OFF MARKET

Listed by Christine Lewis • Brattleboro Area Realty. Bought with Brattleboro Area Realty.

Off Market Aug 2020 for $295K

$594,226

Est. refi paymentEst. refi $1,880/mo

•

5,844

sq ft

585 Upper Dummerston Rd, Brattleboro, VT 05301

About this home

RARE AS RARE CAN BE! Locally, it is so rare to find a nearly 5000 square foot executive ranch in just the right location (across from the golf course and minutes to downtown on a paved road), featuring an incredibly private court yard, private master suite (18x24). .. .supports that king sized bed. .. ,dressing room, tiled full bath and that ever needed extra 1/2 bath and sliders to your own private garden deck and a private wing for the mom (have her near you and age in place gracefully). This incredible home is great for the x generation, not quite ready to leave home, has lots of space for an at home office, nanny, or other fun uses. This is a must see for anyone just waiting for the right one level home to come to the market!

Single-familyProperty Type

1967Year Built

0.93 acresLot Size

$102Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Christine Lewis • Brattleboro Area Realty

Bought with Christine Lewis • Brattleboro Area Realty

Redfin checked: a minute ago

•Source:PrimeMLS #4795117

Redfin Estimate

$594,226

$299K since sold in August 2020$59K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 31.1% higher than the average sale price ($453K) of 6 comparable homes.

SOLD JUL 13, 2026
$296,000
A
5 beds3 baths3,660 sq ft
110 Washington St, Brattleboro, VT 05301
SOLD JUN 26, 2026
$615,000
B
5 beds3.5 baths2,520 sq ft
143 Hillwinds Rd, Brattleboro, VT 05301
SOLD APR 10, 2026
$497,408
C
4 beds2 baths2,656 sq ft
204 Meetinghouse Ln, Brattleboro, VT 05301
SOLD FEB 10, 2026
$385,000
D
4 beds3 baths3,616 sq ft
198 Hillcrest Ter, Brattleboro, VT 05301
SOLD NOV 20, 2025
$476,000
E
4 beds3 baths2,372 sq ft
187 Hillwinds Rd, Brattleboro, VT 05301
SOLD MAY 15, 2026
$450,000
F
4 beds2.5 baths2,756 sq ft
214 Putney 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 July 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

99.2%

+2.1% MoM

Median sale price

$385K

$5K MoM

Avg. days on market

50d

9 days MoM

Recently sold homes

14 MoM

New listings for sale

OPEN TODAY, 10AM TO 12PM
$299,000
6 beds3 baths3,125 sq ft
75 Moreland Ave, Brattleboro, VT 05301
$16,900
2 beds1 bath672 sq ft
11 Crescent Dr, Brattleboro, VT 05301
$499,000
2 beds2 baths1,775 sq ft
171 Buttonwood Dr, Brattleboro, VT 05301
OPEN TODAY, 11AM TO 1PM
$525,000
3 beds2.5 baths2,330 sq ft
205 Wantastiquet Dr, Brattleboro, VT 05301
$479,000
2 beds2 baths1,775 sq ft
162 Buttonwood Dr, Brattleboro, VT 05301
$439,000
2 beds2 baths1,550 sq ft
77 Buttonwood Dr, Brattleboro, VT 05301
$289,000
2 beds1 bath925 sq ft
45 Kopkind Rd, Guilford, VT 05301
$615,000
4 beds2.5 baths2,212 sq ft
354 Orchard St, Brattleboro, VT 05301
$275,000
Studio— baths1,200 sq ft
752 Butternut Rd, Guilford, VT 05301
$290,000
5 beds1.5 baths2,167 sq ft
207 Elliot St, Brattleboro, VT 05301
See all

Provided by Redfin

Sale history for 585 Upper Dummerston Rd

Date

Event

Price

PrimeMLS #4795117

Aug 3, 2020

Sold

$295,000

$50/sq ft

May 21, 2020

Pending

—

Feb 24, 2020

Listed

$329,000

$56/sq ft

PrimeMLS #2

Oct 18, 2019

Price Changed

$329,000

$56/sq ft

PrimeMLS #1

Dec 4, 2018

Price Changed

$359,000

$61/sq ft

Sep 14, 2018

Price Changed

$375,000

$64/sq ft

Jun 28, 2018

Price Changed

$385,000

$66/sq ft

Public Records

Jul 29, 2010

Sold

$390,000

$67/sq ft

PrimeMLS #4001373

Jul 29, 2010

Sold

$380,000

$65/sq ft

May 25, 2010

Listed

$380,000

$65/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$6,195 (−1.9%)

