Is parking easy in Brattleboro, VT?

As of early 2026, 92% of users say parking is easy

Is Brattleboro, VT dog-friendly?

As of early 2026, 91% of users say it's dog friendly

Are yards well-kept in Brattleboro, VT?

As of early 2026, 82% of users say yards are well-kept

Does Brattleboro, VT show holiday spirit?

As of early 2026, 81% of users say there's holiday spirit

Is a car needed in Brattleboro, VT?

As of early 2026, 81% of users say car is needed

Is there wildlife in Brattleboro, VT?

As of early 2026, 80% of users say there's wildlife

Would people walk alone at night in Brattleboro, VT?

As of early 2026, 72% of users say people would walk alone at night

Is Brattleboro, VT walkable to restaurants?

As of early 2026, 66% of users say it's walkable to restaurants

Does Brattleboro, VT have sidewalks?

As of early 2026, 62% of users say there are sidewalks

Are neighbors friendly in Brattleboro, VT?

As of early 2026, 60% of users say neighbors are friendly

Is Brattleboro, VT walkable to grocery stores?

As of early 2026, 58% of users say it's walkable to grocery stores

Do kids play outside in Brattleboro, VT?

As of early 2026, 55% of users say kids play outside

Are the streets well-lit in Brattleboro, VT?

As of early 2026, 50% of users say streets are well-lit

Are there community events in Brattleboro, VT?

As of early 2026, 50% of users say there are community events

Do residents of Brattleboro, VT plan to stay at least 5 years?

As of early 2026, 48% of users say they plan to stay for at least 5 years

Is Brattleboro, VT quiet?

As of early 2026, 38% of users say it's quiet

What is 55 Kipling Rd estimated to be worth?

Trulia's estimated value for 55 Kipling Rd in Brattleboro, VT is $392,300 .

What is the price history for 55 Kipling Rd?

55 Kipling Rd in Brattleboro, VT last sold for $189,000 in November 2015.

Is Brattleboro a buyer's or seller's market?

Brattleboro is currently a balanced 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 55 Kipling Rd have laundry facilities?

Yes, 55 Kipling Rd in Brattleboro, VT has in-unit laundry.

How big is the lot at 55 Kipling Rd?

The lot at 55 Kipling Rd in Brattleboro, VT is about 1.9 acres .

OFF MARKET

$392,300

Trulia Estimate

3 Beds
2 Baths
1,800 sqft (on 1.92 acres)

55 Kipling Rd, Brattleboro, VT 05301

Est. Refi. Payment $2,833/mo*

Refinance Your Home

Currently Off Market - Sold Nov 30, 2015 for $189,000

Home Value

Trulia Estimate

$392K

Since last month

$4K (-0.9%)

Since last year

$13K (-3.2%)

Since last sale

$204K (+108.1%)

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 +104% in the last 10 years

Month	Estimated value
2026
October 2026	$393K
September 2026	$395K
August 2026	$397K
July 2026	$407K
June 2026	$408K
May 2026	$421K
April 2026	$411K
March 2026	$407K
February 2026	$395K
January 2026	$390K
2025
December 2025	$394K
November 2025	$398K
October 2025	$402K
September 2025	$406K
August 2025	$406K
July 2025	$411K
June 2025	$409K
May 2025	$410K
April 2025	$409K
March 2025	$397K
February 2025	$395K
January 2025	$392K
2024
December 2024	$400K
November 2024	$398K
October 2024	$397K
September 2024	$399K
August 2024	$404K
July 2024	$403K
June 2024	$405K
May 2024	$399K
April 2024	$391K
March 2024	$388K
February 2024	$381K
January 2024	$381K
2023
December 2023	$375K
November 2023	$377K
October 2023	$386K
September 2023	$392K
August 2023	$384K
July 2023	$387K
June 2023	$382K
May 2023	$375K
April 2023	$366K
March 2023	$359K
February 2023	$350K
January 2023	$350K
2022
December 2022	$354K
November 2022	$361K
October 2022	$365K
September 2022	$366K
August 2022	$368K
July 2022	$373K
June 2022	$371K
May 2022	$362K
April 2022	$351K
March 2022	$341K
February 2022	$328K
January 2022	$324K
2021
December 2021	$323K
November 2021	$323K
October 2021	$323K
September 2021	$319K
August 2021	$320K
July 2021	$318K
June 2021	$316K
May 2021	$315K
April 2021	$306K
March 2021	$289K
February 2021	$288K
January 2021	$288K
2020
December 2020	$282K
November 2020	$277K
October 2020	$276K
September 2020	$276K
August 2020	$277K
July 2020	$276K
June 2020	$276K
May 2020	$277K
April 2020	$277K
March 2020	$277K
February 2020	$280K
January 2020	$282K
2019
December 2019	$284K
November 2019	$282K
October 2019	$281K
September 2019	$281K
August 2019	$280K
July 2019	$276K
June 2019	$268K
May 2019	$274K
April 2019	$269K
March 2019	$267K
February 2019	$267K
January 2019	$248K
2018
December 2018	$224K
November 2018	$207K
October 2018	$206K
September 2018	$205K
August 2018	$205K
July 2018	$204K
June 2018	$204K
May 2018	$204K
April 2018	$204K
March 2018	$203K
February 2018	$202K
January 2018	$202K
2017
December 2017	$202K
November 2017	$200K
October 2017	$199K
September 2017	$199K
August 2017	$198K
July 2017	$197K
June 2017	$197K
May 2017	$197K
April 2017	$196K
March 2017	$196K
February 2017	$195K
January 2017	$195K
2016
December 2016	$194K
November 2016	$194K
October 2016	$193K

