SOLD JUN 26, 2026

Listed by Christine Lewis • Brattleboro Area Realty. Bought with Brattleboro Area Realty.

Sold on Jun 2026

$615,000

•

2,520

sq ft

143 Hillwinds Rd, Brattleboro, VT 05301

Track this home’s value and nearby sales activity

About this home

Welcome to Hillwinds and this lovely colonial. With 200 acres of conserved land and trails behind and a wonderful meadow view in the front, this house truly feels a part of the landscape. The main house has four bedrooms and two and a half baths and invites you to step right into your new life in this well cared for and lovingly maintained home. The gardens are in, the drive paved and the garden shed with power is standing ready. The sweet sun room is a nice addition to the living area, just off the kitchen/family room so a great place to expand when entertaining in the warmer months. It overlooks the very peaceful conservancy and is a special place for a quiet read or fun games in the rain. No worries of power outages here with both a gas generator and the new Tesla Powerwall! Above the garage is a versatile space that can be used as a studio, guest room, mother-in-law suite, or a study boasting a mini-split, refrigerator, and three-quarter bath. Enjoy the fire pit in the evening, under the stars. Watch the bluebirds at the birdhouses as they raise their families, the chipmunks that scurry, and the turkeys in the meadow. This is a wonderful neighborhood. Make it yours. Open house Saturday, April 25th 11am - 1pm

Single-familyProperty Type

1974Year Built

1.19 acresLot Size

$244Price/Sq.Ft.

2 car garageParking

Listed by Christine Lewis • Brattleboro Area Realty

Bought with Christine Lewis • Brattleboro Area Realty

Redfin checked: 2 minutes ago

•Source:PrimeMLS #5082786

Redfin Estimate

$615,740

$740 since sold in June 2026$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 23.7% higher than the average sale price ($498K) of 6 comparable homes.

SOLD NOV 20, 2025
$476,000
A
4 beds3 baths2,372 sq ft
187 Hillwinds Rd, Brattleboro, VT 05301
SOLD AUG 19, 2026
$540,000
B
4 beds3 baths2,240 sq ft
3333 W River Rd, Dummerston, VT 05301
SOLD MAY 26, 2026
$365,000
C
5 beds3 baths2,254 sq ft
85 Stockwell Dr, Brattleboro, VT 05301
SOLD APR 10, 2026
$497,408
D
4 beds2 baths2,656 sq ft
204 Meetinghouse Ln, Brattleboro, VT 05301
SOLD JUL 10, 2026
$528,000
E
6 beds3 baths1,600 sq ft
25-27 Gingko Ln, Brattleboro, VT 05301
SOLD JUN 30, 2026
$580,000
F
4 beds2.5 baths2,573 sq ft
11 Strawberry Hl, Brattleboro, VT 05301

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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

$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
$275,000
Studio— baths1,200 sq ft
752 Butternut Hill Rd, Guilford, VT 05301
See all

Provided by Redfin

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Rental estimate

Est. $3,939 per month, based on comparable rentals

Sale and tax history for 143 Hillwinds Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2025

$6,676 (−1.9%)

$68,800 + $282,720

$351,520

2024

$6,804 (+10.5%)

$68,800 + $282,720

$351,520

2023

$6,159 (−43.0%)

$68,800 + $282,720

$351,520

2022

$10,810 (+0.9%)

$68,800 + $282,720

$351,520

2021

$10,715 (+1.8%)

$68,800 + $282,720

$351,520

2020

$10,524 (+3.0%)

$68,800 + $282,720

$351,520

2019

$10,214 (+1.6%)

$68,800 + $282,720

$351,520

2018

$10,049 (+1.4%)

$68,800 + $282,720

$351,520

2017

$9,909 (+0.2%)

$68,800 + $282,720

$351,520

2016

$9,886 (−0.9%)

$68,800 + $282,720

$351,520

2015

$9,974 (+400.5%)

$68,800 + $282,720

$351,520

2014

$1,993

$68,800 + $282,720

$351,520

2013

$68,800 + $282,720

$351,520

Public record

Public record
Zoning

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

1.19 Acres

Year renovated

—

Sq. Ft.

