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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. †
3D Property Tour
Property Location
81 Main Street Chester
Property Details
List Price $475,000
Total Rooms 15
List Date Jun 18th, 2026
Cooperation Fee Unknown
Lot Size 0.44 Acres
Taxes $8,894
MLS# 5095551
Days on Market 1 Days
Tax Year 2025
Type House
Stories 2 1/2
Road Frontage
Bedrooms 5
Style Historic Vintage, Other, Victorian
Water Frontage
Full Bathrooms 2
Finished 3,865 Sqft
Construction No, Existing
3/4 Bathrooms 2
Above Grade 3,865 Sqft
Seasonal No
Half Bathrooms 0
Below Grade 0 Sqft
Year Built 1880
1/4 Bathrooms 0
Garage Size 1 Car
County Windsor
Interior Features
Equipment & AppliancesRefrigerator, Mini Fridge, Dishwasher, Washer, Dryer, Electric Stove
ConstructionWood Frame
BasementUnfinished
Exterior Features
Disability Features
Foundation
House Color
Floors Carpet,Laminate,Tile,Wood
Building Certifications
Roof Slate, Slate
HERS Index
DirectionsGPS is accurate. Across from the Chester-Andover Elementary School.
Lot DescriptionLevel, Major Road Frontage, Sidewalks, Street Lights, In Town, Near Shopping, Near Skiing, Near Snowmobile Trails, Near Public Transport, Near School(s)
Garage & Parking
Road Frontage Type Paved,Public,Public Maintained Road
Water Access
Suitable Use
Water Type
Driveway Paved
Water Body
Flood Zone No
Zoning Village Center
School District Two Rivers Supervisory Union
Middle Green Mountain UHSD #35
Elementary Chester-Andover Elementary
High Green Mountain UHSD #35
Heating Propane, Oil, Forced Air
Items Excluded
Cooling Wall AC Units
Negotiable
Sewer Public, Public Sewer On-Site
Parcel Access ROW
Water Public, Public Water On-Site
ROW for Other Parcel
Water Heater
Financing
Cable Co
Documents
Electric Circuit Breaker(s)
Tax ID 144-045-11906
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† The remarks published on this webpage originate from Listed By Betsy Adamovich of Real Broker LLC via the PrimeMLS IDX Program and do not represent the views and opinions of Coldwell Banker Hickok & Boardman. Coldwell Banker Hickok & Boardman cannot be held responsible for possible violations of copyright resulting from the posting of any data from the PrimeMLS IDX Program.