135 Upper Dummerston Road, Brattleboro, VT 05301
OFF MARKET

135 Upper Dummerston Road
Brattleboro, VT 05301

  • 5 Beds
  • 3.5 Baths
  • 3,600 sqft (on 0.90 acres)

$550,300

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $3,716/mo*
Refinance Your Home

$550,300

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $3,716/mo*
Refinance Your Home
5 Beds
3.5 Baths
3,600 sqft
(on 0.90 acres)

Home Value

Trulia Estimate
$550K
Since last month
Increased$3K (+0.5%)
Since last year
Increased$28K (+5.4%)
Since last sale
Increased$26K (+5%)
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 +109% in the last 10 years
MonthEstimated value
2026
August 2026$551K
July 2026$548K
June 2026$544K
May 2026$541K
April 2026$542K
March 2026$532K
February 2026$533K
January 2026$526K
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
155 Upper Dummerston Road, Brattleboro, VT
0.05
Single-Family Home
$407,000
11/21/25
3
1.5
1,655
214 Putney Road, Brattleboro, VT
0.92
Single-Family Home
$450,000
05/15/26
4
2.5
2,756
58 Oak Street, Brattleboro, VT
1.18
Single-Family Home
$595,000
08/07/26
5
4
3,748
49 Tyler Street, Brattleboro, VT
1.16
Single-Family Home
$625,000
10/03/25
3
2
2,731
76 Spruce Street, Brattleboro, VT
1.17
Single-Family Home
$408,065
03/12/26
4
3
3,314
41 Chapin Street, Brattleboro, VT
1.10
Single-Family Home
$495,000
07/30/26
4
2.5
2,874
11 Strawberry Hill, Brattleboro, VT
1.24
Single-Family Home
$580,000
06/30/26
4
2.5
2,573
672 East Orchard Street, Brattleboro, VT
1.05
Single-Family Home
$470,000
09/26/25
3
3
3,148
23 Meetinghouse Lane, Brattleboro, VT
1.28
Single-Family Home
$495,000
12/29/25
3
2.5
3,415
16 Vermont Avenue, Brattleboro, VT
0.88
Single-Family Home
$425,000
12/29/25
3
1.5
1,846

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
155 Upper Dummerston Road, Brattleboro, VT 05301
0.05
$407,000
3
1.5
1,655
Recently Sold
Lot #4 Bittersweet Lane, Brattleboro, VT 05301
0.76
-
-
-
-
Off Market
Lot #5 Bittersweet Lane, Brattleboro, VT 05301
0.76
-
-
-
-
Off Market
139 Buttonwood Drive, Brattleboro, VT 05301
0.75
$455,000
2
2
1,390
Recently Sold
568 West River Road, Brattleboro, VT 05301
0.76
$376,600
2
1.5
1,312
Off Market
72 Landmark Hill Drive, Brattleboro, VT 05301
0.75
$550,000
8
4
6,466
Recently Sold
162 Buttonwood Drive, Brattleboro, VT 05301
0.79
$479,000
2
2
1,775
For Sale
77 Buttonwood Drive, Brattleboro, VT 05301
0.83
$439,000
2
2
1,550
For Sale
84 Magnolia Drive, Brattleboro, VT 05301
0.84
$570,000
2
2
1,900
Recently Sold
316 Putney Road, Brattleboro, VT 05301
0.85
$187,100
3
1.5
1,531
Off Market
322 Putney Road, Brattleboro, VT 05301
0.86
$328,700
3
1.5
1,388
Off Market

Local Information

  • Map ViewExplore the area around 135 Upper Dummerston Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1910
Lot Size
0.9 acres
Living Area
3,600 sqft
Price/Sqft
$153
Parking
Garage
Last check for updates: about 3 hours ago
Listed by Susan LeCours
Barrett & Valley Assoc. Inc, (802) 843-2390
Bought with: Laura D'Angelo, Berkley & Veller Greenwood Country, (802) 254-6400
Source: PrimeMLS, MLS#4993919

