74 Winchester Road Rd, Brattleboro, VT 05358

Listed by Deborah Quigley • Palmiter Realty Group. Bought with Barrett and Valley Associates Inc.

Off market may 2005 for $600K

$880,762

•

4,000

sq ft

74 Winchester Road Rd, Brattleboro, VT 05358

About this home

Single-familyProperty Type

1976Year Built

100 acresLot Size

$220Est. Price/Sq.Ft.

2 car garageParking

Listed by Deborah Quigley • Palmiter Realty Group

Bought with Susan LeCours • Barrett and Valley Associates Inc.

Redfin checked: 2 minutes ago

•Source:PrimeMLS #3103042

Redfin Estimate

$880,762

$281K since sold in May 2005$7,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.7% higher than the average sale price ($833K) of 6 comparable homes.

SOLD OCT 21, 2026
$1,850,000
A
5 beds4.5 baths4,200 sq ft
32 Steep Hill Rd, Wilmington, VT 05363
SOLD SEP 25, 2026
$599,000
B
5 beds2.5 baths2,147 sq ft
146 Minor Rd, Wilmington, VT 05363
SOLD AUG 3, 2026
$586,500
C
3 beds3 baths2,670 sq ft
2079 Ames Hill Rd, Marlboro, VT 05344
SOLD JUL 21, 2026
$538,000
D
4 beds2.5 baths2,567 sq ft
1041 Church Hollow Rd, Brattleboro, VT 05301
SOLD OCT 15, 2026
$775,000
E
4 beds3 baths3,550 sq ft
25 Yeaw Rd, East Dover, VT 05341
SOLD SEP 4, 2026
$650,000
F
5 beds2 baths2,378 sq ft
389 Boyd Hill Rd, Wilmington, VT 05363

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

Earn from this home

Rent

$3,709/mo

Redfin rental estimate

List your home for rent

Market trends in 05301, VT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

98.3%

0.3% MoM

Median sale price

$339K

$41K MoM

Avg. days on market

66d

5 days MoM

Recently sold homes

4 MoM

New listings for sale

NEW 17 HRS AGO
$295,000
— beds2 baths1,885 sq ft
100 Clark St, Brattleboro, VT 05301
$339,000
3 beds1.5 baths1,400 sq ft
12 Thorn Ln, Brattleboro, VT 05301
$439,000
2 beds2 baths1,635 sq ft
160 Wantastiquet Dr, Brattleboro, VT 05301
$265,000
3 beds2 baths1,865 sq ft
17 Paul's Rd, Guilford, VT 05301
$239,900
2 beds1.5 baths1,056 sq ft
78 Morningside Cmns, Brattleboro, VT 05301
$219,000
2 beds1.5 baths1,248 sq ft
9 Robin Way, Brattleboro, VT 05301
$250,000
2 beds1 bath1,485 sq ft
56 Fuller Dr, Brattleboro, VT 05301
See all

Provided by Redfin

Sale history for 74 Winchester Road Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,463 (−4.3%)

$149,000 + $278,200

$427,200

2024

$6,755 (+10.1%)

$149,000 + $278,200

$427,200

2023

$6,134 (−37.9%)

$149,000 + $278,200

$427,200

2022

$9,870 (−9.3%)

$149,000 + $278,200

$427,200

2021

$10,880 (+25.6%)

$149,000 + $278,200

$427,200

2020

$8,665 (−30.7%)

$137,200 + $225,000

$362,200

2019

$12,510 (−0.5%)

$160,200 + $428,200

$588,400

2018

$12,570 (−1.4%)

$160,200 + $428,200

$588,400

2017

$12,743 (−4.4%)

$160,200 + $428,200

$588,400

2016

$13,326 (+3.3%)

$160,200 + $428,200

$588,400

2015

$12,900 (+20.4%)

$160,200 + $428,200

$588,400

2014

$10,716

$160,200 + $428,200

$588,400

2013

$160,200 + $428,200

$588,400

Tax history for 74 Winchester Road Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,463 (−4.3%)

$149,000 + $278,200

$427,200

2024

$6,755 (+10.1%)

$149,000 + $278,200

$427,200

2023

$6,134 (−37.9%)

$149,000 + $278,200

$427,200

2022

$9,870 (−9.3%)

$149,000 + $278,200

$427,200

2021

$10,880 (+25.6%)

$149,000 + $278,200

$427,200

2020

$8,665 (−30.7%)

$137,200 + $225,000

$362,200

2019

$12,510 (−0.5%)

$160,200 + $428,200

$588,400

2018

$12,570 (−1.4%)

$160,200 + $428,200

$588,400

2017

$12,743 (−4.4%)

$160,200 + $428,200

$588,400

2016

$13,326 (+3.3%)

$160,200 + $428,200

$588,400

2015

$12,900 (+20.4%)

$160,200 + $428,200

$588,400

2014

$10,716

$160,200 + $428,200

$588,400

2013

$160,200 + $428,200

$588,400

*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

100 Acres

Year renovated

—

Sq. Ft.

