1468 Upper Dummerston Rd, Brattleboro, VT 05301

Listed by Adam Palmiter • Palmiter Realty Group. Bought with Palmiter Realty Group.

Off market sep 2013 for $450K

$873,050

Est. refi paymentEst. refi $1,399/mo

•

10,605

sq ft

1468 Upper Dummerston Rd, Brattleboro, VT 05301

About this home

What an opportunity! This farm has amazing history and character, abuts Hillwinds, and has plenty of space for anything you could imagine. The property consists of a main home which sits on 22+ acres with barn and two guest houses. The property originally was a site for raising horses and training them, but has been converted into apartments and storage spaces. With some work, this could easily be brought back to its original character. The main farmhouse is 8 apts at over 8000 square feet, which breathtaking views of the fields, and down the West River. The horse barn is over 16,000 square feet and has the original stalls still in it. The first 1975 white guest house is 2 bedrooms and 828 square feet, while the second 1981 red guest house is already subdivided on 1.14 acre and two floors, each a 2-bedroom unit. With this kind of space and history just a short walk or drive to the Brattleboro Country Club and easy access to town on a paved road, this is a must see!

Single-familyProperty Type

1918Year Built

22.24 acresLot Size

$82Est. Price/Sq.Ft.

2 car garageParking

Listed by Adam Palmiter • Palmiter Realty Group

Bought with Adam Palmiter • Palmiter Realty Group

Redfin checked: 2 minutes ago

•Source:PrimeMLS #4228924

Redfin Estimate

$873,050

$423K since sold in September 2013$46K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.2% higher than the average sale price ($799K) of 6 comparable homes.

SOLD AUG 7, 2026
$550,000
A
8 beds4 baths6,466 sq ft
72 Landmark Hill Dr, Brattleboro, VT 05301
SOLD AUG 24, 2026
$1,175,000
B
4 beds3.5 baths4,491 sq ft
390 Pleasant Valley Rd, Brattleboro, VT 05301
SOLD OCT 14, 2026
$762,900
C
4 beds3 baths3,600 sq ft
5 Hillwinds N, Brattleboro, VT 05301
SOLD OCT 16, 2026
$599,000
D
4 beds2.5 baths3,576 sq ft
179 Hillwinds N, Brattleboro, VT 05301
SOLD JUL 23, 2026
$1,095,000
E
7 beds5.5 baths7,367 sq ft
218 Depot Rd, Williamsville, VT 05362
SOLD JUN 26, 2026
$615,000
F
5 beds3.5 baths2,520 sq ft
143 Hillwinds Rd, Brattleboro, VT 05301

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Market trends in 05301, VT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

98.3%

0.3% MoM

Median sale price

$339K

$41K MoM

Avg. days on market

66d

5 days MoM

Recently sold homes

4 MoM

New listings for sale

NEW 1 HR AGO
$295,000
— beds2 baths1,885 sq ft
100 Clark St, Brattleboro, VT 05301
$339,000
3 beds1.5 baths1,400 sq ft
12 Thorn Ln, Brattleboro, VT 05301
$439,000
2 beds2 baths1,635 sq ft
160 Wantastiquet Dr, Brattleboro, VT 05301
$265,000
3 beds2 baths1,865 sq ft
17 Paul's Rd, Guilford, VT 05301
$239,900
2 beds1.5 baths1,056 sq ft
78 Morningside Cmns, Brattleboro, VT 05301
$219,000
2 beds1.5 baths1,248 sq ft
9 Robin Way, Brattleboro, VT 05301
$250,000
2 beds1 bath1,485 sq ft
56 Fuller Dr, Brattleboro, VT 05301
See all

Provided by Redfin

Sale history for 1468 Upper Dummerston Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,667 (−2.2%)

$154,290 + $396,870

$551,160

2024

$9,881 (+11.7%)

$154,290 + $396,870

$551,160

2023

$8,848 (−44.9%)

$154,290 + $396,870

$551,160

2022

$16,050 (−0.9%)

$154,290 + $396,870

$551,160

2021

$16,201 (+1.3%)

$154,290 + $396,870

$551,160

2020

$15,993 (+3.8%)

