What you're looking at today started more than 100 years ago as a working barn, one with deep ties to Kentucky's Thoroughbred history. In 2019, it was extensively renovated and thoughtfully transformed into the one-of-a-kind home you see today. Throughout the conversion, the character and history of the original structure were preserved while creating a residence designed for modern living. The result is a property filled with architectural details you simply can't recreate in a new build, complemented by polished concrete floors, custom murals by local artist Wylie Caudill and modern systems and finishes throughout. The first floor offers two living spaces, a dining area and gas fireplace, along with two bedrooms, two walk-in closets and two spacious full bathrooms. The kitchen features stainless steel appliances and a large island with granite countertops, while the baths include quartz-topped vanities, tiled showers and a Whirlpool tub. Accessible from the main residence, the second floor offers multiple flexible spaces, including a studio apartment-style layout with a full bathroom, wet bar and large walk-in closet. Two additional private apartments are accessed by their own separate entrances and spiral staircases, each featuring a bedroom, full bathroom and wet bar/kitchenette with mini refrigerator. These spaces offer exceptional flexibility for guests, extended family, staff or potential short-term rental income. Set on 1.797 acres surrounded by farmland, the outdoor spaces are equally impressive. The saltwater pool features bubble lights, a stamped-concrete deck, new waterfall, 2026 liner and pool cover, while a hot tub provides another place to relax and unwind. A detached four-car garage offers abundant parking along with two large unfinished multi-purpose spaces ready to adapt to the next owner's needs. Behind the historic character is modern infrastructure designed for comfort, convenience and even self-sufficiency. All major systems date to 2019 or newer and include mini-split heating and cooling, a tankless water heater with plumbing in place for a second system if needed, septic system, Pella windows along the rear of the home and garage, and an automatic generator utilizing solar and gas. The property is even equipped with the ability to operate off-grid if needed, and the asphalt driveway was redone in 2026. But what makes this property especially interesting is what it could become for its next owner. It can be an extraordinary private residence, a memorable setting for hosting and hospitality, or an opportunity to combine your home with potential income from the property's private apartments. More than a century of history, reimagined for what's next. Being sold as-is, with inspections welcome!