3,248

Year built

1975

Style

Single Family Residential

County

Windham County

APN

27608710656

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 23, 2026.

Rural Residential District

The purpose of the Rural Residential District is to provide for residential development and compatible light industrial & light commercial uses at moderate densities which are easily accessible to Class 2 and 3 public roads. It is anticipated that the bulk of new residential and light commercial growth will take place within this district. Special care should be taken to protect the rural-residential character of this district, to locate proposed development off of productive agricultural lands, and to minimize forest fragmentation. Non-residential development proposed in the RR District shall be carefully reviewed on a case-by-case basis utilizing the standards established under Conditional Use Approval, and elsewhere throughout this Zoning Regulation including, but not limited to General Performance Standards, Landscaping Requirements, and Article 5 Special Regulations, as applicable.

Permitted uses

Include but are not limited to:

Agriculture
Housing-Single unit
Housing-Multiple units
Bed & breakfast
Office
Cemetery

Property details

Parking

Parking & Garage
Garage Capacity: 2

Interior

Bathroom Information
# of Baths (full): 4

Basement Information
Basement Access: Walkout
Other, Partially Finished

Other Interior Features
# of Rooms: 10
Flooring: Carpet, Softwood, Vinyl

Equipment & Appliance Information
Dishwasher, Dryer, Exhaust Hood, Microwave, Other, Range - Gas, Refrigerator, Washer, Water Heater - Oil

Room 1 Information
Kitchen
Kitchen
Dimensions: 20x12
Level: 1

Room 2 Information
Dining Room
Dimensions: 12x10
Level: 1

Room 3 Information
Living Room
Dimensions: 20x12
Level: 1

Room 4 Information
Family Room
Dimensions: 24x24

Room 5 Information
Kitchen

Room 6 Information
Foyer
Foyer

Room 7 Information
Master Bedroom
Dimensions: 12x15
Level: 1

Room 8 Information
Bedroom
Dimensions: 20x15
Level: 2

Room 9 Information
Bedroom
Dimensions: 15x10
Level: 2

Room 10 Information
Bedroom
Dimensions: 20x15
Level: 2

Room 11 Information
Bedroom
Dimensions: 20x24
Level: 2

Room 12 Information
Rec Room

Room 13 Information
Other
Dimensions: 10x15
Level: 1

Room 16 Information
Full Bath
Level: 1

Room 17 Information
Full Bath
Level: 2

Room 18 Information
Full Bath
Level: 2

Room 19 Information
Full Bath
Level: Basement

Exterior

Building Information
Architectural Style: Cape, Other
Construction Status: New Construction
Construction Materials: Brick Exterior, Clapboard Exterior
Approximate Sq. Ft. Total Finished: 4000
Color: white
Roof: Shingle - Other

Driveway
Gravel

Lot, Zoning, & Easement Information
Common Land Acres: 0
Lot Features: Trail/Near Trail, Wooded

Other Property & Lot Information
Year Built: 1976

Financial

Tax Information
Tax Year: 2004
Gross Amount Tax: 5500

Utilities

Heating & Cooling Information
Heat: Oil, Hot Air

Sewer Information
Septic

Electric Information
220 Plug

Water Information
Water Source: Drilled Well

Location

School Information
Elementary School: Halifax West School
Elementary School: Halifax West School
Middle/Jr School: Choice
School - High: Choice

Road Information
Road Frontage: Yes
Road Frontage Length: 2300

Other Location Information
Directions: Route 100 to 9 East to Shearer Hill Road Left on Hatch School Road Left on Winchester Road. House on right
Development / Subdivision: None (Hal)

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 3,248
Stories: —
Lot Size: 100 acres
Style: Single Family Residential
Year Built: 1975
Year Renovated: —
County: Windham County
APN: 27608710656

Home facts updated by county records on Sep 23, 2026

Other

Documents & Disclosures
Documents Available: Other

Around this home

Schools

K - 12
Preschool & daycare

Some nearby schools may not be within this home's attendance zone. Please check the Halifax School District website to verify.

