Listed by Jane Sonntag • Berkley & Veller Greenwood Country. Bought with Brattleboro Area Realty.

Off Market Aug 2014 for $370K

$592,773

Est. refi paymentEst. refi $2,355/mo

•

3,010

sq ft

288 Hillwinds Rd, Brattleboro, VT 05301

About this home

Long mountain views abound from the main living spaces of this bright and airy home in the Hillwinds area, on a paved, city plowed, road. This home is single-level living if preferred, but the master/ guest suite is privately situated upstairs. The lower level has a large, bright, finished, multi-purpose (office, game room, studio, gym) with it's own entrance. Rooms are spacious and have large double paned Andersen windows and hardwood floors. A deck off the family room overlooks the back yard and the mountain views. This home is in excellent shape, lovingly maintained, and is move-in ready. You'll have the security provided by the 15 KW whole house, propane powered generator. You'll enjoy having a little over one acre with professionally landscaped gardens, and the home sits at the edge of a large parcel of conserved farmland. As a plus, with the Hillwinds Association land trust, there are over 200 acres of forest & trails. Sale contingent upon sellers finding suitable housing.

Single-familyProperty Type

1974Year Built

1.17 acresLot Size

$197Est. Price/Sq.Ft.

2 car garageParking

Listed by Jane Sonntag • Berkley & Veller Greenwood Country

Bought with Victoria Woods • Brattleboro Area Realty

Redfin checked: 2 minutes ago

•Source:PrimeMLS #4340446

Redfin Estimate

$592,773

$223K since sold in August 2014$17K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 27.6% higher than the average sale price ($465K) of 6 comparable homes.

SOLD DEC 29, 2025
$495,000
A
3 beds2.5 baths3,415 sq ft
23 Meetinghouse Ln, Brattleboro, VT 05301
SOLD JUN 26, 2026
$615,000
B
5 beds3.5 baths2,520 sq ft
143 Hillwinds Rd, Brattleboro, VT 05301
SOLD APR 10, 2026
$497,408
C
4 beds2 baths2,656 sq ft
204 Meetinghouse Ln, Brattleboro, VT 05301
SOLD JUL 31, 2026
$320,000
D
3 beds2 baths1,703 sq ft
1089 Marlboro Rd, Brattleboro, VT 05301
SOLD NOV 20, 2025
$476,000
E
4 beds3 baths2,372 sq ft
187 Hillwinds Rd, Brattleboro, VT 05301
SOLD JUN 1, 2026
$385,000
F
3 beds2.5 baths2,128 sq ft
135 Country Hl, Brattleboro, VT 05301

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Earn from this home

Refinance

Est. cash available

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Rent

$3,167/mo

Redfin rental estimate

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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

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$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
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See all

Provided by Redfin

Sale history for 288 Hillwinds Rd

Date

Event

Price

PrimeMLS #4340446

Aug 14, 2014

Sold

$370,000

$123/sq ft

Mar 7, 2014

Listed

$395,000

$131/sq ft

PrimeMLS #4001772

May 20, 2011

Sold

$310,000

$103/sq ft

May 27, 2010

Listed

$337,500

$112/sq ft

Motivated Seller! Check this one out even if it is a bit above your price range! This contemporary style home enjoys large airy rooms with lots of windows looking out to a private back yard and view over conserved Retreat Farm land. Most of the home is single level living except for the 2nd floor master suite and a partly finished lower level. The kitchen is spacious and open to the formal dining room, the living room has a fireplace and the family room opens to a private back deck. The first floor also has 2 bedrooms, an open concept office area and a full bath with laundry hookups. The neighborhood benefits from the abutting 207 acre Hillwinds Conservation Lands that has lots of trails for hiking, biking and cross country skiing! This is a great opportunity. Sale is subject to tenants rights and notice is needed for showings. Homestead taxes = $9,325+/-. Submit All Offers.

Year

Property tax

Land + Additions

Assessment*

2025

$6,021 (−1.9%)

$68,400 + $248,630

$317,030

2024

$6,136 (+10.5%)

$68,400 + $248,630

$317,030

2023

$5,555 (−43.0%)

$68,400 + $248,630

$317,030

2022

$9,749 (+0.9%)

$68,400 + $248,630

$317,030

2021

$9,663 (+1.8%)

$68,400 + $248,630

$317,030

2020

$9,492 (+3.0%)

$68,400 + $248,630

$317,030

2019

$9,212 (+1.6%)

$68,400 + $248,630

$317,030

2018

$9,063 (+1.4%)

$68,400 + $248,630

$317,030

2017

$8,937 (+0.2%)

$68,400 + $248,630

$317,030

2016

$8,916 (−0.9%)

$68,400 + $248,630

$317,030

2015

$8,996 (+0.8%)

$68,400 + $248,630

$317,030

2014

$8,926

$68,400 + $248,630

$317,030

Tax history for 288 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,021 (−1.9%)

$68,400 + $248,630

$317,030

2024

$6,136 (+10.5%)

$68,400 + $248,630

$317,030

2023

$5,555 (−43.0%)

$68,400 + $248,630

$317,030

2022

$9,749 (+0.9%)

$68,400 + $248,630

$317,030

2021

$9,663 (+1.8%)

$68,400 + $248,630

$317,030

2020

$9,492 (+3.0%)

$68,400 + $248,630

$317,030

2019

$9,212 (+1.6%)

$68,400 + $248,630

$317,030

2018

$9,063 (+1.4%)

$68,400 + $248,630

$317,030

2017

$8,937 (+0.2%)

$68,400 + $248,630

$317,030

2016

$8,916 (−0.9%)

$68,400 + $248,630

$317,030

2015

$8,996 (+0.8%)

$68,400 + $248,630

$317,030

2014

$8,926

$68,400 + $248,630

$317,030

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

1.17 Acres

Year renovated

—

Sq. Ft.

