OFF MARKET

Listed by Robert Doyle • Berkley & Veller Greenwood Country. Bought with Berkley & Veller Greenwood Country.

Off Market Dec 2005 for $295K

$435,622

Est. refi paymentEst. refi $1,243/mo

•

1,720

sq ft

414 Hillwinds, Brattleboro, VT 05301

About this home

Single-familyProperty Type

1974Year Built

1 acresLot Size

$253Est. Price/Sq.Ft.

1 car garageParking

Listed by Robert Doyle • Berkley & Veller Greenwood Country

Bought with Robert Hinrichs • Berkley & Veller Greenwood Country

Redfin checked: 3 minutes ago

•Source:PrimeMLS #3023067

Redfin Estimate

$435,622

$141K since sold in December 2005$5,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 23.8% higher than the average sale price ($352K) of 6 comparable homes.

SOLD JUL 31, 2026
$320,000
A
3 beds2 baths1,703 sq ft
1089 Marlboro Rd, Brattleboro, VT 05301
SOLD DEC 17, 2025
$335,000
B
3 beds2 baths1,728 sq ft
290 Guilford St, Brattleboro, VT 05301
SOLD AUG 12, 2026
$317,000
C
3 beds1 bath1,522 sq ft
69 Carriage Hill Rd, Brattleboro, VT 05301
SOLD JUN 26, 2026
$330,000
D
3 beds2 baths1,521 sq ft
255 Guilford St, Brattleboro, VT 05301
SOLD MAY 13, 2026
$439,000
E
4 beds2 baths1,568 sq ft
387 Meadow Brook Rd, Brattleboro, VT 05301
SOLD APR 2, 2026
$370,000
F
3 beds2 baths1,820 sq ft
115 Country Hl, Brattleboro, VT 05301

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Earn from this home

Refinance

Est. cash available

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Rent

$2,780/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

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
$289,000
2 beds1 bath925 sq ft
45 Kopkind Rd, Guilford, VT 05301
See all

Provided by Redfin

Sale history for 414 Hillwinds

Date

Event

Price

PrimeMLS #3023067

Dec 9, 2005

Sold

$295,000

$172/sq ft

Sep 29, 2005

Listed

$297,500

$173/sq ft

PrimeMLS #3004322

Nov 2, 2000

Sold

$195,000

$113/sq ft

Aug 30, 2000

Listed

$197,500

$115/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$4,354 (−1.9%)

$65,000 + $164,250

$229,250

2024

$4,437 (+20.6%)

$65,000 + $164,250

$229,250

2023

$3,680 (−44.9%)

$65,000 + $164,250

$229,250

2022

$6,676 (−0.9%)

$65,000 + $164,250

$229,250

2021

$6,739 (+1.3%)

$65,000 + $164,250

$229,250

2020

$6,652 (+3.8%)

$65,000 + $164,250

$229,250

2019

$6,410 (−2.2%)

$65,000 + $164,250

$229,250

2018

$6,554 (+1.4%)

$65,000 + $164,250

$229,250

2017

$6,463 (+0.2%)

$65,000 + $164,250

$229,250

2016

$6,447 (−0.9%)

$65,000 + $164,250

$229,250

2015

$6,505 (+0.8%)

$65,000 + $164,250

$229,250

2014

$6,454

$65,000 + $164,250

$229,250

2013

$65,000 + $164,250

$229,250

Tax history for 414 Hillwinds

Year

Property tax

Land + Additions

Assessment*

2025

$4,354 (−1.9%)

$65,000 + $164,250

$229,250

2024

$4,437 (+20.6%)

$65,000 + $164,250

$229,250

2023

$3,680 (−44.9%)

$65,000 + $164,250

$229,250

2022

$6,676 (−0.9%)

$65,000 + $164,250

$229,250

2021

$6,739 (+1.3%)

$65,000 + $164,250

$229,250

2020

$6,652 (+3.8%)

$65,000 + $164,250

$229,250

2019

$6,410 (−2.2%)

