OFF MARKET

Listed by Amanda Stearns • Barrett and Valley Associates Inc. Bought with Engel & Volkers Okemo.

Off Market Nov 2021 for $419K

$529,021

Est. refi paymentEst. refi $2,723/mo

•

2,775

sq ft

372 Main St, Chester, VT 05143

About this home

This exquisite home has been tastefully renovated throughout. The front porch invites a bit of respite and observation with a pause now and then as folks walk by with a hello. A visit offers quite a surprise in terms of the spacious floor plan and great flow! Family and friends easily gather throughout the common space, yet plenty of quiet time area is available. The modern kitchen is open, with ample stone counter tops, and newer appliances. The pantry has been saved and serves as incredible storage! A large office or den is adjacent to an expansive great room combination. A full bath is located just off the kitchen. The second floor landing is comfortable introducing four bedrooms and a full bath and a laundry. The great carriage barn retains it's one holer and has had substantial work done to add to it's long life. It is an incredible building to explore! The side yard is level and enjoys a patio offering expanded fair weather family enjoyment.

Single-familyProperty Type

1850Year Built

0.81 acresLot Size

$191Est. Price/Sq.Ft.

1 car garageParking

Listed by Amanda Stearns • Barrett and Valley Associates Inc.

Listed by Joan Morey • Barrett and Valley Associates Inc.

Bought with Geralyn Donohue • Engel & Volkers Okemo

Redfin checked: 2 minutes ago

•Source:PrimeMLS #4880263

Redfin Estimate

$529,021

$110K since sold in November 2021$6,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 50.9% higher than the average sale price ($351K) of 6 comparable homes.

SOLD MAR 27, 2026
$299,000
A
4 beds2 baths1,782 sq ft
147 South St, Springfield, VT 05156
SOLD APR 13, 2026
$563,000
B
4 beds3 baths2,794 sq ft
95 Church St, Chester, VT 05143
SOLD AUG 6, 2026
$275,000
C
4 beds3 baths3,332 sq ft
397 River St, Chester, VT 05143
SOLD APR 20, 2026
$379,000
D
2 beds2 baths2,751 sq ft
3466 VT Route 103 N, Chester, VT 05143
SOLD AUG 28, 2026
$288,000
E
3 beds2.5 baths2,174 sq ft
147 Park St, Springfield, VT 05156
SOLD AUG 21, 2026
$299,900
F
3 beds2 baths2,048 sq ft
87 Fairground Rd, Springfield, VT 05156

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Earn from this home

Refinance

Est. cash available

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Rent

$2,993/mo

Redfin rental estimate

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Market trends in 05143, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.2%

0.5% MoM

Median sale price

$289K

$70K MoM

Avg. days on market

58d

8 days MoM

Recently sold homes

8 MoM

New listings for sale

VIDEO TOUR
$1,300,000
3 beds3 baths4,714 sq ft
1337 Andover Ridge Rd, Andover, VT 05161
$695,000
3 beds2.5 baths2,232 sq ft
717 Horsenail Hill Rd, Chester, VT 05359
$340,000
3 beds2 baths3,608 sq ft
145 S Main St, Chester, VT 05143
$700,000
2 beds3 baths1,556 sq ft
1260 Grafton Rd, Chester, VT 05143
See all

Provided by Redfin

Sale history for 372 Main St

Year

Property tax

Land + Additions

Assessment*

2025

$5,309 (+16.4%)

$37,900 + $247,200

$285,100

2024

$4,562 (+4.4%)

$37,900 + $247,200

$285,100

2023

$4,371 (−34.1%)

$37,900 + $247,200

$285,100

2022

$6,632 (−1.4%)

$37,900 + $247,200

$285,100

2021

$6,727 (+5.8%)

$37,900 + $247,200

$285,100

2020

$6,360 (+0.8%)

$37,900 + $247,200

$285,100

2019

$6,310 (+0.7%)

$105,700 + $215,800

$321,500

2018

$6,267 (−0.3%)

$105,700 + $215,800

$321,500

2016

$6,284 (−2.9%)

$105,700 + $215,800

$321,500

2015

$6,471

$105,700 + $215,800

$321,500

2013

$105,700 + $215,800

$321,500

Tax history for 372 Main St

Year

Property tax

Land + Additions

Assessment*

2025

$5,309 (+16.4%)

$37,900 + $247,200

$285,100

2024

$4,562 (+4.4%)

$37,900 + $247,200

$285,100

2023

$4,371 (−34.1%)

$37,900 + $247,200

$285,100

2022

$6,632 (−1.4%)

$37,900 + $247,200

$285,100

2021

$6,727 (+5.8%)

$37,900 + $247,200

$285,100

2020

$6,360 (+0.8%)

$37,900 + $247,200

$285,100

2019

$6,310 (+0.7%)

$105,700 + $215,800

$321,500

2018

$6,267 (−0.3%)

$105,700 + $215,800

$321,500

2016

$6,284 (−2.9%)

$105,700 + $215,800

$321,500

2015

$6,471

$105,700 + $215,800

$321,500

2013

$105,700 + $215,800

$321,500

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

—

Lot width

—

Lot depth

—

Lot size

1.19 Acres

Year renovated

—

Sq. Ft.

