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 161 Hillwinds Rd estimated to be worth?

Trulia's estimated value for 161 Hillwinds Rd in Brattleboro, VT is $599,200 .

What is the price history for 161 Hillwinds Rd?

161 Hillwinds Rd in Brattleboro, VT last sold for $330,500 in December 2016.

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 161 Hillwinds Rd have laundry facilities?

Yes, 161 Hillwinds Rd in Brattleboro, VT has in-unit laundry.

How big is the lot at 161 Hillwinds Rd?

The lot at 161 Hillwinds Rd in Brattleboro, VT is about 1.1 acres .

OFF MARKET

$599,200

Trulia Estimate

4 Beds
5 Baths
2,600 sqft (on 1.09 acres)

161 Hillwinds Rd, Brattleboro, VT 05301

Est. Refi. Payment $4,218/mo*

Refinance Your Home

Currently Off Market - Sold Dec 21, 2016 for $330,500

Home Value

Trulia Estimate

$599K

Since last month

$4K (-0.7%)

Since last year

$4K (-0.7%)

Since last sale

$264K (+79.9%)

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 +83% in the last 10 years

Month	Estimated value
2026
September 2026	$595K
August 2026	$599K
July 2026	$609K
June 2026	$613K
May 2026	$615K
April 2026	$595K
March 2026	$589K
February 2026	$579K
January 2026	$574K
2025
December 2025	$580K
November 2025	$584K
October 2025	$605K
September 2025	$599K
August 2025	$593K
July 2025	$584K
June 2025	$593K
May 2025	$594K
April 2025	$584K
March 2025	$574K
February 2025	$564K
January 2025	$561K
2024
December 2024	$572K
November 2024	$574K
October 2024	$591K
September 2024	$602K
August 2024	$615K
July 2024	$606K
June 2024	$606K
May 2024	$600K
April 2024	$585K
March 2024	$579K
February 2024	$570K
January 2024	$570K
2023
December 2023	$556K
November 2023	$561K
October 2023	$593K
September 2023	$602K
August 2023	$585K
July 2023	$580K
June 2023	$576K
May 2023	$563K
April 2023	$547K
March 2023	$543K
February 2023	$535K
January 2023	$535K
2022
December 2022	$544K
November 2022	$556K
October 2022	$567K
September 2022	$571K
August 2022	$569K
July 2022	$570K
June 2022	$564K
May 2022	$551K
April 2022	$535K
March 2022	$527K
February 2022	$517K
January 2022	$522K
2021
December 2021	$532K
November 2021	$531K
October 2021	$533K
September 2021	$522K
August 2021	$518K
July 2021	$521K
June 2021	$526K
May 2021	$434K
April 2021	$426K
March 2021	$404K
February 2021	$397K
January 2021	$392K
2020
December 2020	$388K
November 2020	$382K
October 2020	$376K
August 2020	$383K
July 2020	$383K
June 2020	$381K
May 2020	$380K
April 2020	$384K
March 2020	$386K
February 2020	$381K
January 2020	$379K
2019
December 2019	$374K
November 2019	$372K
October 2019	$370K
September 2019	$369K
August 2019	$368K
July 2019	$366K
June 2019	$364K
May 2019	$363K
April 2019	$361K
March 2019	$359K
February 2019	$357K
January 2019	$353K
2018
December 2018	$352K
November 2018	$352K
October 2018	$350K
September 2018	$349K
August 2018	$349K
July 2018	$349K
June 2018	$348K
May 2018	$348K
April 2018	$347K
March 2018	$346K
February 2018	$345K
January 2018	$344K
2017
December 2017	$343K
November 2017	$341K
October 2017	$340K
September 2017	$339K
August 2017	$338K
July 2017	$337K
June 2017	$336K
May 2017	$335K
April 2017	$334K
March 2017	$333K
February 2017	$332K
January 2017	$331K
2016
December 2016	$331K
November 2016	$320K
October 2016	$324K
September 2016	$325K

