OFF MARKET

Listed by Desiree Stango • Berkley & Veller Greenwood Country (Off: 802-254-6400). Bought with Berkley & Veller Greenwood Country.

Off Market Aug 2025 for $668K

$619,140

Est. refi paymentEst. refi $4,380/mo

•

2,226

sq ft

395 Hillwinds Rd, Brattleboro, VT 05301

About this home

Turnkey Home in Sought-After Hillwinds! Located in the desirable Hillwinds neighborhood and nestled among the trees, your dream home awaits! This charming and functional home offers open, sun-filled living spaces, softwood floors, and abundant storage. The kitchen is a cook’s dream, featuring granite countertops, a gas stove, farmhouse sink, and a unique pull-out cabinet on wheels for added versatility and easy access to storage. The open-concept kitchen flows seamlessly into the living room, complete with a brick mantel and cozy gas fireplace—perfect for relaxing evenings. With four spacious bedrooms and three bathrooms, there’s room for everyone. The primary suite offers a walk-in closet and a skylit bathroom with radiant heated floors for year-round comfort. A convenient first-floor washer and dryer add to the home’s functionality, and if the interior isn’t enough—just wait until you step outside! Enjoy beautifully landscaped gardens with shrubs and mulched beds throughout the yard. A stone patio offers the perfect spot for small gatherings around the fire pit. Off the three-season room, you’ll find a private hot tub—ideal for unwinding after a long day. A private backyard path leads directly to the scenic Hillwinds trails. Don’t miss the chance to own this special home that blends nature, comfort, and thoughtful design. Delayed Showings begin Saturday 7/5/25 with an OPEN HOUSE 11am-2pm.

Single-familyProperty Type

1985Year Built

1.25 acresLot Size

$278Est. Price/Sq.Ft.

3 car garageParking

Listed by Desiree Stango • Berkley & Veller Greenwood Country

Listed by Claire Renaud • Berkley & Veller Greenwood Country

Contact: Off: 802-254-6400

Bought with John Hatton • Berkley & Veller Greenwood Country

Redfin checked: 2 minutes ago

•Source:PrimeMLS #5049724

Redfin Estimate

$619,140

$49K since sold in August 2025$34K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 28.6% higher than the average sale price ($481K) of 6 comparable homes.

SOLD AUG 19, 2026
$540,000
A
4 beds3 baths2,240 sq ft
3333 W River Rd, Dummerston, VT 05301
SOLD MAY 26, 2026
$365,000
B
5 beds3 baths2,254 sq ft
85 Stockwell Dr, Brattleboro, VT 05301
SOLD NOV 20, 2025
$476,000
C
4 beds3 baths2,372 sq ft
187 Hillwinds Rd, Brattleboro, VT 05301
SOLD JUN 26, 2026
$615,000
D
5 beds3.5 baths2,520 sq ft
143 Hillwinds Rd, Brattleboro, VT 05301
SOLD AUG 31, 2026
$395,000
E
4 beds2.5 baths2,100 sq ft
785 Brattleboro Rd, Hinsdale, NH 03451
SOLD APR 10, 2026
$497,408
F
4 beds2 baths2,656 sq ft
204 Meetinghouse Ln, Brattleboro, VT 05301

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,129/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

99.1%

0.5% MoM

Median sale price

$382K

$3K MoM

Avg. days on market

62d

2 days MoM

Recently sold homes

5 MoM

New listings for sale

NEW 6 HRS AGO
$1,195,000
5 beds3.5 baths3,536 sq ft
1845 Hatch School Rd, Brattleboro, VT 05358
NEW 11 HRS AGO
$299,000
2 beds2 baths1,139 sq ft
104 Morningside Cmns, Brattleboro, VT 05301
COMING SOON
$589,000
3 beds2 baths2,336 sq ft
3042 Sweet Pond Rd, Guilford, VT 05301
$379,000
4 beds2 baths1,704 sq ft
19 Blakeslee St, Brattleboro, VT 05301
$179,000
1 bed1 bath700 sq ft
40 Brookside Dr #2, Brattleboro, VT 05301
$350,000
3 beds1.5 baths1,406 sq ft
36 Pine St, Brattleboro, VT 05301
$399,000
3 beds2.5 baths2,108 sq ft
135 Winterbell Dr, East Dummerston, VT 05301
$270,000
2 beds1 bath1,061 sq ft
41 Organ St, Brattleboro, VT 05301
$319,000
2 beds2 baths1,883 sq ft
59 Highland St, Brattleboro, VT 05301
$299,000
3 beds1 bath1,104 sq ft
48 Wilsons Woods Rd, Brattleboro, VT 05301
See all

Provided by Redfin

Sale history for 395 Hillwinds Rd

Date

Event

Price

PrimeMLS #5049724

Aug 12, 2025

Sold

$668,000

$300/sq ft

Jul 10, 2025

Contingent

—

Jul 2, 2025

Listed

$649,000

$292/sq ft

Public Records

Apr 4, 2022

Sold

$475,000

$213/sq ft

PrimeMLS #4011034

Dec 28, 2010

Sold

$307,500

$138/sq ft

Jul 9, 2010

Listed

$334,000

$150/sq ft

This appealing, owner built, traditional post & beam high-posted cape is conveniently located a short drive from downtown Brattleboro, on a quiet cul-de-sac abutting 100 acres of conserved woodland(Hillwinds Conservation Lands Inc. ) Ideal for the buyer who wants a newer, yet period style home with energy efficiency, plaster walls, wide pine floors, custom built-ins & a floor plan featuring a 1st floor master bedroom, full bath & open concept kitchen, dining & living room with brick hearth and fireplace. The stone patio and steps and woodland gardens and landscaping add to the appeal.