$62,900 + $267,130

$330,030

2024

$6,316 (+12.8%)

$62,900 + $267,130

$330,030

2023

$5,598 (−44.3%)

$62,900 + $267,130

$330,030

2022

$10,047 (+3.6%)

$62,900 + $267,130

$330,030

2021

$9,701 (+1.3%)

$62,900 + $267,130

$330,030

2020

$9,576 (−21.7%)

$62,900 + $267,130

$330,030

2019

$12,224 (−2.2%)

$62,900 + $374,250

$437,150

2018

$12,497 (+1.4%)

$62,900 + $374,250

$437,150

2017

$12,323 (+0.2%)

$62,900 + $374,250

$437,150

2016

$12,295 (−0.9%)

$62,900 + $374,250

$437,150

2015

$12,404 (+0.8%)

$62,900 + $374,250

$437,150

2014

$12,308

$62,900 + $374,250

$437,150

Tax history for 585 Upper Dummerston Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,195 (−1.9%)

$62,900 + $267,130

$330,030

2024

$6,316 (+12.8%)

$62,900 + $267,130

$330,030

2023

$5,598 (−44.3%)

$62,900 + $267,130

$330,030

2022

$10,047 (+3.6%)

$62,900 + $267,130

$330,030

2021

$9,701 (+1.3%)

$62,900 + $267,130

$330,030

2020

$9,576 (−21.7%)

$62,900 + $267,130

$330,030

2019

$12,224 (−2.2%)

$62,900 + $374,250

$437,150

2018

$12,497 (+1.4%)

$62,900 + $374,250

$437,150

2017

$12,323 (+0.2%)

$62,900 + $374,250

$437,150

2016

$12,295 (−0.9%)

$62,900 + $374,250

$437,150

2015

$12,404 (+0.8%)

$62,900 + $374,250

$437,150

2014

$12,308

$62,900 + $374,250

$437,150

*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

3.75

Stories

Lot width

—

Lot depth

—

Lot size

40,510

Year renovated

2021

Sq. Ft.

5,844

Year built

1967

Style

Single Family Residential

County

Windham County

APN

08102511835

Parking Spaces

Basement

Yes

Accessible

Yes

HOA Dues

—

Garage

Yes

Features

—

Last updated by owner on Jun 8, 2022.

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
Auto Open, Direct Entry, Heated, Storage Above
Parking Spaces 6+

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Interior
Bulkhead, Climate Controlled, Finished, Frost Wall, Full, Stairs - Exterior, Stairs - Interior, Storage Space, Sump Pump

Other Interior Features
# of Rooms: 11
Flooring: Carpet, Ceramic Tile, Marble
Water Heater: Off Boiler
Cedar Closet, Ceiling Fan, In-Law Apartment, In-Law Suite, Laundry Hook-ups, Master Bedroom With Bath, Laundry - 1st Floor

Accessibility Information
1st Floor 1/2 Bathroom, 1st Floor 3/4 Bathroom, 1st Floor Full Bathroom, 1st Floor Hrd Surfce Flor, 1st Floor Low-Pile Carpet, Access Parking, Bathroom w/5 Ft. Diameter, Bathroom w/Step-in Shower, No Stairs, One-Level Home

Equipment & Appliance Information
Dishwasher, Dryer, Range - Electric, Refrigerator
Window AC, Carbon Monoxide Detector, Security System, Smoke Detector, Smoke Detectr-Battery Powered, Smoke Detectr-Hard Wired With Battery

