Listed by Monica Sumner • BHG Masiello Brattleboro. Bought with BHG Masiello Brattleboro.

Off market may 2015 for $175K

$349,867

Est. refi paymentEst. refi $1,162/mo

•

856

sq ft

344 Winn Rd, West Halifax, VT 05358

About this home

50 ACRES, COMPLETELY PRIVATE RETREAT WITH MAGNIFICANT VIEW FROM EXPANSIVE DECKAdorable cabin has full basement, drilled well and septic, 2 bedrooms, 3/4 bath, wood burning all-nighter stove and propane heater. Free standing, 2 story barn with gambrel roof near cabin. Direct access to snow mobile trail which is on the property. Land is enrolled in Vermont Land Use program which reduces your taxes greatly. A great investment if you are looking for a beautiful peaceful location, Close to many lakes and skiing here in Southern Vermont. Power is in and completed.

Single-familyProperty Type

1965Year Built

49.7 acresLot Size

$409Est. Price/Sq.Ft.

6 spacesParking

Listed by Monica Sumner • BHG Masiello Brattleboro

Bought with Monica Sumner • BHG Masiello Brattleboro

Redfin checked: a few seconds ago

•Source:PrimeMLS #4374515

Redfin Estimate

$349,867

$175K since sold in May 2015$42K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.1% higher than the average sale price ($346K) of 6 comparable homes.

SOLD SEP 25, 2026
$349,000
A
2 beds1 bath883 sq ft
443 East Rd, Whitingham, VT 05361
SOLD MAY 14, 2026
$273,500
B
2 beds1 bath936 sq ft
2378 Deer Park Rd, West Halifax, VT 05358
SOLD SEP 18, 2026
$248,900
C
3 beds1.5 baths1,080 sq ft
2448 Burrington Hill Rd, Whitingham, VT 05361
SOLD AUG 3, 2026
$369,000
D
2 beds1 bath936 sq ft
127 County Rd, Rowe, MA 01367
SOLD SEP 23, 2026
$396,000
E
3 beds1.5 baths1,908 sq ft
1408 Hatch School Rd, Brattleboro, VT 05358
SOLD OCT 28, 2026
$439,000
F
3 beds1 bath1,508 sq ft
147 Gilbert Rd, Marlboro, VT 05344

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$1,481/mo

Redfin rental estimate

List your home for rent

Market trends in 05342, VT

Last updated October 2026

Sale-to-list price

95.0%

0.0% MoM

Median sale price

$285K

$0 MoM

Avg. days on market

71d

0 days MoM

Recently sold homes

0 MoM

Provided by Redfin

Sale history for 344 Winn Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,238 (−10.7%)

$99,100 + $87,200

$186,300

2024

$3,626 (+19.8%)

$99,100 + $87,200

$186,300

2023

$3,028 (−35.6%)

$99,100 + $87,200

$186,300

2022

$4,700 (−4.5%)

$99,100 + $87,200

$186,300

2021

$4,920 (−20.6%)

$99,100 + $87,200

$186,300

2020

$6,196 (+4.4%)

$172,900 + $76,000

$248,900

2019

$5,938 (+3.9%)

$172,900 + $76,000

$248,900

2018

$5,717 (+0.9%)

$172,900 + $76,000

$248,900

2017

$5,666 (−4.1%)

$172,900 + $76,000

$248,900

2016

$5,910 (+1,173.7%)

$172,900 + $76,000

$248,900

2011

$464

$168,200 + $76,000

$244,200

Tax history for 344 Winn Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,238 (−10.7%)

$99,100 + $87,200

$186,300

2024

$3,626 (+19.8%)

$99,100 + $87,200

$186,300

2023

$3,028 (−35.6%)

$99,100 + $87,200

$186,300

2022

$4,700 (−4.5%)

$99,100 + $87,200

$186,300

2021

$4,920 (−20.6%)

$99,100 + $87,200

$186,300

2020

$6,196 (+4.4%)

$172,900 + $76,000

$248,900

2019

$5,938 (+3.9%)

$172,900 + $76,000

$248,900

2018

$5,717 (+0.9%)

$172,900 + $76,000

$248,900

2017

$5,666 (−4.1%)

$172,900 + $76,000

$248,900

2016

$5,910 (+1,173.7%)

$172,900 + $76,000

$248,900

2011

$464

$168,200 + $76,000

$244,200

*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

49.7 Acres

Year renovated

—

Sq. Ft.

