Chester, VT | 81 Main Street

Christie's International Real Estate
$445,000
MLS#: 5095551
3,865
Sq Ft
0.44
Acres
4
Baths
5
Bedrooms
General Property Information
Property Status
Active
Price
$445, 000
Property Type
Single Family
County
VT-Windsor
Agency / Brokerage
Betsy Adamovich
Real Broker LLC
List Date
6/17/2026 8:00 PM
Acres
0.44
Year Built
1880
Bedrooms
5
Total Baths
4
Sq. Ft. (Total)
3,865
Tax Year
2025
Taxes
$8,894

Virtual Tour

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, 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.

Map

Interior Features
# Of Stories
2.5
Sq. Ft. (Total)
3,865
Sq. Ft. (Above Ground)
3,865
Sq. Ft. (Below Ground)
0
Sq. Ft. Unfinished
400
Rooms
15
Bedrooms
5
Baths
4
Interior Desc
Bar, Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace Screens/Equip, Wood Fireplace, 1 Fireplace, Primary BR w/ BA, Soaking Tub, Wet Bar, 1st Floor Laundry, Walkup Attic
Appliances Included
Dishwasher, Dryer, Mini Fridge, Refrigerator, Washer, Electric Stove
Flooring
Carpet, Laminate, Tile, Wood
Heating
Propane, Oil, Forced Air
Basement Desc
Unfinished

Town Market Snapshot

Source: Data provided by PrimeMLS, graph generated by Pall Spera Company

Exterior Features
Style of Residence
Historic Vintage, Other, Victorian
Time Share
No
Exterior Details
Building, Garden Space, Natural Shade, Outbuilding, Porch, Covered Porch
Land Desc.
Level, Major Road Frontage, Sidewalks, Street Lights, In Town, Near Shopping, Near Skiing, Near Snowmobile Trails, Near Public Transport, Near School(s)
Roof Desc.
Shingle, Slate
Driveway Desc.
Paved
Foundation Desc.
Concrete, Stone
Sewer Desc.
Public, Public Sewer On-Site
Garage / Parking
Yes
Garage Spaces
1
Road Frontage
0
Zoning
Village Center
Elementary School
Chester-Andover Elementary
Middle School
Green Mountain UHSD #35
High School
Green Mountain UHSD #35

Affordability Estimate

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