OFF MARKET

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

Off Market Nov 2016 for $357K

$614,635

Est. refi paymentEst. refi $2,275/mo

•

2,445

sq ft

177 Hillwinds Rd, Brattleboro, VT 05301

About this home

Wow! If you are looking for a great neighborhood this is it! This home is uniquely situated between conservation land, a small meadow in the front and acres of pond, walking trails and preserved woodland in the back! The home itself has been meticulously maintained and upgraded with style and grace. With an open concept kitchen/dining/family room, 2 sided fireplace and lovely cherry handcrafted built-ins, the central living area is just right for the now lifestyle! First floor bedroom to accommodate aging in place, and a 2nd floor master that is a great size with en suite dressing area and private bath. Spend the summer on the private back deck with in-ground pool for lovely long lazy days. a must see for anyone looking for quality and lifestyle.

Single-familyProperty Type

1974Year Built

1.36 acresLot Size

$251Est. Price/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 #4495215

Redfin Estimate

$614,635

$257K since sold in November 2016$7,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 18.8% higher than the average sale price ($517K) of 6 comparable homes.

SOLD APR 10, 2026
$497,408
A
4 beds2 baths2,656 sq ft
204 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 JUN 30, 2026
$580,000
C
4 beds2.5 baths2,573 sq ft
11 Strawberry Hl, Brattleboro, VT 05301
SOLD AUG 31, 2026
$395,000
D
4 beds2.5 baths2,100 sq ft
785 Brattleboro Rd, Hinsdale, NH 03451
SOLD NOV 20, 2025
$476,000
E
4 beds3 baths2,372 sq ft
187 Hillwinds Rd, Brattleboro, VT 05301
SOLD AUG 19, 2026
$540,000
F
4 beds3 baths2,240 sq ft
3333 W River Rd, Dummerston, VT 05301

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,166/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

NEW 8 HRS AGO
$830,000
5 beds5.5 baths5,064 sq ft
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OPEN SEP 7, 10:30AM TO 12:30PM
$149,900
3 beds2 baths1,232 sq ft
14 Deepwood Park, Brattleboro, VT 05301
NEW 34 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 177 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,770 (−1.9%)

$72,200 + $284,310

$356,510

2024

$6,901 (+10.5%)

$72,200 + $284,310

$356,510

2023

$6,246 (−43.0%)

$72,200 + $284,310

$356,510

2022

$10,963 (+0.9%)

$72,200 + $284,310

$356,510

2021

$10,867 (+1.8%)

$72,200 + $284,310

$356,510

2020

$10,674 (+3.0%)

$72,200 + $284,310

$356,510

2019

$10,359 (+1.6%)

$72,200 + $284,310

$356,510

2018

$10,192 (+8.6%)

$72,200 + $284,310

$356,510

2017

$9,385 (−4.8%)

$72,200 + $278,370

$350,570

2016

$9,860 (−0.9%)

$72,200 + $278,370

$350,570

2015

$9,947 (+0.8%)

$72,200 + $278,370

$350,570

2014

$9,870

$72,200 + $278,370

$350,570

2013

$72,200 + $278,370

$350,570

Tax history for 177 Hillwinds Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,770 (−1.9%)

$72,200 + $284,310

$356,510

2024

$6,901 (+10.5%)

$72,200 + $284,310

$356,510

2023

$6,246 (−43.0%)

$72,200 + $284,310

$356,510

2022

$10,963 (+0.9%)

$72,200 + $284,310

$356,510

2021

$10,867 (+1.8%)

$72,200 + $284,310

$356,510

2020

$10,674 (+3.0%)

$72,200 + $284,310

$356,510

2019

$10,359 (+1.6%)

$72,200 + $284,310

$356,510

2018

$10,192 (+8.6%)

$72,200 + $284,310

$356,510

2017

$9,385 (−4.8%)

$72,200 + $278,370

$350,570

2016

$9,860 (−0.9%)

$72,200 + $278,370

$350,570

2015

$9,947 (+0.8%)

$72,200 + $278,370

$350,570

2014

$9,870

$72,200 + $278,370

$350,570

2013

$72,200 + $278,370

$350,570

*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

2.25

Stories

Lot width

—

Lot depth

—

Lot size

59,241

Year renovated

—

Sq. Ft.

2,445

Year built

1974

Style

Single Family Residential

County

Windham County

APN

08102513934

Parking Spaces

Basement

Yes

Accessible

Yes

HOA Dues

—

Garage

Yes

Features

—

Last updated by owner on Jul 17, 2022.