2,520

Year built

1974

Style

Single Family Residential

County

Windham County

APN

08102513927

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): 1
# of Baths (3/4): 2
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Bulkhead, Concrete, Crawl Space, Concrete Floor, Exterior Access, Frost Wall, Full, Interior Access, Storage Space, Stairs - Basement, Stairs - Interior, Unfinished

Other Interior Features
# of Rooms: 9
Flooring: Carpet, Laminate, Tile, Vinyl, Wood

Equipment & Appliance Information
Dishwasher, Dishwasher - Energy Star, Dryer, Dryer - Energy Star, Microwave, Range - Gas, Refrigerator, Refrigerator-Energy Star, Washer, Washer - Energy Star, Water Heater - Electric, Water Heater - Owned, Water Heater - Separate, Water Heater - Heat Pump, Exhaust Fan, Vented Exhaust Fan, Water Heater

Room 1 Information
Family Room
Family Room
Dimensions: 13x18
Level: 1

Room 2 Information
Kitchen
Dimensions: 13x18
Level: 1

Room 3 Information
Dining Room
Dimensions: 11x13
Level: 1

Room 4 Information
Living Room
Dimensions: 14x28
Level: 1

Room 5 Information
Bedroom
Dimensions: 12x12
Level: 2

Room 6 Information
Bedroom
Bedroom
Dimensions: 13x15
Level: 2

Room 7 Information
Bedroom
Dimensions: 10x12
Level: 2

Room 8 Information
Bedroom
Dimensions: 13x14
Level: 2

Room 9 Information
Bedroom
Dimensions: 13x24
Level: 2

Room 10 Information
1/2 Bath
Dimensions: 07x08
Level: 1

Room 11 Information
Full Bath
Dimensions: 12x06
Level: 2

Room 12 Information
3/4 Bath
Dimensions: 05x08
Level: 2

Room 13 Information
3/4 Bath
Dimensions: 05x10
Level: 2

Exterior

Building Information
Architectural Style: Colonial
Construction Status: Existing
Construction Materials: Wood Frame, Vinyl Siding
Approximate Sq. Ft. Total Finished: 2520
Approximate Sq. Ft. Total: 3495
Roof: Shingle - Asphalt

Driveway
Paved

Lot, Zoning, & Easement Information
Lot Features: Conserved Land, Country Setting, Deed Restricted, Landscaped, Level, Open, Slight, Sloping, Trail/Near Trail, View, Walking Trails, Abuts Conservation, Near Country Club, Near Golf Course, Near Paths, Neighborhood

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1974

Financial

Tax Information
Tax Year: 2025
Gross Amount Tax: 12242
SPAN Number: 081-025-13927

Other Tax Information
Page Deed: 348

Utilities

Heating & Cooling Information
Cooling: Attic Fan, Mini Split, Other
Heat: Oil, Baseboard, Hot Water, Multi Zone, Mini Split

Sewer Information
On-Site Septic Exists

Electric Information
Electric Company: GMP
220 Plug, Circuit Breaker(s), Energy Storage Device, Generator, On-Site

Water Information
Water Source: Drilled Well

Other Utilities Information
Internet: High Speed Intrnt -Avail
Cable Company: xfinity
Fuel Company: Cota & Cota Discount
Cable - Available, Gas - LP/Bottle, Telephone Available

Location

Road Information
Road Frontage Type: Cul-de-Sac, Paved, Public
Road Frontage: Yes
Road Frontage Length: 175

Other Location Information
Directions: RT 30 to Upper Dummerston Rd. to Hillwinds. Straight up to first house on right. Don't take Hillwinds North Rd right turn.

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 2,520
Stories: 2.0
Lot Size: 1.19 acres
Style: Single Family Residential
Year Built: 1974
Year Renovated: —
County: Windham County
APN: 08102513927

Home facts updated by county records on Jul 8, 2026

Other

Documents & Disclosures
Documents Available: Aerials, 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 • 2.8mi

6/10

Green Street School

Public PreK-6 • 3.3mi

8/10

Neighborhood Schoolhouse

Private PreK-8 • 2.9mi

Provided by GreatSchools

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 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

89/ 100

Very good sunlight

Sunscore

This home ranks in the top 18% for direct sun exposure in the zip code. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.1 hrs

5.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$585,000 – $709,000

Sell confidently with a local market expert in Brattleboro.

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Home values near 143 Hillwinds Rd

Data from public records.

Address	Redfin Estimate
122 Hillwinds Rd, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1330 Sq. Ft.	$418,929
161 Hillwinds Rd, Brattleboro, VT 4 Beds \| 4.5 Baths \| 2600 Sq. Ft.	$593,732

Address	Redfin Estimate
10 Hillwinds N, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1482 Sq. Ft.	$447,230
155 Hillwinds N, Brattleboro, VT 4 Beds \| 3.5 Baths \| 3685 Sq. Ft.	$878,302

Address	Redfin Estimate
148 Hillwinds N, Brattleboro, VT 3 Beds \| 3.5 Baths \| 3040 Sq. Ft.	$616,894
306 Hillwinds Rd, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2590 Sq. Ft.	$584,379

Property information provided by PrimeMLS when last listed in 2026. This data may not match . Learn more.

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143 Hillwinds Rd, Brattleboro, VT 05301

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About this home

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Market trends in 05301, VT

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Sale and tax history for 143 Hillwinds Rd

Public record

Property details

Parking

Interior

Exterior

Financial

Utilities

Location

Public facts

Other

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05301

Home values near 143 Hillwinds Rd

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