SOLD NOV 20, 2025

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

Off Market Nov 2025 for $476K

$565,489

Est. refi paymentEst. refi $3,029/mo

•

2,372

sq ft

187 Hillwinds Rd, Brattleboro, VT 05301

About this home

Welcome home! The four bedroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A private office provides the perfect space for remote work or creative projects. Upstairs, the primary suite includes a fireplace, en-suite bath, with three additional bedrooms and ample bathrooms for family or guests. Set in a friendly, vibrant neighborhood, this home is close to shopping, dining, arts, and year-round recreation. A rare opportunity to enjoy both community and nature in a prime location! Delayed showings begin Saturday 9/20/25.

Single-familyProperty Type

1976Year Built

1.3 acresLot Size

$238Est. Price/Sq.Ft.

2 car garageParking

Listed by Claire Renaud • Berkley & Veller Greenwood Country

Contact: Off: 802-254-6400

Bought with Liz LaVorgna • Berkley & Veller Greenwood Country

Redfin checked: a minute ago

•Source:PrimeMLS #5061423

Redfin Estimate

$565,489

$89K since sold in November 2025$8,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.9% higher than the average sale price ($534K) of 6 comparable homes.

SOLD JUL 31, 2026
$790,000
A
4 beds3.5 baths3,212 sq ft
104 Juniper Ridge Rd, Brattleboro, VT 05301
SOLD JUN 26, 2026
$615,000
B
5 beds3.5 baths2,520 sq ft
143 Hillwinds Rd, Brattleboro, VT 05301
SOLD AUG 19, 2026
$540,000
C
4 beds3 baths2,240 sq ft
3333 W River Rd, Dummerston, VT 05301
SOLD APR 10, 2026
$497,408
D
4 beds2 baths2,656 sq ft
204 Meetinghouse Ln, Brattleboro, VT 05301
SOLD MAY 26, 2026
$365,000
E
5 beds3 baths2,254 sq ft
85 Stockwell Dr, Brattleboro, VT 05301
SOLD AUG 31, 2026
$395,000
F
4 beds2.5 baths2,100 sq ft
785 Brattleboro Rd, Hinsdale, NH 03451

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,710/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 32 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
$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 187 Hillwinds Rd

Date

Event

Price

PrimeMLS #5061423

Nov 20, 2025

Sold

$476,000

$201/sq ft

Oct 15, 2025

Contingent

—

Oct 9, 2025

Price Changed

$499,000

$210/sq ft

Sep 15, 2025

Listed

$550,000

$232/sq ft

PrimeMLS #3030168

Apr 2, 2007

Sold

$319,950

$135/sq ft

Jul 16, 2006

Listed

$329,500

$139/sq ft

Located in desirable Hillwinds, this handsome colonial is sited on over an acre of land and features easterly winter views and is bordered by the Hillwinds Conservation Lands. The fenced rear yard provides an in-ground pool, hot tub and raised bed garden. Features include: Hardwood flooring, two fireplaces, formal dining and living rooms, family room, three and a half baths and much more. A wonderful place to call home!

Year

Property tax

Land + Additions

Assessment*

2025

$6,183 (−1.9%)

$71,000 + $254,570

$325,570

2024

$6,302 (+10.5%)

$71,000 + $254,570

$325,570

2023

$5,704 (−43.0%)

$71,000 + $254,570

$325,570

2022

$10,012 (+0.9%)

$71,000 + $254,570

$325,570

2021

$9,924 (+1.8%)

$71,000 + $254,570

$325,570

2020

$9,747 (+3.0%)

$71,000 + $254,570

$325,570

2019

$9,460 (+1.6%)

$71,000 + $254,570

$325,570

2018

$9,307 (+1.4%)

$71,000 + $254,570

$325,570

2017

$9,178 (+0.2%)

$71,000 + $254,570

$325,570

2016

$9,156 (−0.9%)

$71,000 + $254,570

$325,570

2015

$9,238 (+0.8%)

$71,000 + $254,570

$325,570

2014

$9,166

$71,000 + $254,570

$325,570

Tax history for 187 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,183 (−1.9%)

$71,000 + $254,570

$325,570

2024

$6,302 (+10.5%)

$71,000 + $254,570

$325,570

2023

$5,704 (−43.0%)

$71,000 + $254,570

$325,570

2022

$10,012 (+0.9%)

$71,000 + $254,570

$325,570

2021

$9,924 (+1.8%)