720

Year built

1960

Style

Single Family Residential

County

Windham County

APN

27608710659

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
Driveway, Parking Spaces 6+, Unassigned

Interior

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

Basement Information
Basement: Yes
Basement Access: Walkout
Bulkhead, Concrete, Full, Unfinished

Other Interior Features
# of Rooms: 5
Flooring: Softwood, Tile
Ceiling Fan, Draperies, Hearth, Kitchen/Dining, Lead/Stain Glass, Natural Woodwork, Vaulted Ceiling, Window Treatment, Wood Stove Hook-up

Accessibility Information
1st Floor 3/4 Bathroom

Equipment & Appliance Information
Microwave, Range - Gas, Refrigerator, Water Heater-Gas-LP/Bttle, Water Heater - Owned
Smoke Detector, Smoke Detectr-Battery Powered

Room 1 Information
Kitchen
Kitchen
Level: 1

Room 3 Information
Living Room
Level: 1

Room 13 Information
Other
Level: 1

Exterior

Building Information
Architectural Style: Cabin
Construction Status: Existing
Construction Materials: Wood Frame, Clapboard Exterior
Approximate Sq. Ft. Total Finished: 856
Color: Natural
Barn, Deck
Foundation: Concrete
Roof: Shingle - Asphalt

Driveway
Gravel, Right-Of-Way (ROW)

Lot, Zoning, & Easement Information
Lot Features: Country Setting, Landscaped, Mountain View, Secluded, Ski Area, Sloping, Trail/Near Trail, View, Walking Trails, Wooded, Near Snowmobile Trails, Rural

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1965

Financial

Assessment Information
Assessment Amount: 208700
Assessment Year: 2013

Tax Information
Tax Year: 2013
Gross Amount Tax: 3054.18
SPAN Number: 651-205-10817

Other Tax Information
Page Deed: 131

Financing Information
Cash Only, Conventional, Portfolio

Utilities

Heating & Cooling Information
Heat: Propane, Wood, Gas Heater, Stove, Stove - Gas, Stove - Wood, Wall Furnace

Sewer Information
Septic

Electric Information
Electric Company: GMP
100 Amp, Circuit Breaker(s)

Water Information
Water Source: Drilled Well

Other Utilities Information
Internet: DSL
Phone Company: Fairpoint

Location

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

Road Information
Road Frontage Type: Dead End, Gravel, Public

Other Location Information
Directions: From the village of West Halifax, take Reed Hill Rd about 1 mile to 3rd road on the left. Winn Rd is a dead end. There is a red farm house at the end. The driveway which is the right of way to the cabin is before the last home on the left. You cannot see the cabin from the road. No drive-bys please.
Development / Subdivision: NO

Public facts

Beds: 1
Baths: 1.0
Sq. Ft.: 720
Stories: —
Lot Size: 49.7 acres
Style: Single Family Residential
Year Built: 1960
Year Renovated: —
County: Windham County
APN: 27608710659

Home facts updated by county records on Sep 23, 2026

Other

Documents & Disclosures
Documents Available: Deed, Plot Plan, Property Disclosure, Survey

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 • 1.4mi

6/10

Twin Valley Middle High School

Public 6-12 • 2.4mi

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 89° 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

West Halifax, VT • 05358

Average low and high temperatures (°F)

