OFF MARKET

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

Off market sep 2017 for $453K

$903,890

Est. refi paymentEst. refi $2,990/mo

•

2,660

sq ft

279 Winn Rd, West Halifax, VT 05358

About this home

Priceless privacy with a spectacular view! An end of the road location offering solitude, tranquility and just wonderful peaceful quietness! This beautifully restored circa 1780's post and beam farmhouse on 95.2 acres is a gem. The home has a charming brick fireplace, spacious rooms, including 3 bedrooms, a large parlor, formal dining room and a bright country kitchen. A screened in porch and a stone patio add to the charm. Its pastoral setting offers views to the south. A spring feed pond for the wildlife is in the meadow. Attached 1 car garage/shed and a 3 bay tractor shed for the big boy toys!

Single-familyProperty Type

1782Year Built

95.2 acresLot Size

$340Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Monica Sumner • BHG Masiello Brattleboro

Bought with Monica Sumner • BHG Masiello Brattleboro

Redfin checked: 3 minutes ago

•Source:PrimeMLS #4632856

Redfin Estimate

$903,890

$451K since sold in September 2017$29K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 88.8% higher than the average sale price ($479K) of 6 comparable homes.

SOLD SEP 1, 2026
$675,000
A
3 beds2 baths2,245 sq ft
442 Josh Rd, Brattleboro, VT 05358
SOLD AUG 27, 2026
$488,000
B
3 beds1.5 baths2,400 sq ft
3524 Deer Park Rd, Brattleboro, VT 05358
SOLD JUL 24, 2026
$550,000
C
3 beds2 baths2,697 sq ft
193 Rt.9 E, Wilmington, VT 05363
SOLD SEP 17, 2026
$449,000
D
3 beds2 baths2,001 sq ft
520 Legate Hl, Charlemont, MA 01339
SOLD SEP 23, 2026
$396,000
E
3 beds1.5 baths1,908 sq ft
1408 Hatch School Rd, Brattleboro, VT 05358
SOLD JAN 9, 2026
$315,000
F
3 beds2 baths2,910 sq ft
597 Gates Pond Rd, Jacksonville, VT 05342

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,893/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 279 Winn Rd

Year

Property tax

Land + Additions

Assessment*

2025

$11,351 (−10.7%)

$135,200 + $518,000

$653,200

2024

$12,715 (+19.8%)

$135,200 + $518,000

$653,200

2023

$10,616 (−35.6%)

$135,200 + $518,000

$653,200

2022

$16,479 (−4.5%)

$135,200 + $518,000

$653,200

2021

$17,250 (+39.9%)

$135,200 + $518,000

$653,200

2020

$12,330 (+15.3%)

$167,600 + $327,700

$495,300

2019

$10,692 (+3.9%)

$198,900 + $249,300

$448,200

2018

$10,295 (+7.8%)

$198,900 + $249,300

$448,200

2017

$9,548 (−4.5%)

$198,900 + $249,300

$448,200

2016

$9,993 (−24.6%)

$198,900 + $249,300

$448,200

2015

$13,249 (+116.5%)

$286,400 + $322,400

$608,800

2014

$6,119

$286,400 + $207,300

$493,700

Tax history for 279 Winn Rd

Year

Property tax

Land + Additions

Assessment*

2025

$11,351 (−10.7%)

$135,200 + $518,000

$653,200

2024

$12,715 (+19.8%)

$135,200 + $518,000

$653,200

2023

$10,616 (−35.6%)

$135,200 + $518,000

$653,200

2022

$16,479 (−4.5%)

$135,200 + $518,000

$653,200

2021

$17,250 (+39.9%)

$135,200 + $518,000

$653,200

2020

$12,330 (+15.3%)

$167,600 + $327,700

$495,300

2019

$10,692 (+3.9%)

$198,900 + $249,300

$448,200

2018

$10,295 (+7.8%)

$198,900 + $249,300

$448,200

2017

$9,548 (−4.5%)

$198,900 + $249,300

$448,200

2016

$9,993 (−24.6%)

$198,900 + $249,300

$448,200

2015

$13,249 (+116.5%)

$286,400 + $322,400

$608,800

2014

$6,119

$286,400 + $207,300

$493,700

*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

95.2 Acres

Year renovated

—

Sq. Ft.

3,909

Year built

2017

Style

Single Family Residential

County

Windham County

APN

27608710658

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: 3
Location: Detached
Unassigned
Driveway, Parking Spaces 6+

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Walkout
Concrete, Partial, Stairs - Interior, Unfinished

Other Interior Features
# of Rooms: 6
Flooring: Softwood, Tile
Water Heater: Electric
Attic, Cedar Closet, Dining Area, Fireplace - Wood, Fireplaces - 1, Hearth, Laundry Hook-ups, Soaking Tub, Walk-in Closet, Wood Stove Insert, Laundry - 1st Floor

Accessibility Information
1st Floor Full Bathroom

Equipment & Appliance Information
Dishwasher, Range - Gas, Refrigerator, Stove - Wood Cook
Carbon Monoxide Detector, Smoke Detector, Smoke Detectr-Battery Powered

