939 Upper Dummerston Rd, Brattleboro, VT 05301
Property image
Property image
OFF MARKET

$413,300

Trulia Estimate
  • 2 Beds
  • 1.5 Baths
  • 1,650 sqft (on 4.15 acres)

939 Upper Dummerston Rd, Brattleboro, VT 05301

Refinance Your Home
Currently Off Market - Sold Sep 4, 2020 for $285,000

Home Value

Trulia Estimate
$413K
Since last month
Increased$600 (+0.1%)
Since last year
Increased$9K (+2.2%)
Since last sale
Increased$128K (+45%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +89% in the last 10 years
MonthEstimated value
2026
September 2026$413K
August 2026$409K
July 2026$413K
June 2026$413K
May 2026$410K
April 2026$402K
March 2026$398K
February 2026$383K
January 2026$385K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
211 Pleasant Valley Road, Brattleboro, VT
0.68
Single-Family Home
$525,000
08/31/26
2
1
1,576
1082 W River Road, Brattleboro, VT
0.46
Single-Family Home
$305,000
09/23/25
3
1
1,222
672 East Orchard Street, Brattleboro, VT
0.59
Single-Family Home
$470,000
09/26/25
3
3
3,148
1644 Upper Dummerston Road, Dummerston, VT
1.38
Single-Family Home
$325,000
08/12/26
2
2
1,499
187 Hillwinds Road, Brattleboro, VT
0.64
Single-Family Home
$476,000
11/20/25
4
3
2,372
131 Pleasant Valley Rd, Brattleboro, VT
0.75
Single-Family Home
$15,000
05/13/26
2
1
792
137 Pleasant Valley Road, Brattleboro, VT
0.79
Single-Family Home
$389,000
05/08/26
1
1
650
143 Hillwinds Road, Brattleboro, VT
0.67
Single-Family Home
$615,000
06/26/26
5
3.5
2,520
155 Upper Dummerston Road, Brattleboro, VT
1.35
Single-Family Home
$407,000
11/21/25
3
1.5
1,655
387 Meadow Brook Road, Brattleboro, VT
1.20
Single-Family Home
$439,000
05/13/26
4
2
1,568

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
863 Upper Dummerston Road, Brattleboro, VT 05301
0.15
$580,300
3
2.5
2,112
Off Market
1073 Upper Dummerston Road, Brattleboro, VT 05301
0.24
$557,200
3
2
2,456
Off Market
395 Hillwinds Road, Brattleboro, VT 05301
0.30
$709,700
4
2.5
2,226
Off Market
94 Brets Road, Brattleboro, VT 05301
0.35
$475,000
3
2.5
2,594
Recently Sold
336 Hillwinds Road, Brattleboro, VT 05301
0.38
$751,200
4
3
3,257
Off Market
335 Hillwinds Road, Brattleboro, VT 05301
0.41
$608,800
4
3.5
2,544
Off Market
1082 W River Road, Brattleboro, VT 05301
0.46
$321,900
3
1
1,222
Off Market
680 West River Road, Brattleboro, VT 05301
0.48
$145,000
-
-
-
Recently Sold
672 East Orchard Street, Brattleboro, VT 05301
0.59
$495,800
3
3
3,148
Off Market
187 Hillwinds Road, Brattleboro, VT 05301
0.64
$476,000
4
3
2,372
Recently Sold
143 Hillwinds Road, Brattleboro, VT 05301
0.67
$615,000
5
3.5
2,520
Recently Sold
0 East Orchard Street, Brattleboro, VT 05301
0.67
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 939 Upper Dummerston Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1948
4.15 acre lot
1,650 sqft
$250/sqft

About this House

For only the second time since it was built in 1948, this Saltbox style house is on the market. Throughout the early 2010's the home was thoughtfully renovated with features such as new kitchen/bath cabinetry and fixtures, granite countertops, refinished red oak flooring, new tile, fresh paint inside and out, and a deck overlooking the hayfield nearby.  In 2016, a sunny mudroom was built to improve the entry, complete with new washer and dryer.  An efficient Avalon wood stove and Nest thermostat were also installed at that time to help mitigate oil usage.  The plot features lovely perennials and open grassy lawn, and down the ravine you'll find roughly 3 wooded acres and a trail to the Meadow Brook waterfall. The plot benefits from morning to evening sun exposure, and the house has ample windows to bring in maximum light. This home is located just 6 minutes from Main Street Brattleboro, one mile from the Brattleboro Country Club/Outing Club, and 5 minutes from the Retreat Farm and Trails.  The mountains are not far either; just 30 minutes to Mt. Snow and 40 minutes to Stratton. 
939 Upper Dummerston Rd, Brattleboro, VT 05301 is a 2 bedroom, 2 bathroom, 1,650 sqft single-family home built in 1948. It last sold for $285,000 on Sep 4, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $413,300, with a rent estimate of $2,476/month.

