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

585 Upper Dummerston Rd
Brattleboro, VT 05301

  • 4 Beds
  • 4 Baths
  • 5,844 sqft (on 0.93 acres)

$606,300

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $4,166/mo*
Refinance Your Home

$606,300

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $4,166/mo*
Refinance Your Home
4 Beds
4 Baths
5,844 sqft
(on 0.93 acres)

Local Information

  • Map ViewExplore the area around 585 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
1967
Lot Size
0.93 acres
Living Area
5,844 sqft
Price/Sqft
$104
Parking
Garage

About this House

This single-family home is located at 585 Upper Dummerston Rd, Brattleboro, VT. 585 Upper Dummerston Rd is in Brattleboro, VT and in ZIP code 05301. This property has 4 bedrooms, 3 bathrooms and approximately 5,844 sqft of floor space. This property has a lot size of 0.93 acres and was built in 1967.
585 Upper Dummerston Rd, Brattleboro, VT 05301 is a 4 bedroom, 3 bathroom, 5,844 sqft single-family home built in 1967. It last sold for $295,000 on Aug 3, 2020. It is currently off market. The Trulia Estimate is $606,300, with a rent estimate of $4,598/month.

Home Details for 585 Upper Dummerston Rd

Interior Features

Interior Details
BasementIn-law unitTypes of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Solarium Atrium, Sun Room
Heating & Cooling
Heating: Baseboard, Electric, OilHeating Fuel: Baseboard
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigerator
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Concrete, Hardwood, Linoleum Vinyl
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodGardenPatioPorch
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1967
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Lot Information

Lot Area: 0.93 acres

Price History for 585 Upper Dummerston Rd

DatePriceEventSource
08/03/2020$295,000Sold
PrimeMLS #4795117
10/18/2019$329,000PriceChange
Agent Provided
09/09/2019$339,000Listed For SaleAgent Provided
02/15/2019$359,000ListingRemovedAgent Provided
12/04/2018$359,000PriceChange
Agent Provided
09/14/2018$375,000PriceChange
Agent Provided
06/28/2018$385,000PriceChange
Agent Provided
09/29/2017$395,000Listed For SaleAgent Provided
10/15/1997$305,000Sold
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$330,030
Home facts updated by county records

Comparable Sales for 585 Upper Dummerston Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
672 East Orchard Street, Brattleboro, VT
0.24
Single-Family Home
$470,000
09/26/25
3
3
3,148
395 Hillwinds Road, Brattleboro, VT
0.86
Single-Family Home
$668,000
08/12/25
4
2.5
2,226
155 Upper Dummerston Road, Brattleboro, VT
0.81
Single-Family Home
$407,000
11/21/25
3
1.5
1,655
1073 Upper Dummerston Road, Brattleboro, VT
0.84
Single-Family Home
$525,000
08/19/25
3
2
2,456
187 Hillwinds Road, Brattleboro, VT
1.23
Single-Family Home
$476,000
11/20/25
4
3
2,372
23 Meetinghouse Lane, Brattleboro, VT
1.05
Single-Family Home
$495,000
12/29/25
3
2.5
3,415
387 Meadow Brook Road, Brattleboro, VT
0.94
Single-Family Home
$439,000
05/13/26
4
2
1,568
143 Hillwinds Road, Brattleboro, VT
1.28
Single-Family Home
$615,000
06/26/26
5
3.5
2,520
1082 W River Road, Brattleboro, VT
1.00
Single-Family Home
$305,000
09/23/25
3
1
1,222
155 Hillwinds North Road, Brattleboro, VT
1.51
Single-Family Home
$868,000
09/09/25
4
3.5
3,685

Nearby homes

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Assigned Schools

These are the assigned schools for 585 Upper Dummerston Rd.
View nearby schools on GreatSchools
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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Apartments for Rent

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Explore by feature - Pet Friendly

8 pet-friendly rentals in Brattleboro, VT

Explore by feature - Air Conditioning

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11 rentals with a washer/dryer in Brattleboro, VT

Homes for sale near 585 Upper Dummerston Rd

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Off Market Homes Near 585 Upper Dummerston Rd

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