OFF MARKET

Listed by John Hatton • Berkley & Veller Greenwood Country. Bought with Berkley & Veller Greenwood Country.

Off Market Dec 2018 for $270K

$461,092

Est. refi paymentEst. refi $1,674/mo

•

2,180

sq ft

357 Hillwinds Rd, Brattleboro, VT 05301

About this home

Tucked back from the road, surrounded by woodland and bordering conserved land, is this Japan-influenced, passive-solar home, designed with clean, simple lines, a close connection to nature, and light-filled rooms from plentiful windows and carefully placed skylights. The main floor open-concept living/dining/kitchen area has large open spaces, lovely birch flooring warmed by radiant heat, walls of windows, and a three-sided central fireplace. There is a master bedroom, a bath with clawfoot tub and a 12x25 screened porch overlooking the woods--perfect for warm weather meals, yoga, and bird watching. The lower level has 2 bedrooms, bath, laundry and a huge family room or studio with a woodstove hookup and radiant heat. All the lower level rooms are walk-out and bright, with sliders overlooking the conserved woodlands with miles of hiking and groomed x-c ski trails. Excellent downhill skiing is only 30 minutes away. The house design provides passive solar and passive cooling which is supplemented by a new photovoltaic--solar panel--system. This is a remarkable, inviting home in a desirable location that is both private and convenient. The Hillwinds area, on the edge of Brattleboro, offers a strong community, and is a wonderful place to raise children, walk your dog, and get to know your friendly neighbors.

Single-familyProperty Type

1997Year Built

1.5 acresLot Size

$212Est. Price/Sq.Ft.

2 car garageParking

Listed by John Hatton • Berkley & Veller Greenwood Country

Bought with Bill Murray • Berkley & Veller Greenwood Country

Redfin checked: a few seconds ago

•Source:PrimeMLS #4722950

Redfin Estimate

$461,092

$191K since sold in December 2018$4,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.8% higher than the average sale price ($420K) of 6 comparable homes.

SOLD APR 2, 2026
$370,000
A
3 beds2 baths1,820 sq ft
115 Country Hl, Brattleboro, VT 05301
SOLD JUN 1, 2026
$385,000
B
3 beds2.5 baths2,128 sq ft
135 Country Hl, Brattleboro, VT 05301
SOLD JUL 31, 2026
$320,000
C
3 beds2 baths1,703 sq ft
1089 Marlboro Rd, Brattleboro, VT 05301
SOLD JUN 26, 2026
$330,000
D
3 beds2 baths1,521 sq ft
255 Guilford St, Brattleboro, VT 05301
SOLD MAY 18, 2026
$590,000
E
3 beds2.5 baths1,995 sq ft
299 Sunset Lake Rd, Brattleboro, VT 05301
SOLD JUL 31, 2026
$525,000
F
3 beds2.5 baths2,182 sq ft
160 Akley Rd, Guilford, VT 05301

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,429/mo

Redfin rental estimate

List your home for rent

Market trends in 05301, VT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.7%

+0.5% MoM

Median sale price

$387K

$2K MoM

Avg. days on market

59d

9 days MoM

Recently sold homes

8 MoM

New listings for sale

OPEN SEP 7, 10:30AM TO 12:30PM
$149,900
3 beds2 baths1,232 sq ft
14 Deepwood Park, Brattleboro, VT 05301
NEW 22 HRS AGO
$395,000
2 beds2 baths1,400 sq ft
215 Gilbert Rd, Marlboro, VT 05344
$190,000
2 beds1 bath930 sq ft
39 Brookside Dr #5, Brattleboro, VT 05301
$120,000
2 beds1 bath924 sq ft
21 Winding Hl, Brattleboro, VT 05301
$499,000
2 beds2 baths1,775 sq ft
171 Buttonwood Dr, Brattleboro, VT 05301
$525,000
3 beds2.5 baths2,330 sq ft
205 Wantastiquet Dr, Brattleboro, VT 05301
$479,000
2 beds2 baths1,775 sq ft
162 Buttonwood Dr, Brattleboro, VT 05301
$439,000
2 beds2 baths1,550 sq ft
77 Buttonwood Dr, Brattleboro, VT 05301
$289,000
2 beds1 bath925 sq ft
45 Kopkind Rd, Guilford, VT 05301
$615,000
4 beds2.5 baths2,212 sq ft
354 Orchard St, Brattleboro, VT 05301
See all

