OFF MARKET

Listed by Sunny Breen • Josiah Allen Real Estate, Inc. Bought with Four Seasons Sotheby's Int'l Realty.

Off market may 2021 for $800K

$1,355,353

Est. refi paymentEst. refi $5,348/mo

•

4,512

sq ft

2069 Upper Hollow Rd, Dorset, VT 05251

About this home

Nestled within the rolling hills of the enchanting Dorset Upper Hollow and tucked in on 8+ private and serene acres, sits a charming renovated, antique post and beam barn. Revealing a stunning open floor plan, graced with Palladian windows allowing an abundance of light and majestic mountain views. Four ample size bedrooms, and second floor loft which is perfect for home office, three baths with lower level partially finished off bonus room, laundry room and attached two car garage, this lovely home has it all. .. Waiting for a new family to take Stewardship, lots of walking trails, very accessible to the wonderful amenities that Dorset has to offer.

Single-familyProperty Type

1987Year Built

8.8 acresLot Size

$300Est. Price/Sq.Ft.

2 car garageParking

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

Bought with Kevin Moran • Four Seasons Sotheby's Int'l Realty

Redfin checked: a minute ago

•Source:PrimeMLS #4848341

Redfin Estimate

$1,355,353

$555K since sold in May 2021$4,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 53.9% higher than the average sale price ($881K) of 6 comparable homes.

SOLD JAN 28, 2026
$1,200,000
A
4 beds4 baths4,266 sq ft
693 Longview Dr, Manchester, VT 05254
SOLD AUG 4, 2026
$776,000
B
4 beds3.5 baths4,282 sq ft
267 Eagle Rdg, Dorset, VT 05251
SOLD AUG 13, 2026
$1,100,000
C
3 beds3 baths2,797 sq ft
227 Birchstone Ln, East Dorset, VT 05253
SOLD JUN 22, 2026
$684,000
D
3 beds2.5 baths4,683 sq ft
2744 Danby Mountain Rd, Dorset, VT 05251
SOLD DEC 19, 2025
$875,000
E
4 beds3.5 baths4,650 sq ft
81 Windward Hl, Dorset, VT 05251
SOLD JUN 15, 2026
$650,000
F
4 beds4 baths3,161 sq ft
413 Dutch Hill Rd, Danby, VT 05739

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Earn from this home

Refinance

Est. cash available

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Market trends in 05251, VT

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.3%

0.9% MoM

Median sale price

$776K

$228 MoM

Avg. days on market

74d

27 days MoM

Recently sold homes

2 MoM

New listings for sale

$2,250,000
4 beds3.5 baths4,831 sq ft
122 Blue Heron Ln, Dorset, VT 05251
$6,250,000
6 beds7.5 baths10,739 sq ft
300 Nims Rd, Dorset, VT 05251
See all

Provided by Redfin

Sale history for 2069 Upper Hollow Rd

Date

Event

Price

Public Records

Jun 18, 2021

Sold

$800,000

$177/sq ft

PrimeMLS #4848341

May 7, 2021

Sold

$800,000

$177/sq ft

Apr 2, 2021

Pending

—

Mar 6, 2021

Contingent

—

Feb 24, 2021

Listed

$825,000

$183/sq ft

PrimeMLS #4021883

Oct 26, 2010

Sold

$495,000

$110/sq ft

Sep 2, 2010

Listed

$495,000

$110/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$11,012 (−9.5%)

$331,900 + $669,800

$1,001,700

2024

$12,166 (+14.3%)

$276,000 + $344,630

$620,630

2023

$10,639 (−11.7%)

$276,000 + $344,630

$620,630

2022

$12,049 (+2.8%)

$276,000 + $344,630

$620,630

2021

$11,723 (+1.6%)

$276,000 + $344,630

$620,630

2020

$11,536 (+5.6%)

$276,000 + $344,630

$620,630

2019

$10,923 (+0.6%)

$276,000 + $344,630

$620,630

2018

$10,858 (+1.2%)

$276,000 + $344,630

$620,630

2017

$10,731 (+1.7%)

$276,000 + $344,630

$620,630

2016

$10,554 (+3.3%)

$276,000 + $344,630

$620,630

2015

$10,216

$276,000 + $344,630

$620,630

2013

$288,700 + $276,700

$565,400

Tax history for 2069 Upper Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$11,012 (−9.5%)

$331,900 + $669,800

$1,001,700

2024

$12,166 (+14.3%)

$276,000 + $344,630

$620,630

2023

$10,639 (−11.7%)

$276,000 + $344,630

$620,630

2022

$12,049 (+2.8%)

$276,000 + $344,630

$620,630

2021

$11,723 (+1.6%)

$276,000 + $344,630

$620,630

2020

$11,536 (+5.6%)

$276,000 + $344,630

$620,630

2019

$10,923 (+0.6%)

$276,000 + $344,630

$620,630

2018

$10,858 (+1.2%)

$276,000 + $344,630

$620,630

2017

$10,731 (+1.7%)

$276,000 + $344,630

$620,630

2016

$10,554 (+3.3%)

