OFF MARKET

Listed by Chelsea Cary • Barrett & Valley Assoc. Inc. Bought with Berkley & Veller Greenwood Country.

Off Market Sep 2018 for $276K

$471,602

Est. refi paymentEst. refi $1,759/mo

•

1,904

sq ft

348 Hillwinds Rd, Brattleboro, VT 05301

About this home

Are you looking for the perfect combination of privacy and convenience? Great neighborhood with a country feel? Tucked away in the northern corner of Brattleboro lies the desirable Hillwinds Road, just minutes to the Brattleboro Country Club and gorgeous walking trails. This home sits on 1.1 acres and overlooks 30+ acres of conserved land. Sit on your back porch, look out over your in-ground pool and watch deer frolic through the fields. Or take a 5 minute drive and be in downtown Brattleboro, filled with shopping, restaurants, and night life. This 3 bedroom, 2 bathroom home has ample space in the finished basement for a library, game room, or man cave, and has a new sliding glass door that open up to the pool. Owners since 2012 have replaced the roof, windows, oil tank, water pump, water heater, the plumbing for the pool, and more! This home has a little bit of everything- come and see for yourself.

Single-familyProperty Type

1970Year Built

1.1 acresLot Size

$248Est. Price/Sq.Ft.

2 car garageParking

Listed by Chelsea Cary • Barrett & Valley Assoc. Inc

Bought with Jane Sonntag • Berkley & Veller Greenwood Country

Redfin checked: a minute ago

•Source:PrimeMLS #4695133

Redfin Estimate

$471,602

$196K since sold in September 2018$5,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 31% higher than the average sale price ($360K) of 6 comparable homes.

SOLD JUL 31, 2026
$320,000
A
3 beds2 baths1,703 sq ft
1089 Marlboro Rd, Brattleboro, VT 05301
SOLD DEC 17, 2025
$335,000
B
3 beds2 baths1,728 sq ft
290 Guilford St, Brattleboro, VT 05301
SOLD AUG 12, 2026
$317,000
C
3 beds1 bath1,522 sq ft
69 Carriage Hill Rd, Brattleboro, VT 05301
SOLD MAY 13, 2026
$439,000
D
4 beds2 baths1,568 sq ft
387 Meadow Brook Rd, Brattleboro, VT 05301
SOLD JUL 15, 2026
$379,000
E
3 beds2 baths1,966 sq ft
25 Speno Ct, Brattleboro, VT 05301
SOLD APR 2, 2026
$370,000
F
3 beds2 baths1,820 sq ft
115 Country Hl, Brattleboro, VT 05301

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,442/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

NEW 8 HRS AGO
$830,000
5 beds5.5 baths5,064 sq ft
253 Sugar House Hl, Guilford, VT 05301
OPEN SEP 7, 10:30AM TO 12:30PM
$149,900
3 beds2 baths1,232 sq ft
14 Deepwood Park, Brattleboro, VT 05301
NEW 34 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
See all

Provided by Redfin

Sale history for 348 Hillwinds Rd

Date

Event

Price

PrimeMLS #4695133

Sep 6, 2018

Sold

$276,000

$145/sq ft

Jun 7, 2018

Contingent

—

May 23, 2018

Listed

$276,000

$145/sq ft

PrimeMLS #4145306

Nov 7, 2012

Sold

$215,000

$113/sq ft

Mar 28, 2012

Listed

$225,000

$118/sq ft

Location, Location, Location! This charming home is sited in desirable Hillwinds on 1.10+/- acres with beautiful views, landscaping, stone walls and an 18X36 in-ground pool. The rear yard is private and overlooks conserved lands. Providing 3 bedrooms, 2 baths, family room, office, formal living and dining rooms and kitchen with granite counters, it is a fine offering in a great location. Huge deck, bluestone patio and detached 2-car garage all add to the appeal.

Year

Property tax

Land + Additions

Assessment*

2025

$4,523 (−1.9%)

$67,000 + $171,150

$238,150

2024

$4,610 (+10.5%)

$67,000 + $171,150

$238,150

2023

$4,173 (−43.0%)

$67,000 + $171,150

$238,150

2022

$7,324 (+0.9%)

$67,000 + $171,150

$238,150

2021

$7,259 (+1.8%)

$67,000 + $171,150

$238,150

2020

$7,130 (+7.1%)

$67,000 + $171,150

$238,150

2019

$6,659 (−2.2%)

$67,000 + $171,150

$238,150

2018

$6,808 (+1.4%)

$67,000 + $171,150

$238,150

2017

$6,713 (+0.2%)