About this House

An ideal location from which to enjoy the countless in-town and country activities available in the Brattleboro area! This circa 1910 arts and crafts style cedar shingle house was one of Brattleboro’s historic downtown homes and was moved to its current enviable location in 1996. The house sits 1/8th of a mile off of Route 30, within one mile of downtown Brattleboro and even closer to the active Retreat Farm (with its seasonal music and food truck roundups), the Meadows (water related activities) and the extensive Retreat trail system. The house is under 1/4 mile from the Brattleboro Country Club for golf, cross-country skiing and dining. The home offers an exceptional combination of country living and accessibility and features wood floors with radiant heat, a wood burning fireplace with built-in bookcase surrounds, high ceilings throughout, a formal dining room, office, and a kitchen with informal kitchen dining area with abundant natural light. The second floor is home to four spacious bedrooms and a full bathroom. The primary bedroom includes another private ensuite bath. There is ample outdoor common area including a 440 square foot deck above the home’s two-bay garage and a covered entry porch which looks to the property’s yard and surrounding woods. The walkout level basement is currently utilized as a rented apartment with one bedroom, an office space, and an open plan kitchen and living/dining space. Showings Begin 5/4! Contact us to discuss this special offering!
135 Upper Dummerston Road, Brattleboro, VT 05301 is a 5 bedroom, 4 bathroom, 3,600 sqft single-family home built in 1910. It last sold for $525,000 on May 16, 2025 (12% below the $599,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $550,300, with a rent estimate of $3,827/month.

Home Details for 135 Upper Dummerston Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Concrete,Concrete Floor,Daylight,Interior Access,Basement Stairs,Interior EntryNumber of Rooms: 12
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3600 Square Feet
Appliances & Utilities
Utilities: Cable at Site, Telephone at Site
Heating & Cooling
Heating: Oil,In Floor,Radiant,RadiatorNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Flooring: Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Wood
View
No View

Exterior Features

Exterior Home Features
Roof: SlateFoundation: Concrete
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageParking Spaces: 2Parking: Circular Driveway,Concrete
Frontage
Road Frontage: PublicRoad Surface Type: Paved
Water & Sewer
Sewer: Private Sewer, Septic Tank
Farm & Range
Frontage Length: Road frontage: 293
Finished Area
Finished Area (above surface): 2460 Square FeetFinished Area (below surface): 1140 Square Feet

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Arts and Crafts
Building
Construction Materials: Wood Frame, Shingle Siding, Wood Exterior, Wood SidingNot a New Construction

Price & Status

Price
List Price: $599,000

Location

Direction & Address
City: Brattleboro

Building

Building Area
Building Area: 5130 Square Feet

Lot Information

Lot Area: 0.90 acres

Miscellaneous

BasementMls Number: 4993919Above Grade Unfinished Area: 2460Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 300Below Grade Unfinished Area Source: EstimatedBelow Grade Unfinished Area Units: Square Feet

Price and Tax history

DateEventPrice
May 16, 2025
Source: PrimeMLS #4993919
Sold
$525,000
Jan 3, 2025
Source: PrimeMLS #4993919
Listed For Sale
$599,000
Sep 5, 2024
Source: PrimeMLS #4993919
ListingRemoved
$599,000
Jun 12, 2024
Source: PrimeMLS #4993919
PriceChange
$599,000
Price decreased by 7%
May 2, 2024
Source: PrimeMLS #4993919
Listed For Sale
$645,000

Market trends in Brattleboro

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32

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

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-08-25 09:56:45 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

Frequently asked questions about 135 Upper Dummerston Road

  • What is 135 Upper Dummerston Road estimated to be worth?
    Trulia's estimated value for 135 Upper Dummerston Road in Brattleboro, VT is $550,300.
  • What is the price history for 135 Upper Dummerston Road?
    135 Upper Dummerston Road in Brattleboro, VT last sold for $525,000 in May 2025.
  • 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.
  • How big is the lot at 135 Upper Dummerston Road?
    The lot at 135 Upper Dummerston Road in Brattleboro, VT is about 0.90 acres (39,204 sq ft).
  • Does 135 Upper Dummerston Road have a garage?
    Yes, 135 Upper Dummerston Road in Brattleboro, VT has a garage.

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