OFF MARKET
Google street view image for 244 Hillwinds Rd, Brattleboro, VT 05301
OFF MARKET
$351,482
4
bd
•
1.5 ba
•
1,440
sq ft

244 Hillwinds Rd, Brattleboro, VT 05301

map-entry

About this home

244 Hillwinds Rd is a 1,440 square foot house on a 1.64 acre lot with 4 bedrooms and 1.5 bathrooms. Based on Redfin's Brattleboro data, we estimate the home's value is $351,482.
Single-familyProperty Type
1970Year Built
1.64 acresLot Size
$244Est. Price/Sq.Ft.
Source:Public Records

Redfin Estimate

$351,482
$7,000 since August

This home's estimate is 4.3% lower than the average sale price ($367K) of 6 comparable homes.

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

Earn from this home

Rent
$2,302/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
55

8 MoM

New listings for sale

Provided by Redfin

Sale history for 244 Hillwinds Rd

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

Tax history for 244 Hillwinds Rd

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

Zoning

RR

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

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 • 2.6mi

6/10
Green Street School

Public PreK-6 • 3.1mi

8/10
Neighborhood Schoolhouse

Private PreK-8 • 2.7mi

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)
30
15
33
16
48
28
60
38
67
48
79
57
85
63
80
56
75
52
63
40
49
32
35
20
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
$334,000 – $405,000

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

Nearby similar homes

$1,650,000
4 beds3.5 baths3,268 sq ft
161 Depot Rd, Williamsville, VT 05362
3D & VIDEO TOUR
$674,000
3 beds2 baths1,660 sq ft
85 Brown's Rd, Newfane, VT 05345
NEW 33 HRS AGO
$395,000
2 beds2 baths1,400 sq ft
215 Gilbert Rd, Marlboro, VT 05344
$299,000
3 beds2 baths1,400 sq ft
68 E Bonnyvale Ln, Brattleboro, VT 05301
$340,000
4 beds2 baths2,745 sq ft
120 Western Ave, Brattleboro, VT 05301
$375,000
4 beds2.5 baths2,066 sq ft
313 Dover Rd, Newfane, VT 05345

New listings for sale in 05301

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 33 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

Home values near 244 Hillwinds Rd

Data from public records.

More real estate resources

Wilmington homes for sale
Keene homes for sale
Greenfield homes for sale
Download the Redfin App on the Apple App Store
Download the Redfin App from the Google Play Store

Join us

Become an Agent
Get referrals
Careers

Find homes faster

Download the Redfin App on the Apple App Store
Download the Redfin App from the Google Play Store

About us

Why Redfin?
Community Impact
Inclusion
Culture
Press
Investors
Blog
Real Estate News

Find us

Contact Us
Help Center
Advertise

Subsidiaries

Rent.
ApartmentGuide

Affiliated Business

Rocket Close
Rocket Mortgage

Countries

US flagUnited States

Canadian flagCanada

Copyright: © 2026 Redfin. All rights reserved.

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.