81 Main St Chester, VT 05143
Estimated payment $3,306/month
Highlights
- Very Popular Property
- Property is near public transit, schools, and shops
- Wood Flooring
- Public Water Access
- Cathedral Ceiling
- Victorian Architecture
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.
Open House Schedule
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Saturday, June 27, 202611:00 am to 1:00 pm6/27/2026 11:00:00 AM +00:006/27/2026 1:00:00 PM +00:00Add to Calendar
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $8,894
Year Built
- Built in 1880
Lot Details
- 19,166 Sq Ft Lot
- Level Lot
- Garden
- Historic Home
- Property is zoned Village Center
Parking
- 1 Car Garage
- Off-Street Parking
Home Design
- Victorian Architecture
- Concrete Foundation
- Stone Foundation
- Wood Frame Construction
- Shingle Roof
- Slate Roof
Interior Spaces
- Property has 2.5 Levels
- Wet Bar
- Bar
- Cathedral Ceiling
- Ceiling Fan
- Wood Burning Fireplace
- Screen For Fireplace
- Dining Area
- Basement
- Interior Basement Entry
- Walkup Attic
Kitchen
- Electric Range
- Dishwasher
Flooring
- Wood
- Carpet
- Laminate
- Tile
Bedrooms and Bathrooms
- 5 Bedrooms
- En-Suite Bathroom
- Soaking Tub
Laundry
- Laundry on main level
- Dryer
- Washer
Outdoor Features
- Public Water Access
- Covered Patio or Porch
- Outbuilding
Location
- Property is near public transit, schools, and shops
Schools
- Chester-Andover Elementary School
- Green Mountain Uhsd #35 Middle School
- Green Mountain Uhsd #35 High School
Utilities
- Cooling System Mounted In Outer Wall Opening
- Window Unit Cooling System
- Forced Air Heating System
- Pellet Stove burns compressed wood to generate heat
- Heating System Uses Oil
- Heating System Uses Propane
- Propane
Community Details
- Snowmobile Trail
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $8,480 | $305,700 | $29,400 | $276,300 |
| 2024 | $8,480 | $305,700 | $29,400 | $276,300 |
| 2023 | $4,853 | $305,700 | $29,400 | $276,300 |
| 2022 | $7,289 | $305,700 | $29,400 | $276,300 |
| 2021 | $7,502 | $305,700 | $29,400 | $276,300 |
| 2020 | $7,210 | $305,700 | $29,400 | $276,300 |
| 2019 | $7,640 | $364,000 | $77,600 | $286,400 |
| 2018 | $7,491 | $364,000 | $77,600 | $286,400 |
| 2017 | $0 | $364,000 | $77,600 | $286,400 |
| 2016 | $0 | $364,000 | $77,600 | $286,400 |
| 2015 | -- | $3,640 | $0 | $0 |
| 2014 | -- | $3,640 | $0 | $0 |
| 2013 | -- | $4,260 | $0 | $0 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 06/18/2026 06/18/26 | For Sale | $475,000 | +3.3% | $123 / Sq Ft | |
| 02/10/2023 02/10/23 | Sold | $460,000 | -4.0% | $119 / Sq Ft | View Prior Sale |
| 12/21/2022 12/21/22 | Pending | -- | -- | -- | |
| 10/18/2022 10/18/22 | For Sale | $479,000 | 0.0% | $124 / Sq Ft | |
| 09/22/2022 09/22/22 | Pending | -- | -- | -- | |
| 09/09/2022 09/09/22 | For Sale | $479,000 | -- | $124 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $460,000 | -- | |
| Grant Deed | $255,000 | -- | |
| Grant Deed | $40,000 | -- | |
| Grant Deed | $40,000 | -- |
Source: PrimeMLS
MLS Number: 5095551
APN: 144-045-11906
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display 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.
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