266 Main Street

Closed 8/31/22
Closed 8/31/22
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Sold
Last Sold Price
$535,000
9 beds5,242 sqft
266 Main St, Chester, VT 05143
Single FamilyProperty Type
0.75 acresLot Size
1780Year Built
$102/sq ftPrice per sq ft
2 carsParking Spaces

Description

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. Currently rented out as an extended stay rental and generating $8,800 monthly. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished...This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. Currently rented out as an extended stay rental and generating $8,800 monthly. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches.   The main floor is easily accessible with first floor accommodations for those needing to avoid stairs.   Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

    Sold By New England Landmark Realty LTD

    • Listed by: Daire Gibney • Barrett and Valley Associates Inc.
    Listing closed: 08/31/2022 12:00 AM • Source: New England Real Estate Network, MLS#: 4907617

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    $3,826 per month

    30 year fixed, 7.03% Interest

    Principal and Interest

    $2,856

    Property Taxes

    $970

    HOA Dues

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    Property Information for 266 Main Street

    Property Details
    • Taxes: $11,643 / year
    • MLS Type: Residential / Single Family
    • County: Windsor County
    • Parking: Driveway, Garage, On-Site, On Street, Parking Spaces 6+, Paved
    • Zoning: Village Center
    Building Information
    • Stories: 2
    • Year Built: 1780
    • Lot Size: 0.75 AC / 32,670 SF
    Summary
    Location and General Information
    • Area Description: Historic District, In Town
    • City: Chester
    • County: VT-Windsor
    • Directions: Located in the center of Chester Village across from the village common and 2 doors up the street from the historic society and the information center.
    • Latitude: 43.264994948277348
    • Longitude: -72.599400613255341
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Street
    • Zip Code: 05143
    Taxes and HOA Information
    • SPAN Number: 144-045-10050
    • Tax - Gross Amount: $11,643.00
    • Tax Year: 2021
    • Taxes TBD: No
    School Information
    • School - High: Green Mountain UHSD #35
    • School - District: Chester School District
    • School - Elementary: Chester-Andover Elementary
    • School - Middle/Jr: Green Mountain UHSD #35
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Paved
    Property
    Lot Information
    • Lot - Sqft: 32670.0
    • Lot Size Acres: 0.75
    • Road Frontage Length: 99.0
    • Square Feet Apx Finished Above Grade: 5242.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Finished BG Source: Public Records
    • Square Feet Apx Total: 5242.0
    • Square Feet Apx Total Finished: 5242.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Public Records
    • Square Feet Apx Unfinished Below Grade: 0.0
    • Square Feet Apx Unfinished BG Source: Public Records
    Property and Assessments
    • Current Use: No
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: Unknown
    • Foundation: Concrete, Fieldstone
    • PreConstruction: No
    • Resort: No
    • Surveyed: Unknown
    • Year Built: 1780
    Utilities
    • Electric Company: GMP
    • Electric: 200 Amp
    • Sewer: Public
    • Utilities: Fiber Optic Internt Avail
    Interior and Exterior Features
    Exterior Features
    • Features - Accessibility: Access Common Use Areas, Access Parking, Paved Parking
    • Features - Exterior: Barn, Deck, Garden Space, Porch
    • Roads: Paved, Public
    • Roof: Other, Shingle - Other
    Interior Features
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Interior Access
    • Baths - Total: 9
    • Baths - Full: 8
    • Half Baths: 1
    • One Quarter Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 15
    • Bedrooms - Total: 9
    • Features - Interior: Bar, Dining Area, Fireplace - Gas, Fireplace - Wood, Fireplaces - 3+, Furnished, Natural Woodwork, Storage - Indoor
    • Flooring: Hardwood, Softwood, Tile
    • Heat Fuel: Oil
    • Heating: Baseboard
    • Cooling: None
    • Total Stories: 2

    Property History for 266 Main Street

    DateEvent & SourcePriceAppreciation
    Aug 31, 2022

    Sold

    New England Real Estate Network #4907617

    		$535,000—
    May 13, 2022

    Active Under Contract

    New England Real Estate Network #4907617

    		—
    May 2, 2022

    Listed (Active)

    New England Real Estate Network #4907617

    		$529,000—
    DateEvent & SourcePrice
    08/31/2022

    Sold

    New England Real Estate Network #4907617

    $535,000
    05/13/2022

    Active Under Contract

    New England Real Estate Network #4907617

    —
    05/02/2022

    Listed (Active)

    New England Real Estate Network #4907617

    $529,000

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

    Public Records for 266 Main Street

    Taxable ValueLand$32,500Additions$451,800Total$484,300
    Tax Record2025$9,039 ($753 / month)
    Home Facts
    Baths7.5Total Finished SqFt4,972 SqFtAbove Grade Finished SqFt4,972 SqFtUnfinished Basement SqFt1,584 SqFtLot Size32,670 SqFtStyleMiscellaneous CommercialYear Built1825Year Renovated1825CountyWINDSORAPN(045) 605102

    Schools near 266 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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    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.

    Listing Courtesy of Barrett and Valley Associates Inc.

    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 10/01/2026 05:16 AM