OFF MARKET

Listed by Sunny Breen • Josiah Allen Real Estate, Inc. Bought with Josiah Allen Real Estate, Manchester Branch Office.

Off Market Nov 2020 for $975K

$2,018,827

Est. refi paymentEst. refi $6,377/mo

•

3,808

sq ft

274 Upper Hollow Rd, Dorset, VT 05251

About this home

Single-familyProperty Type

1930Year Built

4.72 acresLot Size

$530Est. Price/Sq.Ft.

3 car garageParking

Listed by Sunny Breen • Josiah Allen Real Estate, Inc.

Bought with Sara Buckley • Josiah Allen Real Estate, Manchester Branch Office

Redfin checked: 2 minutes ago

•Source:PrimeMLS #4824394

Redfin Estimate

$2,018,827

$1.0M since sold in November 2020$247K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 89.4% higher than the average sale price ($1.07M) of 6 comparable homes.

SOLD JUL 31, 2026
$1,700,000
A
5 beds4.5 baths3,218 sq ft
5491 VT Route 315, Rupert, VT 05776
SOLD JUL 24, 2026
$825,000
B
4 beds3.5 baths3,237 sq ft
1731 Three Maple Dr, Manchester Center, VT 05255
SOLD JUN 1, 2026
$1,245,000
C
4 beds5 baths4,272 sq ft
1016 West Rd, Manchester, VT 05254
SOLD JUL 17, 2026
$1,075,000
D
4 beds4.5 baths3,584 sq ft
5173 Route 30, Dorset, VT 05251
SOLD AUG 4, 2026
$776,000
E
4 beds3.5 baths4,282 sq ft
267 Eagle Rdg, Dorset, VT 05251
SOLD APR 8, 2026
$775,000
F
4 beds3 baths3,659 sq ft
445 Canterbury Rd, Manchester Center, VT 05255

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Earn from this home

Refinance

Est. cash available

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Market trends in 05251, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

99.2%

+0.9% MoM

Median sale price

$776K

$92K MoM

Avg. days on market

47d

16 days MoM

Recently sold homes

0 MoM

Provided by Redfin

Sale history for 274 Upper Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$10,890 (−36.9%)

$327,900 + $662,700

$990,600

2024

$17,262 (+14.3%)

$404,080 + $476,480

$880,560

2023

$15,096 (−11.7%)

$404,080 + $476,480

$880,560

2022

$17,097 (+2.8%)

$404,080 + $476,480

$880,560

2021

$16,635 (+2.9%)

$404,080 + $476,480

$880,560

2020

$16,168 (+7.3%)

$404,080 + $476,480

$880,560

2019

$15,071 (−3.5%)

$404,080 + $476,480

$880,560

2018

$15,621 (−5.5%)

$404,080 + $476,480

$880,560

2017

$16,523 (+9.5%)

$404,080 + $476,480

$880,560

2016

$15,092 (−0.6%)

$404,080 + $476,480

$880,560

2015

$15,183

$404,080 + $476,480

$880,560

2013

Tax history for 274 Upper Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$10,890 (−36.9%)

$327,900 + $662,700

$990,600

2024

$17,262 (+14.3%)

$404,080 + $476,480

$880,560

2023

$15,096 (−11.7%)

$404,080 + $476,480

$880,560

2022

$17,097 (+2.8%)

$404,080 + $476,480

$880,560

2021

$16,635 (+2.9%)

$404,080 + $476,480

$880,560

2020

$16,168 (+7.3%)

$404,080 + $476,480

$880,560

2019

$15,071 (−3.5%)

$404,080 + $476,480

$880,560

2018

$15,621 (−5.5%)

$404,080 + $476,480

$880,560

2017

$16,523 (+9.5%)

$404,080 + $476,480

$880,560

2016

$15,092 (−0.6%)

$404,080 + $476,480

$880,560

2015

$15,183

$404,080 + $476,480

$880,560

2013

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

4.72 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Bennington County

APN

18005710314

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 3
Location: Detached

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 3
# of Baths (3/4): 1
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Concrete Floor, Full, Stairs - Exterior, Stairs - Interior, Unfinished, Exterior Access, Stairs - Basement

