Exceptional mixed-use opportunity with strong visibility on South Main Street in downtown Chester. Offered at an attractive 8% cap rate, this versatile property features two residential apartments-a 2-bedroom, 1-bath unit and a 1-bedroom, 1-bath unit-alongside two commercial spaces, creating a diverse and stable income stream. A large barn adds tremendous upside with the potential for additional units or expanded uses, subject to local approvals. Positioned in the heart of one of Southern Vermont's most charming villages, the property benefits from excellent exposure and convenient access to Chester's vibrant downtown, local shops, restaurants, and year-round events. Ample parking provides added convenience for residents, customers, and tenants alike. Whether you're looking to expand your portfolio, establish a business presence, or capitalize on future development potential, this well-located property offers the ideal blend of cash flow, visibility, and long-term opportunity. 3D Virtual Tour available upon request.

More Info

Tax Information

Tax Year2025

Basic Information

StatusACT
Modification Date06/30/2026
TypeBusiness, Multi-Family, Office, Retail
List Price$385,000
Broker NameNancy Jenkins Real Estate
Listing Agent NameThe Nancy Jenkins Team
Lister Office NameNancy Jenkins Real Estate
MLS Number5097411
MLS StatusActive

Location

Building Number145
StreetSouth Main Street
TownChester
StateVT
Zip05143
CountyWindsor
Address145 South Main Street

Building

Year Built1880
ConstructionWood Frame
NumberOfUnitsInCommunity5
Square Feet3,608
BasementUnfinished

Property

Acreage0.8
Parking Spaces
Property TypeCommercial Sale
AreaVT-Windsor
Lot Sqft34,848

Exterior

RoofSlate

Utilities

Heating CoolingBaseboard, Hot Air, Propane, Oil

Amenities

PricePerSqFt106.71

Legal

Taxes$7,811
NOI30610
OtherStructuresBuilding Only
ZoningCommercial

Other

Date Listed06/30/2026

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated July 1, 2026 7:38 AM UTC

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