About 21 Main Street
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.
Features of 21 Main Street
| MLS® # | 24148717 |
|---|---|
| Price | $995,000 |
| Bathrooms | 1.00 |
| Full Baths | 1 |
| Square Footage | 3,000 |
| Square Footage | Approximate |
| Acres | 0.02 |
| Type | Commercial For Sale |
| Status | Active |
Community Information
| Address | 21 Main Street |
|---|---|
| Area | N/A |
| City | Chester |
| County | Middlesex |
| State | Connecticut |
| Zip Code | 06412 |
Amenities
| Utilities | Electric, Gas |
|---|---|
| Is Waterfront | No |
| Has Pool | No |
Interior
| Interior | Wood |
|---|---|
| Heating | Hot Air, Electric, Propane |
| Cooling | Window Unit |
| Fireplace | No |
| Has Basement | No |
Exterior
| Lot Description | N/A |
|---|---|
| Roof | Asphalt Shingle |
Additional Information
| Date Listed | January 13th, 2026 |
|---|---|
| Days on Market | 252 |
| Zoning | C |
| RE / Bank Owned | No |