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MLS 24144188 For Sale Updated March 3, 2026
21 Main Street

Chester, Connecticut 06412

$1,200,000
On market 61 days
21 Main Street
1 / 37

About This Property

Opportunities like this rarely come along. Perfectly positioned in the very heart of downtown Chester, this 1830 mixed-use building offers unmatched visibility, foot traffic, and charm. For the past 17 years, the street-level space has operated as a successful and beloved art gallery, benefiting from its prominent Main Street presence and steady stream of visitors drawn to Chester's vibrant shops, dining, and cultural events. The upper level features a bright and inviting short-term rental, fully furnished, beautiful outdoor seating area above the Pattaconk brook-ideal for continued income generation or personal use. Additional storage space in the attic & alley way. With flexible mixed-use zoning, the building supports a wide range of possibilities; retail, gallery, studio, office, or live-work combinations. Blending historic character with modern opportunity, this is a rare chance to own a cornerstone property in one of Connecticut's most desirable village centers. Location, history, and versatility right where everyone wants to be.

Property Details

Interior

Heat
Hot Air — Propane
Cooling
Wall Unit
Flooring
Wood
Interior Features
Security System Window Display

Exterior & Lot

Roof
NULL
Construction
Construction
Exterior Features
Sidewalk

Utilities & Systems

Water Source
Public Water Connected
Sewer
Public Sewer Connected

Community & Schools

Elementary
NULL
Middle
NULL
High
NULL

21 Main Street

Chester , Connecticut 06412

$1,200,000

On market 61 days

Beds
-
Baths
-
SqFt
3,000
Type
Business
County Middlesex
Garage -
Rooms -
Lot Size -
Property Tax -
Assessed Value -
Year Built 1830

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
Open the full mortgage calculator →

Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: RAVE51.

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