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.

The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Name

Your Email Address

Phone

Message Send me the deed for 21 Main Street Chester CT 06412 (ID#:24148717)

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Name

Your Email Address

Phone

Message Send me the survey or tax map for 21 Main Street Chester CT 06412 (ID#:24148717)

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Name

Your Email Address

Phone

Message I would like more information for 21 Main Street Chester CT 06412 (ID#:24148717)

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Welcome Home

21 Main StreetChester, CT 06412Price: $1,200,000

$/month over payments

Listing Tools

Property Details of 21 Main Street

Map Location

Driving Directions

Simply Sold Real Estate

Contact

Quick Links

Welcome Home

21 Main StreetChester, CT 06412Price: $1,200,000

$/month over payments

Listing Tools

$/month over payments

Hi there! How can we help you?

Send to a friend

Property Details of 21 Main Street

Map Location

Driving Directions

Hi there! How can we help you?

Hi there! How can we help you?

Hi there! How can we help you?

Simply Sold Real Estate

Contact

Quick Links