559 Upper Dummerston Rd, Brattleboro, VT 05301
OFF MARKET

559 Upper Dummerston Rd
Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,536 sqft (on 0.48 acres)

$539,200

Trulia Estimate
as of Aug 12, 2026

$539,200

Trulia Estimate
as of Aug 12, 2026
3 Beds
2 Baths
2,536 sqft
(on 0.48 acres)

Home Value

Trulia Estimate
$539K
Since last month
Decreased$16K (-2.9%)
Since last year
Decreased$10K (-1.8%)
Since last sale
Increased$210K (+63.6%)
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 +60% in the last 10 years
MonthEstimated value
2026
August 2026$539K
July 2026$552K
June 2026$556K
May 2026$546K
April 2026$532K
March 2026$531K
February 2026$517K
January 2026$523K
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
672 East Orchard Street, Brattleboro, VT
0.27
Single-Family Home
$470,000
09/26/25
3
3
3,148
155 Upper Dummerston Road, Brattleboro, VT
0.77
Single-Family Home
$407,000
11/21/25
3
1.5
1,655
387 Meadow Brook Road, Brattleboro, VT
0.96
Single-Family Home
$439,000
05/13/26
4
2
1,568
1073 Upper Dummerston Road, Brattleboro, VT
0.87
Single-Family Home
$525,000
08/19/25
3
2
2,456
395 Hillwinds Road, Brattleboro, VT
0.90
Single-Family Home
$668,000
08/12/25
4
2.5
2,226
1082 W River Road, Brattleboro, VT
1.02
Single-Family Home
$305,000
09/23/25
3
1
1,222
84 Magnolia Drive, Brattleboro, VT
1.08
Single-Family Home
$570,000
04/29/26
2
2
1,900
23 Meetinghouse Lane, Brattleboro, VT
1.04
Single-Family Home
$495,000
12/29/25
3
2.5
3,415
139 Buttonwood Drive, Brattleboro, VT
1.08
Single-Family Home
$455,000
03/04/26
2
2
1,390
204 Meetinghouse Lane, Brattleboro, VT
1.34
Single-Family Home
$497,408
04/10/26
4
2
2,656

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
672 East Orchard Street, Brattleboro, VT 05301
0.27
$483,700
3
3
3,148
Off Market
680 West River Road, Brattleboro, VT 05301
0.34
$145,000
-
-
-
Recently Sold
0 East Orchard Street, Brattleboro, VT 05301
0.33
-
-
-
-
Off Market
568 West River Road, Brattleboro, VT 05301
0.39
$374,800
2
1.5
1,312
Off Market
0 Gibson Road Lot #56, Brattleboro, VT 05301
0.43
-
-
-
-
Off Market
863 Upper Dummerston Road, Brattleboro, VT 05301
0.50
$582,500
3
2.5
2,112
Off Market
94 Brets Road, Brattleboro, VT 05301
0.51
$475,000
3
2.5
2,594
Recently Sold
396 East Orchard Street, Brattleboro, VT 05301
0.58
$798,600
4
5
4,300
Off Market
155 Upper Dummerston Road, Brattleboro, VT 05301
0.77
$407,000
3
1.5
1,655
Recently Sold
135 Upper Dummerston Road, Brattleboro, VT 05301
0.82
$545,400
5
3.5
3,600
Off Market
0 Orchard Street Lot 59, Brattleboro, VT 05301
0.79
$70,000
-
-
-
Recently Sold
Lot #4 Bittersweet Lane, Brattleboro, VT 05301
0.85
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 559 Upper Dummerston Rd.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1960
Lot Size
0.48 acres
Living Area
2,536 sqft
Price/Sqft
$213

About this House

This handsome contemporary single level home is located on prestigious Upper Dummerston Road and provides lovely views of Fairwinds Farm, The Country Club and distant mountains. Just minutes from downtown, the location is choice and country. The interior is bright and inviting and includes large principal rooms, notably: Spectacular country Kitchen/Family Room, spacious Living Room with fireplace, formal Dining Room, Bedroom wing with master with en suite bath and two additional bedrooms with shared second bath and a lower level office. Beautiful stone walls, 2-car garage, stone house accents and large rear deck all add to the appeal. A wonderful place to call home!!!
559 Upper Dummerston Rd, Brattleboro, VT 05301 is a 3 bedroom, 2 bathroom, 2,536 sqft single-family home built in 1960. It last sold for $329,500 on Jun 29, 2015. It is currently off market. The Trulia Estimate is $539,200, with a rent estimate of $2,741/month.

Home Details for 559 Upper Dummerston Rd

Interior Features

Heating & Cooling
Heating: Baseboard, Gas, Oil, Wood PelletCooling System: OtherHeating Fuel: Baseboard
Interior Details
Additional StorageNumber of Rooms: 8Types of Rooms: Dining RoomStorageCeiling Fan
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltDeckPorch

Property Information

Year Built
Year Built: 1960
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Building

Levels, Entrance, & Accessibility
Disabled Access

Lot Information

Lot Area: 0.48 acres

Price and Tax history

DateEventPrice
Jun 29, 2015
Source: N/A
Sold
$329,500
Jun 2, 2015
Source: Agent Provided
Pending
$339,500
Aug 8, 2014
Source: Agent Provided
PriceChange
$339,500
Price decreased by 5%
Apr 19, 2014
Source: Agent Provided
Listed For Sale
$359,000
Dec 6, 2006
Source: N/A
Sold
$314,900

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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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
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 559 Upper Dummerston Rd

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Off Market Homes Near 559 Upper Dummerston Rd

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Frequently asked questions about 559 Upper Dummerston Rd

  • What is 559 Upper Dummerston Rd estimated to be worth?
    Trulia's estimated value for 559 Upper Dummerston Rd in Brattleboro, VT is $539,200.
  • What is the price history for 559 Upper Dummerston Rd?
    559 Upper Dummerston Rd in Brattleboro, VT last sold for $329,500 in June 2015.
  • 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 559 Upper Dummerston Rd have air conditioning?
    Yes, 559 Upper Dummerston Rd in Brattleboro, VT has air conditioning.
  • Does 559 Upper Dummerston Rd have laundry facilities?
    Yes, 559 Upper Dummerston Rd in Brattleboro, VT has in-unit laundry.