$154,290 + $396,870

$551,160

2019

$15,412 (+0.2%)

$154,290 + $396,870

$551,160

2018

$15,381 (+4.2%)

$154,290 + $396,870

$551,160

2017

$14,755

$154,290 + $396,870

$551,160

2016

$14,753 (+0.4%)

$154,290 + $396,870

$551,160

2015

$14,691 (−0.3%)

$154,290 + $396,870

$551,160

2014

$14,730

$154,290 + $396,870

$551,160

Tax history for 1468 Upper Dummerston Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,667 (−2.2%)

$154,290 + $396,870

$551,160

2024

$9,881 (+11.7%)

$154,290 + $396,870

$551,160

2023

$8,848 (−44.9%)

$154,290 + $396,870

$551,160

2022

$16,050 (−0.9%)

$154,290 + $396,870

$551,160

2021

$16,201 (+1.3%)

$154,290 + $396,870

$551,160

2020

$15,993 (+3.8%)

$154,290 + $396,870

$551,160

2019

$15,412 (+0.2%)

$154,290 + $396,870

$551,160

2018

$15,381 (+4.2%)

$154,290 + $396,870

$551,160

2017

$14,755

$154,290 + $396,870

$551,160

2016

$14,753 (+0.4%)

$154,290 + $396,870

$551,160

2015

$14,691 (−0.3%)

$154,290 + $396,870

$551,160

2014

$14,730

$154,290 + $396,870

$551,160

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

Public record

Public record
Zoning

Beds

—

Baths

—

Stories

Lot width

—

Lot depth

—

Lot size

17.44 Acres

Year renovated

—

Sq. Ft.

—

Year built

1918

Style

Multi-Family (5+ Unit)

County

Windham County

APN

08102514396

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 23, 2026.

Rural Residential District

The Rural Residential District encompasses land primarily west of Interstate 91 that is rural in character but is relatively close to the developed areas of town and accessible from improved public roads, which has made these areas a suitable and attractive location for low-density residential development. This land is generally not served by municipal water and sewer, and extension of infrastructure into this district is discouraged. The purpose of this district is to provide opportunities for rural housing and to encourage thoughtful siting of new development in order to protect rural character, farmland, forestland, open space and important natural resources in accordance with the policies of the Brattleboro Town Plan.

Permitted uses

Include but are not limited to:

Agriculture
Religious facility
Housing-Single unit
Housing-Multiple units
Housing-Senior
Infrastructure
Golf related
Cemetery
Park & open space
Timberland

Property details

Parking

Parking & Garage
Garage Capacity: 2
Location: Attached
Unassigned
Driveway

Interior

Bathroom Information
# of Baths (full): 8

Basement Information
Basement: Yes
Basement Access: Walkout
Finished, Full

Other Interior Features
# of Rooms: 20
Flooring: Carpet, Vinyl
Water Heater: Electric
Attic, Dining Area, Hearth, In-Law Apartment

Room 3 Information
Living Room

Room 4 Information
Family Room

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 10605
Color: White
Barn, Deck, Guest House, Outbuilding, Porch - Covered
Foundation: Concrete
Roof: Membrane, Shingle - Architectural
Exterior: Wood

Driveway
Dirt

Lot, Zoning, & Easement Information
Lot: 1
Country Setting, Farm, Farm - Horse/Animal, Field/Pasture, Mountain View

Other Property & Lot Information
Year Built: 1918

Financial

Tax Information
Tax Year: 2012
Gross Amount Tax: 14691.17
SPAN Number: 08102514396

Other Tax Information
Page Deed: 193

Financing Information
Conventional

Utilities

Heating & Cooling Information
Heat: Alternative Heat Stove, Baseboard, Stove - Wood
Heat Fuel: Electric, Oil

Sewer Information
Public

Electric Information
Circuit Breaker(s)

Water Information
Drilled Well

Location

School Information
Elementary School: Brattleboro Elem Schools
Elementary School: Brattleboro Elem Schools
Middle/Jr School: Brattleboro Area Middle School

Neighborhood Information
Valley

Road Information
Road Frontage: Yes
Road Frontage Length: 500
Paved

Other Location Information
Directions: Upper Dummerston Road to Hillwinds Farm.