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, Direct Entry, Storage Above
Driveway

Interior

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

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

Other Interior Features
# of Rooms: 8
Flooring: Hardwood, Laminate
Water Heater: Domestic
Blinds, Cathedral Ceiling, Ceiling Fan, Dining Area, Draperies, Fireplace - Gas, Fireplace - Screens/Equip, Fireplace - Wood, Fireplaces - 2, Hearth, Kitchen Island, Kitchen/Dining, Laundry Hook-ups, Master Bedroom With Bath, Skylight, Vaulted Ceiling, Window Treatment, Wood Stove Hook-up

Accessibility Information
1st Floor 1/2 Bathroom, 1st Floor Full Bathroom, 1st Floor Hrd Surfce Flor, 1st Floor Low-Pile Carpet, Bathroom w/Step-in Shower, Bathroom w/Tub

Equipment & Appliance Information
Disposal, Dryer, Microwave, Range - Electric, Refrigerator, Washer
Air Conditioner, Window AC, Carbon Monoxide Detector, Dehumidifier, Smoke Detector, Smoke Detectr-Battery Powered

Room 1 Information
Kitchen
Kitchen
Dimensions: 14x12
Level: 1

Room 2 Information
Dining Room
Dimensions: 18x13
Level: 1

Room 3 Information
Living Room
Dimensions: 13x18
Level: 1

Room 4 Information
Family Room
Dimensions: 18x13
Level: 1

Room 5 Information
Office/Study
Level: 1

Room 7 Information
Master Bedroom
Dimensions: 13x17
Level: 2

Room 8 Information
Bedroom
Dimensions: 12x18
Level: 2

Room 9 Information
Bedroom
Dimensions: 14x14
Level: 2

Room 10 Information
Bedroom
Dimensions: 12x11
Level: 1

Room 13 Information
Other
Dimensions: 09x08
Level: 2

Room 14 Information
Other
Dimensions: 06x08
Level: 2

Room 15 Information
Other
Dimensions: 05x05
Level: 1

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 2445
Approximate Sq. Ft. Total: 3525
Color: red
Deck, Outbuilding, Pool - In Ground, Shed, Window Screens
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle - Asphalt
Exterior: Clapboard, Wood

Driveway
Paved

Lot, Zoning, & Easement Information
Country Setting, Landscaped, Level, Sloping, Walking Trails

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1974

Financial

Tax Information
Tax Year: 2015
Gross Amount Tax: 9947.77
SPAN Number: 08102513934

Other Tax Information
Page Deed: 112

Financing Information
Conventional, Portfolio, VA

Utilities

Heating & Cooling Information
Cooling: Multi Zone
Heat: Baseboard, Hot Water, Multi Zone
Heat Fuel: Oil

Sewer Information
Private, Septic

Electric Information
Circuit Breaker(s)

Water Information
Drilled Well, Private

Other Utilities Information
Cable, Internet - Cable

Location

School Information
Elementary School: Brattleboro Elem Schools
Elementary School: Brattleboro Elem Schools
Middle/Jr School: Brattleboro Area Middle School

Neighborhood Information
Abuts Conservation

Road Information
Road Frontage: Yes
Road Frontage Length: 137
Paved, Public

Other Location Information
Directions: RT 30 to Upper Dummerston Rd to HIllwinds, straight ahead @ intersection to sign on right

Public facts

Beds: 4
Baths: 2.25
Sq. Ft.: 2,445
Stories: 2.0
Parking Spaces: 2
Basement: Yes
Accessible: Yes
Lot Size: 1.36 acres
Style: Single Family Residential
Year Built: 1974
Year Renovated: —
County: Windham County
APN: 08102513934
HOA Dues: —
Garage: Yes
Features: —

Home facts updated by owner on Jul 17, 2022

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 • 2.7mi

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

$584,000 – $707,000

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

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Home values near 177 Hillwinds Rd

Data from public records.

Address	Redfin Estimate
122 Hillwinds Road, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1330 Sq. Ft.	$410,325
336 Hillwinds Road, Brattleboro, VT 4 Beds \| 3 Baths \| 3257 Sq. Ft.	$736,857

Address	Redfin Estimate
10 Hillwinds North, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1482 Sq. Ft.	$431,846
335 Hillwinds Road, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2544 Sq. Ft.	$556,962

Address	Redfin Estimate
148 Hillwinds North, Brattleboro, VT 3 Beds \| 3.5 Baths \| 3040 Sq. Ft.	$616,916
161 Hillwinds Road, Brattleboro, VT 4 Beds \| 4.5 Baths \| 2600 Sq. Ft.	$591,142

Property information provided by PrimeMLS when last listed in 2016. This data may not show owner updates. 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 177 Hillwinds Rd

Tax history for 177 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 177 Hillwinds Rd

More real estate resources