357 Hillwinds Rd, Brattleboro, VT 05301
Property image
Property image
OFF MARKET

$504,300

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,180 sqft (on 1.50 acres)

357 Hillwinds Rd, Brattleboro, VT 05301

Est. Refi. Payment $3,411/mo*
Refinance Your Home
Currently Off Market - Sold Dec 27, 2018 for $270,000

Home Value

Trulia Estimate
$504K
Since last month
Decreased$600 (-0.1%)
Since last year
Increased$8K (+1.6%)
Since last sale
Increased$233K (+86.3%)
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 +87% in the last 10 years
MonthEstimated value
2026
August 2026$503K
July 2026$504K
June 2026$507K
May 2026$510K
April 2026$501K
March 2026$497K
February 2026$485K
January 2026$480K
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
187 Hillwinds Road, Brattleboro, VT
0.34
Single-Family Home
$476,000
11/20/25
4
3
2,372
1082 W River Road, Brattleboro, VT
0.54
Single-Family Home
$305,000
09/23/25
3
1
1,222
143 Hillwinds Road, Brattleboro, VT
0.41
Single-Family Home
$615,000
06/26/26
5
3.5
2,520
155 Hillwinds North Road, Brattleboro, VT
0.66
Single-Family Home
$868,000
09/09/25
4
3.5
3,685
672 East Orchard Street, Brattleboro, VT
0.83
Single-Family Home
$470,000
09/26/25
3
3
3,148
65 Hillwinds North Road, Brattleboro, VT
0.55
Single-Family Home
$925,000
10/01/25
5
4.5
4,150
65 Hillwinds N, Brattleboro, VT
0.56
Single-Family Home
$925,000
10/06/25
5
5
4,150
137 Pleasant Valley Road, Brattleboro, VT
0.73
Single-Family Home
$389,000
05/08/26
1
1
650
1644 Upper Dummerston Road, Dummerston, VT
1.16
Single-Family Home
$325,000
08/12/26
2
2
1,499
387 Meadow Brook Road, Brattleboro, VT
1.26
Single-Family Home
$439,000
05/13/26
4
2
1,568

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
335 Hillwinds Road, Brattleboro, VT 05301
0.07
$616,200
4
3.5
2,544
Off Market
395 Hillwinds Road, Brattleboro, VT 05301
0.06
$697,100
4
2.5
2,226
Off Market
336 Hillwinds Road, Brattleboro, VT 05301
0.10
$754,700
4
3
3,257
Off Market
1073 Upper Dummerston Road, Brattleboro, VT 05301
0.29
$547,400
3
2
2,456
Off Market
187 Hillwinds Road, Brattleboro, VT 05301
0.34
$476,000
4
3
2,372
Recently Sold
143 Hillwinds Road, Brattleboro, VT 05301
0.41
$615,000
5
3.5
2,520
Recently Sold
863 Upper Dummerston Road, Brattleboro, VT 05301
0.46
$576,800
3
2.5
2,112
Off Market
65 Hillwinds North Road, Brattleboro, VT 05301
0.55
$959,900
5
4.5
4,150
Off Market
1082 W River Road, Brattleboro, VT 05301
0.54
$316,800
3
1
1,222
Off Market
94 Brets Road, Brattleboro, VT 05301
0.51
$475,000
3
2.5
2,594
Recently Sold
390 Pleasant Valley Road, Brattleboro, VT 05301
0.57
$1,175,000
4
3.5
4,491
Recently Sold
0 Pleasant Valley Road, Brattleboro, VT 05301
0.62
$198,000
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For Sale

Local Information

  • Map ViewExplore the area around 357 Hillwinds Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Lot Size
1.5 acres
Living Area
2,180 sqft
Price/Sqft
$231
Parking
Garage

About this House

Walls of windows bring you close to nature in this classy, contemporary, Japanese-influenced house in a prestigious Brattleboro neighborhood. The look inside is sleak with clean line; white walls; and all hardwood birch, ceramic tile or concrete floors. The open concept living/dining/kitchen space wraps around the three-way wood-burning fireplace. Special details include granite counter tops in the kitchen, a double refrigerator, a gas range, a dishwasher, a claw foot bathtub, a full laundry rooom, 4 skylights, blinds on some windows, a 12' x 25' screened porch, sliders to the porch and rear yard, a mini-mudroom, an attached 2-car garage, radiant heat and passive solar heating and cooling, supplemented by a photovoltaic solar panel system. Sited next to the Hillwinds Trails conservation area, you will be able to hike or cross country ski from your door. This hilltop house is just minutes away from downtown Brattleboro.

Room dimensions: LR 24'8" x 15'3"; DR 16'4" x 14'11"; KIT 17' x 11'3"; BR 18'5" x 15'7"; Family room 30'5" x 17'11" + 17'3" x 6'6"; BR 13'4" x 10'5"; BR 12'1" x 10'5".

Comcast available.

First, last and security to move in.

No pets.

No smoking.

No showings until 6/16/20.

NOTE: We do not require any payment until the application is submitted. If someone solicits a payment from you, it could be a scam.

Owner pays septic and water. Tenant pays heat, hot water, electricity, trash removal, snow removal and landscaping.
357 Hillwinds Rd, Brattleboro, VT 05301 is a 3 bedroom, 2 bathroom, 2,180 sqft single-family home built in 1997. It last sold for $270,000 on Dec 27, 2018. More recently, it was listed as a rental in May 2020 with an asking price of $1,800 per month. That rental listing was removed on June 8, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $504,300, with a rent estimate of $2,700/month.

Home Details for 357 Hillwinds Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasHeating Fuel: Forced Air
Interior Details
Number of Rooms: 7Types of Rooms: Dining Room
Appliances & Utilities
DryerWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Lot Information

Lot Area: 1.50 acres

Price and Tax history

DateEventPrice
Jun 8, 2020
Source: Agent Provided
ListingRemoved
$1,800
May 28, 2020
Source: Agent Provided
Listed For Rent
$1,800
Mar 20, 2020
Source: Agent Provided
ListingRemoved
$1,700
Mar 6, 2020
Source: Agent Provided
Listed For Rent
$1,700
May 12, 2019
Source: Agent Provided
ListingRemoved
$1,700

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 357 Hillwinds Rd

  • What is 357 Hillwinds Rd estimated to be worth?
    Trulia's estimated value for 357 Hillwinds Rd in Brattleboro, VT is $504,300.
  • What is the price history for 357 Hillwinds Rd?
    357 Hillwinds Rd in Brattleboro, VT last sold for $270,000 in December 2018.
  • 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 357 Hillwinds Rd have laundry facilities?
    Yes, 357 Hillwinds Rd in Brattleboro, VT has in-unit laundry.
  • How big is the lot at 357 Hillwinds Rd?
    The lot at 357 Hillwinds Rd in Brattleboro, VT is about 1.5 acres.

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