$65,000 + $164,250

$229,250

2018

$6,554 (+1.4%)

$65,000 + $164,250

$229,250

2017

$6,463 (+0.2%)

$65,000 + $164,250

$229,250

2016

$6,447 (−0.9%)

$65,000 + $164,250

$229,250

2015

$6,505 (+0.8%)

$65,000 + $164,250

$229,250

2014

$6,454

$65,000 + $164,250

$229,250

2013

$65,000 + $164,250

$229,250

*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

Stories

Lot width

—

Lot depth

—

Lot size

1 Acre

Year renovated

—

Sq. Ft.

1,504

Year built

1974

Style

Single Family Residential

County

Windham County

APN

08102513912

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: 1
Location: Attached
Auto Open

Interior

Bathroom Information
# of Baths (full): 2

Basement Information
Basement Access: Walkout
Full, Other

Other Interior Features
# of Rooms: 7
Flooring: Carpet, Hardwood, Vinyl
Water Heater: Domestic
Fireplace - Wood, Fireplaces - 1, Kitchen Island

Equipment & Appliance Information
Dishwasher, Disposal, Dryer, Microwave, Range - Electric, Refrigerator, Washer

Room 1 Information
Kitchen
Kitchen
Dimensions: 18x11`6
Level: 1

Room 2 Information
Dining Room
Dimensions: 12`2x8`8
Level: 1

Room 3 Information
Living Room
Dimensions: 18x12`6
Level: 1

Room 4 Information
Family Room
Dimensions: 13`6x12`6
Level: 1

Room 7 Information
Master Bedroom
Dimensions: 13x18
Level: 2

Room 8 Information
Bedroom
Dimensions: 13x18
Level: 2

Room 9 Information
Bedroom
Dimensions: 12`6x10
Level: 1

Room 16 Information
Full Bath
Level: 1

Room 17 Information
Full Bath
Level: 2

Exterior

Building Information
Approximate Sq. Ft. Total Finished: 1720
Color: GREY
Deck
Foundation: Concrete
Roof: Shingle - Other
Exterior: Clapboard

Driveway
Paved

Lot, Zoning, & Easement Information
Common Land Acres: 0

Other Property & Lot Information
Year Built: 1974

Financial

Tax Information
Tax Year: 2005
Gross Amount Tax: 4604

Financing Information
Cash Only

Utilities

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

Sewer Information
Septic

Electric Information
Circuit Breaker(s)

Water Information
Drilled Well

Location

School Information
Elementary School: Brattleboro Elem Schools
Elementary School: Brattleboro Elem Schools

Road Information
Road Frontage: Yes
Road Frontage Length: 0
Cul-de-Sac

Other Location Information
Directions: At the very end of Hillwinds Road.
Development / Subdivision: None (Bratt)

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 1,504
Stories: 2.0
Lot Size: 1 acres
Style: Single Family Residential
Year Built: 1974
Year Renovated: —
County: Windham County
APN: 08102513912

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 • 2.3mi

6/10

Green Street School

Public PreK-6 • 2.8mi

8/10

Neighborhood Schoolhouse

Private PreK-8 • 2.4mi

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

2/10 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

$414,000 – $501,000

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

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Home values near 414 Hillwinds

Data from public records.

Address	Redfin Estimate
357 Hillwinds Road, Brattleboro, VT 3 Beds \| 2 Baths \| 2180 Sq. Ft.	$461,092
409 Hillwinds Road, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1638 Sq. Ft.	$412,987

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

Address	Redfin Estimate
335 Hillwinds Road, Brattleboro, VT 4 Beds \| 3.5 Baths \| 2544 Sq. Ft.	$556,962
297 Hillwinds Road, Brattleboro, VT 3 Beds \| 2 Baths \| 1408 Sq. Ft.	$423,931

Property information provided by PrimeMLS when last listed in 2005. 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 414 Hillwinds

Tax history for 414 Hillwinds

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 414 Hillwinds

More real estate resources