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: 3.0
Lot Size: 17.44 acres
Style: Multi-Family (5+ Unit)
Year Built: 1918
Year Renovated: —
County: Windham County
APN: 08102514396

Home facts updated by county records on Sep 23, 2026

Other

Documents & Disclosures
Documents Available: Deed

Around this home

Schools

K - 12
Preschool & daycare

Some nearby schools may not be within this home's attendance zone. Please check the Windham Southeast Unified Union School District #96 website to verify.

Academy School

Public PreK-6 • 3.1mi

7/10

Neighborhood Schoolhouse

Private PreK-8 • 3.2mi

Community Schoolhouse

Private 1-9 • 3.4mi

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

3/10 Heat Factor

7 days above 93° expected this year, 17 days in 30 years

4/10 Wind Factor

9% 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

Brattleboro, VT • 05301

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 3.9 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

3.9 hrs

JuneDecember

Provided by Shadowmap

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Home values near 1468 Upper Dummerston Rd

Data from public records.

Address	Redfin Estimate
1628 Upper Dummerston Road, Dummerston, VT 4 Beds \| 3 Baths \| 3373 Sq. Ft.	$465,769
1381 Upper Dummerston Road, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1440 Sq. Ft.	$267,089
1577 Upper Dummerston Road, Dummerston, VT 2 Beds \| 3 Baths \| 4142 Sq. Ft.	$1,017,379
155 Hillwinds North, Brattleboro, VT 4 Beds \| 3.5 Baths \| 3685 Sq. Ft.	$875,061
197 Hillwinds North, Brattleboro, VT 4 Beds \| 2.5 Baths \| 2412 Sq. Ft.	$569,257
208 Hillwinds North, Brattleboro, VT 3 Beds \| 2.5 Baths \| 2632 Sq. Ft.	$599,551
106 Hillwinds North, Brattleboro, VT 5 Beds \| 3 Baths \| 2696 Sq. Ft.	$584,439

Address	Redfin Estimate
1343 Upper Dummerston Road, Brattleboro, VT 1 Beds \| 1 Baths \| 805 Sq. Ft.	$276,714
1347 Upper Dummerston Road, Brattleboro, VT 1 Beds \| 1 Baths \| 720 Sq. Ft.	$265,754
10 Hillwinds North, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1482 Sq. Ft.	$427,097
189 Hillwinds North, Brattleboro, VT 3 Beds \| 3 Baths \| 2594 Sq. Ft.	$569,424
65 Hillwinds North, Brattleboro, VT 5 Beds \| 4.5 Baths \| 4150 Sq. Ft.	$829,332
179 Hillwinds North, Brattleboro, VT 4 Beds \| 2.5 Baths \| 3576 Sq. Ft.	$598,149
30 Hillwinds North, Brattleboro, VT 4 Beds \| 3 Baths \| 2066 Sq. Ft.	$498,144

Address	Redfin Estimate
1443 Upper Dummerston Road, Brattleboro, VT 4 Beds \| 2 Baths \| 1650 Sq. Ft.	$353,870
1313 Upper Dummerston Road, Brattleboro, VT 2 Beds \| 1 Baths \| 1350 Sq. Ft.	$305,739
148 Hillwinds North, Brattleboro, VT 3 Beds \| 3.5 Baths \| 3040 Sq. Ft.	$617,098
62 Hillwinds North, Brattleboro, VT 3 Beds \| 2 Baths \| 1890 Sq. Ft.	$453,306
5 Hillwinds North, Brattleboro, VT 4 Beds \| 3 Baths \| 3600 Sq. Ft.	$748,593
45 Hillwinds North, Brattleboro, VT 5 Beds \| 5.5 Baths \| 3880 Sq. Ft.	$694,261
297 Hillwinds North, Brattleboro, VT 3 Beds \| 2 Baths \| 1700 Sq. Ft.	$432,626

Property information provided by PrimeMLS when last listed in 2013. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05301, VT

Sale history for 1468 Upper Dummerston Rd

Tax history for 1468 Upper Dummerston Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Is this your home?

Nearby similar homes

New listings for sale in 05301

Home values near 1468 Upper Dummerston Rd

More real estate resources