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	0.06	Single-Family Home	$476,000	11/20/25	4	3	2,372
143 Hillwinds Road, Brattleboro, VT	0.05	Single-Family Home	$615,000	06/26/26	5	3.5	2,520
65 Hillwinds North Road, Brattleboro, VT	0.21	Single-Family Home	$925,000	10/01/25	5	4.5	4,150
65 Hillwinds N, Brattleboro, VT	0.23	Single-Family Home	$925,000	10/06/25	5	5	4,150
1644 Upper Dummerston Road, Dummerston, VT	0.77	Single-Family Home	$325,000	08/12/26	2	2	1,499
390 Pleasant Valley Road, Brattleboro, VT	0.77	Single-Family Home	$1,175,000	08/24/26	4	3.5	4,491
1555 W River Road, Dummerston, VT	0.75	Single-Family Home	$243,000	02/26/26	2	1	903
672 East Orchard Street, Brattleboro, VT	1.22	Single-Family Home	$470,000	09/26/25	3	3	3,148
211 Pleasant Valley Road, Brattleboro, VT	0.91	Single-Family Home	$525,000	08/31/26	2	1	1,576
183 Bear Hill Road, Brattleboro, VT	1.51	Single-Family Home	$385,000	06/02/26	3	1.5	2,433

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
143 Hillwinds Road, Brattleboro, VT 05301	0.05	$615,000	5	3.5	2,520	Recently Sold
187 Hillwinds Road, Brattleboro, VT 05301	0.06	$499,200	4	3	2,372	Off Market
65 Hillwinds North Road, Brattleboro, VT 05301	0.21	$978,000	5	4.5	4,150	Off Market
155 Hillwinds North Road, Brattleboro, VT 05301	0.27	$921,000	4	3.5	3,685	Off Market
336 Hillwinds Road, Brattleboro, VT 05301	0.32	$748,000	4	3	3,257	Off Market
335 Hillwinds Road, Brattleboro, VT 05301	0.33	$606,900	4	3.5	2,544	Off Market
395 Hillwinds Road, Brattleboro, VT 05301	0.44	$709,700	4	2.5	2,226	Off Market
1073 Upper Dummerston Road, Brattleboro, VT 05301	0.48	$557,200	3	2	2,456	Off Market
1082 W River Road, Brattleboro, VT 05301	0.56	$322,900	3	1	1,222	Off Market
1555 W River Road, Dummerston, VT 05301	0.75	$243,000	2	1	903	Recently Sold
390 Pleasant Valley Road, Brattleboro, VT 05301	0.77	$1,175,000	4	3.5	4,491	Recently Sold
1644 Upper Dummerston Road, Dummerston, VT 05301	0.77	$325,000	2	2	1,499	Recently Sold

Local Information

Map ViewExplore the area around 161 Hillwinds Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1975

1.09 acre lot

2,600 sqft

$230/sqft

Garage

About this House

This single-family home is located at 161 Hillwinds Rd, Brattleboro, VT. 161 Hillwinds Rd is in Brattleboro, VT and in ZIP code 05301. This property has 4 bedrooms, 5 bathrooms and approximately 2,600 sqft of floor space. This property has a lot size of 1.09 acres and was built in 1975.

161 Hillwinds Rd, Brattleboro, VT 05301 is a 4 bedroom, 5 bathroom, 2,600 sqft single-family home built in 1975. It last sold for $330,500 on Dec 21, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $599,200, with a rent estimate of $4,428/month.

Home Details for 161 Hillwinds Rd

Interior Features
Heating & Cooling Heating: Baseboard, OilHeating Fuel: Baseboard
Interior Details Types of Rooms: Dining Room
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility Floors: Tile, Carpet, Hardwood, Linoleum Vinyl

Exterior Features
Exterior Home Features Roof: Asphalt, Metal
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1975
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 1.09 acres

Price and Tax history

Date	Event	Price
Dec 21, 2016 Source: PrimeMLS #4499319	Sold	$330,500
Jul 20, 2016 Source: Agent Provided	PriceChange	$339,000 Price decreased by 3%
Jun 21, 2016 Source: Agent Provided	Listed For Sale	$349,000

Year	Property tax	Tax assessment
2024	Unavailable	$352,070

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
4mo 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 161 Hillwinds Rd

What is 161 Hillwinds Rd estimated to be worth?
Trulia's estimated value for 161 Hillwinds Rd in Brattleboro, VT is $599,200.
What is the price history for 161 Hillwinds Rd?
161 Hillwinds Rd in Brattleboro, VT last sold for $330,500 in December 2016.
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 161 Hillwinds Rd have laundry facilities?
Yes, 161 Hillwinds Rd in Brattleboro, VT has in-unit laundry.
How big is the lot at 161 Hillwinds Rd?
The lot at 161 Hillwinds Rd in Brattleboro, VT is about 1.1 acres.