322 South Main Street

Closed 3/25/19
Closed 3/25/19
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Sold
Last Sold Price
$93,500
2 beds768 sqft$122/sqft
322 S Main St, Chester, VT 05143
Single FamilyProperty Type
0.87 acresLot Size
1900Year Built
$122/sq ftPrice per sq ft
3 carsParking Spaces

Description

A remarkable little house near the village of Chester on Main Street. A cape with two bedrooms and 2 bathrooms on .87 acres. Sit comfortably by the gas fireplace or on the deck overlooking the river. Wander along the river. Very pretty spot on Main Street and zoned residential/commercial. Just 20 minutes to Okemo. And 40 minutes to the Upper Valley. Offered at great price in a great town.A remarkable little house near the village of Chester on Main Street. A cape with two bedrooms and 2 bathrooms on .87 acres. Sit comfortably by the gas fireplace or on the deck overlooking the river. Wander along the river. Very pretty spot on Main Street and zoned residential/commercial. Just 20 minutes to Okemo. And 40 minutes to the Upper Valley. Offered at great price in a great town.

    Sold By BHG Masiello Brattleboro

    • Listed by: Catherine Fisher • Coldwell Banker Watson Realty/ Ludlow
    Listing closed: 03/25/2019 12:00 AM • Source: New England Real Estate Network, MLS#: 4694673

    Recent comparable sales

    Median sold price

    $272,500

    Avg days on market

    25

    Sale-to-list ratio

    94.6%

    Chester, VT

    9 comparable properties found

    $359,000 | 1470 Flamstead Road, Chester, VT 05143
    1/43
    1

    $359,000

    Sold 11/05/25

    2
    Bedrooms
    803
    Square Feet
    2.66
    Acres

    1470 Flamstead Road, Chester, VT 05143

    $550,000 | 1937 Green Mountain Turnpike, Chester, VT 05143
    1/54
    2

    $550,000

    Sold 10/06/25

    2
    Bedrooms
    1,812
    Square Feet
    0.81
    Acres

    1937 Green Mountain Turnpike, Chester, VT 05143

    $229,000 | 87 Kevadus Circle, Chester, VT 05143
    1/2
    3

    $229,000

    Sold 08/29/25

    3
    Bedrooms
    840
    Square Feet
    0.5
    Acres

    87 Kevadus Circle, Chester, VT 05143

    a front view of a house with a yard
    1/16
    4

    $90,700

    Sold 12/09/25

    2
    Bedrooms
    858
    Square Feet
    0.11
    Acres

    515 Myrtle Street, Chester, SC 29706

    $425,000 | 115 Orcutt Drive, Chester, VT 05143
    1/37
    5

    $425,000

    Sold 07/30/25

    2
    Bedrooms
    1,360
    Square Feet
    0.75
    Acres

    115 Orcutt Drive, Chester, VT 05143

    $270,000 | 203 Marcs Drive, Chester, VT 05143
    1/27
    6

    $270,000

    Sold 02/05/25

    2
    Bedrooms
    1,005
    Square Feet
    2.2
    Acres

    203 Marcs Drive, Chester, VT 05143

    $275,000 | 230 Kevadus Circle, Chester, VT 05143
    1/14
    7

    $275,000

    Sold 09/10/25

    3
    Bedrooms
    894
    Square Feet
    0.25
    Acres

    230 Kevadus Circle, Chester, VT 05143

    8

    $84,000

    Sold 08/14/25

    1
    Bedrooms
    1
    Bathrooms
    800
    Square Feet
    2
    Acres

    1622 Highway 103, Chester, VT 05143

    $95,000 | 207 Doty Street, Chester, WI 53963
    9

    $95,000

    Sold 11/07/24

    2
    Bedrooms
    900
    Square Feet
    0.17
    Acres

    207 Doty Street, Chester, WI 53963

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    $712 per month

    30 year fixed, 6.71% Interest

    Principal and Interest

    $483

    Property Taxes

    $228

    HOA Dues

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    Property Information for 322 South Main Street