Provided by Redfin

Sale history for 357 Hillwinds Rd

Date

Event

Price

PrimeMLS #4722950

Dec 27, 2018

Sold

$270,000

$124/sq ft

Nov 12, 2018

Contingent

—

Oct 10, 2018

Listed

$297,000

$136/sq ft

PrimeMLS #4404448

Nov 25, 2015

Sold

$263,000

$121/sq ft

Oct 5, 2015

Contingent

—

May 7, 2015

Price Changed

$289,000

$133/sq ft

Feb 25, 2015

Listed

$316,000

$145/sq ft

+22

Tucked back from the road, surrounded by woodland and bordering conserved land in back, this lovely Hillwinds home offers both convenience and privacy. The main floor open-concept living/dining/kitchen area has large open spaces, lovely birch flooring, lots of windows, a central fireplace and beautiful light. There is a good sized bedroom, a bath with clawfoot tub and a 12x25 screened porch overlooking the woods-perfect for summertime meals and a hammock. The lower level has 2 bedrooms, bath, laundry and a huge family room or studio with a woodstove hookup and radiant heat. All the lower level rooms are walk-out and bright, with sliders overlooking lovely conserved woodland in back. There are hiking and x-c ski trails right out your door! This is a sweet, light-filled home in a wonderful location.

Year

Property tax

Land + Additions

Assessment*

2025

$4,826 (−9.4%)

$75,000 + $200,180

$275,180

2024

$5,326 (+20.6%)

$75,000 + $200,180

$275,180

2023

$4,417 (−44.9%)

$75,000 + $200,180

$275,180

2022

$8,014 (−0.9%)

$75,000 + $200,180

$275,180

2021

$8,089 (+1.3%)

$75,000 + $200,180

$275,180

2020

$7,985 (+3.8%)

$75,000 + $200,180

$275,180

2019

$7,695 (−2.2%)

$75,000 + $200,180

$275,180

2018

$7,867 (+1.4%)

$75,000 + $200,180

$275,180

2017

$7,757 (−12.7%)

$75,000 + $200,180

$275,180

2016

$8,888 (+5.5%)

$75,000 + $241,030

$316,030

2015

$8,423 (−0.3%)

$75,000 + $241,030

$316,030

2014

$8,445

$75,000 + $241,030

$316,030

Tax history for 357 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,826 (−9.4%)

$75,000 + $200,180

$275,180

2024

$5,326 (+20.6%)

$75,000 + $200,180

$275,180

2023

$4,417 (−44.9%)

$75,000 + $200,180

$275,180

2022

$8,014 (−0.9%)

$75,000 + $200,180

$275,180

2021

$8,089 (+1.3%)

$75,000 + $200,180

$275,180

2020

$7,985 (+3.8%)

$75,000 + $200,180

$275,180

2019

$7,695 (−2.2%)

$75,000 + $200,180

$275,180

2018

$7,867 (+1.4%)

$75,000 + $200,180

$275,180

2017

$7,757 (−12.7%)

$75,000 + $200,180

$275,180

2016

$8,888 (+5.5%)

$75,000 + $241,030

$316,030

2015

$8,423 (−0.3%)

$75,000 + $241,030

$316,030

2014

$8,445

$75,000 + $241,030

$316,030

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1.5 Acres

Year renovated

—

Sq. Ft.

1,380

Year built

1997

Style

Single Family Residential

County

Windham County

APN

08102515668

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 8, 2026.

Rural Residential District

The Rural Residential District encompasses land primarily west of Interstate 91 that is rural in character but is relatively close to the developed areas of town and accessible from improved public roads, which has made these areas a suitable and attractive location for low-density residential development. This land is generally not served by municipal water and sewer, and extension of infrastructure into this district is discouraged. The purpose of this district is to provide opportunities for rural housing and to encourage thoughtful siting of new development in order to protect rural character, farmland, forestland, open space and important natural resources in accordance with the policies of the Brattleboro Town Plan.

Permitted uses

Include but are not limited to:

Agriculture
Religious facility
Housing-Single unit
Housing-Multiple units
Housing-Senior
Infrastructure
Golf related
Cemetery
Park & open space
Timberland

Property details

Parking

Parking & Garage
Garage Capacity: 2
Location: Attached
Auto Open
Driveway, Garage

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 2

Basement Information
Basement: Yes
Basement Access: Interior
Concrete Floor, Partially Finished, Walkout

Other Interior Features
# of Rooms: 7
Level B: Bedroom, Level B: Full Bath, Level B: Den
Flooring: Concrete, Hardwood
Water Heater: Off Boiler
Dining Area, Walk-in Pantry

