357 Hillwinds Rd, Brattleboro, VT 05301
OFF MARKET

357 Hillwinds Rd
Brattleboro, VT 05301

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

$510,100

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $3,420/mo*
Refinance Your Home

$510,100

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $3,420/mo*
Refinance Your Home
3 Beds
2 Baths
2,180 sqft
(on 1.50 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 357 Hillwinds Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasCooling System: OtherHeating 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 History for 357 Hillwinds Rd

DatePriceEventSource
06/08/2020$1,800ListingRemovedAgent Provided
05/28/2020$1,800Listed For RentAgent Provided
03/20/2020$1,700ListingRemovedAgent Provided
03/06/2020$1,700Listed For RentAgent Provided
05/12/2019$1,700ListingRemovedAgent Provided
04/29/2019$1,700Listed For RentAgent Provided
12/27/2018$270,000Sold
PrimeMLS #4722950
10/10/2018$297,000Listed For SaleAgent Provided
11/30/2015$263,000Sold
N/A
10/05/2015$289,000PendingAgent Provided
05/07/2015$289,000PriceChange
Agent Provided
02/26/2015$316,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax
Assessment$275,180
Home facts updated by county records

Comparable Sales for 357 Hillwinds Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1073 Upper Dummerston Road, Brattleboro, VT
0.29
Single-Family Home
$525,000
08/19/25
3
2
2,456
395 Hillwinds Road, Brattleboro, VT
0.06
Single-Family Home
$668,000
08/12/25
4
2.5
2,226
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
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
387 Meadow Brook Road, Brattleboro, VT
1.26
Single-Family Home
$439,000
05/13/26
4
2
1,568

Nearby homes

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Assigned Schools

These are the assigned schools for 357 Hillwinds Rd.
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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

  • 65 % 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 there are community events

  • 49 % Say streets are well-lit

  • 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
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357 Hillwinds Rd, Brattleboro, VT 05301 is a 3 bedroom, 2 bathroom, 2,180 sqft single-family home built in 1997. This property is not currently available for sale. 357 Hillwinds Rd was last sold on Dec 27, 2018 for $270,000. The current Trulia Estimate for 357 Hillwinds Rd is $510,100.