Prime mixed-use investment opportunity on the iconic Chester Green, offering strong visibility, multiple income streams, and timeless village charm. Listed at an attractive 8% cap rate, this unique property features two 1-bedroom, 1-bath residential apartments along with three commercial spaces boasting excellent storefront frontage and a prominent presence in the heart of downtown Chester. Surrounded by historic architecture, vibrant shops, restaurants, and year-round community events, the property enjoys one of the most desirable locations in Southern Vermont. The combination of residential and commercial tenants provides diversification and stability, while the highly walkable setting enhances appeal for both businesses and residents. Whether expanding an investment portfolio or seeking a distinctive asset in a thriving village center, this rare Chester Green offering combines character, visibility, and exceptional income potential. 3D Virtual Tours available upon request.

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Tax Information

Tax Year2025

Building

Year Built1880
ConstructionWood Frame
NumberOfUnitsInCommunity5
FoundationStone
Square Feet3,940
BasementUnfinished

Exterior

RoofSlate

Utilities

Heating CoolingBaseboard, Propane

Other

Date Listed06/30/2026

Basic Information

StatusACT
Modification Date06/30/2026
TypeBusiness, Multi-Family, Office, Retail
List Price$465,000
Broker NameNancy Jenkins Real Estate
Listing Agent NameThe Nancy Jenkins Team
Lister Office NameNancy Jenkins Real Estate
MLS Number5097413
MLS StatusActive

Amenities

PricePerSqFt118.02

Location

Building Number34
StreetSchool Street
TownChester
StateVT
Zip05143
CountyWindsor
Address34 School Street

Property

Acreage0.07
Parking Spaces
Property TypeCommercial Sale
AreaVT-Windsor
Lot Sqft3,049

Legal

Taxes$6,454
NOI37428
OtherStructuresBuilding Only
ZoningCommercial

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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