$67,000 + $171,150

$238,150

2016

$6,698 (−0.9%)

$67,000 + $171,150

$238,150

2015

$6,757 (+210.5%)

$67,000 + $171,150

$238,150

2014

$2,176

$67,000 + $171,150

$238,150

Tax history for 348 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,523 (−1.9%)

$67,000 + $171,150

$238,150

2024

$4,610 (+10.5%)

$67,000 + $171,150

$238,150

2023

$4,173 (−43.0%)

$67,000 + $171,150

$238,150

2022

$7,324 (+0.9%)

$67,000 + $171,150

$238,150

2021

$7,259 (+1.8%)

$67,000 + $171,150

$238,150

2020

$7,130 (+7.1%)

$67,000 + $171,150

$238,150

2019

$6,659 (−2.2%)

$67,000 + $171,150

$238,150

2018

$6,808 (+1.4%)

$67,000 + $171,150

$238,150

2017

$6,713 (+0.2%)

$67,000 + $171,150

$238,150

2016

$6,698 (−0.9%)

$67,000 + $171,150

$238,150

2015

$6,757 (+210.5%)

$67,000 + $171,150

$238,150

2014

$2,176

$67,000 + $171,150

$238,150

*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

1.1 Acres

Year renovated

—

Sq. Ft.

1,138

Year built

1972

Style

Single Family Residential

County

Windham County

APN

08102513292

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: Detached

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 2

Basement Information
Basement: Yes
Basement Access: Walkout
Finished, Full

Other Interior Features
# of Rooms: 8
Level B: Den, Level B: Library
Flooring: Carpet, Hardwood
Water Heater: Electric
Kitchen/Dining, Storage - Indoor

Accessibility Information
1st Floor Bedroom, 1st Floor Full Bathroom, Paved Parking

Equipment & Appliance Information
Dishwasher, Refrigerator, Stove - Electric
Smoke Detector, Stove-Gas

Room 1 Information
Kitchen
Kitchen
Dimensions: 10x11
Level: 1

Room 2 Information
Dining Room
Dimensions: 16x11
Level: 1

Room 3 Information
Living Room
Dimensions: 22x10
Level: 1

Room 4 Information
Den
Dimensions: 26x20
Level: Basement

Room 5 Information
Library
Dimensions: 24x11
Level: Basement

Room 6 Information
Bedroom
Bedroom
Dimensions: 10x15
Level: 1

Room 7 Information
Bedroom
Dimensions: 13x11
Level: 1

Room 8 Information
Bedroom
Dimensions: 11x9
Level: 1

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 1904
Approximate Sq. Ft. Total: 2276
Color: yellow
Deck, Garden Space, Outbuilding, Pool - In Ground, Shed
Construction: Modular Prefab
Foundation: Poured Concrete
Roof: Shingle
Exterior: Clapboard, Vinyl

Driveway
Paved

Lot, Zoning, & Easement Information
Country Setting, Mountain View, View

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1970

Financial

Tax Information
Tax Year: 2018
Gross Amount Tax: 6713.44
SPAN Number: 081-025-13292

Other Tax Information
Page Deed: 686-688

Utilities

Heating & Cooling Information
Heat: Baseboard, Hot Water, Stove - Gas
Heat Fuel: Oil

Sewer Information
1000 Gallon, Leach Field - On-Site, Septic

Electric Information
100 Amp, Circuit Breaker(s)

Water Information
Drilled Well, Private

Location

School Information
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: 300
Paved, Public

Other Location Information
Directions: From Exit 2 off I-91, turn right onto VT-9 West (signs for VT-30). Turn right onto Orchard Street, and then another right onto East Orchard Street. Left on Upper Dummerston Road, and then another left onto Hillwinds Rd. Turn left to stay on Hillwinds, and house will be on the left.

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 1,138
Stories: 1.0
Lot Size: 1.1 acres
Style: Single Family Residential
Year Built: 1972
Year Renovated: —
County: Windham County
APN: 08102513292

Home facts updated by county records on Jul 8, 2026

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 • 2.5mi

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

3/10 Heat Factor

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

4/10 Wind Factor

9% 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

$449,000 – $543,000

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

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Home values near 348 Hillwinds Rd

Data from public records.

Address	Redfin Estimate
357 Hillwinds Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 2180 Sq. Ft.	$461,092
409 Hillwinds Rd, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1638 Sq. Ft.	$412,987

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

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

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 348 Hillwinds Rd

Tax history for 348 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 348 Hillwinds Rd

More real estate resources