OFF MARKET

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

Off Market Dec 2016 for $330K

$591,142

Est. refi paymentEst. refi $2,103/mo

•

2,600

sq ft

161 Hillwinds Rd, Brattleboro, VT 05301

About this home

Great opportunity to own a fantastic home in Hillwinds and enjoy the summer cooling off in the beautiful in-ground pool! Hardwood floors grace most of the interior and there are many options for your family to spread out from the formal living room to the family room, 2 dens or the screen room out on the back deck. There is also a private accessory apartment above the garage that includes a bedroom, bath and living/partial kitchen area for in-laws or guests. Lovely gardens and flowering trees & shrubs surround the home, plus there is some lawn for the kids to play and a fenced dog pen for your pets. YouÃ¢ll enjoy the protection of having conserved land behind you and across the street. Like to hike, bike, snowshoe or cross country ski? The Hillwinds trails provide year round options for you and your family. Don't miss out on this fine home, make an appointment today! Sellers reserve right to remove some Peonies & Mountain Laurel.

Single-familyProperty Type

1975Year Built

1.09 acresLot Size

$227Est. Price/Sq.Ft.

2 car garageParking

Listed by Jane Sonntag • Berkley & Veller Greenwood Country

Bought with Wilma Skovinski • Berkley & Veller Greenwood Country

Redfin checked: a minute ago

•Source:PrimeMLS #4499319

Redfin Estimate

$591,142

$261K since sold in December 2016$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 22.8% higher than the average sale price ($481K) of 6 comparable homes.

SOLD JUN 26, 2026
$615,000
A
5 beds3.5 baths2,520 sq ft
143 Hillwinds Rd, Brattleboro, VT 05301
SOLD NOV 20, 2025
$476,000
B
4 beds3 baths2,372 sq ft
187 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 AUG 31, 2026
$395,000
E
4 beds2.5 baths2,100 sq ft
785 Brattleboro Rd, Hinsdale, NH 03451
SOLD MAY 26, 2026
$365,000
F
5 beds3 baths2,254 sq ft
85 Stockwell Dr, Brattleboro, VT 05301

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

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,805/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

OPEN SEP 7, 10:30AM TO 12:30PM
$149,900
3 beds2 baths1,232 sq ft
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NEW 10 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
$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
See all

Provided by Redfin

Sale history for 161 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,686 (−1.9%)

$66,800 + $285,270

$352,070

2024

$6,815 (+10.5%)

$66,800 + $285,270

$352,070

2023

$6,169 (−43.0%)

$66,800 + $285,270

$352,070

2022

$10,827 (+0.9%)

$66,800 + $285,270

$352,070

2021

$10,731 (+1.8%)

$66,800 + $285,270

$352,070

2020

$10,541 (+3.0%)

$66,800 + $285,270

$352,070

2019

$10,230 (+1.6%)

$66,800 + $285,270

$352,070

2018

$10,065 (+6.8%)

$66,800 + $285,270

$352,070

2017

$9,425

$66,800 + $285,270

$352,070

2016

$9,424 (+0.4%)

$66,800 + $285,270

$352,070

2015

$9,384 (−5.3%)

$66,800 + $285,270

$352,070

2014

$9,912

$66,800 + $285,270

$352,070

2013

$66,800 + $285,270

$352,070

Tax history for 161 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,686 (−1.9%)

$66,800 + $285,270

$352,070

2024

$6,815 (+10.5%)

$66,800 + $285,270

$352,070

2023

$6,169 (−43.0%)

$66,800 + $285,270

$352,070

2022

$10,827 (+0.9%)

$66,800 + $285,270

$352,070

2021

$10,731 (+1.8%)

$66,800 + $285,270

$352,070

2020

$10,541 (+3.0%)

$66,800 + $285,270

$352,070

2019

$10,230 (+1.6%)

$66,800 + $285,270

$352,070

2018

$10,065 (+6.8%)

$66,800 + $285,270

$352,070

2017

$9,425

$66,800 + $285,270

$352,070

2016

$9,424 (+0.4%)

$66,800 + $285,270

$352,070

2015

$9,384 (−5.3%)

$66,800 + $285,270

$352,070

2014

$9,912

$66,800 + $285,270

$352,070

2013

$66,800 + $285,270

$352,070

*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

4.5

Stories

Lot width

—

Lot depth

—

Lot size

1.09 Acres

Year renovated

—

Sq. Ft.