27°

14°

30°

15°

45°

27°

56°

37°

64°

47°

76°

58°

80°

62°

77°

57°

72°

52°

59°

41°

46°

33°

32°

19°

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

$333,000 – $403,000

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

Nearby similar homes

$725,000

5 beds1 bath1,224 sq ft

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3 beds3 baths2,401 sq ft

783 Wilmington Cross Rd, Whitingham, VT 05361

72 acre playground • Covered porch • Large family room

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5 beds3 baths2,415 sq ft

511 Shearer Hill Rd, Wilmington, VT 05363

95 acres • Easy access • Pastoral setting

$599,000

5 beds2 baths2,350 sq ft

9282 VT Rte 100, Whitingham, VT 05361

41 acres • Post and beam barn • Access to skiing

$624,900

4 beds2.5 baths2,904 sq ft

37 Stowe Hill Rd, Wilmington, VT 05363

Restored farmhouse • Modern amenities • Historic details

$259,000

3 beds2.5 baths1,568 sq ft

1806 Bosley Hill Rd, Readsboro, VT 05350

Large front deck • 10 acre lot • Garage

Home values near 344 Winn Rd

Data from public records.

Address	Redfin Estimate
279 Winn Rd, West Halifax, VT 3 Beds \| 2 Baths \| 2660 Sq. Ft.	$903,890
1452 Vt Route 8A, Jacksonville, VT 3 Beds \| 2 Baths \| 1690 Sq. Ft.	$334,263
1886 Reed Hill Rd, West Halifax, VT 2 Beds \| 2 Baths \| 1780 Sq. Ft.	$682,721
204 Bellow Rd, West Halifax, VT 3 Beds \| 2 Baths \| 1674 Sq. Ft.	$646,980
1613 Vt Route 112, Jacksonville, VT 2 Beds \| 1 Baths \| 950 Sq. Ft.	$213,210
1843 VT-112, Halifax, VT 4 Beds \| 2.5 Baths \| 2074 Sq. Ft.	$403,385
104 Karen Day Rd, Halifax, VT 4 Beds \| 1 Baths \| 1560 Sq. Ft.	$544,155

Address	Redfin Estimate
616 Vt Route 8A, Jacksonville, VT 2 Beds \| 1 Baths \| 1200 Sq. Ft.	$319,131
2247 Vt Route 112, Jacksonville, VT 3 Beds \| 2.5 Baths \| 2201 Sq. Ft.	$338,511
228 Smith Rd, Wilmington, VT 3 Beds \| 3.5 Baths \| 4344 Sq. Ft.	$754,086
76 Larrabee Rd, Brattleboro, VT 2 Beds \| 1 Baths \| 1560 Sq. Ft.	$251,236
1843 Vt Route 112, Jacksonville, VT 4 Beds \| 2.5 Baths \| 2074 Sq. Ft.	$384,533
496 VT Rte 8A, Whitingham, VT 4 Beds \| 4.5 Baths \| 4033 Sq. Ft.	$752,053

Address	Redfin Estimate
1424 Vt Route 112, Jacksonville, VT 5 Beds \| 1 Baths \| 1730 Sq. Ft.	$372,157
1787 Vt Route 112, Jacksonville, VT 1 Beds \| 1.5 Baths \| 1536 Sq. Ft.	$380,891
710 Larrabee Rd, Jacksonville, VT 4 Beds \| 2 Baths \| 1926 Sq. Ft.	$373,395
1524 Vt Route 112, Jacksonville, VT 3 Beds \| 1.5 Baths \| 2120 Sq. Ft.	$587,828
1787 Vt Route 112 Rd, Halifax, VT 3 Beds \| 1.5 Baths \| 1536 Sq. Ft.	$377,625
3671 Vermont 112 Rte, Halifax, VT 2 Beds \| 2 Baths \| 1010 Sq. Ft.	$295,187

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 05342, VT

Sale history for 344 Winn Rd

Tax history for 344 Winn Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

Home values near 344 Winn Rd

More real estate resources