Single Family Residence at 81 Main Street, Chester

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58 photos

$450,000

81 Main Street

Chester, VT 05143

Listed by Betsy Adamovich · Real Broker LLC

Bedrooms

Bathrooms

Living area

N/A

Year built

1880

About this home

Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning fireplace and a large entertainment room complete with a wet bar, creating an ideal setting for gatherings, celebrations, or relaxing at home. The thoughtfully designed primary suite features a beautiful en-suite bathroom, while first-floor laundry adds everyday convenience. The flexible floor plan provides abundant space for family, guests, remote work, hobbies, or multi-generational living. Outside, a paved driveway leads to a detached one-car garage, and the level backyard offers plenty of room for recreation, gardening, pets, or outdoor entertaining. Mature trees and established landscaping create a natural buffer from the road, providing a sense of privacy while remaining just moments from Chester's village amenities, shops, restaurants, and community events. Combining historic character, generous living space, and a highly desirable location, this is a rare opportunity to own one of Chester's classic homes. Conveniently located just minutes from I-91 and within easy reach of Okemo Mountain Resort, Magic Mountain, Bromley Mountain, Stratton Mountain, and other Southern Vermont outdoor destinations, this property offers year-round access to skiing, hiking, recreation, and travel throughout the region.

Property details

MLS #: 5095551
Property type: Single Family Residence
Subdivision: N/A
Status: Active
Days on market: 55
On market date: N/A
Stories: N/A
Total bathrooms: 2
Garage spaces: 1
Parking spaces: N/A
Lot size: 0.44 acres

Location

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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary

Charlestown Primary School

9.22 mi away · Grades -1-5

Nearest school -- attendance-zone data not available here

5.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 217
Student:teacher ratio: 9.9:1
District: Fall Mountain Regional School District

Middle

Charlestown Middle School

9.03 mi away · Grades 6-8

Nearest school -- attendance-zone data not available here

5.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 146
Student:teacher ratio: 11.2:1
District: Fall Mountain Regional School District

High

None found nearby

Mortgage calculator

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Interest rate

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Est. monthly payment

$2,860/mo

$90,000 down

$360,000 loan

Principal & interest$2,335

Property tax (est.)$375

Home insurance (est.)$150

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Copyright 2026 PrimeMLS. 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 07/20/26.