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$1,200,000
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Property Description
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.
Full Property Details
Full Property Details for 21 Main St
General
- Price: $1,200,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Commercial
- Source: SMARTMLS
- MLS ID: 24148717
- Updated: 1/13/2026
- Added to Site: 15 day(s) ago
Business
- Business Included: Yes
Interior
- Flooring: Wood
Rooms
Bathrooms
- Total Bathrooms: 1
- Full Bathrooms: 1
Location
- County: Middlesex
- Driving Directions: Downtown Chester Ct,
Heating & Cooling
- Cooling Type: Window Unit
- Heating Type: Hot Air, Electric, Propane
- Heating Fuel: Electric, Propane
Utilities
- Sewer: Public Sewer Connected
- Water: Public Water Connected
- Utility Description: Electric, Gas
Structural Information
- Roof: Asphalt Shingle
- Square Feet: 3,000
- Sq. Ft. Source: Approximate
- Year Built: 1830
Unit Information
Unit 1
- Unit Description: 1 Bedroom
- Square Feet: 1000
- Total Bathrooms: 1
Lot Features
- Lot Size (Acres): 0.02
- Frontage: Municipal Street
- Zoning: C
- Lot Description: N/A
Financial Considerations
- Assessment Amount: $275,730
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Documents Avail.: None
- Property ID: 941205
Listed by William Raveis Real Estate, Maureen Evans
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Price & Sales History for 21 Main St
Date
Details
Price
Change
Source
1/13/2026
Listed
$1,200,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 21 Main St
Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,467
11%
$275,730
—
2023
$6,742
-8%
$275,730
12%
2023
$7,299
1%
$245,760
—
2022
$7,250
—
$245,760
—
2021
$7,250
3%
$245,760
—
2020
$7,034
-1%
$245,760
—
2019
$7,075
8%
$245,760
2%
2018
$6,529
3%
$240,820
—
2017
$6,348
3%
$240,820
—
2016
$6,158
1%
$240,820
—
2015
$6,098
2%
$240,820
—
2014
$5,977
10%
$240,820
-2%
2011
$5,413
—
$246,590
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 21 Main St
21 Main Street, Chester, CT 06412 (MLS# 24148717) is a Commercial property. 21 Main Street is currently listed for $1,200,000 and was received on December 31, 2025. Want to learn more about 21 Main Street? Do you have questions about finding other Commercial real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

