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$395,000
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Property Description
Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe, retail, or service business! The second floor offers a spacious 3-bedroom apartment with many recent updates, a new roof, windows, a deck, a kitchen, and an on-demand hot water system. The unit was renovated down to the studs. Separate gas and electric meters make it ideal for owner-occupy or investment use. On-street parking only, but surrounded by other downtown businesses with strong walkability and visibility. Excellent location near Highland Lake, Route 44, and all downtown amenities. Great opportunity to live and work in the same building or generate dual rental income. Bring your vision and make this Main Street property shine again! Also listed under multi-family- MLS# 24138050
Full Property Details
Full Property Details for 720 Main St
General
- Price: $395,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Commercial
- Source: SMARTMLS
- MLS ID: 24138743
- Updated: 11/26/2025
- Added to Site: 67 day(s) ago
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 1
- Half Bathrooms: 1
- Restrooms: 1
Location
- County: Litchfield
- Driving Directions: GPS Friendly
Heating & Cooling
- Cooling Type: None
- Heating Type: Baseboard, Hot Air, Natural Gas
- Heating Fuel: Natural Gas
Utilities
- Sewer: Public Sewer Connected
- Water: Public Water Connected
- Utility Description: Gas
Structural Information
- Roof: Asphalt Shingle, Rubber
- Square Feet: 1,909
- Sq. Ft. Source: Public Records
- Living Area: 760 Sq. Ft.
- Retail: 1,149 Sq. Ft.
- Year Built: 1900
Unit Information
Unit 1
- Unit Description: Retail
- Square Feet: 1149
- Total Bathrooms: 1
- Partial Bathrooms: 1
Unit 2
- Unit Description: 3 Bedrooms
- Square Feet: 760
- Total Bathrooms: 1
Lot Features
- Lot Size (Acres): 0.07
- Frontage: State Road
- Zoning: CB-3
- Lot Description: Level Lot
Financial Considerations
- Assessment Amount: $47,810
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Documents Avail.: None
- Property ID: 927576
Listed by The Washington Agency, Ryan Marconi
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Schools
Schools serving 720 Main St
School District:Winchester School District
| Name | Grades | Distance |
|---|---|---|
Pearson Middle School 2 Wetmore Avenue, Winsted, CT 06098 | 3-6 | 0.4 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 720 Main St
Date
Details
Price
Change
Source
11/12/2025
Listed
$395,000
243.48%
MLS
6/01/2024
Sold
$115,000
—
Public Record
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 720 Main St
Year
Property Taxes
Change
Tax Assessment
Change
2024
$1,395
7%
$47,810
—
2023
$1,302
3%
$47,810
—
2023
$1,262
10%
$47,810
40%
2022
$1,148
—
$34,230
—
2021
$1,148
—
$34,230
—
2020
$1,148
—
$34,230
—
2019
$1,148
—
$34,230
—
2018
$1,148
-38%
$34,230
-38%
2017
$1,855
-11%
$55,300
-11%
2016
$2,094
3%
$62,440
—
2015
$2,042
3%
$62,440
—
2014
$1,992
2%
$62,440
—
2011
$1,948
—
$62,440
—
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 720 Main St
720 Main Street, Winchester, CT 06098 (MLS# 24138743) is a Commercial property. 720 Main Street is currently listed for $395,000 and was received on November 12, 2025. Want to learn more about 720 Main Street? Do you have questions about finding other Commercial real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