Room 1 Information
Kitchen
Kitchen
Dimensions: 11'2 x 17'1
Level: 1

Room 2 Information
Dining Room
Dimensions: 163 x 14'11.5
Level: 1

Room 3 Information
Living Room
Dimensions: 24'9 x 12'9.75
Level: 1

Room 5 Information
Den
Dimensions: 17'11.5 x 29'4.75
Level: Basement

Room 6 Information
Other
Other
Dimensions: 7'2.5 x 3'5.75
Level: 1

Room 7 Information
Porch
Dimensions: 10' x 32'
Level: 1

Room 10 Information
Master Bedroom
Dimensions: 15'7 x 18'5.75
Level: 1

Room 11 Information
Bedroom
Dimensions: 10'5 x 10'8.5
Level: Basement

Room 12 Information
Bedroom
Dimensions: 13'1 x 10'5
Level: Basement

Room 16 Information
Full Bath
Dimensions: 9'9.25 x 9
Level: 1

Room 17 Information
Full Bath
Dimensions: 8'3 x 8'6
Level: Basement

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 2180
Approximate Sq. Ft. Total: 2760
Color: Brown
Porch - Screened, Windows - Double Pane
Construction: Wood Frame
Foundation: Concrete, Poured Concrete
Roof: Shingle - Asphalt
Exterior: T-111
Fixed Rack
Mount Location: Roof
Power Production Year Ins: 2017
Power Production Year Ins: 2017
Power Production Type: Photovoltaics

Driveway
Gravel

Lot, Zoning, & Easement Information
Country Setting

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1997

Financial

Tax Information
Tax Year: 2018
Gross Amount Tax: 7866
SPAN Number: 081-025-15688

Other Tax Information
Page Deed: 461

Utilities

Heating & Cooling Information
Heat: Hot Water, Radiant
Heat Fuel: Gas - Liquid Propane Bottle

Sewer Information
Leach Field, Septic

Electric Information
100 Amp, Circuit Breaker(s)

Water Information
Drilled Well

Power Production Information
Power Production Ownership: Seller Owned

Other Utilities Information
Internet - Cable

Location

School Information
School District: Brattleboro School District
Elementary School: Brattleboro Elem Schools
Elementary School: Brattleboro Elem Schools
Middle/Jr School: Brattleboro Area Middle School

Road Information
Road Frontage: Yes
Road Frontage Length: 180
Paved, Public

Other Location Information
Directions: Rt. 30 to Upper Dummerston Rd. to Hillwinds. #357, see sign.

Public facts

Beds: 1
Baths: 2.0
Sq. Ft.: 1,380
Stories: 1.0
Lot Size: 1.5 acres
Style: Single Family Residential
Year Built: 1997
Year Renovated: —
County: Windham County
APN: 08102515668

Home facts updated by county records on Jul 8, 2026

Other

Documents & Disclosures
Documents Available: Deed, Property Disclosure, Tax Map

Around this home

Schools

Some nearby schools may not be within this home's attendance zone. Please check the Windham Southeast Unified Union School District #96 website to verify.

Academy School

Public PreK-6 • 2.4mi

6/10

Green Street School

Public PreK-6 • 2.9mi

8/10

Neighborhood Schoolhouse

Private PreK-8 • 2.5mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

2/10 Heat Factor

7 days above 94° expected this year, 16 days in 30 years

4/10 Wind Factor

8% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Brattleboro, VT • 05301

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 3.9 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

3.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$439,000 – $531,000

Sell confidently with a local market expert in Brattleboro. 3 minutes to get started.

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New listings for sale in 05301

OPEN SEP 7, 10:30AM TO 12:30PM

$149,900

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14 Deepwood Park, Brattleboro, VT 05301

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171 Buttonwood Dr, Brattleboro, VT 05301

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205 Wantastiquet Dr, Brattleboro, VT 05301

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162 Buttonwood Dr, Brattleboro, VT 05301

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Home values near 357 Hillwinds Rd

Data from public records.

Address	Redfin Estimate
336 Hillwinds Road, Brattleboro, VT 4 Beds \| 3 Baths \| 3257 Sq. Ft.	$736,857
306 Hillwinds Road, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2590 Sq. Ft.	$576,619

Address	Redfin Estimate
335 Hillwinds Road, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2544 Sq. Ft.	$556,962
297 Hillwinds Road, Brattleboro, VT 3 Beds \| 2 Baths \| 1408 Sq. Ft.	$423,931

Address	Redfin Estimate
409 Hillwinds Road, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1638 Sq. Ft.	$412,987
321 Hillwinds Road, Brattleboro, VT 4 Beds \| 2.5 Baths \| 2464 Sq. Ft.	$506,184

Property information provided by PrimeMLS when last listed in 2018. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05301, VT

Sale history for 357 Hillwinds Rd

Tax history for 357 Hillwinds Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05301

Home values near 357 Hillwinds Rd

More real estate resources