Well-maintained second-floor office condo in excellent condition, offering a versatile and efficient layout for a variety of professional uses. The space features three private offices, a generous bullpen area that can accommodate 4-6 desks, and ample storage throughout. The property offers ample parking, making it convenient for both staff and clients. Located just minutes from downtown, the building is home to a strong mix of professional neighbors, including an eye doctor, dentist, civil engineering firm, and attorney-an ideal setting for any business seeking a convenient and professional environment.
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
Exceptional Investment Opportunity, Business & Building for Sale! Discover this rare gem located at 354 Main Street, Winsted, CT, a one of a kind commercial property offering both business and real estate ownership. This historic movie theatre is among the few in the nation that allow guests to enjoy food and alcoholic beverages while watching on the big screen. The property features two full size theatres with seating for up to 200 guests, a separate restaurant, and a lounge bar spread across the first and second floors, creating multiple income streams under one roof. Recent capital improvements include a $200,000 Fire Sprinkler System and a brand new $30,000 Digital Marquee, ensuring modern safety and visibility. With Town Center (TC) Zoning, this space offers endless possibilities, continue operating the successful theatre business, or transform it into a music venue, event space, brewery, or mixed-use entertainment hub. Whether you're an investor seeking a turnkey opportunity or a visionary entrepreneur ready to bring new life to a local landmark, this property is your ticket to success.
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***
Unlock the potential of this solid 7-unit brick building, featuring a versatile mix of 5 residential apartments and 2 commercial office spaces. Ideal for investors seeking reliable cash flow or developers exploring expansion opportunities, this property offers both immediate income and long-term upside. With proper zoning and approvals, the two office spaces could be converted into additional residential units. The owner currently covers electric for the office spaces. Owner also covers heat and water for all units. A spacious rear lot provides ample off-street parking for tenants. Conveniently located near Routes 8 and 44, this property offers easy access to shopping, dining, Northwestern Connecticut Community College, and a variety of recreational options, making it a consistently easy to rent location. Property to be sold "AS IS." Property may be purchased a portfolio with 106 Birch Street, Manchester.
Open 10:30-12:30 Sunday 11/9/25. Motivated Seller! Seller financing available. A wonderful opportunity to own a mixed use property in the town center of Winsted. Currently used as a cleaner and tailoring shop on the first floor with an apartment on the second floor. Opportunity exists for the new owner to take over a turn key business with a strong existing client base and several commercial clients. The second floor offers the opportunity for a live in space, rental residential space with 3 bedrooms, a kitchen, living room and bathroom or the opportunity for office space. This building is located on a main road with great road frontage and a brand new freshly paved parking lot and some new siding on the building. The location offers an opportunity for a new owner to take over the existing business or completely start a new one in this prime location. Book your showing today.
Prime Commercial Property at 1 Lake Street. This 4,852-square-foot commercial building is located in the heart of the highly desirable Litchfield County, positioned on a prominent corner lot with exceptional visibility and easy access. Surrounded by thriving businesses and a strong consumer base, this property is perfectly suited for a variety of commercial uses. The building's open layout allows for versatile customization, making it ideal for a range of industries, including retail, office space, showrooms, or even a combination of these uses. Currently, the space is divided into four large sections, each approximately 700 square feet, along with 300 square feet of dedicated office space. Additionally, the building features separate men's and women's bathrooms (each with three fixtures), a handicap/family restroom, and a modest-sized kitchen. With clear-span construction, the interior walls are easily movable, offering maximum flexibility for redesign or reconfiguration to suit your business needs. The property is zoned as Town Center, allowing for numerous potential uses, such as: Accessory Residential Uses,Artisan Production, Bakery, Banks & Financial Institutions (without Drive-Thru), Commissary, Cultural Institutions Small Format Drug Store, Family Day Care Home, Home Occupation, Small Format Medical Offices, Business & Professional Offices, Restaurants, Small Format Grocery Retail, Personal Service Retail, Small Shops
Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.
Prime commercial opportunity in downtown Winsted, 115 Willow Street offers high traffic exposure, versatile space, and outstanding visibility from Main Street. Currently operating as a monument company, the well-maintained property features both office and garage areas, making it ideal for a variety of businesses. Potential uses include auto-related services (detail shop, repair, tire services), contractor services (plumbing, electrical, HVAC), retail or showroom space (home improvement, specialty retail), professional offices (real estate, insurance, accounting), health & wellness (physical therapy, chiropractic), creative/art-based uses (studio, photography, design), Pet Salon and Take-out businesses (burgers/hot dogs, tacos, ice cream and more). The building's location benefits from significant daily traffic, providing excellent advertising and customer engagement opportunities. This property offers easy access to local amenities and presents a unique chance to establish or expand your business in a thriving area with a professional appearance and strong community ties.

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.