Commercial For Sale near Highland Lake

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

Property Details

  • Beds: 0
  • Baths: 2.0
  • Sq Feet: 1909
  • Year Built: 1900
  • Location: Highland Lake
  • Acres: 0.070
  • County: Litchfield County
  • Heat/AC: Baseboard, Natural Gas
  • Roof: Asphalt, Rubber, Shingle
  • MLS #: 24138743

Location

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Contact Information:

Contact Agent
Listing Agent: Ryan Marconi, The Washington Agency, 860-960-6946, 860-482-7044 Listing Site, Listing Status: Active
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Ad Statistics:

Lake Commercial For Sale in Winchester, Connecticut
Ad Number : 6823406
Viewed: 5 times
Added: Nov 13, 2025
Updated on: Jan 10, 2026
All information provided is deemed reliable but is not guaranteed and should be independently verified.