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$395,000

  • For Sale
  • Active
  • Multi-Family
  • 3 Total Beds
See This Home
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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-occupier 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 as a commercial property- MLS# 24138743

Full Property Details for 720 Main St

General

  • Price: $395,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Multi-Family
  • Source: SMARTMLS
  • MLS ID: 24138050
  • Updated: 11/26/2025
  • Added to Site: 65 day(s) ago

Interior

  • Number of Rooms: 7

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Exterior

  • Exterior Features: Deck

Parking

  • Parking: None

Location

  • County: Litchfield
  • Driving Directions: GPS Friendly

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Baseboard, Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, Domestic, Tankless Hotwater

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Units on different Floors, Other
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: None
  • Roof: Asphalt Shingle, Flat
  • Square Feet: 1,909
  • Above Ground: 1,909 Sq. Ft.
  • Year Built: 1900

Unit Information

Unit 1

  • Square Feet: 1149
  • Total Bathrooms: 1
  • Partial Bathrooms: 1

Unit 2

  • Square Feet: 760
  • Total Bathrooms: 1
  • Bedrooms: 3

Lot Features

  • Lot Size (Acres): 0.07
  • Zoning: CB-3
  • Lot Description: Level Lot

Financial Considerations

  • Assessment Amount: $47,810
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 927576

Listed by The Washington Agency, Ryan Marconi

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Listing agent

— 720 Main St —

  • Ryan Marconi

    The Washington Agency

Agent Contact: (860) 960-6946 Office Contact: (860) 482-7044

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 720 Main St

School District:Winchester School District
NameGradesDistance
Pearson Middle School
2 Wetmore Avenue, Winsted, CT 06098
3-60.4 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/12/2025
Listed
$395,000
243.48%
MLS
6/01/2024
Sold
$115,000
—
Public Record
Get Price Alerts and Save Property
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 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
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by The Washington Agency, Ryan Marconi

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720 Main Street, Winchester, CT 06098 (MLS# 24138050) is a Multi-Family property with 2 units containing 3 bedrooms, 1 full bathroom and 1 partial bathroom. 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 Multi-Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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