511 Upper Hollow Road

Closed 11/25/19
Closed 11/25/19
Gallery Image 1
Sold
Last Sold Price
$750,000
5 beds4,306 sqft
511 Upper Hollow Rd, Dorset, VT 05251
Single FamilyProperty Type
10.20 acresLot Size
1791Year Built
$174/sq ftPrice per sq ft
2 carsParking Spaces

Description

Dorset's Upper Hollow Road Treasure! Curb appeal always draws as this stately C.1791 Colonial captivates interest in its refinement and restored expanse. All of the 10 level pastoral acres graciously embrace the Vermont Tradition surrounded by 360 degree mountain hollow views. There's old growth trees and wide stone walled gardens greeting guests upon approach. Enter through the wide center hall with a simple staircase as the front to back living room is to the left, the architectural details are...Dorset's Upper Hollow Road Treasure! Curb appeal always draws as this stately C.1791 Colonial captivates interest in its refinement and restored expanse. All of the 10 level pastoral acres graciously embrace the Vermont Tradition surrounded by 360 degree mountain hollow views. There's old growth trees and wide stone walled gardens greeting guests upon approach. Enter through the wide center hall with a simple staircase as the front to back living room is to the left, the architectural details are evident, from the raised paneled fireplace offering a beautiful "key" style mantle, a library alcove at one end and the extended deep & private side porch beyond. To the right a lovey study with powder room. Across the back of the center hall one enters the elegantly preserved dining room boasting wide beaded panels, chair rail and receded cupboard. Original main level wide board flooring is found throughout the original structure. As time expanded the "back house", a sunny kitchen wing evolved wrapped around the raised hearth fireplace which can easily open to the original dining room creating "great room" appeal. The side entrance offers a spacious sense with very practical storage for household needs. The front and rear staircases lead to 5 comfortable en-suite bedrooms offering marble baths. Off the kitchen there's an office w direct access garden shed inspiring an herb garden. Oversized 2 car garage. The privately sited heated pool & cabana patio is a Dorset Hollow Splendor!

    Sold By Josiah Allen Real Estate, Inc.

    • Listed by: Laura Beckwith • Josiah Allen Real Estate, Inc.
    Listing closed: 11/25/2019 12:00 AM • Source: New England Real Estate Network, MLS#: 4741614

    Recent comparable sales

    Median sold price

    $1,275,000

    Avg days on market

    35

    Sale-to-list ratio

    92.4%

    Dorset, VT

    9 comparable properties found

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

    $939,000

    Sold 10/11/24

    5
    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

    $1,672,500 | 75 Church Street, Dorset, VT 05251
    1/59
    3

    $1,672,500

    Sold 08/25/25

    5
    Bedrooms
    6,165
    Square Feet
    0.46
    Acres

    75 Church Street, Dorset, VT 05251

    $1,275,000 | 3360 Dorset West Road, Dorset, VT 05251
    1/51
    4

    $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
    5

    $1,250,000

    Sold 11/21/25

    5
    Bedrooms
    4,686
    Square Feet
    4.7
    Acres

    7 Timberbrook North, Dorset, VT 05251

    $2,850,000 | 86 Church Street, Dorset, VT 05251
    1/54
    6

    $2,850,000

    Sold 09/18/26

    5
    Bedrooms
    6,182
    Square Feet
    0.8
    Acres

    86 Church Street, Dorset, VT 05251

    $2,150,000 | 341 Danby Mountain Road, Dorset, VT 05251
    1/61
    7

    $2,150,000

    Sold 09/04/25

    4
    Bedrooms
    4,975
    Square Feet
    23.90
    Acres

    341 Danby Mountain Road, 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

    $1,075,000 | 5173 Highway 30, Dorset, VT 05251
    1/45
    9

    $1,075,000

    Sold 07/17/26

    4
    Bedrooms
    3,584
    Square Feet
    0.85
    Acres

    5173 Highway 30, Dorset, VT 05251

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    $5,459 per month

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    Principal and Interest

    $3,876

    Property Taxes

    $1,583

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    Property Information for 511 Upper Hollow Road

