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 348 Hillwinds Rd estimated to be worth?

Trulia's estimated value for 348 Hillwinds Rd in Brattleboro, VT is $406,800 .

What is the price history for 348 Hillwinds Rd?

348 Hillwinds Rd in Brattleboro, VT last sold for $56,652 in April 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 .

Does 348 Hillwinds Rd have a pool?

Yes, 348 Hillwinds Rd in Brattleboro, VT has a pool.

How big is the lot at 348 Hillwinds Rd?

The lot at 348 Hillwinds Rd in Brattleboro, VT is about 1.1 acres .

OFF MARKET

$406,800

Trulia Estimate

3 Beds
2 Baths
1,904 sqft (on 1.10 acres)

348 Hillwinds Rd, Brattleboro, VT 05301

Refinance Your Home

Currently Off Market - Sold Apr 11, 2025 for $56,652

Home Value

Trulia Estimate

$407K

Since last month

$5K (-1.1%)

Since last year

$60K (+17%)

Since last sale

$354K (+624.4%)

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 +74% in the last 10 years

Month	Estimated value
2026
September 2026	$410K
August 2026	$407K
July 2026	$415K
June 2026	$408K
May 2026	$400K
April 2026	$398K
March 2026	$389K
February 2026	$374K
January 2026	$388K
2025
December 2025	$373K
November 2025	$380K
October 2025	$371K
September 2025	$373K
August 2025	$351K
July 2025	$309K
June 2025	$283K
May 2025	$229K
April 2025	$239K
March 2025	$433K
February 2025	$427K
January 2025	$425K
2024
December 2024	$434K
November 2024	$435K
October 2024	$439K
September 2024	$442K
August 2024	$442K
July 2024	$444K
June 2024	$441K
May 2024	$441K
April 2024	$435K
March 2024	$428K
February 2024	$424K
January 2024	$423K
2023
December 2023	$413K
November 2023	$421K
October 2023	$424K
September 2023	$434K
August 2023	$429K
July 2023	$433K
June 2023	$429K
May 2023	$422K
April 2023	$413K
March 2023	$407K
February 2023	$396K
January 2023	$394K
2022
December 2022	$400K
November 2022	$406K
October 2022	$410K
September 2022	$412K
August 2022	$414K
July 2022	$418K
June 2022	$416K
May 2022	$409K
April 2022	$398K
March 2022	$389K
February 2022	$378K
January 2022	$374K
2021
December 2021	$371K
November 2021	$370K
October 2021	$372K
September 2021	$368K
August 2021	$365K
July 2021	$367K
June 2021	$370K
May 2021	$324K
April 2021	$320K
March 2021	$318K
February 2021	$317K
January 2021	$309K
2020
December 2020	$308K
November 2020	$306K
October 2020	$301K
September 2020	$300K
August 2020	$299K
July 2020	$302K
June 2020	$301K
May 2020	$300K
April 2020	$296K
March 2020	$295K
February 2020	$294K
January 2020	$295K
2019
December 2019	$294K
November 2019	$293K
October 2019	$293K
September 2019	$292K
August 2019	$291K
July 2019	$290K
June 2019	$289K
May 2019	$287K
April 2019	$286K
March 2019	$284K
February 2019	$283K
January 2019	$279K
2018
December 2018	$279K
November 2018	$278K
October 2018	$277K
September 2018	$276K
August 2018	$266K
July 2018	$270K
June 2018	$263K
May 2018	$265K
April 2018	$248K
March 2018	$247K
February 2018	$248K
January 2018	$246K
2017
December 2017	$244K
November 2017	$239K
October 2017	$243K
September 2017	$243K
August 2017	$243K
July 2017	$240K
June 2017	$239K
May 2017	$240K
April 2017	$240K
March 2017	$236K
February 2017	$232K
January 2017	$233K
2016
December 2016	$236K
November 2016	$237K
October 2016	$239K
September 2016	$236K

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
187 Hillwinds Road, Brattleboro, VT	0.31	Single-Family Home	$476,000	11/20/25	4	3	2,372
1082 W River Road, Brattleboro, VT	0.45	Single-Family Home	$305,000	09/23/25	3	1	1,222
143 Hillwinds Road, Brattleboro, VT	0.36	Single-Family Home	$615,000	06/26/26	5	3.5	2,520
65 Hillwinds North Road, Brattleboro, VT	0.49	Single-Family Home	$925,000	10/01/25	5	4.5	4,150
65 Hillwinds N, Brattleboro, VT	0.50	Single-Family Home	$925,000	10/06/25	5	5	4,150
211 Pleasant Valley Road, Brattleboro, VT	0.65	Single-Family Home	$525,000	08/31/26	2	1	1,576
672 East Orchard Street, Brattleboro, VT	0.86	Single-Family Home	$470,000	09/26/25	3	3	3,148
1644 Upper Dummerston Road, Dummerston, VT	1.11	Single-Family Home	$325,000	08/12/26	2	2	1,499
131 Pleasant Valley Rd, Brattleboro, VT	0.78	Single-Family Home	$15,000	05/13/26	2	1	792
137 Pleasant Valley Road, Brattleboro, VT	0.81	Single-Family Home	$389,000	05/08/26	1	1	650

