Welcome to this beautifully maintained 6 bedroom, 3.5 bath two-family home in Winsted, set on a generous 1.25 acres of fully fenced yard. Warm wood flooring flows throughout the home, creating a welcoming feel from the moment you step inside. The layout on both levels offers generous sized bedrooms with high ceilings, large living rooms and the second floor has a spacious sunroom; an ideal spot to unwind or enjoy your morning coffee. Stainless steel appliances complement the home, and the eat-in kitchens provides a cozy space for casual dining and everyday living. Designed with convenience in mind, the home features laundry on both floors, gas heat and central air. Outside, the fully fenced backyard offers space to entertain, garden, or play, enhanced by a concrete walkway and a driveway freshly paved last year. The original post and beam 2 story carriage barn has a workshop and serves as a large 2 car garage that can easily fit 3 cars with plenty of storage space! Recent updates include almost all new windows, newly installed central air on the second floor, and a new hot water storage tank, and solar panels adding comfort and peace of mind. This property offers space, functionality, and thoughtful updates perfect for both owners and investors alike.
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
One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year track record of success and a loyal customer base, this restaurant has earned recognition in top publications including the New York Times, Wall Street Journal, Hartford Courant, CT Magazine, and numerous local publications - Sale includes the business and comes fully equipped with all infrastructure items. This is a rare opportunity to step into a thriving, reputable restaurant with an exceptional reputation-ready to operate from day one - Numerous infrastructure items are included in the sale totaling well over 100k (See list in attached docs)***Price includes thriving restaurant with 10 year track record with all equipment included. See attachment for equipment list***
Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS #24112471. Property has brand new paved parking lot not shown in current picture and some new siding on outside. Come see this great investment opportunity.
THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas heating system! 1.08 acres 2. Updated 960 sq ft ranch. 3 bed, 1 bath, walk out basement, great backyard with tons of potential. .37 acres. 3. 2.9 acres of undeveloped land. Potential for multiple access points. Condo's? Apartments? Parking garage? Bring your ideas and imagination. All properties sold together. Tax & Square footage is total for all three properties.

Winchester is located in Connecticut. Winchester, Connecticut has a population of 10,335. Winchester is less family-centric than the surrounding county with 20.73% of the households containing married families with children. The county average for households married with children is 26.17%.
The median household income in Winchester, Connecticut is $65,537. The median household income for the surrounding county is $84,797 compared to the national median of $69,021. The median age of people living in Winchester is 50.7 years.
The average high temperature in July is 80.7 degrees, with an average low temperature in January of 13.6 degrees. The average rainfall is approximately 52.3 inches per year, with 52.6 inches of snow per year.