Room 1 Information
Kitchen
Kitchen
Dimensions: 25.6x13.8
Level: 1

Room 2 Information
Dining Room
Dimensions: 15.6x11.4
Level: 1

Room 3 Information
Living Room
Dimensions: 24.4x15.6
Level: 1

Room 7 Information
Master Bedroom
Dimensions: 19.7x19.4
Level: 2

Room 8 Information
Bedroom
Dimensions: 15.6x13
Level: 2

Room 9 Information
Bedroom
Dimensions: 14.10x12
Level: 2

Room 13 Information
Other
Level: 1

Room 14 Information
Other
Dimensions: 9.2x9.2
Level: 2

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 2660
Approximate Sq. Ft. Total: 3350
Color: Red
Fence - Partial, Outbuilding, Patio, Porch, Porch - Covered, Porch - Enclosed, Porch - Screened, Shed, Window Screens
Construction: Post and Beam, Wood Frame
Foundation: Concrete, Stone
Roof: Shingle - Asphalt
Exterior: Clapboard

Driveway
Gravel

Lot, Zoning, & Easement Information
Country Setting, Field/Pasture, Landscaped, Level, Mountain View, Open, Pond, Pond Frontage, Pond Site, Secluded, Ski Area, Trail/Near Trail, View

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1782
Waterfront: Yes
Water Body Access: Yes

Financial

Tax Information
Tax Year: 2016
Gross Amount Tax: 6849
SPAN Number: 276-087-10658

Other Tax Information
Page Deed: 265

Financing Information
Cash Only, Conventional, FHA, VTFHA

Utilities

Heating & Cooling Information
Cooling: Attic Fan
Heat: Hot Air, Stove, Stove - 2, Stove - Wood
Heat Fuel: Electric, Gas - Liquid Propane Bottle, Oil, Wood

Sewer Information
1000 Gallon, Concrete, Private, Septic

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

Water Information
Drilled Well, Private

Other Utilities Information
Phone Company: Fairpoint
DSL

Location

School Information
Elementary School: Halifax School
Elementary School: Halifax School
Middle/Jr School: Halifax School

Neighborhood Information
Near Snowmobile Trails, Rural

Road Information
Road Frontage: TBD
Public

Other Location Information
Directions: Take Reed Hill Road from Jacksonville Vt to Winn Road on the right. Travel to the end of this road.

Public facts

Beds: 4
Baths: 4.5
Sq. Ft.: 3,909
Stories: —
Lot Size: 95.2 acres
Style: Single Family Residential
Year Built: 2017
Year Renovated: —
County: Windham County
APN: 27608710658

Home facts updated by county records on Sep 23, 2026

Other

Water Body Information
Pond
Name: Pond
Access: Owned

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 • 2.5mi

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, 17 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

$859,000 – $1.04M

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

Nearby similar homes

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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

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5 beds1 bath1,224 sq ft

6036 Jacksonville Stage Rd, Halifax, VT 05358

Serene woodlands • Historic stone walls • Wetland area

$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

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3 beds2.5 baths1,568 sq ft

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Home values near 279 Winn Rd

Data from public records.

Address	Redfin Estimate
344 Winn Road, West Halifax, VT 2 Beds \| 1 Baths \| 856 Sq. Ft.	$349,867
2247 Vt Route 112, Jacksonville, VT 3 Beds \| 2.5 Baths \| 2201 Sq. Ft.	$338,511
1886 Reed Hill Road, West Halifax, VT 2 Beds \| 2 Baths \| 1780 Sq. Ft.	$682,721
355 Larrabee Road, Brattleboro, VT 4 Beds \| 4 Baths \| 3544 Sq. Ft.	$585,575
1524 Vt Route 112, Jacksonville, VT 3 Beds \| 1.5 Baths \| 2120 Sq. Ft.	$587,828
1787 Vt Route 112 Road, Halifax, VT 3 Beds \| 1.5 Baths \| 1536 Sq. Ft.	$377,625
104 Karen Day Road, Halifax, VT 4 Beds \| 1 Baths \| 1560 Sq. Ft.	$544,155

Address	Redfin Estimate
2704 Vt Route 112, Jacksonville, VT 3 Beds \| 1 Baths \| 1532 Sq. Ft.	$334,165
1787 Vt Route 112, Jacksonville, VT 1 Beds \| 1.5 Baths \| 1536 Sq. Ft.	$380,891
228 Smith Road, Wilmington, VT 3 Beds \| 3.5 Baths \| 4344 Sq. Ft.	$754,086
710 Larrabee Road, Jacksonville, VT 4 Beds \| 2 Baths \| 1926 Sq. Ft.	$373,395
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

Address	Redfin Estimate
2770 Vt Route 112, Jacksonville, VT 3 Beds \| 1 Baths \| 1373 Sq. Ft.	$259,415
300 Smith Road, Jacksonville, VT 3 Beds \| 1 Baths \| 1492 Sq. Ft.	$321,638
889 Larrabee Road, Jacksonville, VT 3 Beds \| 2 Baths \| 1352 Sq. Ft.	$252,807
76 Larrabee Road, 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
3671 Vermont 112 Route, Halifax, VT 2 Beds \| 2 Baths \| 1010 Sq. Ft.	$295,187

Property information provided by PrimeMLS when last listed in 2017. 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 279 Winn Rd

Tax history for 279 Winn Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

Home values near 279 Winn Rd

More real estate resources