44 Cherry St, Brattleboro, VT 05301
Property image
Property image
OFF MARKET

44 Cherry St
Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,133 sqft

$457,100

Trulia Estimate
as of Aug 16, 2026

$457,100

Trulia Estimate
as of Aug 16, 2026
3 Beds
2 Baths
2,133 sqft

Home Value

Trulia Estimate
$457K
Since last month
Increased$9K (+2%)
Since last year
Increased$36K (+8.7%)
Since last sale
Increased$330K (+274.7%)
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 +81% in the last 10 years
MonthEstimated value
2026
August 2026$450K
July 2026$446K
June 2026$441K
May 2026$438K
April 2026$444K
March 2026$413K
February 2026$406K
January 2026$411K
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
144 Belmont Avenue, Brattleboro, VT
0.16
Single-Family Home
$339,000
12/12/25
3
1.5
1,520
177 Fairview Street, Brattleboro, VT
0.21
Single-Family Home
$350,000
10/06/25
3
1.5
1,768
76 Belmont Avenue, Brattleboro, VT
0.21
Single-Family Home
$391,000
06/25/26
3
2
1,686
11 Maple Street, Brattleboro, VT
0.17
Single-Family Home
$322,500
09/23/25
4
2
1,548
44 Brook Street, Brattleboro, VT
0.22
Single-Family Home
$319,000
03/09/26
4
1.5
1,584
16 Willow Street, Brattleboro, VT
0.20
Single-Family Home
$399,900
06/02/26
3
1.5
1,339
140 Washington Street, Brattleboro, VT
0.24
Single-Family Home
$365,000
08/29/25
5
2
1,962
48 Central St, Brattleboro, VT
0.43
Single-Family Home
$65,251
09/30/25
4
2
2,744
321 Williams Street, Brattleboro, VT
0.55
Single-Family Home
$69,420
05/29/26
4
2
2,108
155 Oak Grove Avenue, Brattleboro, VT
0.31
Single-Family Home
$415,000
11/07/25
4
2
1,446

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
95 Maple Street, Brattleboro, VT 05301
0.04
$475,000
4
2
1,970
Off Market
25 Cottage Street, Brattleboro, VT 05301
0.07
$380,000
6
4
3,264
For Sale
11 Maple Street, Brattleboro, VT 05301
0.17
$332,000
4
2
1,548
Off Market
10 Birge Street, Brattleboro, VT 05301
0.16
$350,000
5
4
3,002
For Sale
31 Pleasant Street, Brattleboro, VT 05301
0.13
$401,900
1
2
1,560
Off Market
144 Belmont Avenue, Brattleboro, VT 05301
0.16
$339,000
3
1.5
1,520
Recently Sold
116 Birge Street #2, Brattleboro, VT 05301
0.16
$255,000
1
1
1,320
For Sale
116 Birge Street #3, Brattleboro, VT 05301
0.16
$239,000
1
1
2,000
For Sale
76 Belmont Avenue, Brattleboro, VT 05301
0.21
$391,000
3
2
1,686
Recently Sold
157 Pine Street, Brattleboro, VT 05301
0.22
$358,800
3
1.5
1,435
Off Market
52 Belmont Avenue, Brattleboro, VT 05301
0.22
$320,800
3
1.5
1,300
Off Market
22 Chestnut Street #5, Brattleboro, VT 05301
0.16
$215,800
3
1
1,250
Off Market

Local Information

  • Map ViewExplore the area around 44 Cherry St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Living Area
2,133 sqft
Price/Sqft
$214

About this House

Gorgeous house on a quiet street just a block from BMH. This house is truly a gem: Victorian exterior laced with gingerbread accents, not to mention the Arts and Crafts interior ripe with rambling fir floors and original oak trim. Brass doors plates, stained glass windows, and beautiful built-ins are just a few of the easter eggs one will encounter when exploring this house.

Bask in the glow of huge sun-filled windows whilst looking out over stunning gardens; meticulously curated perennials and mature fruit trees, all of which were cultivated with the upmost care over the last 20 years.

Close to town, one minute drive to grocery stores, steps from the hospital.

Washer and dryer in the basement
Off-street parking

Tenant is responsible for heat, electric, Wi-Fi

Landlord pays for plow and water/sewer.
44 Cherry St, Brattleboro, VT 05301 is a 3 bedroom, 2 bathroom, 2,133 sqft single-family home. It last sold for $120,000 on Jul 12, 1999 (4,900% above the $2,400 asking price). More recently, it was listed as a rental in January 2026 with an asking price of $2,400 per month. That rental listing was removed on February 2, 2026. It is currently off market. The Trulia Estimate is $457,100, with a rent estimate of $2,878/month.

Home Details for 44 Cherry St

Interior Features

Heating & Cooling
Heating: Forced Air, Heat PumpHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Price and Tax history

DateEventPrice
Feb 2, 2026
Source: Zillow Rentals
ListingRemoved
$2,400
Jan 5, 2026
Source: Zillow Rentals
Listed For Rent
$2,400
Dec 25, 2025
Source: Zillow Rentals
ListingRemoved
$2,400
Oct 14, 2025
Source: Zillow Rentals
PriceChange
$2,400
Price decreased by 8%
Sep 22, 2025
Source: Zillow Rentals
PriceChange
$2,600
Price decreased by 7%

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
Skip to last item
  • Results are loading
Skip to first item

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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

11 pet-friendly rentals in Brattleboro, VT

Explore by feature - Air Conditioning

13 rentals with air conditioning in Brattleboro, VT

Explore by feature - Washer/dryer

12 rentals with a washer/dryer in Brattleboro, VT

Homes for sale near 44 Cherry St

Skip to last item
Skip to first item

Off Market Homes Near 44 Cherry St

Skip to last item
Skip to first item

Frequently asked questions about 44 Cherry St

  • What is 44 Cherry St estimated to be worth?
    Trulia's estimated value for 44 Cherry St in Brattleboro, VT is $457,100.
  • What is the price history for 44 Cherry St?
    44 Cherry St in Brattleboro, VT last sold for $120,000 in July 1999.
  • 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 44 Cherry St have laundry facilities?
    Yes, 44 Cherry St in Brattleboro, VT has in-unit laundry.
  • Does 44 Cherry St have parking?
    Yes, 44 Cherry St in Brattleboro, VT has on-site parking.