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Investment Highlights

  • Unique opportunity to own a versatile property in one of Connecticut’s most picturesque towns
  • Prime location near local landmarks and major routes

Executive Summary

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 Facts

Sale Type
Investment or Owner User
Property Type
Retail
Property Subtype
Freestanding
Building Size
3,000 SF
Building Class
C
Year Built
1830
Price
$1,658,880 CAD
Price Per SF
$552.96 CAD
Tenancy
Single
Building Height
2 Stories
Building FAR
3.00
Lot Size
0.02 AC
Zoning
VD - Village District
Frontage
40’ on Main Street

Amenities

  • Air Conditioning
Somewhat walkable
20/100
Exceptionally drivable
100/100
Limited public transit
30/100
Fairly bikeable
40/100

Property Taxes

Property Taxes

Parcel Number
CHES-000014-000000-000547
Land Assessment
$174,182 CAD
Improvements Assessment
$618,444 CAD
Total Assessment
$792,627 CAD
  • Listing ID: 38949990

  • Date on Market: 2026-01-02

  • Last Updated:

  • Address: 21 Main St, Chester, CT 06412

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