2,775

Year built

1850

Style

Single Family Residential

County

Windsor County

APN

14404510176

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 2, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 1
Location: Detached

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 2

Basement Information
Basement: Yes
Basement Access: Interior
Stairs - Interior

Other Interior Features
# of Rooms: 11
Water Heater: Electric, Rented

Room 1 Information
Eat-in Kitchen
Eat-In Kitchen
Dimensions: 22.10 x 12.3
Level: 1

Room 2 Information
Dining Room
Dimensions: 10.11 x 15
Level: 1

Room 3 Information
Office/Study
Dimensions: 16 x 14.3
Level: 1

Room 4 Information
Living Room
Dimensions: 20.6 x 15.4
Level: 1

Room 5 Information
Bonus Room
Dimensions: 9.10 x 6.5
Level: 1

Room 6 Information
Bedroom
Bedroom
Dimensions: 11 x 11.2
Level: 2

Room 7 Information
Bedroom
Dimensions: 11.3 x 10.3
Level: 2

Room 8 Information
Bedroom
Dimensions: 17 x 15.8
Level: 2

Room 9 Information
Bedroom
Dimensions: 14.5 x 14.4
Level: 2

Room 10 Information
Laundry Room
Dimensions: 10.9 x 10
Level: 2

Room 11 Information
Family Room
Dimensions: 22.4 x 13.7
Level: 2

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 2775
Approximate Sq. Ft. Total: 3400
Color: Straw
Construction: Wood Frame
Foundation: Fieldstone, Stone
Roof: Metal, Shingle - Asphalt, Slate
Exterior: Clapboard, Wood

Driveway
Paved

Lot, Zoning, & Easement Information
Corner, Level, Sidewalks

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1850

Financial

Tax Information
Tax Year: 2021
Gross Amount Tax: 6726.94
SPAN Number: 144-045-10176
Taxes TBD: Yes

Other Tax Information
Page Deed: 36

Utilities

Heating & Cooling Information
Heat: Forced Air
Heat Fuel: Oil

Sewer Information
Public

Electric Information
Electric Company: Green Mountain Power
Circuit Breaker(s)

Water Information
Public

Other Utilities Information
Cable Company: Comcast
Fuel Company: HB Fuels
Phone Company: Vtel
Cable, High Speed Intrnt -AtSite, Internet - Fixed Wireless, Telephone At Site

Location

School Information
School District: Two Rivers Supervisory Union
Elementary School: Chester-Andover Elementary
Elementary School: Chester-Andover Elementary
Middle/Jr School: Green Mountain UHSD #35

Road Information
Road Frontage: Yes
Road Frontage Length: 114
Public

Other Location Information
Directions: From the Chester Village Green travel West on Rt 11. Turn right Senior Circle. See sign.

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 2,775
Stories: —
Lot Size: 1.19 acres
Style: Single Family Residential
Year Built: 1850
Year Renovated: —
County: Windsor County
APN: 14404510176

Home facts updated by county records on Sep 2, 2026

Around this home

Schools

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

Chester-Andover Unified School District #29

Public PreK-6 • 0.3mi

6/10

Green Mountain Uhsd #35

Public 7-12 • 1.3mi

7/10

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

3/10 Heat Factor

7 days above 90° expected this year, 17 days in 30 years

3/10 Wind Factor

7% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Chester, VT • 05143

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 8.6 hours in June and 3.6 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

3.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$503,000 – $609,000

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

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3D WALKTHROUGH

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3D WALKTHROUGH

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New listings for sale in 05161

VIDEO TOUR

$1,300,000

3 beds3 baths4,714 sq ft

1337 Andover Ridge Rd, Andover, VT 05161

$695,000

3 beds2.5 baths2,232 sq ft

717 Horsenail Hill Rd, Chester, VT 05359

$340,000

3 beds2 baths3,608 sq ft

145 S Main St, Chester, VT 05143

$700,000

2 beds3 baths1,556 sq ft

1260 Grafton Rd, Chester, VT 05143

Home values near 372 Main St

Data from public records.

Address	Redfin Estimate
278 Main St, Chester, VT 4 Beds \| 3.5 Baths \| 3236 Sq. Ft.	$437,809
460 Main St, Chester, VT 3 Beds \| 1 Baths \| 1143 Sq. Ft.	$208,762

Address	Redfin Estimate
308 Main St, Chester, VT 7 Beds \| 2 Baths \| 5044 Sq. Ft.	$657,432
407 Main St, Chester, VT 5 Beds \| 3.5 Baths \| 2047 Sq. Ft.	$398,917

Address	Redfin Estimate
442 Main St, Chester, VT 4 Beds \| 1 Baths \| 2264 Sq. Ft.	$324,919
447 Main St, Chester, VT 6 Beds \| 4.5 Baths \| 3096 Sq. Ft.	$467,386

Property information provided by PrimeMLS when last listed in 2021. This data may not match . 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 05143, VT

Sale history for 372 Main St

Tax history for 372 Main St

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05161

Home values near 372 Main St

More real estate resources