Room 1 Information
Full Bath
Full Bath
Dimensions: 12x09
Level: 1

Room 2 Information
Bedroom
Dimensions: 14x15
Level: 1

Room 3 Information
Kitchen
Dimensions: 09x10
Level: 1

Room 4 Information
Living Room
Dimensions: 15x15
Level: 1

Room 5 Information
Dining Room
Dimensions: 12x09
Level: 1

Room 6 Information
Family Room
Family Room
Dimensions: 36x21
Level: 1

Room 7 Information
Living Room
Dimensions: 23x15
Level: 1

Room 8 Information
Kitchen
Dimensions: 11x18
Level: 1

Room 9 Information
Sunroom
Dimensions: 10x16
Level: 1

Room 10 Information
Dining Room
Dimensions: 12x15
Level: 1

Room 11 Information
Bedroom
Dimensions: 10x11
Level: 1

Room 12 Information
1/2 Bath
Dimensions: 05x07
Level: 1

Room 13 Information
Bedroom
Dimensions: 12x23
Level: 1

Room 14 Information
Full Bath
Dimensions: 05x07
Level: 1

Room 15 Information
Master Bedroom
Dimensions: 18x26
Level: 1

Room 16 Information
1/2 Bath
Dimensions: 06x06
Level: 1

Room 17 Information
Other
Dimensions: 06x2.6
Level: 1

Room 18 Information
Full Bath
Dimensions: 15x10
Level: 1

Room 19 Information
Level: 1

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 5844
Approximate Sq. Ft. Total: 6324
Color: grey
Deck, Patio, Porch - Enclosed, Window Screens
Construction: Wood Frame
Foundation: Below Frost Line, Concrete
Roof: Shingle - Architectural, Shingle - Fiberglass
Exterior: Clapboard, Wood

Driveway
Circular, Paved

Lot, Zoning, & Easement Information
Lot: 35
Country Setting, Landscaped, Level, Trail/Near Trail

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1967

Financial

Tax Information
Tax Year: 2019
Gross Amount Tax: 12224
SPAN Number: 08102511835

Other Tax Information
Page Deed: 980

Utilities

Heating & Cooling Information
Cooling: Multi Zone
Heat: Baseboard, Hot Water, Multi Zone
Heat Fuel: Oil

Sewer Information
Private, Septic

Electric Information
Electric Company: GMP
Circuit Breaker(s), Generator, Generator Ready

Water Information
Drilled Well

Other Utilities Information
Cable Company: Comcast
Phone Company: FairPoint
Cable, DSL, Internet - Cable

Location

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

Neighborhood Information
Abuts Conservation, Rural, Near Public Transportatn

Road Information
Road Frontage: Yes
Road Frontage Length: 249
Public

Other Location Information
Directions: From Brattleboro, RT 30 to left on Upper Dummerston Road, house on right across from golf course

Public facts

Beds: 4
Baths: 3.75
Sq. Ft.: 5,844
Stories: 2.0
Parking Spaces: 6
Basement: Yes
Accessible: Yes
Lot Size: 0.93 acres
Style: Single Family Residential
Year Built: 1967
Year Renovated: 2021
County: Windham County
APN: 08102511835
HOA Dues: —
Garage: Yes
Features: —

Home facts updated by owner on Jun 8, 2022

Other

Water Body Information
Flood Zone: Unknown

Documents & Disclosures
Documents Available: Deed, Plot Plan, Property Disclosure

Around this home

Schools

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 • 1.8mi

6/10

Green Street School

Public PreK-6 • 2.0mi

8/10

Neighborhood Schoolhouse

Private PreK-8 • 1.7mi

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 94° expected this year, 16 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

Estimated sale price

$560,000 – $677,000

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

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Home values near 585 Upper Dummerston Rd

Data from public records.

Address	Redfin Estimate
559 Upper Dummerston Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 2536 Sq. Ft.	$515,850
651 Upper Dummerston Rd, Brattleboro, VT 5 Beds \| 3 Baths \| 3426 Sq. Ft.	$548,315

Address	Redfin Estimate
799 Upper Dummerston Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 2100 Sq. Ft.	$653,763
475 Upper Dummerston Rd, Brattleboro, VT 4 Beds \| 2.5 Baths \| 2860 Sq. Ft.	$863,282

Address	Redfin Estimate
750 Upper Dummerston Rd, Brattleboro, VT 3 Beds \| 1 Baths \| 1989 Sq. Ft.	$360,446
736 Upper Dummerston Rd, Brattleboro, VT 3 Beds \| 1 Baths \| 1633 Sq. Ft.	$371,804

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

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About this home

Redfin Estimate

Earn from this home

Market trends in 05301, VT

Sale history for 585 Upper Dummerston Rd

Tax history for 585 Upper Dummerston Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05301

Home values near 585 Upper Dummerston Rd

More real estate resources