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81 Main Street, Chester, VT 05143

$450,000
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Active Price Reduced $10,000 on July 20th, 2026
BEDS5 BATHS4 full SQUARE FEET3,865 MLS#5095551
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLTwo Rivers Supervisory Union

Listing Courtesy of: Real Broker LLC
Agency Phone: 855-450-0442
Associate Name: Betsy Adamovich
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Property 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.

81 Main Street | MLS# 5095551

This single family home located at 81 Main Street, Chester, VT 05143 is currently listed for sale with an asking price of $450,000. This property was built in 1880 and has 5 bedrooms and 4 full baths with 3865 sq. ft. Main Street is located within the Two Rivers Supervisory Union school district. Search Chester real estate on www.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Unfinished
Cooling: Wall AC Units
Garage: 1
Heating: Propane, Oil, Forced Air
Home Style: Historic Vintage, Other, Victorian
Lot Size: 0.44 Acres
Roof Type: Shingle, Slate
Stories: 2.5
Taxes: $8,894
Year Built: 1880

Amenities

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
Building
Garden Space
Natural Shade
Outbuilding
Porch
Covered Porch

Feature Descriptions

Appliances: Dishwasher, Dryer, Mini Fridge, Refrigerator, Washer, Electric Stove
Baths 3/4: 2
Baths Full: 2
Construction: Wood Frame
Construction Status: Existing
Days on Site: 33
Driveway: Paved
Electric: Circuit Breaker(s)
Equipment: Window AC, Pellet Stove
Exterior: Wood Frame
Flood Zone: No
Flooring: Carpet, Laminate, Tile, Wood
Foundation: Concrete, Stone
Lot: Level, Major Road Frontage, Sidewalks, Street Lights, In Town, Near Shopping, Near Skiing, Near Snowmobile Trails, Near Public Transport, Near School(s)
Number of Rooms: 15
Parking: Off Street, Paved
Roads: Paved, Public, Public Maintained Road
Sewer: Public, Public Sewer On-Site
Sq. Ft. Above Grade Finished: 3865
Sq. Ft. Total Finished: 3865
Total Stories: 2.5
Water: Public, Public Water On-Site
Zoning: Village Center

Local Schools

High School: Green Mountain UHSD #35
Middle School: Green Mountain UHSD #35
Elementary School: Chester-Andover Elementary
School District: Two Rivers Supervisory Union

Listed By / Shown By

Listed By

Agency Name: Real Broker LLC
Agent Name: Betsy Adamovich
Agency Phone: 855-450-0442

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Estimated Payment

$ 1,873.92 per month $1,001.50 Principal & Interest $741.17 Property Tax $131.25 Homeowner's Insurance

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