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$389,900
9 Beds ⋅ 6 Baths ⋅ 26020069 MLS
Exceptional investment opportunity! This fully occupied triplex is a turnkey addition to any investment portfolio, offering three spacious units, each with approximately 1,116 square feet, 3 bedrooms, and 1.5 bathrooms. With strong rental potential and separately metered utilities paid by the tenants, this property provides an excellent income-producing opportunity. Each unit features a well-designed two-story floor plan with a welcoming foyer, spacious living room, kitchen, utility area, and half bath on the main level. Upstairs, you'll find three generously sized bedrooms and a full bathroom, creating a comfortable layout that appeals to long-term tenants. Additional features include private decks, ceiling fans, window blinds, ample off-street parking, and generously sized yards. Conveniently maintained and fully leased, this multifamily property offers immediate cash flow with minimal owner responsibilities. Showings are available by appointment only with advance notice to accommodate the tenants.

341-345 Carolina Ave, Winchester
$374,000
25508602 MLS
Turn Key Ready! This well established business is equipped and ready for someone to live out their dream. All equipment stays. Two pool tables, barstools, tables, televisions, pool sticks, dartboard, and all inventory stays. HVAC unit, walk in compressors, and cooler recently replaced. Great location in historic downtown Winchester. One of the very few liquor stores in Kentucky that can serve mixed drinks and open liquor. The business has a very well established clientele. Call to schedule a private tour while this one last.

137 E Broadway St, Winchester
$1,950,000
26018115 MLS
Located directly across from the Clark County Hospital this 12,042 office building has been occupied by the Clark County Board of Education since 1969. There is an additional 4,092 sf building located behind the main office that has been finished with office and storage space. This incredible location could be the right site for a multi-tenant renovation, single-use office, or a new beginning.

1600 W Lexington Ave, Winchester
$515,000
26002170 MLS
This versatile mixed-use property offers a rare opportunity to combine business potential with built-in residential income. Formerly operated as a neighborhood market, the commercial building spans over 3,000 square feet and is thoughtfully equipped with a full kitchen and laundry area, making it ideal for a wide range of business concepts. Whether you envision a café, restaurant, retail shop, office space, event venue, service-based business, or creative studio, the layout and infrastructure provide a flexible foundation ready to be reimagined. With strong visibility and a neighborhood presence, this property is well-positioned for an owner-operator or investor seeking adaptability and long-term value. Adding to its appeal is the separate 3-bedroom residential home located at 35 Hays, which is currently income-producing and leased through 2027. This creates an immediate revenue stream while you develop, occupy, or lease the commercial space a powerful advantage for offsetting costs or maximizing returns. Opportunities like this offering commercial flexibility, residential income, and long-term potential are increasingly rare. Whether you're expanding a business, launching something new, or investing with vision, this property delivers the space, structure, and upside to make it happen.

35-37 Hays St, Winchester
$340,000
4 Beds ⋅ 5 Baths ⋅ 26010324 MLS
Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units! Basement for extra storage room with freight elevator. Two new HVAC units and a new roof within the last 2 years! Approximately 16 parking spaces. All 3 units are currently occupied.

502 W Lexington Ave, Winchester
$699,000
26004697 MLS
Operated for over 20 years as a physician's office this two-story building features a "ready to go" office on the main floor with two large apartments on the second floor with walkup, outside entry. The entire structure is on an unfinished basement perfect for storage and access to the mechanical systems. There is also a detached 3-bay garage for parking and storage as well as an asphalt parking lot with more room for more than 25 vehicles.

218 S Maple St, Winchester
$1,200,000
16 Beds ⋅ 16 Baths ⋅ 26007993 MLS
You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof replacement in 2022, new siding in 2023, and 6 of the AC units were replaced in the last three years. The main electrical service mast was replaced in 2023, and all 100-amp breakers were replaced in 2025. Most units have been updated with LVP flooring.

16 Linden Ave, Winchester
$825,000
26015570 MLS
308 West Lexington has been renovated recently as an office space for a medical practice. The main space consists of a bright reception area, large office, file room, 5 exam rooms and kitchen area. The back of the building has two suites that could be leased out separately or incorporated into the main space. The basement area is unfinished but could be up-fitted for additional office space. The parking lot is generous in size and has access to a back alley way. This property could also be leased. Gateway to the downtown district, close to the Bypass and I-64. Very accessible area. Property Highlights: -Recently renovated -Great location -Multiple Opportunities

308 W Lexington Ave, Winchester
$299,999
25001584 MLS
The building may be old, but everything about it is new! That includes a new roof, 4 new skylights, exposed beams, new hardwood floors throughout, plumbed for 4 bathrooms, laundry room and back office with a window looking into the main space. All of the electrical and plumbing has been done as well. This property boasts the largest back parking lot in the Downtown area making parking for customers and staff a dream. There are numerous grants available as well for this property. Winchester wants your business! 7 new, high-end apartments are going in across the street, there are 5 delicious restaurants on this block, and numerous shops, and the Leeds Center for the Arts is also across the street. Property Highlights: -Recently renovated with a new roof, 4 new skylights, exposed beams, new hardwood floors, new plumbing and new electrical. -Winchester periodically offers numerous building and business grants to kick start your new business. -The property is located directly across from a brand-new apartment building and is surrounded by retail and restaurants. -The property boasts the largest back parking lot in the downtown area

16 N Main St, Winchester
$199,000
26001995 MLS
Business / Investment Opportunity!! 2 commercial units zoned B-3 in the heart of Winchester just off of Lexington Ave. Currently an indoor self storage mini warehouse business with the ability to easily convert to many other options. 10' ceiling height, newer roof, motion sensor lighting, security system, code entry door, parking in front and rear. Units are deeded individually, this listing is for both units (103 & 105 Talbott). 1,404 sq ft each unit, currently no interior dividing wall. Build this business or convert to storefront, salon, larger warehouse space, church, etc.

103 Talbott Ave Unit 2,3, Winchester