2,504

Year built

1975

Style

Single Family Residential

County

Windham County

APN

08102512450

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
Location: Attached
Auto Open
Driveway

Interior

Bathroom Information
# of Baths (full): 1
# of Baths (3/4): 3
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Bulkhead, Concrete, Full, Stairs - Interior, Storage Space, Unfinished

Other Interior Features
# of Rooms: 12
Flooring: Carpet, Ceramic Tile, Hardwood, Vinyl
Water Heater: Domestic, Off Boiler, Oil
Fireplace - Wood, Fireplaces - 1, Hearth, In-Law Apartment, Kitchen/Dining, Master Bedroom With Bath

Accessibility Information
1st Floor 3/4 Bathroom, 1st Floor Bedroom

Equipment & Appliance Information
Dishwasher, Dryer, Exhaust Hood, Microwave, Range - Electric, Refrigerator, Washer
Smoke Detectr-Battery Powered

Room 1 Information
Kitchen
Kitchen
Dimensions: 11'8x10'7
Level: 1

Room 2 Information
Dining Room
Dimensions: 10'6x13'4
Level: 1

Room 3 Information
Living Room
Dimensions: 13'4x15'7
Level: 1

Room 4 Information
Family Room
Dimensions: 11'11x18'8
Level: 1

Room 5 Information
Office/Study
Dimensions: 8'11x11'11
Level: 1

Room 6 Information
Utility Room
Utility Room
Dimensions: 9'2x9'11
Level: 1

Room 7 Information
Master Bedroom
Dimensions: 13'5x13'8
Level: 2

Room 8 Information
Bedroom
Dimensions: 10x14'8
Level: 2

Room 9 Information
Bedroom
Dimensions: 13'5'x13'8
Level: 2

Room 13 Information
Other
Dimensions: 9x9
Level: 2

Room 14 Information
Other
Dimensions: 12'2x17'10
Level: 2

Room 15 Information
Other
Dimensions: 11'8x13'4
Level: 1

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 2600
Approximate Sq. Ft. Total: 3900
Color: Cream
Deck, Fence - Dog, Pool - In Ground, Porch - Screened, Window Screens
Construction: Wood Frame
Foundation: Concrete
Roof: Metal, Shingle - Asphalt
Exterior: Clapboard

Driveway
Paved

Lot, Zoning, & Easement Information
Country Setting, Landscaped

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1975

Financial

Assessment Information
Assessment Amount: 352070

Tax Information
Tax Year: 2016
Gross Amount Tax: 9424
SPAN Number: 081-025-12450

Other Tax Information
Page Deed: 226

Utilities

Heating & Cooling Information
Heat: Baseboard, Hot Water, Stove - Wood
Heat Fuel: Oil, Wood

Sewer Information
1000 Gallon, Concrete, Leach Field

Electric Information
100 Amp, Circuit Breaker(s)

Water Information
Drilled Well, Private

Other Utilities Information
Cable, Internet - Cable

Location

Neighborhood Information
Abuts Conservation

Road Information
Road Frontage: Yes
Road Frontage Length: 173
Paved, Public

Other Location Information
Directions: Upper Dummerston Rd. to Hillwinds Rd, at top of hill, go straight to second house on right.

Public facts

Beds: 4
Baths: 4.5
Sq. Ft.: 2,504
Stories: 2.0
Lot Size: 1.09 acres
Style: Single Family Residential
Year Built: 1975
Year Renovated: —
County: Windham County
APN: 08102512450

Home facts updated by county records on Jul 8, 2026

Other

Documents & Disclosures
Documents Available: 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 • 2.8mi

6/10

Green Street School

Public PreK-6 • 3.3mi

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

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

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

$562,000 – $680,000

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

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Home values near 161 Hillwinds Rd

Data from public records.

Address	Redfin Estimate
122 Hillwinds Road, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1330 Sq. Ft.	$410,325
155 Hillwinds North, Brattleboro, VT 4 Beds \| 3.5 Baths \| 3685 Sq. Ft.	$878,866

Address	Redfin Estimate
10 Hillwinds North, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1482 Sq. Ft.	$431,846
306 Hillwinds Road, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2590 Sq. Ft.	$576,619

Address	Redfin Estimate
148 Hillwinds North, Brattleboro, VT 3 Beds \| 3.5 Baths \| 3040 Sq. Ft.	$616,916
297 Hillwinds Road, Brattleboro, VT 3 Beds \| 2 Baths \| 1408 Sq. Ft.	$423,931

Property information provided by PrimeMLS when last listed in 2016. 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 161 Hillwinds Rd

Tax history for 161 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 161 Hillwinds Rd

More real estate resources