Main House used as short term rental w/2 Bedrooms (3 actual Beds) + Caretaker's House w/ 1 Bedroom + Second Story Suite in Event Hall Building with 1 Bedroom. A wonderful opportunity to own 16 acres of rolling Tennessee countryside with two residences, expansive entertaining spaces, and an established winery and vineyard! Situated along the scenic Natchez Trace corridor, Natchez Hills Vineyard & Winery offers a unique combination of private country living, recreational opportunities, and income-producing potential. The property features a recently renovated 1,340-square-foot cottage, ideal as a primary residence, private retreat, or short-term rental. A separate 692-square-foot caretaker's house provides additional accommodations for guests, extended family, or on-site property management. Surrounded by picturesque countryside and an established vineyard, the setting offers privacy, natural beauty, and room to create a truly one-of-a-kind estate. Beyond the residences, the property offers an impressive collection of improvements designed for entertaining, hospitality, and agricultural use. A 4,832-square-foot event venue features a stage, bar, commercial kitchen, and former recording studio that could serve as additional overnight flex space with a full bathroom. Outdoor gathering areas provide beautiful views of the surrounding landscape, while a 728-square-foot maintenance shed offers additional storage and utility space. Also included is a fully equipped 6,050-square-foot winery production facility and tasting room, complete with wine production equipment and an established vineyard. With two residences, substantial existing infrastructure, ample parking, and versatile improvements across 16 acres, the possibilities extend far beyond a traditional residential property. Please do not visit the property without an agent.