow Road

Closed 4/23/19
Closed 4/23/19
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Sold
Last Sold Price
$750,000
4 beds2,864 sqft
444 Upper Hollow Rd, Dorset, VT 05251
Single FamilyProperty Type
10.02 acresLot Size
1978Year Built
$262/sq ftPrice per sq ft
2 carsParking Spaces

Description

Timeless and ideal Dorset Hollow Location! Close to town and set back on Upper Hollow Road, this restored farmhouse exudes warmth and charm, offering big views on 10+ scenic acres. A beautiful setting with circular drive and mature trees give this parcel special curb appeal featuring level and gently rolling meadows throughout the entire property. The home consists of four bedrooms including a master bedroom suite on the main floor and with three additional baths. The charming Post and Beam floor...Timeless and ideal Dorset Hollow Location! Close to town and set back on Upper Hollow Road, this restored farmhouse exudes warmth and charm, offering big views on 10+ scenic acres. A beautiful setting with circular drive and mature trees give this parcel special curb appeal featuring level and gently rolling meadows throughout the entire property. The home consists of four bedrooms including a master bedroom suite on the main floor and with three additional baths. The charming Post and Beam floor plan includes a cozy stone fireplace and wide Pine floors with an open living and dining arrangement making it ideal for entertaining family and guests. Amazing mountain views can be enjoyed from the slate patio or the wonderful three season porch. This special home also has a new, efficient furnace and is being offered at a very reasonable price so come take a look at this Dorset Hollow gem!

    Sold By Four Seasons Sotheby's Int'l Realty

    • Listed by: David Shehadi • Josiah Allen Real Estate, Inc.
    Listing closed: 04/23/2019 12:00 AM • Source: New England Real Estate Network, MLS#: 4732189

    Recent comparable sales

    Median sold price

    $776,000

    Avg days on market

    27

    Sale-to-list ratio

    97.7%

    Dorset, VT

    9 comparable properties found

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

    $650,000

    Sold 10/07/24

    4
    Bedrooms
    4,228
    Square Feet
    3.2
    Acres

    364 Barrows Heights, Dorset, VT 05251

    $670,000 | 1489 Highway 30, Dorset, VT 05251
    1/36
    2

    $670,000

    Sold 12/02/24

    3
    Bedrooms
    2,924
    Square Feet
    3.2
    Acres

    1489 Highway 30, Dorset, VT 05251

    $2,600,000 | 198 Church Street, Dorset, VT 05251
    1/46
    3

    $2,600,000

    Sold 07/29/26

    4
    Bedrooms
    2,338
    Square Feet
    0.76
    Acres

    198 Church Street, 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

    $875,000 | 81 Windward Hill, Dorset, VT 05251
    1/39
    5

    $875,000

    Sold 12/19/25

    4
    Bedrooms
    4,650
    Square Feet
    5.8
    Acres

    81 Windward Hill, Dorset, VT 05251

    $709,000 | 253 Owl's Head Hill Lane South, Dorset, VT 05251
    1/30
    6

    $709,000

    Sold 03/18/26

    3
    Bedrooms
    2,262
    Square Feet
    1.8
    Acres

    253 Owl's Head Hill Lane South, Dorset, VT 05251

    $1,450,000 | 17 Farwell Lane, Dorset, VT 05251
    1/61
    7

    $1,450,000

    Sold 10/17/25

    3
    Bedrooms
    3,294
    Square Feet
    2.9
    Acres

    17 Farwell Lane, Dorset, VT 05251

    $380,000 | 567 Kirby Hollow Road, Dorset, VT 05251
    1/33
    8

    $380,000

    Sold 11/22/24

    4
    Bedrooms
    1,332
    Square Feet
    0.44
    Acres

    567 Kirby Hollow Road, Dorset, VT 05251

    $776,000 | 267 Eagle Ridge, Dorset, VT 05251
    1/15
    9

    $776,000

    Sold 08/04/26

    4
    Bedrooms
    4,282
    Square Feet
    5.92
    Acres

    267 Eagle Ridge, Dorset, VT 05251

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    $4,927 per month

    30 year fixed, 6.71% Interest

    Principal and Interest

    $3,876

    Property Taxes

    $1,051

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    Property Information for 444 Upper Hollow Road