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
84 Magnolia Drive, Brattleboro, VT	0.24	Single-Family Home	$570,000	04/29/26	2	2	1,900
139 Buttonwood Drive, Brattleboro, VT	0.35	Single-Family Home	$455,000	03/04/26	2	2	1,390
155 Upper Dummerston Road, Brattleboro, VT	1.07	Single-Family Home	$407,000	11/21/25	3	1.5	1,655
75 Ryan Road, Dummerston, VT	0.96	Single-Family Home	$615,000	05/11/26	4	2.5	2,511
16 Vermont Avenue, Brattleboro, VT	1.69	Single-Family Home	$425,000	12/29/25	3	1.5	1,846
138 Wantastiquet Drive, Brattleboro, VT	1.77	Single-Family Home	$405,000	10/08/26	3	2	1,934
187 Hillwinds Road, Brattleboro, VT	1.82	Single-Family Home	$476,000	11/20/25	4	3	2,372
214 Putney Road, Brattleboro, VT	1.75	Single-Family Home	$450,000	05/15/26	4	2.5	2,756
1644 Upper Dummerston Road, Dummerston, VT	2.17	Single-Family Home	$325,000	08/12/26	2	2	1,499
143 Hillwinds Road, Brattleboro, VT	1.79	Single-Family Home	$615,000	06/26/26	5	3.5	2,520

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
30 Kipling Rd #T, Brattleboro, VT 05301	0.03	-	-	-	-	Off Market
253 Black Mountain Rd, Brattleboro, VT 05301	0.05	$378,800	3	2.5	2,660	Off Market
57 Kipling Rd, Brattleboro, VT 05301	0.08	$331,000	Studio	-	-	Off Market
249 Black Mountain Rd, Brattleboro, VT 05301	0.09	$296,000	3	1	1,701	Off Market
237 Black Mountain Rd, Brattleboro, VT 05301	0.11	$269,700	3	1	1,584	Off Market
5 Crescent Dr, Brattleboro, VT 05301	0.12	-	Studio	-	-	Off Market
4 Crescent Dr, Brattleboro, VT 05301	0.12	$111,000	Studio	-	-	Off Market
6 Crescent Dr, Brattleboro, VT 05301	0.12	-	Studio	-	-	Off Market
59 Kipling Rd, Brattleboro, VT 05301	0.13	$549,500	Studio	-	-	Off Market
10 Crescent Dr, Brattleboro, VT 05301	0.14	-	Studio	-	-	Off Market
9 Crescent Dr, Brattleboro, VT 05301	0.14	-	Studio	-	-	Off Market
12 Crescent Dr, Brattleboro, VT 05301	0.15	$56,800	2	1	480	Off Market
16 Crescent Drive, Brattleboro, VT 05301	0.15	$84,900	2	1	784	Off Market
13 Crescent Dr, Brattleboro, VT 05301	0.15	$51,500	2	1	728	Off Market
14 Crescent Dr, Brattleboro, VT 05301	0.16	-	Studio	-	-	Off Market
14 Crescent Dr, Brattleboro, VT 05301	0.16	$121,900	Studio	-	-	Off Market
7 Crescent Dr, Brattleboro, VT 05301	0.16	$127,700	3	2	1,026	Off Market
15 Crescent Dr, Brattleboro, VT 05301	0.16	-	Studio	-	-	Off Market
17 Crescent Dr, Brattleboro, VT 05301	0.17	-	Studio	-	-	Off Market
19 Crescent Dr, Brattleboro, VT 05301	0.18	$52,700	Studio	-	-	Off Market

Local Information

Map ViewExplore the area around 55 Kipling Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1968

1.92 acre lot

1,800 sqft

$218/sqft

Garage

About this House

MOTIVATED SELLERS - SUGGEST ALL OFFERS. Located on Kipling Rd. close to SIT, this country setting offers the best of both worlds, privately situated, yet an easy distance to nearby stores and services. Attractive and well cared for, the house provides ample room for family, or in-home business. A galley kitchen adjoins the inviting multi-purpose great room with cathedral ceiling, along with a 3-season porch, two bedrooms and full bath. The original portion of the house includes a dining/living room, office, additional bedroom, laundry and full bath. The spacious basement is complete with storage room, 2-furnaces, workshop space and attached, over-sized garage. Additionally there is a space for equipment storage. The property is enhanced by mature trees, perennials and a beautiful stone patio.