Home Details for 939 Upper Dummerston Rd

Interior Features

Interior Details
BasementAdditional StorageNumber of Rooms: 8Types of Rooms: Breakfast Nook, Family Room, Laundry Room, Mud RoomStorage
Heating & Cooling
Heating: Forced Air, Stove, Oil, Wood PelletHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood, Linoleum Vinyl

Exterior Features

Exterior Home Features
Roof: MetalDeckExterior: WoodLawn

Property Information

Year Built
Year Built: 1948
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 4.15 acres

Additional Information

On Site Laundry Available

Price and Tax history

DateEventPrice
Mar 1, 2021
Source: N/A
ListingRemoved
Sep 4, 2020
Source: N/A
Sold
$285,000
Jun 5, 2020
Source: N/A
Pending
$285,000
Jun 1, 2020
Source: N/A
Listed For Sale
$285,000
Sep 26, 2016
Source: N/A
Sold
$225,000

Market trends in Brattleboro

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
33
1MoM

Around this home

What Locals Say about Brattleboro

At least 47 Trulia users voted on each feature.

  • 92 % Say parking is easy

  • 91 % Say it's dog friendly

  • 82 % Say yards are well-kept

  • 81 % Say there's holiday spirit

  • 81 % Say car is needed

  • 80 % Say there's wildlife

  • 72 % Say people would walk alone at night

  • 66 % Say it's walkable to restaurants

  • 62 % Say there are sidewalks

  • 60 % Say neighbors are friendly

  • 58 % Say it's walkable to grocery stores

  • 55 % Say kids play outside

  • 50 % Say streets are well-lit

  • 50 % Say there are community events

  • 48 % Say they plan to stay for at least 5 years

  • 38 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.
  • Greycella
    "Great neighborhood for learning to ride bikes, trick-or-treating, making friends with other families."
    0
    Flag
  • Brenda Nichols
    "Yes! Lots of space for walking and running around with dogs. Quiet countryside with not a lot of traffic."
    0
    Flag
  • Kelly Dias
    "People watch out for each other, sometimes we go Christmas caroling, we watch each others’ pets; we have a messaging group for neighborhood news"
    1
    Flag
  • Kelly Dias
    "It’s a great neighborhood to walk dogs. Sometimes bears come through so if it’s bear season you have to be careful. People are respectful and greet each other and we know each others’ dogs. "
    0
    Flag
  • Jessica Brown
    "I drive through downtown to work and there is some negativity on the streets by way of homelessness and drug abuse/ mental illness. But this neighborhood is still overall a place that I love to live . "
    0
    Flag
  • Kelly Dias
    "Pet friendly, willing to help out and get to know pets. Lots if grass and forested trails for walking and hiking with dogs. "
    0
    Flag
  • Isaac S.
    "Great small town in New England-artsy, funky, liberal. Nice amenities for the size of the town. Still some amount of crime-like everywhere these days."
    5
    Flag
  • Isaac S.
    "Dogs are welcome. Neighbor s are friendly. Houses are well maintained. I feel safe. Walkable neighborhood."
    3
    Flag
  • Jcoursem3
    "Neighbors are friendly and help each other out. Get together’s are organic and easy because of our close proximity. "
    0
    Flag
  • Deanshippee
    "A lot of people trust their dogs without a leash. It’s really annoying especially when every dog owner in. Brattleboro should know about our leash law."
    7
    Flag
  • Isaac S.
    "Car, 5 minutes to work. Few stoplights in town. Friendly drivers except those from Massachusetts and New York. Main Street gets bogged down with traffic but there are several back ways to get around town. Good city for driving in general."
    3
    Flag
  • Grace
    "I grew up in this neighborhood & am raising my daughter here. I love how bike friendly the neighborhood is and that we can walk both downtown & to the farmer’s market."
    11
    Flag
  • rhc3vt
    "Deteriorating economics, falling home prices, difficult to sell homes, few jobs, really bad schools, more and more poor people in trailer parks. There's not much of a future here."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 939 Upper Dummerston Rd

  • What is 939 Upper Dummerston Rd estimated to be worth?
    Trulia's estimated value for 939 Upper Dummerston Rd in Brattleboro, VT is $413,300.
  • What is the price history for 939 Upper Dummerston Rd?
    939 Upper Dummerston Rd in Brattleboro, VT last sold for $285,000 in September 2020.
  • Is Brattleboro a buyer's or seller's market?
    Brattleboro is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Brattleboro?
    Residents describe Brattleboro, VT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Brattleboro, VT.
  • Does 939 Upper Dummerston Rd have laundry facilities?
    Yes, 939 Upper Dummerston Rd in Brattleboro, VT has in-unit laundry.
  • How big is the lot at 939 Upper Dummerston Rd?
    The lot at 939 Upper Dummerston Rd in Brattleboro, VT is about 4.2 acres.

Explore by feature - Pet Friendly

7 pet-friendly rentals in Brattleboro, VT

Explore by feature - Air Conditioning

8 rentals with air conditioning in Brattleboro, VT

Explore by feature - Washer/dryer

16 rentals with a washer/dryer in Brattleboro, VT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 939 Upper Dummerston Rd

Skip to last item
Skip to first item

Homes for sale near 939 Upper Dummerston Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item