Timeless character on 4.5 picturesque acres in Woodford County. This remarkable residence, with origins tracing back to 1790, has been meticulously reimagined over the past two decades, including a Tom Padgett renovation. At the heart of the home, a stunning chef's kitchen invites gathering and celebration, showcasing an oversized island, Thermador Professional appliances, and abundant cabinetry. The main level offers a luxurious primary suite, a spacious living and dining area ideal for entertaining, a generous laundry room, and the home's original room—now a charming office with original beamed ceiling that nods to its storied past. Wide-plank Ash, Poplar, and Pine floors run throughout, complemented by soaring windows that flood the interiors with natural light. Upstairs, you'll find an additional primary suite, a guest room with ensuite bath, and a cozy traveler's room with its own staircase—plus two more bedrooms and a full bath on the third level. Outside, expansive patios and a covered front porch overlook rolling pastureland and mature trees. A detached two-car garage with storage, a barn, and a run-in shed complete the property. Just minutes from Keeneland, Bluegrass Airport, and The Kentucky Castle, this extraordinary estate embodies the grace and soul of Kentucky's countryside.