55 Kipling Rd, Brattleboro, VT 05301 is a 3 bedroom, 2 bathroom, 1,800 sqft single-family home built in 1968. It last sold for $189,000 on Nov 30, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $392,300, with a rent estimate of $2,537/month.

Home Details for 55 Kipling Rd

Interior Features
Heating & Cooling Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 1Floors: Carpet, Hardwood, Laminate, Linoleum Vinyl
Interior Details Additional StorageNumber of Rooms: 8Types of Rooms: Dining RoomStorageCeiling Fan
Appliances & Utilities Cable ReadyDishwasherDryerRefrigeratorWasher

Exterior Features
Exterior Home Features Roof: MetalDeckExterior: VinylPorch
Parking & Garage GarageParking: Carport, Garage Attached

Property Information
Year Built Year Built: 1968
Property Type / Style Property Type: Single Family HomeArchitecture: Contemporary

Building
Levels, Entrance, & Accessibility Disabled Access

Lot Information
Lot Area: 1.92 acres

Price and Tax history

Date	Event	Price
Nov 30, 2015 Source: N/A	Sold	$189,000
Sep 4, 2015 Source: Agent Provided	Pending	$189,000
Aug 11, 2015 Source: Agent Provided	PriceChange	$189,000 Price decreased by 5%
Jul 14, 2015 Source: Agent Provided	PriceChange	$199,000 Price decreased by 9%
May 19, 2015 Source: Agent Provided	PriceChange	$219,000 Price decreased by 7%
Sep 6, 2014 Source: Agent Provided	PriceChange	$235,000 Price decreased by 6%
Jun 5, 2014 Source: Agent Provided	PriceChange	$249,000 Price decreased by 4%
Sep 6, 2013 Source: Agent Provided	Listed For Sale	$259,000
Aug 11, 2005 Source: N/A	Sold	$210,000

Year	Property tax	Tax assessment
2024	Unavailable	$214,550

Additional Cost

Market trends in Brattleboro

Last updated September 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Sourced by Trulia Market Trends

Around this home

Green Street School
PK-6
Public
237 Students
Windham Southeast Unified Union School District #96
7/10
GreatSchools Rating
Parent Rating Average
This upcoming school year will be my children's second year attending and we love this school!!! I have never witnessed a greater staff or a better principal! He is very involved with the children and their activities. Its so wonderful to see someone in leadership be so "fun like" involved with elementary students like he is.
Parent Review
13y ago
2 Reviews

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

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.

81% say there's holiday spirit
62% say there are sidewalks
60% say neighbors are friendly

Trulia Trick or TreatStart Ghost Hunt

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
Resident
4mo ago
"Great neighborhood for learning to ride bikes, trick-or-treating, making friends with other families."
0
Flag
Brenda Nichols
Resident
11mo ago
"Yes! Lots of space for walking and running around with dogs. Quiet countryside with not a lot of traffic."
0
Flag
Kelly Dias
Resident
1y ago
"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
Resident
1y ago
"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
Resident
2y ago
"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
Resident
2y ago
"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.
Resident
7y ago
"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.
Resident
7y ago
"Dogs are welcome. Neighbor s are friendly. Houses are well maintained. I feel safe. Walkable neighborhood."
3
Flag
Jcoursem3
Resident
7y ago
"Neighbors are friendly and help each other out. Get together’s are organic and easy because of our close proximity. "
0
Flag
Deanshippee
Resident
7y ago
"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.
Resident
7y ago
"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
Resident
8y ago
"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
14y ago
"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 55 Kipling Rd

What is 55 Kipling Rd estimated to be worth?
Trulia's estimated value for 55 Kipling Rd in Brattleboro, VT is $392,300.
What is the price history for 55 Kipling Rd?
55 Kipling Rd in Brattleboro, VT last sold for $189,000 in November 2015.
Is Brattleboro a buyer's or seller's market?
Brattleboro is currently a balanced 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 55 Kipling Rd have laundry facilities?
Yes, 55 Kipling Rd in Brattleboro, VT has in-unit laundry.
How big is the lot at 55 Kipling Rd?
The lot at 55 Kipling Rd in Brattleboro, VT is about 1.9 acres.