81 Main St

Chester, VT 05143

$475,000
Price
5
Beds
3,865 Sq. Ft.
$123 / Sq. Ft.
3,865
Sq. Ft.
$123
per Sq. Ft.
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Open: 6/27 11:00AM - 01:00PMVirtual TourNew
Open: 6/27 11:00AM - 01:00PMVirtual TourNew

Description

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,...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.
  1. Listed by Betsy Adamovich • Real Broker LLC

Property Details for 81 Main Street

Zoning
Village Center

Open Houses

Saturday, Jun 27th11:00 AM - 1:00 PM
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LISTING UPDATED: 06/18/2026 06:46 PM

Property Details for 81 Main Street

StatusActive
MLS #5095551
Days on MarketListed Today
Taxes$8,894 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1880
Lot Size0.44 AC / 19,166 SF
CountyWindsor County
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Location

Listing Courtesy of Real Broker LLC
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Building Information for 81 Main Street

Stories2Year Built1880Building Size-Lot Size0.44 AC / 19,166 SF

Payment Calculator

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$3,108 per month

30 year fixed, 6.36% Interest

Principal and Interest

$2,367

Property Taxes

$741

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 81 Main Street

Summary
Location and General Information
  • City: Chester
  • County: VT-Windsor
  • Directions: GPS is accurate. Across from the Chester-Andover Elementary School.
  • Latitude: 43.263440000001005
  • Longitude: -72.596593999999996
  • Road Frontage: TBD
  • Seasonal: No
  • State: VT
  • Street Designation: Street
  • Zip Code: 05143
Taxes and HOA Information
  • SPAN Number: 144-045-11906
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 1.00
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Level, Major Road Frontage, Sidewalks, Street Lights, In Town, Near Shopping, Near Skiing, Near Snowmobile Trails, Near Public Transport, Near School(s)
  • Lot Size Acres: 0.44
  • Total Finished Area: 3865.0
  • Above Grade Finished Area: 3865.0
  • Above Grade Finished Area Source: Public Records
  • Above Grade Unfinished Area: 0.0
  • Below Grade Finished Area: 0.0
  • Below Grade Unfinished Area: 400.0
  • BelowGradeUnfinishedAreaSource: Public Records
  • Lot Size Square Feet: 19166.0
  • Total Area: 4265.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1880
  • School District: Two Rivers Supervisory Union
  • High School: Green Mountain UHSD #35
  • Middle/Jr School: Green Mountain UHSD #35
  • Elementary School: Chester-Andover Elementary
Utilities
  • Electric Company: Green Mountain Power
  • Fuel Company: James Plumbing
  • Electric: Circuit Breaker(s)
  • Sewer: Public, Public Sewer On-Site
  • Water Source: Public, Public Water On-Site
  • Utilities: Propane
  • Internet: High Speed Intrnt Avail
  • Water Company: Town of Chester
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame
  • Roof: Shingle, Slate
Interior Features
  • Appliances: Dishwasher, Dryer, Mini Fridge, Refrigerator, Washer, Electric Stove
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Unfinished
  • Flooring: Carpet, Laminate, Tile, Wood
  • Heating: Propane, Oil, Forced Air
  • Cooling: Wall AC Units
  • Total Stories: 2.5
  • Rooms Total: 15
  • Bathrooms Full: 2
  • Bathrooms Half: 0
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 2
  • Bedrooms Total: 5
  • Bathrooms Total: 4

Property History for 81 Main Street

DateEvent & SourcePriceAppreciation
Jun 18, 2026

Listed (Active)

New England Real Estate Network #5095551

$475,000—
Feb 10, 2023

Sold (Public Record)

Public Record #1505877210

$460,000—
Feb 10, 2023

Sold

New England Real Estate Network #4929143

$460,000—
DateEvent & SourcePrice
06/18/2026

Listed (Active)

New England Real Estate Network #5095551

$475,000
02/10/2023

Sold (Public Record)

Public Record #1505877210

$460,000
02/10/2023

Sold

New England Real Estate Network #4929143

$460,000

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

Public Records for 81 Main Street

Taxable ValueLand$29,400Additions$276,300Total$305,700
Tax Record2024$8,480 ($707 / month)
Home Facts
Beds6Baths3Total Finished SqFt3,864 SqFtAbove Grade Finished SqFt3,864 SqFtStories3Lot Size19,166 SqFtStyleSingle Family ResidenceYear Built1880CountyWINDSORAPN(045) 605043Fireplace TypeHas Fireplace

Schools near 81 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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More information about 81 Main Street, Chester, VT 05143

81 Main Street is a single family home for sale in Chester, VT 05143. This listing's school district is Green Mountain Unified School District. Nearby schools include Chester-Andover Usd #29 and Green Mountain Uhsd #35. 81 Main Street is a 5-bed, 4-bath, 3,865 sqft single family home built in 1880.

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 Real Broker LLC

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 06/18/2026 11:20 PM