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720 Main Street, Winchester, CT 06098

Multi-Family For Sale · 2 Family

$395,000
$207/sqft

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3
Bedrooms
2
Bathrooms
1,909
Sq Ft
0.07
Acres
1900
Year Built

About This Home

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

Listed by Ryan Marconi (860) 960-6946 with The Washington Agency (860) 482-7044

Listing Snapshot

Price $395,000 Days on Market 126 days
Property Tax $1,395/yr Style Units on different Floors,Other
Year Built 1900 Total Sq Ft 1,909
Lot Size 0.07 acres HOA Fees N/A
Bedrooms 3 Full Bathrooms 1
Total Rooms 7 Half Baths 1

Key Features

Outdoor
  • Deck

Structure & Parking

Construction Frame
Roof Asphalt Shingle,Flat

Systems & Utilities

Heat Baseboard, Hot Air
Fuel Natural Gas
Cooling None
Hot Water Natural Gas, Domestic, Tankless Hotwater
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $116/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Nov 12, 2025 Listed $395,000

Frequently Asked Questions

How much does 720 Main Street in Winchester, CT cost?
This property is listed at $395,000, which works out to $207 per square foot.
How many bedrooms does 720 Main Street have?
This home has 3 bedrooms and 2 bathrooms.
What is the square footage of 720 Main Street?
The home is 1,909 square feet, situated on 0.07 acres.
When was 720 Main Street in Winchester built?
This property was built in 1900.
Is 720 Main Street, Winchester, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 720 Main Street, Winchester in?
This home is served by the Winchester public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 720 Main Street, Winchester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Ryan Marconi · (860) 960-6946

The Washington Agency · (860) 482-7044

MLS# 24138050 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Mar 2, 2026 7:48 PM UTC