$276,000 + $344,630

$620,630

2015

$10,216

$276,000 + $344,630

$620,630

2013

$288,700 + $276,700

$565,400

*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

9 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Bennington County

APN

18005710157

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 2
Location: Attached

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 3

Basement Information
Basement: Yes
Basement Access: Interior
Concrete Floor, Finished, Insulated, Stairs - Interior

Other Interior Features
# of Rooms: 9
Flooring: Carpet, Tile, Wood
Water Heater: Gas
Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace - Gas, Kitchen Island, Master Bedroom With Bath, Natural Light, Natural Woodwork, Security, Skylight, Wood Stove Hook-up, Laundry - Basement

Accessibility Information
1st Floor Bedroom, 1st Floor Full Bathroom

Equipment & Appliance Information
Dishwasher, Dryer, Freezer, Refrigerator, Washer, Stove - Gas
Smoke Detector, Stove-Gas

Room 1 Information
Kitchen
Kitchen
Dimensions: 14x13
Level: 1

Room 2 Information
Dining Room
Dimensions: 16x12
Level: 1

Room 3 Information
Living Room
Dimensions: 23x13
Level: 1

Room 4 Information
Den
Dimensions: 14x13
Level: 1

Room 5 Information
Master Bedroom
Dimensions: 13x16
Level: 1

Room 6 Information
Bedroom
Bedroom
Dimensions: 17x14
Level: 2

Room 7 Information
Bedroom
Dimensions: 14x11
Level: 2

Room 8 Information
Bedroom
Dimensions: 19x12
Level: 2

Room 9 Information
Loft
Level: 2

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 4512
Approximate Sq. Ft. Total: 4512
Color: Grey
Deck
Construction: Post and Beam
Foundation: Concrete
Roof: Shingle
Exterior: Clapboard

Driveway
Gravel

Lot, Zoning, & Easement Information
Country Setting, Field/Pasture, Landscaped, Mountain View, Orchards, Rolling, Trail/Near Trail, Walking Trails

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1987

Financial

Tax Information
Tax Year: 2021
Gross Amount Tax: 11260.16
SPAN Number: 180-057-10157

Other Tax Information
Page Deed: 775

Utilities

Heating & Cooling Information
Heat: Baseboard, Hot Air
Heat Fuel: Gas - Liquid Propane Bottle

Sewer Information
On-Site Septic Exists

Electric Information
Electric Company: GMP
Circuit Breaker(s)

Water Information
On-Site Well Exists

Other Utilities Information
Fuel Company: Dorr
Phone, Gas - At Street, Gas - Underground

Location

School Information
Elementary School: The Dorset School
Elementary School: The Dorset School
Middle/Jr School: The Dorset School

Road Information
Road Frontage: Yes
Road Frontage Length: 550
Dirt

Other Location Information
Directions: Dorset Hollow Road to Upper Hollow Road. Travel approximately 2 miles to 2069 on the left hand side of the road.

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 9 acres
Style: Other
Year Built: —
Year Renovated: —
County: Bennington County
APN: 18005710157

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 • 3.7mi

6/10

Long Trail School

Private 6-12 • 2.3mi

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

8 days above 88° expected this year, 18 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

$1.29M – $1.56M

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

Nearby similar homes

$875,000

3 beds2 baths1,600 sq ft

447 Rock Bottom Ln, Peru, VT 05255

$499,900

3 beds2 baths1,528 sq ft

335 Tinmouth Rd, Danby, VT 05739

$595,000

4 beds3 baths3,272 sq ft

1174 N Main St, Danby, VT 05739

$320,000

4 beds3 baths2,000 sq ft

686 Route 30, Dorset, VT 05261

$750,000

4 beds5.5 baths4,502 sq ft

3373 Main St, Manchester, VT 05254

VIDEO TOUR

$975,000

4 beds4 baths5,164 sq ft

78 Bonnet St, Manchester Center, VT 05255

New listings for sale in 05251

$2,250,000

4 beds3.5 baths4,831 sq ft

122 Blue Heron Ln, Dorset, VT 05251

$6,250,000

6 beds7.5 baths10,739 sq ft

300 Nims Rd, Dorset, VT 05251

Home values near 2069 Upper Hollow Rd

Data from public records.

Address	Redfin Estimate
2199 Lower Hollow Road, Dorset, VT 4 Beds \| 4 Baths \| 5500 Sq. Ft.	$2,766,760
2491 Lower Hollow Road, Dorset, VT 4 Beds \| 2.5 Baths \| 2280 Sq. Ft.	$1,056,600

Address	Redfin Estimate
190 Turkey Run Lane, Dorset, VT 5 Beds \| 6 Baths \| 5033 Sq. Ft.	$2,924,016
393 Red Tail Lane, Dorset, VT 3 Beds \| 4 Baths \| 3967 Sq. Ft.	$1,612,035

Address	Redfin Estimate
2340 Lower Hollow Road, Dorset, VT 4 Beds \| 5 Baths \| 3750 Sq. Ft.	$1,627,969
395 Red Tail Lane, Dorset, VT 5 Beds \| 3.5 Baths \| 4370 Sq. Ft.	$1,759,155

Property information provided by PrimeMLS when last listed in 2021. This data may not match . Learn more.

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