2,652

Year built

1974

Style

Single Family Residential

County

Windham County

APN

08102514685

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
Auto Open, Driveway, Detached

Interior

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

Basement Information
Basement: Yes
Basement Access: Interior
Crawl Space, Daylight, Partial, Partially Finished, Stairs - Interior, Storage Space, Sump Pump

Other Interior Features
# of Rooms: 9
Flooring: Carpet, Ceramic Tile, Hardwood
Ceiling Fan, Kitchen/Dining, Master Bedroom With Bath, Vaulted Ceiling, Walk-in Closet, Walk-in Pantry, Laundry - 1st Floor

Accessibility Information
1st Floor 1/2 Bathroom, 1st Floor Bedroom, 1st Floor Full Bathroom, Access Laundry No Steps

Equipment & Appliance Information
Dishwasher, Dryer, Range - Electric, Refrigerator, Washer, Water Heater - Electric, Water Heater - Owned
Window AC, Dehumidifier, Smoke Detectr-Battery Powered, Smoke Detectr-Hard Wired With Battery

Room 1 Information
Kitchen
Kitchen
Dimensions: 11'2x10
Level: 1

Room 2 Information
Dining Room
Dimensions: 14'7x11'2
Level: 1

Room 3 Information
Living Room
Dimensions: 15'6x25'3
Level: 1

Room 4 Information
Family Room
Dimensions: 24x15

Room 7 Information
Master Bedroom
Dimensions: 15'5x15'5
Level: 2

Room 8 Information
Bedroom
Dimensions: 11'5x11'9
Level: 1

Room 9 Information
Bedroom
Dimensions: 11'10x15
Level: 1

Room 13 Information
Other
Dimensions: 9'9x11'5
Level: 1

Room 14 Information
Other
Dimensions: 24x15
Level: Basement

Exterior

Building Information
Architectural Style: Contemporary
Construction Status: Existing
Construction Materials: Wood Frame, T1-11 Exterior
Approximate Sq. Ft. Total Finished: 3010
Deck, Fence - Invisible Pet, Shed, Window Screens
Foundation: Concrete
Roof: Shingle - Asphalt

Driveway
Paved

Lot, Zoning, & Easement Information
Lot Features: Landscaped, Mountain View, Trail/Near Trail, View, Walking Trails

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1974

Financial

Tax Information
Tax Year: 2014
Gross Amount Tax: 8996.04
SPAN Number: 08102514685

Other Tax Information
Page Deed: 645

Financing Information
Conventional

Utilities

Heating & Cooling Information
Cooling: Central AC
Heat: Hot Air, Stove - Wood
Heat Fuel: Oil, Wood

Sewer Information
1000 Gallon, Concrete, Leach Field, Private, Septic

Electric Information
100 Amp, Circuit Breaker(s), Generator

Water Information
Water Source: Drilled Well, Private

Other Utilities Information
Internet: Internet - Cable
Cable

Location

Homeowners Association
Recreation

School Information
School District: Brattleboro School District
Elementary School: Brattleboro Elem Schools
Elementary School: Brattleboro Elem Schools
Middle/Jr School: Brattleboro Area Middle School
School - High: Brattleboro High School

Neighborhood Information
Abuts Conservation

Road Information
Road Frontage: Yes
Road Frontage Length: 185
Paved, Public

Other Location Information
Directions: From Brattleboro - RT 30 to Upper Dummerston Rd., follow to Hillwinds on left. At top of hill, bear left and follow to 288 on left.

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,652
Stories: 2.0
Lot Size: 1.17 acres
Style: Single Family Residential
Year Built: 1974
Year Renovated: —
County: Windham County
APN: 08102514685

Home facts updated by county records on Jul 8, 2026

Other

Documents & Disclosures
Documents Available: Building Permit, Deed, Plot Plan, Property Disclosure

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)

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

$564,000 – $682,000

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

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Home values near 288 Hillwinds Rd

Data from public records.

Address	Redfin Estimate
357 Hillwinds Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 2180 Sq. Ft.	$461,092
335 Hillwinds Rd, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2544 Sq. Ft.	$556,962

Address	Redfin Estimate
122 Hillwinds Rd, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1330 Sq. Ft.	$410,325
161 Hillwinds Rd, Brattleboro, VT 4 Beds \| 4.5 Baths \| 2600 Sq. Ft.	$591,142

Address	Redfin Estimate
336 Hillwinds Rd, Brattleboro, VT 4 Beds \| 3 Baths \| 3257 Sq. Ft.	$736,857
306 Hillwinds Rd, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2590 Sq. Ft.	$576,619

Property information provided by PrimeMLS when last listed in 2014. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05301, VT

Sale history for 288 Hillwinds Rd

Tax history for 288 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 288 Hillwinds Rd

More real estate resources