    Property Details
    • Taxes: $2,741 / year
    • MLS Type: Residential / Single Family
    • County: Windsor County
    • Parking: Parking Spaces 3
    • Water Body Type: River
    • Water View: Yes
    • Waterfront Property: Yes
    • Zoning: residential/commerical
    Building Information
    • Stories: 1
    • Year Built: 1900
    • Lot Size: 0.87 AC / 37,897 SF
    Summary
    Location and General Information
    • City: Chester
    • County: VT-Windsor
    • Directions: Travel south on Route 11 from Chester Green. On right just before the Country Girl Diner. See sign.
    • Latitude: 43.259611493316619
    • Longitude: -72.590793084655729
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Street
    • Map: 605147
    • Zip: 05143
    Taxes and HOA Information
    • SPAN Number: 14404511496
    • Tax - Gross Amount: $2,741.33
    • Tax Year: 2017
    • Taxes TBD: No
    School Information
    • School - High: Green Mountain UHSD #35
    • School - District: Two Rivers Supervisory Union
    • School - Elementary: Chester-Andover Elementary
    • School - Middle/Jr: Green Mountain UHSD #35
    Parking
    • Garage: No
    • Driveway: Gravel
    Property
    Lot Information
    • Lot - Sqft: 37897.0
    • Lot Size Acres: 0.87
    • Road Frontage Length: 318.0
    • Square Feet Apx Finished Above Grade: 768.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Finished BG Source: Other
    • Square Feet Apx Total: 1536.0
    • Square Feet Apx Total Finished: 768.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Other
    • Square Feet Apx Unfinished Below Grade: 768.0
    • Square Feet Apx Unfinished BG Source: Other
    Property and Assessments
    • Current Use: No
    • Assessment Amount: $138,500
    • Property Class: Residential
    • Property Type: Single Family
    • Easements: Unknown
    • Flood Zone: Yes
    • Foundation: Poured Concrete
    • PreConstruction: No
    • Resort: No
    • ROW - Parcel Access: No
    • ROW to other Parcel: Yes
    • Surveyed: Yes
    • Year Built: 1900
    Utilities
    • Electric: 200 Amp
    • Sewer: Public
    Interior and Exterior Features
    Exterior Features
    • Color: yellow
    • Roads: Paved, Public
    • Roof: Shingle - Asphalt
    Interior Features
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Concrete, Concrete Floor
    • Baths - Total: 2
    • Baths - Full: 1
    • Half Baths: 1
    • One Quarter Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 6
    • Rooms: Level 1: Level 1: Kitchen - Eat-in, Level 1: Living Room
    • Rooms: Level 2: Level 2: Bedroom
    • Bedrooms - Total: 2
    • Heat Fuel: Gas - LP/Bottle
    • Heating: Gas Heater - Vented
    • Cooling: None
    • Total Stories: 1.5
    Room Information
    Room 1
    • Room Level: 2
    • Room Type: Bedroom
    Room 2
    • Room Level: 2
    • Room Type: Bedroom
    Room 3
    • Room Level: 1
    • Room Type: Kitchen - Eat-in
    Room 4
    • Room Level: 1
    • Room Type: Living Room

    Property History for 322 South Main Street

    DateEvent & SourcePriceAppreciation
    Mar 27, 2019

    Sold (Public Record)

    Public Record #641670343

    		$93,500—
    Mar 25, 2019

    Sold

    New England Real Estate Network #4694673

    		$93,500—
    May 22, 2018

    Price Change

    New England Real Estate Network #4694673

    		$130,000—
    DateEvent & SourcePrice
    03/27/2019

    Sold (Public Record)

    Public Record #641670343

    $93,500
    03/25/2019

    Sold

    New England Real Estate Network #4694673

    $93,500
    05/22/2018

    Price Change

    New England Real Estate Network #4694673

    $130,000

    For completeness, we often displays two records for one sale: the MLS record and the public record.

    Public Records for 322 South Main Street

    Taxable ValueLand$27,000Additions$76,500Total$103,500
    Tax Record2025$1,927 ($161 / month)
    Home Facts
    Beds2Baths1.5Total Finished SqFt768 SqFtAbove Grade Finished SqFt768 SqFtUnfinished Basement SqFt384 SqFtLot Size37,897 SqFtStyleSingle Family ResidenceYear Built1900Year Renovated1900CountyWINDSORAPN(045) 605147

    Schools near 322 South Main Street

    This home is within Green Mountain Unified School District.
    Rating
    School
    Type
    Grades
    Distance
    Chester-Andover Usd #29
    		Public - PK to 6
    Green Mountain Uhsd #35
    		Public - 7 to 12
    Rating
    School
    Distance
    Chester-Andover Usd #29
    PublicPK to 6

    Green Mountain Uhsd #35
    Public7 to 12

    School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 322 South Main Street, Chester, VT 05143
    $93,500
    2
    768
    37,897
    268 South Main Street, Chester, VT 05143
    $240,000
    1
    844
    14,810
    269 South Main Street, Chester, VT 05143
    $239,500
    3
    1,700
    24,829
    269 Main Street, Chester, VT 05143
    –
    3
    2.5
    1,680
    23,522
    46 Highway 103, Chester, VT 05143
    $20,000
    –
    –
    1,316
    25,700
    252 River Street, Chester, VT 05143
    $125,000
    3
    1,300
    10,890

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    No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

    Listing Courtesy of Coldwell Banker Watson Realty/ Ludlow

    Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 09/12/2026 01:26 AM