    Property Details
    • Taxes: $12,616 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Zoning: RR
    Building Information
    • Stories: 1
    • Year Built: 1978
    • Lot Size: 10.02 AC / 436,471 SF
    Summary
    Location and General Information
    • City: Dorset
    • County: VT-Bennington
    • Directions: Dorset Hollow Road to Upper Hollow Road. House is up a little way on the right.
    • Latitude: 43.263589241181940
    • Longitude: -73.075940474868787
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip: 05251
    Taxes and HOA Information
    • SPAN Number: 180-057-10805
    • Tax - Gross Amount: $12,616.36
    • Tax Year: 2019
    • Taxes TBD: No
    School Information
    • School - High: Long Trail School
    • School - Elementary: Dorset Elementary School
    • School - Middle/Jr: Dorset Elementary School
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Circular, Gravel
    Property
    Lot Information
    • Lot - Sqft: 436471.0
    • Lot Size Acres: 10.02
    • Road Frontage Length: 300.0
    • Square Feet Apx Finished Above Grade: 2864.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Finished BG Source: Other
    • Square Feet Apx Total: 2864.0
    • Square Feet Apx Total Finished: 2864.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Public Records
    • Square Feet Apx Unfinished Below Grade: 0.0
    • Square Feet Apx Unfinished BG Source: Other
    Property and Assessments
    • Current Use: No
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete
    • PreConstruction: No
    • Surveyed: Unknown
    • Year Built: 1978
    Utilities
    • Electric: 200 Amp
    • Sewer: On-Site Septic Exists
    Interior and Exterior Features
    Exterior Features
    • Roads: Public
    • Roof: Shingle - Architectural
    Interior Features
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Concrete, Unfinished
    • Baths - Total: 4
    • Baths - Full: 2
    • Half Baths: 1
    • One Quarter Baths: 0
    • Three Quarter Bath: 1
    • Rooms - Total: 10
    • Rooms: Level 1: Level 1: Den, Level 1: Dining Room, Level 1: Foyer, Level 1: Kitchen, Level 1: Laundry Room, Level 1: Living Room, Level 1: Master Bedroom
    • Rooms: Level 2: Level 2: Bedroom
    • Bedrooms - Total: 4
    • Heat Fuel: Oil
    • Heating: Baseboard
    • Cooling: None
    • Total Stories: 1.75
    Room Information
    Room 1
    • Room Dimensions: 17 x 12.7
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 14 x 15
    • Room Level: 1
    • Room Type: Den
    Room 3
    • Room Dimensions: 24 x 20
    • Room Level: 1
    • Room Type: Living Room
    Room 4
    • Room Dimensions: 16 x 10
    • Room Level: 1
    • Room Type: Dining Room
    Room 5
    • Room Dimensions: 15 x 20
    • Room Level: 1
    • Room Type: Master Bedroom
    Room 6
    • Room Dimensions: 17 x 13
    • Room Level: 2
    • Room Type: Bedroom
    Room 7
    • Room Dimensions: 17 x 13
    • Room Level: 2
    • Room Type: Bedroom
    Room 8
    • Room Dimensions: 15.6 x 19
    • Room Level: 2
    • Room Type: Bedroom
    Room 9
    • Room Dimensions: 8 x 7
    • Room Level: 1
    • Room Type: Foyer
    Room 10
    • Room Dimensions: 7 x 6
    • Room Level: 1
    • Room Type: Laundry Room

    Property History for 444 Upper Hollow Road

    DateEvent & SourcePriceAppreciation
    Apr 29, 2019

    Sold (Public Record)

    Public Record #643533242

    		$750,000—
    Apr 23, 2019

    Sold

    New England Real Estate Network #4732189

    		$750,000—
    Apr 23, 2019

    Pending

    New England Real Estate Network #4732189

    		—
    DateEvent & SourcePrice
    04/29/2019

    Sold (Public Record)

    Public Record #643533242

    $750,000
    04/23/2019

    Sold

    New England Real Estate Network #4732189

    $750,000
    04/23/2019

    Pending

    New England Real Estate Network #4732189

    —

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

    Public Records for 444 Upper Hollow Road

    Taxable ValueLand$635,100Additions$637,800Total$1,272,900
    Tax Record2025$13,993 ($1,166 / month)
    Home Facts
    Beds0Lot Size436,471 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(057)001282

    Schools near 444 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: 444 Upper Hollow Road, Dorset, VT 05251
    $750,000
    4
    2,864
    436,471
    518 Upper Hollow Road, Dorset, VT 05251
    $292,000
    –
    –
    –
    436,036
    511 Upper Hollow Road, Dorset, VT 05251
    $750,000
    5
    4,306
    444,311
    427 Upper Hollow Road, Dorset, VT 05251
    $600,000
    4
    4,799
    288,367
    590 Upper Hollow Road, Dorset, VT 05251
    $533,333
    –
    –
    –
    132,422
    345 Upper Hollow Road, Dorset, VT 05251
    –
    –
    –
    –
    69,696

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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 09:31 PM