Year

Property tax

Land + Additions

Assessment*

2025

$5,898 (−1.9%)

$70,000 + $240,560

$310,560

2024

$6,011 (+10.5%)

$70,000 + $240,560

$310,560

2023

$5,441 (−39.8%)

$70,000 + $240,560

$310,560

2022

$9,044 (−0.9%)

$70,000 + $240,560

$310,560

2021

$9,129 (+1.3%)

$70,000 + $240,560

$310,560

2020

$9,012 (+3.8%)

$70,000 + $240,560

$310,560

2019

$8,684 (+0.2%)

$70,000 + $240,560

$310,560

2018

$8,666 (+4.2%)

$70,000 + $240,560

$310,560

2017

$8,314 (+2.7%)

$70,000 + $240,560

$310,560

2016

$8,098 (+0.4%)

$70,000 + $232,540

$302,540

2015

$8,064 (−0.3%)

$70,000 + $232,540

$302,540

2014

$8,085

$70,000 + $232,540

$302,540

Tax history for 395 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$5,898 (−1.9%)

$70,000 + $240,560

$310,560

2024

$6,011 (+10.5%)

$70,000 + $240,560

$310,560

2023

$5,441 (−39.8%)

$70,000 + $240,560

$310,560

2022

$9,044 (−0.9%)

$70,000 + $240,560

$310,560

2021

$9,129 (+1.3%)

$70,000 + $240,560

$310,560

2020

$9,012 (+3.8%)

$70,000 + $240,560

$310,560

2019

$8,684 (+0.2%)

$70,000 + $240,560

$310,560

2018

$8,666 (+4.2%)

$70,000 + $240,560

$310,560

2017

$8,314 (+2.7%)

$70,000 + $240,560

$310,560

2016

$8,098 (+0.4%)

$70,000 + $232,540

$302,540

2015

$8,064 (−0.3%)

$70,000 + $232,540

$302,540

2014

$8,085

$70,000 + $232,540

$302,540

*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

1.25 Acres

Year renovated

—

Sq. Ft.

2,226

Year built

1985

Style

Single Family Residential

County

Windham County

APN

08102511714

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: 3

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 2
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Concrete Floor, Insulated, Interior Access

Other Interior Features
# of Rooms: 8
Flooring: Carpet, Tile, Wood

Equipment & Appliance Information
Dishwasher, Dryer, Range - Gas, Refrigerator, Washer, Water Heater - Domestic

Room 1 Information
Kitchen/Dining
Kitchen/Dining
Dimensions: 24X14
Level: 1

Room 3 Information
Living Room
Dimensions: 13X13
Level: 1

Room 6 Information
Office/Study
Office/Study
Dimensions: 10X10.11
Level: 1

Room 7 Information
Den
Dimensions: 5X9
Level: 2

Room 8 Information
Sunroom
Dimensions: 11X14
Level: 1

Room 10 Information
Master Bedroom
Dimensions: 16X13
Level: 1

Room 11 Information
Bedroom
Dimensions: 12X10
Level: 2

Room 12 Information
Bedroom
Dimensions: 11X13
Level: 2

Room 13 Information
Bedroom
Dimensions: 11X10
Level: 2

Exterior

Building Information
Architectural Style: Cape
Construction Status: Existing
Construction Materials: Post and Beam, Wood Frame, Clapboard Exterior
Approximate Sq. Ft. Total Finished: 2226
Approximate Sq. Ft. Total: 3234
Color: Sandstone
Roof: Shingle - Asphalt

Driveway
Paved

Lot, Zoning, & Easement Information
Lot Features: Country Setting, Landscaped, Abuts Conservation

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1985

Financial

Tax Information
Tax Year: 2024
Gross Amount Tax: 10527
SPAN Number: 081-025-11714

Other Tax Information
Page Deed: 389

Utilities

Heating & Cooling Information
Cooling: Mini Split
Heat: Propane, Baseboard, Hot Water, Radiant

Sewer Information
1000 Gallon, On-Site Septic Exists, Private

Electric Information
200 Amp

Water Information
Water Source: Drilled Well

Other Utilities Information
Internet: Internet - Cable
Cable - Available, Telephone Available

Location

School Information
School District: Windham Southeast

Road Information
Road Frontage Type: Cul-de-Sac, Public
Road Frontage: Yes
Road Frontage Length: 150

Other Location Information
Directions: From Route 30 turn onto Upper Dummerston Road, then left on Hillwinds Road to #395. See sign.

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 2,226
Stories: 2.0
Lot Size: 1.25 acres
Style: Single Family Residential
Year Built: 1985
Year Renovated: —
County: Windham County
APN: 08102511714

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 • 2.4mi

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

3/10 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

$589,000 – $713,000

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

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Home values near 395 Hillwinds Rd

Data from public records.

Address	Redfin Estimate
357 Hillwinds Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 2180 Sq. Ft.	$453,135
409 Hillwinds Rd, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1638 Sq. Ft.	$407,956

Address	Redfin Estimate
336 Hillwinds Rd, Brattleboro, VT 4 Beds \| 3 Baths \| 3257 Sq. Ft.	$731,461
306 Hillwinds Rd, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2590 Sq. Ft.	$576,037

Address	Redfin Estimate
335 Hillwinds Rd, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2544 Sq. Ft.	$548,484
297 Hillwinds Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 1408 Sq. Ft.	$419,381

Property information provided by PrimeMLS when last listed in 2025. 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 395 Hillwinds Rd

Tax history for 395 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 05358

Home values near 395 Hillwinds Rd

More real estate resources