81 Main Street Chester, Vermont - For Sale

81 Main Street Chester, Vermont 05143 MLS# 5095551

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For Sale Status

$475,000 List Price

House Type

5 Beds

4 Baths

3,865 Sqft

Saturday, June 27th, 11:00AM - 1:00PM

Listed By Betsy Adamovich of Real Broker LLC
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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.