Other Interior Features
# of Rooms: 10
Water Heater: Oil

Room 1 Information
Living Room
Living Room
Dimensions: 28' 4" x 16' 1"
Level: 1

Room 2 Information
Dining Room
Dimensions: 14' 9" x 16' 3"
Level: 1

Room 3 Information
Den
Dimensions: 11' 11" x 17' 9"
Level: 1

Room 4 Information
Kitchen
Dimensions: 12' x 21'
Level: 1

Room 5 Information
Breakfast Nook
Dimensions: 10' 1" x 11' 2"
Level: 1

Room 6 Information
Master Bedroom
Master Bedroom
Dimensions: 24' 6" x 12'
Level: 2

Room 7 Information
Bedroom
Dimensions: 10' 2" x 12' 4"
Level: 2

Room 8 Information
Bedroom
Dimensions: 12' 10" x 15' 9"
Level: 2

Room 9 Information
Bedroom
Dimensions: 14' 10" x 12' 11"
Level: 2

Room 10 Information
Bedroom
Dimensions: 12' 1" x 14' 5"
Level: 2

Room 11 Information
Den
Dimensions: 9' 7" x 11' 3"
Level: 2

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 3808
Approximate Sq. Ft. Total: 5760
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle
Exterior: Clapboard

Driveway
Circular, Crushed Stone

Lot, Zoning, & Easement Information
Landscaped, Mountain View, Orchards, View

Other Property & Lot Information
Year Built: 1930

Financial

Tax Information
Tax Year: 2020
Gross Amount Tax: 15188.58
SPAN Number: 180-057-10314

Other Tax Information
Page Deed: 454

Utilities

Heating & Cooling Information
Heat: Radiator
Heat Fuel: Oil

Sewer Information
On-Site Septic Exists

Electric Information
Generator, On-Site

Water Information
On-Site Well Exists

Other Utilities Information
Telephone At Site

Location

Road Information
Road Frontage: Yes
Road Frontage Length: 300
Dirt, Public

Other Location Information
Directions: Dorset Hollow road. Bear left onto Upper Hollow Rd. House is 3rd House on the right.

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 4.72 acres
Style: Other
Year Built: —
Year Renovated: —
County: Bennington County
APN: 18005710314

Home facts updated by county records on Jul 15, 2026

Around this home

Schools

Some nearby schools may not be within this home's attendance zone. Please check the Taconic and Green Regional School District website to verify.

Dorset Elementary School

Public PreK-8 • 2.8mi

6/10

Red Fox Community School

Private K-5 • 5.0mi

Long Trail School

Private 6-12 • 1.2mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

1/10 Heat Factor

7 days above 88° expected this year, 16 days in 30 years

3/10 Wind Factor

5% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Dorset, VT • 05251

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$1.92M – $2.32M

Sell confidently with a local market expert in Dorset. 3 minutes to get started.

Nearby similar homes

$595,000

4 beds3 baths3,272 sq ft

1174 N Main St, Danby, VT 05739

$515,000

3 beds2 baths1,528 sq ft

335 Tinmouth Rd, Danby, VT 05739

$599,000

4 beds3 baths2,886 sq ft

209 Kelley Hill Rd, Danby, VT 05739

$925,000

3 beds2 baths2,403 sq ft

99 Holly's Way, West Rupert, VT 05776

$390,000

4 beds2 baths2,352 sq ft

85 Depot Street Ext, Mount Tabor, VT 05739

$835,000

3 beds2.5 baths2,780 sq ft

232 Powderhorn Rd, Manchester Center, VT 05255

Home values near 274 Upper Hollow Rd

Data from public records.

Address	Redfin Estimate
82 Upper Hollow Rd, Dorset, VT 4 Beds \| 3.5 Baths \| 2676 Sq. Ft.	$1,283,493
427 Upper Hollow Rd, Dorset, VT 4 Beds \| 5 Baths \| 4799 Sq. Ft.	$1,822,240

Address	Redfin Estimate
164 Upper Hollow Rd, Dorset, VT 5 Beds \| 5.5 Baths \| 5200 Sq. Ft.	$2,741,765
312 Upper Hollow Rd, Dorset, VT 3 Beds \| 3 Baths \| 2867 Sq. Ft.	$1,809,486

Address	Redfin Estimate
444 Upper Hollow Rd, Dorset, VT 4 Beds \| 3.5 Baths \| 2864 Sq. Ft.	$2,179,664
511 Upper Hollow Rd, Dorset, VT 5 Beds \| 5 Baths \| 4306 Sq. Ft.	$2,230,904

Property information provided by PrimeMLS when last listed in 2020. This data may not match . Learn more.

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