Google street view image for 66 Highlawn Rd, Brattleboro, VT 05301

OFF MARKET

$511,442

•

4 ba

•

3,850

sq ft

66 Highlawn Rd, Brattleboro, VT 05301

About this home

66 Highlawn Rd is a 3,850 square foot property on a 0.27 acre lot with 8 bedrooms and 4 bathrooms. Based on Redfin's Brattleboro data, we estimate the home's value is $511,442.

1890Year Built

0.27 acresLot Size

$133Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$511,442

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 21.5% higher than the average sale price ($421K) of 6 comparable homes.

SOLD JUL 30, 2026
$495,000
A
4 beds2.5 baths2,874 sq ft
41 Chapin St, Brattleboro, VT 05301
SOLD MAR 12, 2026
$408,065
B
4 beds3 baths3,314 sq ft
76 Spruce St, Brattleboro, VT 05301
SOLD AUG 14, 2026
$339,000
C
4 beds2 baths2,250 sq ft
65 Cedar St, Brattleboro, VT 05301
SOLD JUL 30, 2026
$493,000
D
3 beds2.5 baths2,400 sq ft
30 Chapin St, Brattleboro, VT 05301
SOLD FEB 19, 2026
$450,000
E
4 beds2.5 baths1,887 sq ft
230 Western Ave, Brattleboro, VT 05301
SOLD JAN 27, 2026
$341,000
F
4 beds3 baths1,668 sq ft
7 Union St, Brattleboro, VT 05301

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

Market trends in 05301, VT

Last updated July 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

99.2%

+2.1% MoM

Median sale price

$385K

$5K MoM

Avg. days on market

50d

9 days MoM

Recently sold homes

14 MoM

New listings for sale

$299,000
6 beds3 baths3,125 sq ft
75 Moreland Ave, Brattleboro, VT 05301
$16,900
2 beds1 bath672 sq ft
11 Crescent Dr, 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 Rd, Guilford, VT 05301
$290,000
5 beds1.5 baths2,167 sq ft
207 Elliot St, Brattleboro, VT 05301
See all

Provided by Redfin

Sale history for 66 Highlawn Rd

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2025

$4,522 (−2.1%)

$52,800 + $196,800

$249,600

2024

$4,617 (+11.2%)

$52,800 + $196,800

$249,600

2023

$4,153 (−44.1%)

$52,800 + $196,800

$249,600

2022

$7,431 (−0.2%)

$52,800 + $196,800

$249,600

2021

$7,445 (+1.5%)

$52,800 + $196,800

$249,600

2020

$7,334 (+3.5%)

$52,800 + $196,800

$249,600

2019

$7,088 (+0.8%)

$52,800 + $196,800

$249,600

2018

$7,033 (+3.1%)

$52,800 + $196,800

$249,600

2017

$6,823 (+0.1%)

$52,800 + $196,800

$249,600

2016

$6,816 (−0.1%)

$52,800 + $196,800

$249,600

2015

$6,824 (+0.2%)

$52,800 + $196,800

$249,600

2014

$6,812

$52,800 + $196,800

$249,600

2013

$52,800 + $196,800

$249,600

Tax history for 66 Highlawn Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,522 (−2.1%)

$52,800 + $196,800

$249,600

2024

$4,617 (+11.2%)

$52,800 + $196,800

$249,600

2023

$4,153 (−44.1%)

$52,800 + $196,800

$249,600

2022

$7,431 (−0.2%)

$52,800 + $196,800

$249,600

2021

$7,445 (+1.5%)

$52,800 + $196,800

$249,600

2020

$7,334 (+3.5%)

$52,800 + $196,800

$249,600

2019

$7,088 (+0.8%)

$52,800 + $196,800

$249,600

2018

$7,033 (+3.1%)

$52,800 + $196,800

$249,600

2017

$6,823 (+0.1%)

$52,800 + $196,800

$249,600

2016

$6,816 (−0.1%)

$52,800 + $196,800

$249,600

2015

$6,824 (+0.2%)

$52,800 + $196,800

$249,600

2014

$6,812

$52,800 + $196,800

$249,600

2013

$52,800 + $196,800

$249,600

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

Zoning

Residential Neighborhood District

The Residential Neighborhood District is composed of high- to moderate-density residential neighborhoods extending outward from downtown Brattleboro and West Brattleboro village, and along the Route 9 corridor. While primarily residential in use, these neighborhoods vary significantly in the form and density of housing they offer, and include traditional neighborhoods, post-war suburban-style neighborhoods, multi-family developments, townhouses and mobile home parks. The land within this district is generally served by municipal water and sewer. Walkability and proximity to public transit service, neighborhood stores, schools, parks and other amenities varies by neighborhood. The purpose of this district is to allow a diverse range of housing, encourage an increase in and improvement of the town’s housing stock, and promote more compact, walkable neighborhoods in balance with protection of neighborhood character and quality of life, and in accordance with the policies of the Brattleboro Town Plan.

Property details

Interior

Basement Information
Basement Type: Full

Bathroom Information
# of Full Baths: 4

Room Information
# of Rooms: 18

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Multi-Family
Construction Type: Frame
Exterior Wall: Vinyl
Building Type: Apartment

Property Information
Living Sq. Ft: 3,850
Gross Sq. Ft: 3,850
Building Sq. Ft: 3,850
# of Stories: 2
Legal Description: DWELLING 4 UNIT/GARAGE/LAND

Parking & Garage Information
Parking Type: Detached Garage
Garage / Carport Type: Detached

Lot Information
# of Buildings: 1
Land Sq. Ft: 11,761
Municipality Name: BRATTLEBORO
Acres: 0.27
County Use Description: RESIDENTIAL < 6 ACRES

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 8
Baths: 4.0
Sq. Ft.: 3,850
Stories: 2.0
Lot Size: 0.27 acres
Style: Other
Year Built: 1890
Year Renovated: —
County: Windham County
APN: 08102515515

Home facts updated by county records on Jul 8, 2026

Around this home

Schools

Neighborhood Schoolhouse

Private PreK-8 • 0.2mi

Austine School for the Deaf

Private 2-12 • 0.5mi

William Center At Austine

Private 7-12 • 0.5mi

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

10% 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

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$486,000 – $589,000

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

Nearby similar homes

$399,000

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New listings for sale in 05301

$299,000

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75 Moreland Ave, Brattleboro, VT 05301

$16,900

2 beds1 bath672 sq ft

11 Crescent Dr, Brattleboro, VT 05301

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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

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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 Rd, Guilford, VT 05301

Home values near 66 Highlawn Rd

Data from public records.

Address	Redfin Estimate
34 Highlawn Rd, Brattleboro, VT 2 Beds \| 2 Baths \| 2118 Sq. Ft.	$385,028
42 Highlawn Rd, Brattleboro, VT 4 Beds \| 1.5 Baths \| 1127 Sq. Ft.	$361,168

Address	Redfin Estimate
58 Highlawn Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 1568 Sq. Ft.	$361,688
81 Highlawn Rd, Brattleboro, VT 2 Beds \| 1.5 Baths \| 1288 Sq. Ft.	$299,815

Address	Redfin Estimate
65 Highlawn Rd, Brattleboro, VT 4 Beds \| 1 Baths \| 1718 Sq. Ft.	$358,702
33 Highlawn Rd, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1600 Sq. Ft.	$352,656

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Market trends in 05301, VT

Sale history for 66 Highlawn Rd

Tax history for 66 Highlawn Rd

Zoning

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 66 Highlawn Rd

More real estate resources