1284 Upper Hollow Road

Closed 11/16/20
Closed 11/16/20
Gallery Image 1
Last Sold Price
$1,000,000
4 beds3,938 sqft$254/sqft
1284 Upper Hollow Rd, Dorset, VT 05251

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!
LISTING CLOSED: 11/16/2020 12:00 AM

  1. Listed by Laura Beckwith • Josiah Allen Real Estate, Manchester Branch Office

Sold By Josiah Allen Real Estate, Inc.

Property Details for 1284 Upper Hollow Road

Status
Closed
MLS #
4806732
Days on Market
89
Taxes
$16,848 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential / Single Family
Year Built
1855
Lot Size
25.00 AC / 1,089,000 SF
County
Bennington County
Zoning
residential

Recent comparable sales

Median sold price

$939,000

Avg days on market

26

Sale-to-list ratio

94.9%

Dorset, VT

9 comparable properties found

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

$1,075,000

Sold 07/17/26

4
Bedrooms
3,584
Square Feet
0.85
Acres

5173 Highway 30, Dorset, VT 05251

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

$875,000

Sold 12/19/25

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

Sold 10/11/24

5
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

$897,000 | 3444 Highway 30, Dorset, VT 05251
1/28
7

$897,000

Sold 09/12/24

4
Bedrooms
3,082
Square Feet
0.62
Acres

3444 Highway 30, Dorset, VT 05251

$1,275,000 | 3360 Dorset West Road, Dorset, VT 05251
1/51
8

$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
9

$1,250,000

Sold 11/21/25

5
Bedrooms
4,686
Square Feet
4.7
Acres

7 Timberbrook North, Dorset, VT 05251

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Building Information for 1284 Upper Hollow Road

Stories2Year Built1855Building Size-Lot Size25.00 AC / 1,089,000 SF

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Property Information for 1284 Upper Hollow Road

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 08/26/2026 11:15 PM