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
336 Hillwinds Road, Brattleboro, VT 05301	0.04	$754,700	4	3	3,257	Off Market
335 Hillwinds Road, Brattleboro, VT 05301	0.08	$611,200	4	3.5	2,544	Off Market
395 Hillwinds Road, Brattleboro, VT 05301	0.09	$703,500	4	2.5	2,226	Off Market
1073 Upper Dummerston Road, Brattleboro, VT 05301	0.21	$552,400	3	2	2,456	Off Market
187 Hillwinds Road, Brattleboro, VT 05301	0.31	$476,000	4	3	2,372	Recently Sold
143 Hillwinds Road, Brattleboro, VT 05301	0.36	$615,000	5	3.5	2,520	Recently Sold
1082 W River Road, Brattleboro, VT 05301	0.45	$319,500	3	1	1,222	Off Market
65 Hillwinds North Road, Brattleboro, VT 05301	0.49	$967,900	5	4.5	4,150	Off Market
863 Upper Dummerston Road, Brattleboro, VT 05301	0.45	$576,500	3	2.5	2,112	Off Market
155 Hillwinds North Road, Brattleboro, VT 05301	0.61	$910,900	4	3.5	3,685	Off Market
94 Brets Road, Brattleboro, VT 05301	0.55	$475,000	3	2.5	2,594	Recently Sold
390 Pleasant Valley Road, Brattleboro, VT 05301	0.66	$1,175,000	4	3.5	4,491	Recently Sold

Local Information

Map ViewExplore the area around 348 Hillwinds Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1970

1.1 acre lot

1,904 sqft

$214/sqft

Garage

About this House

This single-family home is located at 348 Hillwinds Rd, Brattleboro, VT. 348 Hillwinds Rd is in Brattleboro, VT and in ZIP code 05301. This property has 3 bedrooms, 2 bathrooms and approximately 1,904 sqft of floor space. This property has a lot size of 1.10 acres and was built in 1970.

348 Hillwinds Rd, Brattleboro, VT 05301 is a 3 bedroom, 2 bathroom, 1,904 sqft single-family home built in 1970. It last sold for $56,652 on Apr 11, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $406,800, with a rent estimate of $2,837/month.

Home Details for 348 Hillwinds Rd

Interior Features
Heating & Cooling Heating: Baseboard, Electric, Gas, OilHeating Fuel: Baseboard
Interior Details Types of Rooms: Dining Room, Library
Appliances & Utilities DishwasherRefrigerator
Levels, Entrance, & Accessibility Floors: Carpet, Hardwood

Property Information
Year Built Year Built: 1970
Property Type / Style Property Type: Single Family Home

Exterior Features
Exterior Home Features DeckExterior: VinylGarden
Pool Pool
Parking & Garage GarageParking: Garage Detached

Lot Information
Lot Area: 1.10 acres

Price and Tax history

Date	Event	Price
Apr 11, 2025 Source: N/A	Sold	$56,652
Sep 6, 2018 Source: PrimeMLS #4695133	Sold	$276,000
Jul 11, 2018 Source: Agent Provided	PendingToActive	$276,000
Jun 7, 2018 Source: Agent Provided	Pending	$276,000
May 24, 2018 Source: Agent Provided	Listed For Sale	$276,000
Nov 7, 2012 Source: N/A	Sold	$215,000
Aug 4, 2012 Source: Agent Provided	PriceChange	$225,000 Price decreased by 10%
Apr 4, 2012 Source: Agent Provided	Listed For Sale	$249,900

Year	Property tax	Tax assessment
2024	Unavailable	$238,150

Additional Cost

Market trends in Brattleboro

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Around this home

Academy School
PK-6
Public
418 Students
Windham Southeast Unified Union School District #96
6/10
GreatSchools Rating
Parent Rating Average
Our last public school experience was at a 10/10 on Great Schools. While we had high hopes for that school, they were only able to meet the needs of one type of learner. Here at Academy, they pride themselves on meeting many different learning styles exactly where they are...we are forever grateful.
Other Review
5y ago
3 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

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
3mo ago
"Great neighborhood for learning to ride bikes, trick-or-treating, making friends with other families."
0
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Brenda Nichols
Resident
10mo 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 348 Hillwinds Rd

What is 348 Hillwinds Rd estimated to be worth?
Trulia's estimated value for 348 Hillwinds Rd in Brattleboro, VT is $406,800.
What is the price history for 348 Hillwinds Rd?
348 Hillwinds Rd in Brattleboro, VT last sold for $56,652 in April 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.
Does 348 Hillwinds Rd have a pool?
Yes, 348 Hillwinds Rd in Brattleboro, VT has a pool.
How big is the lot at 348 Hillwinds Rd?
The lot at 348 Hillwinds Rd in Brattleboro, VT is about 1.1 acres.