Welcome to 8765 Highway 52 - A Historic Gem on Nearly 9 Acres with an Income-Producing Guest House in Charming Loretto, KY! Step back in time and experience the character of this stunning Sears & Roebuck home, originally built in 1900 by the Dant family. Nestled on almost 9 peaceful acres with no neighbors in sight, this one-of-a-kind property offers a rare combination of history, space, and serenity. Inside the main home, you'll find gorgeous hardwood floors throughout and four spacious bedrooms upstairs. Need more room? There's potential for two additional bedrooms—one on the main level and another in the basement, each with its own private entrance. The main living space invites you to cozy up by the fireplace or soak in the sunshine from the large, light-filled sunroom. Entertain with ease in the oversized dining room, and enjoy your morning coffee in the quaint breakfast nook filled with natural light. The kitchen features stainless steel appliances and a convenient pantry. Outside, the property is just as impressive featuring a large detached garage, a charming shed, a historic rebuilt barn complete with a workbench area, and a gazebo perfect for picnics on pretty days. The land even backs up to the old train tracks once used to transport whiskey, adding yet another layer of Kentucky heritage to this truly unique homestead. **Also included is a 2024 newly built guest house with its own separate address, currently operating as a successful short-term rental. This charming space features 1,749sq ft an open-concept layout with rustic charm, along with two bedrooms each with its own private bathroom making it ideal for guests or generating rental income. Don't miss your chance to own a piece of history with income potential in beautiful Loretto, KY. Schedule your private showing today!