400 W Main St

MOTIVATED SELLERS! Step into a piece of Kentucky history with this charming, late-1800s farmhouse, known locally as the McKenna House. Built in 1869 by Irish immigrant and bourbon pioneer, Henry McKenna, this remarkable property offers timeless character, Victorian Folk architecture, and modern comforts. Just up the road, his original distillery remains standing, and his legacy lives through his namesake bourbon, still produced today by Heaven Hill. Set on 4.5+ fully fenced acres, the home features over 3,500 square feet of living space, including 5 bedrooms, 3 full bathrooms, a formal dining room, a fully renovated kitchen, a library, and six fireplaces. Two main-level, spacious primary suites each include their own private parlor, fireplace, a dedicated full bathroom, and a separate interior/exterior entrance - offering both comfort and autonomy. Upstairs, the original winding staircase leads to two additional bedrooms and a third full bath. Updated/replaced plumbing, septic lines, mechanicals, and all new vinyl siding are just a few of many updates to give you peace of mind! And that's just the beginning... In addition to the main residence, the property includes a separate 2,100-square-foot carriage house with 2 bedrooms and 2 full bathrooms—ideal for guests, extended family, or rental opportunities. With its rich history and generous layout, the McKenna House presents endless possibilities: a distinctive primary residence, a multi-generational living opportunity, or a high-performing investment property with proven income & potential for up to four short-term rentals. Ideally located along Kentucky's famed Bourbon Trail, and just minutes from Bardstown, Mount Washington, Bloomfield, and Taylorsville—with Louisville and Lexington under an hour away—this one-of-a-kind property is truly special. Priced well under appraised value & motivated sellers! Schedule your private showing today!