35 Chestnut St, Brattleboro, VT 05301
OFF MARKET

$349,000

Trulia Estimate
  • 3 Beds
  • 1.5 Baths
  • 1,750 sqft (on 0.25 acres)

35 Chestnut St, Brattleboro, VT 05301

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Home Value

Trulia Estimate
$349K
Since last month
Decreased$10K (-2.7%)
Since last year
Increased$8K (+2.2%)
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 +91% in the last 10 years
MonthEstimated value
2026
August 2026$349K
August 2026$348K
July 2026$359K
June 2026$363K
May 2026$358K
April 2026$358K
March 2026$329K
February 2026$317K
January 2026$323K
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
39 Locust Street, Brattleboro, VT
0.16
Single-Family Home
$340,000
08/31/26
4
1.5
1,800
177 Fairview Street, Brattleboro, VT
0.25
Single-Family Home
$350,000
10/06/25
3
1.5
1,768
164 Chestnut Street, Brattleboro, VT
0.20
Single-Family Home
$265,000
08/05/26
3
1
1,323
144 Belmont Avenue, Brattleboro, VT
0.23
Single-Family Home
$339,000
12/12/25
3
1.5
1,520
16 Willow Street, Brattleboro, VT
0.27
Single-Family Home
$399,900
06/02/26
3
1.5
1,339
44 Brook Street, Brattleboro, VT
0.36
Single-Family Home
$319,000
03/09/26
4
1.5
1,584
192 Western Avenue, Brattleboro, VT
0.35
Single-Family Home
$568,000
04/20/26
3
2
2,066
11 Maple Street, Brattleboro, VT
0.38
Single-Family Home
$322,500
09/23/25
4
2
1,548
17 Winter Court, Brattleboro, VT
0.32
Single-Family Home
$265,000
09/12/25
3
1
1,178
15 West Street, Brattleboro, VT
0.23
Single-Family Home
$277,000
04/23/26
4
1
1,374

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
22 Chestnut Street #5, Brattleboro, VT 05301
0.05
$213,400
3
1
1,250
Off Market
105 Chestnut Street, Brattleboro, VT 05301
0.10
$395,000
4
2
2,715
Recently Sold
204 Williams Street, Brattleboro, VT 05301
0.15
$272,200
3
1.5
1,611
Off Market
108 Chestnut Street, Brattleboro, VT 05301
0.13
$341,300
4
1.5
1,544
Off Market
187 Maple Street, Brattleboro, VT 05301
0.13
$371,300
2
1.5
1,272
Off Market
25 Cottage Street, Brattleboro, VT 05301
0.16
$380,000
6
4
3,264
For Sale
116 Birge Street #2, Brattleboro, VT 05301
0.20
$255,000
1
1
1,320
For Sale
39 Locust Street, Brattleboro, VT 05301
0.16
$340,000
4
1.5
1,800
Recently Sold
238 - 240 Fairview Street, Brattleboro, VT 05301
0.18
$360,000
5
2
2,176
Off Market
5 Reynolds Drive, Brattleboro, VT 05301
0.23
$284,000
5
3
2,360
For Sale
100 Whetstone Drive, Brattleboro, VT 05301
0.20
$351,800
2
1.5
1,519
Off Market
33 Frost Place, Brattleboro, VT 05301
0.23
$409,800
3
2.5
1,617
Off Market

Local Information

  • Map ViewExplore the area around 35 Chestnut St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1920
0.25 acre lot
1,750 sqft
$199/sqft
Garage

About this House

This single-family home is located at 35 Chestnut St, Brattleboro, VT. 35 Chestnut St is in Brattleboro, VT and in ZIP code 05301. This property has 3 bedrooms, 2 bathrooms and approximately 1,750 sqft of floor space. This property has a lot size of 10890 sqft and was built in 1920.
35 Chestnut St, Brattleboro, VT 05301 is a 3 bedroom, 2 bathroom, 1,750 sqft single-family home built in 1920. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $349,000, with a rent estimate of $2,357/month.

Home Details for 35 Chestnut St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8Types of Rooms: Dining Room, Mud Room, Office, Pantry
Levels, Entrance, & Accessibility
Stories: 3Floors: Carpet, Hardwood, Linoleum Vinyl
Appliances & Utilities
Cable ReadyDryerRefrigeratorWasher
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: Metal, SlateDeckExterior: ShingleGardenLawnPorch
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1920
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 10890 sqft

Price and Tax history

YearProperty taxTax assessment
2024Unavailable
$204,950
Home facts updated by county records

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

Frequently asked questions about 35 Chestnut St

  • What is 35 Chestnut St estimated to be worth?
    Trulia's estimated value for 35 Chestnut St in Brattleboro, VT is $349,000.
  • 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.
  • What are the closest schools to 35 Chestnut St?
    The closest schools to 35 Chestnut St in Brattleboro, VT are Brattleboro Area Middle School (rated 6/10), Green Street School (Pre-K/Elementary, rated 8/10), Windham Regional Career Center (High).
  • Does 35 Chestnut St have laundry facilities?
    Yes, 35 Chestnut St in Brattleboro, VT has in-unit laundry.
  • How big is the lot at 35 Chestnut St?
    The lot at 35 Chestnut St in Brattleboro, VT is about 0.25 acres (10,890 sq ft).

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