$71,000 + $254,570

$325,570

2020

$9,747 (+3.0%)

$71,000 + $254,570

$325,570

2019

$9,460 (+1.6%)

$71,000 + $254,570

$325,570

2018

$9,307 (+1.4%)

$71,000 + $254,570

$325,570

2017

$9,178 (+0.2%)

$71,000 + $254,570

$325,570

2016

$9,156 (−0.9%)

$71,000 + $254,570

$325,570

2015

$9,238 (+0.8%)

$71,000 + $254,570

$325,570

2014

$9,166

$71,000 + $254,570

$325,570

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

1.3 Acres

Year renovated

—

Sq. Ft.

2,372

Year built

1976

Style

Single Family Residential

County

Windham County

APN

08102512833

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

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Interior
Concrete

Other Interior Features
# of Rooms: 8
Flooring: Hardwood, Tile

Equipment & Appliance Information
Dishwasher, Dryer, Refrigerator, Washer, Stove - Gas, Water Heater - Electric

Room 1 Information
Kitchen/Dining
Kitchen/Dining
Dimensions: 23x13
Level: 2

Room 3 Information
Living Room
Dimensions: 19x11.8
Level: 1

Room 4 Information
Family Room
Dimensions: 19.8x13.5
Level: 1

Room 6 Information
Office/Study
Office/Study
Dimensions: 15.5x9.3
Level: 1

Room 10 Information
Master Bedroom
Dimensions: 18.9x11.11
Level: 2

Room 11 Information
Bedroom
Dimensions: 11.11x9.6
Level: 2

Room 12 Information
Bedroom
Dimensions: 13x13
Level: 2

Room 13 Information
Bedroom
Dimensions: 13.4x9.9
Level: 1

Exterior

Building Information
Architectural Style: Colonial
Construction Status: Existing
Construction Materials: Wood Frame, Wood Siding
Approximate Sq. Ft. Total Finished: 2372
Approximate Sq. Ft. Total: 3380
Color: Blue
Roof: Shingle - Asphalt

Driveway
Paved

Lot, Zoning, & Easement Information
Lot Features: Level, Sloping, Wooded, Neighborhood

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1976

Financial

Tax Information
Tax Year: 2025
Gross Amount Tax: 11338
SPAN Number: 081-025-12833

Other Tax Information
Page Deed: 119

Utilities

Heating & Cooling Information
Heat: Baseboard, Hot Water, Stove - Wood, Furnace - Pellet

Sewer Information
1000 Gallon, Leach Field

Electric Information
Circuit Breaker(s)

Water Information
Water Source: Drilled Well

Other Utilities Information
Internet: High Speed Intrnt -Avail
Cable, Telephone At Site

Location

School Information
School District: Windham Southeast

Road Information
Road Frontage Type: Paved, Public
Road Frontage: Yes
Road Frontage Length: 140

Other Location Information
Directions: From Route 30 turn onto Upper Dummerston Road, then left on Hillwinds Road to #187. See sign.

Public facts

Beds: 3
Baths: 3.5
Sq. Ft.: 2,372
Stories: 2.0
Lot Size: 1.3 acres
Style: Single Family Residential
Year Built: 1976
Year Renovated: —
County: Windham County
APN: 08102512833

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 • 2.7mi

6/10

Green Street School

Public PreK-6 • 3.2mi

8/10

Neighborhood Schoolhouse

Private PreK-8 • 2.9mi

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 93° 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

$538,000 – $651,000

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

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New listings for sale in 05301

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Home values near 187 Hillwinds Rd

Data from public records.

Address	Redfin Estimate
122 Hillwinds Road, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1330 Sq. Ft.	$410,325
336 Hillwinds Road, Brattleboro, VT 4 Beds \| 3 Baths \| 3257 Sq. Ft.	$736,857

Address	Redfin Estimate
10 Hillwinds North, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1482 Sq. Ft.	$431,846
335 Hillwinds Road, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2544 Sq. Ft.	$556,962

Address	Redfin Estimate
148 Hillwinds North, Brattleboro, VT 3 Beds \| 3.5 Baths \| 3040 Sq. Ft.	$616,916
161 Hillwinds Road, Brattleboro, VT 4 Beds \| 4.5 Baths \| 2600 Sq. Ft.	$591,142

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 187 Hillwinds Rd

Tax history for 187 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 187 Hillwinds Rd

More real estate resources