REQUEST A TOUR If you would like to see this home without being there in person, select the "Virtual Tour" option and your agent will contact you to discuss available opportunities.

In-PersonVirtual Tour

Nick Regan

nick@reganrealtygroup.com +1(603) 759-8169

Listed by Betsy Adamovich • Real Broker LLC

$ 475,000

Est. payment -/mo

Save Virtual Tour

Open 6/27 11AM-1PM

81 Main ST Chester, VT 05143

5 Beds

4 Baths

3,865 SqFt

Open House

Sat Jun 27, 11:00am - 1:00pm

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family

Listing Status Active

Purchase Type For Sale

Square Footage 3,865 sqft

Price per Sqft $122

MLS Listing ID 5095551

Style Historic Vintage,Other,Victorian

Bedrooms 5

Full Baths 2

Three Quarter Bath 2

Construction Status Existing

Year Built 1880

Annual Tax Amount $8,894

Tax Year 2025

Lot Size 0.440 Acres

Acres 0.44

Property Sub-Type Single Family

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.

Location

State VT

County Vt-windsor

Area Vt-Windsor

Zoning Village Center

Rooms

Basement Entrance Interior

Basement Unfinished

Interior

Heating Propane, Oil, Forced Air

Cooling Wall AC Units

Flooring Carpet, Laminate, Tile, Wood

Exterior

Parking Features Yes

Garage Spaces 1.0

Utilities Available Propane

Roof Type Shingle,Slate

Building

Lot Description Level, Major Road Frontage, Sidewalks, Street Lights, In Town, Near Shopping, Near Skiing, Near Snowmobile Trails, Near Public Transport, Near School(s)

Story 2.5

Sewer Public, Public Sewer On-Site

Water Public, Public Water On-Site

Architectural Style Historic Vintage, Other, Victorian

Construction Status Existing

Schools

Elementary Schools Chester-Andover Elementary

Middle Schools Green Mountain Uhsd #35

High Schools Green Mountain Uhsd #35

School District Two Rivers Supervisory Union

Others

Virtual Tour https://my.matterport.com/show/?m=32yKyW4SQ6H

Nick Regan

Agent

+1(603) 759-8169

Nick Regan

81 Main ST Chester, VT 05143

Open House

Key Details

Location

Rooms

Interior

Exterior

Building

Schools

Others

GET MORE INFORMATION

Go tour this home

81 Main ST