Halifax West School

Public PreK-8 • 2.9mi

6/10

Marlboro Elementary School

Public PreK-8 • 4.3mi

6/10

Twin Valley Middle High School

Public 6-12 • 4.1mi

3/10

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

1/10 Heat Factor

7 days above 88° expected this year, 16 days in 30 years

4/10 Wind Factor

8% 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 • 05358

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 8.5 hours in June and 3.8 hours in December, placing it below the U.S. average for solar exposure.

8.5 hrs

3.8 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$837,000 – $1.01M

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

Nearby similar homes

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New listings for sale in 05301

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Fully renovated • New kitchens • New baths

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First floor living • Finished basement • Separate office

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17 Paul's Rd, Guilford, VT 05301

Easy access • Privacy • Drilled well

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2 beds1.5 baths1,056 sq ft

78 Morningside Cmns, Brattleboro, VT 05301

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$219,000

2 beds1.5 baths1,248 sq ft

9 Robin Way, Brattleboro, VT 05301

End unit townhouse • Second floor deck • Private patio

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2 beds1 bath1,485 sq ft

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Two bonus rooms • One-car garage • Attached breezeway

Home values near 74 Winchester Road Rd

Data from public records.

Address	Redfin Estimate
221 Winchester Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 1880 Sq. Ft.	$447,263
1691 Hanson, Brattleboro, VT 2 Beds \| 1 Baths \| 756 Sq. Ft.	$231,176
229 Wheeler Rd, Brattleboro, VT 2 Beds \| 2 Baths \| 1492 Sq. Ft.	$306,781
53 Wheeler Rd, Brattleboro, VT 2 Beds \| 1.5 Baths \| 892 Sq. Ft.	$231,783
171 Wheeler Rd, Brattleboro, VT 1 Beds \| 1 Baths \| 1152 Sq. Ft.	$233,336
102 Wheeler Rd, Brattleboro, VT 4 Beds \| 2 Baths \| 1800 Sq. Ft.	$273,799
305 Wheeler Rd, Brattleboro, VT 3 Beds \| 2 Baths \| 1008 Sq. Ft.	$283,298

Address	Redfin Estimate
1581 Hanson Rd, Brattleboro, VT 5 Beds \| 3 Baths \| 3482 Sq. Ft.	$640,173
1211 Hatch School Rd, Brattleboro, VT 3 Beds \| 3.5 Baths \| 1400 Sq. Ft.	$380,502
253 Wheeler Rd, Brattleboro, VT 3 Beds \| 2.5 Baths \| 2842 Sq. Ft.	$420,161
60 Wheeler Rd, Brattleboro, VT 3 Beds \| 1.5 Baths \| 2154 Sq. Ft.	—
149 Wheeler Rd, Brattleboro, VT 5 Beds \| 2 Baths \| 1443 Sq. Ft.	$246,679
1437 Hatch School Rd, Brattleboro, VT 2 Beds \| - Baths \| 544 Sq. Ft.	$224,870
1543 Hatch School Rd, Brattleboro, VT 1 Beds \| 1 Baths \| 1568 Sq. Ft.	$372,696

Address	Redfin Estimate
1189 Hatch School Rd, Brattleboro, VT 2 Beds \| 1 Baths \| 1500 Sq. Ft.	$309,796
1408 Hatch School Rd, Brattleboro, VT 3 Beds \| 1.5 Baths \| 1908 Sq. Ft.	$420,155
88 Wheeler Rd, Brattleboro, VT 4 Beds \| 2 Baths \| 840 Sq. Ft.	$258,663
Wheeler Rd, Dummerston, VT 4 Beds \| 2 Baths \| 1198 Sq. Ft.	$215,404
15 Wheeler Rd, Brattleboro, VT 1 Beds \| 1 Baths \| 1600 Sq. Ft.	$231,297
119 Wheeler Rd, Brattleboro, VT 2 Beds \| 1 Baths \| 1548 Sq. Ft.	$195,283
15 Wheeler Rd, Halifax, VT 1 Beds \| 1 Baths \| 1692 Sq. Ft.	$92,359

Property information provided by PrimeMLS when last listed in 2004. 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 74 Winchester Road Rd

Tax history for 74 Winchester Road 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 74 Winchester Road Rd

More real estate resources