939 Upper Dummerston Rd, Brattleboro, VT 05301
OFF MARKET

939 Upper Dummerston Rd
Brattleboro, VT 05301

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

$413,800

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $2,874/mo*
Refinance Your Home

$413,800

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $2,874/mo*
Refinance Your Home
2 Beds
1.5 Baths
1,650 sqft
(on 4.15 acres)

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

Property Type
Single-Family Home
Year Built
1948
Lot Size
4.15 acres
Living Area
1,650 sqft
Price/Sqft
$251

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. It is currently off market. The Trulia Estimate is $413,800, with a rent estimate of $2,473/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 History for 939 Upper Dummerston Rd

DatePriceEventSource
03/01/2021ListingRemovedN/A
09/04/2020$285,000Sold
N/A
06/05/2020$285,000PendingN/A
06/01/2020$285,000Listed For SaleN/A
09/26/2016$225,000Sold
N/A
09/09/2015$224,900ListingRemovedAgent Provided
10/03/2014$224,900Listed For SaleAgent Provided
03/13/2013$42,000Sold
N/A

Market trends in Brattleboro

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
9MoM
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Property Tax and Assessment

Year2024
Tax
Assessment$238,720
Home facts updated by county records

Comparable Sales for 939 Upper Dummerston Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1073 Upper Dummerston Road, Brattleboro, VT
0.24
Single-Family Home
$525,000
08/19/25
3
2
2,456
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
395 Hillwinds Road, Brattleboro, VT
0.30
Single-Family Home
$668,000
08/12/25
4
2.5
2,226
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 homes

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Assigned Schools

These are the assigned schools for 939 Upper Dummerston Rd.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
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Explore by feature - Pet Friendly

9 pet-friendly rentals in Brattleboro, VT

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Homes for sale near 939 Upper Dummerston Rd

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Off Market Homes Near 939 Upper Dummerston Rd

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