    Property Details
    • Taxes: $19,000 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Parking: Garage, Parking Spaces 6+, Paved
    • Water Body Type: Stream
    • Zoning: Residential
    Building Information
    • Stories: 2
    • Year Built: 1791
    • Lot Size: 10.20 AC / 444,311 SF
    Summary
    Location and General Information
    • City: Dorset
    • County: VT-Bennington
    • Directions: RT 30 to Dorset Hollow Road bear Right and then Bear Left to Upper Hollow Road 511 will be on your Left... Sign
    • Latitude: 43.264890193004028
    • Longitude: -73.074905644180319
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip: 05251
    Taxes and HOA Information
    • SPAN Number: 180-057-11164
    • Tax - Gross Amount: $19,000.00
    • Tax Year: 19
    • Tax Year Notes: estimated
    • 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: 2.00
    • Driveway: Paved
    Property
    Lot Information
    • Lot - Sqft: 444312.0
    • Lot Size Acres: 10.2
    • Road Frontage Length: 540.0
    • Square Feet Apx Finished Above Grade: 4306.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Total: 5006.0
    • Square Feet Apx Total Finished: 4306.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished Below Grade: 700.0
    • Square Feet Apx Unfinished BG Source: Public Records
    • Water Frontage Length: 507.0
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete, Stone
    • PreConstruction: No
    • Surveyed: Yes
    • Year Built: 1791
    Utilities
    • Electric: 200 Amp, 220 Volt, Circuit Breaker(s), Generator
    • Sewer: 1000 Gallon, Alternative System, Concrete, Holding Tank, Leach Field
    • Utilities: Cable
    Interior and Exterior Features
    Exterior Features
    • Color: White
    • Features - Exterior: Garden Space, Natural Shade, Outbuilding, Patio, Pool - In Ground, Porch - Covered, Shed
    • Roads: Gravel, Public
    • Roof: Metal, Slate
    Interior Features
    • Appliances: Dishwasher, Disposal, Dryer, Range - Electric, Refrigerator, Washer
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Bulkhead, Concrete Floor, Partial, Stairs - Interior, Unfinished
    • Baths - Total: 6
    • Baths - Full: 3
    • Half Baths: 2
    • One Quarter Baths: 0
    • Three Quarter Bath: 1
    • Rooms - Total: 13
    • Rooms: Level 1: Level 1: Dining Room, Level 1: Foyer, Level 1: Kitchen, Level 1: Living Room, Level 1: Mudroom, Level 1: Office/Study
    • Rooms: Level 2: Level 2: Bedroom, Level 2: Master Bedroom, Level 2: Nursery, Level 2: Other
    • Bedrooms - Total: 5
    • Equipment: CO Detector, Dehumidifier, Security System, Smoke Detector
    • Features - Interior: Cedar Closet, Fireplace - Wood, Fireplaces - 3+, Kitchen/Dining, Master BR w/ BA, Natural Light, Natural Woodwork, Security, Storage - Indoor, Wood Stove Insert, Laundry - 1st Floor
    • Flooring: Hardwood, Marble, Slate/Stone, Softwood, Tile
    • Heat Fuel: Oil
    • Heating: Baseboard, Multi Zone, Radiator
    • Cooling: None
    • Total Stories: 2
    Room Information
    Room 1
    • Room Dimensions: 20 x 16
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 25 x 14
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 29 x 14
    • Room Level: 1
    • Room Type: Living Room
    Room 4
    • Room Dimensions: 15 x 13
    • Room Level: 1
    • Room Type: Office/Study
    Room 5
    • Room Dimensions: 11 x 10
    • Room Level: 1
    • Room Type: Office/Study
    Room 6
    • Room Dimensions: 25 x 14
    • Room Level: 1
    • Room Type: Mudroom
    Room 7
    • Room Dimensions: 16 x 10
    • Room Level: 1
    • Room Type: Foyer
    Room 8
    • Room Dimensions: 25 x 15
    • Room Level: 2
    • Room Type: Master Bedroom
    Room 9
    • Room Dimensions: 15 x 13
    • Room Level: 2
    • Room Type: Bedroom
    Room 10
    • Room Dimensions: 14 x 13
    • Room Level: 2
    • Room Type: Other
    Room 11
    • Room Dimensions: 19 x 12
    • Room Level: 2
    • Room Type: Bedroom
    Room 12
    • Room Dimensions: 19 x 18
    • Room Level: 2
    • Room Type: Bedroom
    Room 13
    • Room Dimensions: 13 x 10
    • Room Level: 2
    • Room Type: Bedroom
    Room 14
    • Room Level: 2
    • Room Type: Nursery

    Property History for 511 Upper Hollow Road

    DateEvent & SourcePriceAppreciation
    Nov 26, 2019

    Sold (Public Record)

    Public Record #657637944

    		$750,000

    +201.8% / yr

    Nov 25, 2019

    Sold

    New England Real Estate Network #4741614

    		$750,000—
    Nov 5, 2019

    Pending

    New England Real Estate Network #4741614

    		—
    DateEvent & SourcePrice
    11/26/2019

    Sold (Public Record)

    Public Record #657637944

    $750,000

    +201.8% / yr

    11/25/2019

    Sold

    New England Real Estate Network #4741614

    $750,000
    11/05/2019

    Pending

    New England Real Estate Network #4741614

    —

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

    Public Records for 511 Upper Hollow Road

    Taxable ValueLand$536,300Additions$822,000Total$1,358,300
    Tax Record2025$12,549 ($1,046 / month)
    Home Facts
    Beds0Lot Size444,312 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(057)001270

    Schools near 511 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: 511 Upper Hollow Road, Dorset, VT 05251
    $750,000
    5
    4,306
    444,311
    518 Upper Hollow Road, Dorset, VT 05251
    $292,000
    –
    –
    –
    436,036
    444 Upper Hollow Road, Dorset, VT 05251
    $750,000
    4
    2,864
    436,471
    590 Upper Hollow Road, Dorset, VT 05251
    $533,333
    –
    –
    –
    132,422
    427 Upper Hollow Road, Dorset, VT 05251
    $600,000
    4
    4,799
    288,367
    100 Twin Willows Lane, Unit 8, Dorset, VT 05251
    $450,000
    –
    –
    –
    747,925

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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 02:06 PM