Situated in the peaceful countryside of Madisonville in scenic Monroe County, this versatile East Tennessee property offers an outstanding combination of privacy, comfort, recreation, and usable acreage. Available in two options consisting of the home with 57.1± acres or the home with 271.28± acres, this property is well-suited for buyers seeking a private residence, recreational retreat, family compound, or long-term investment opportunity. The centerpiece of the property is a spacious custom home offering approximately 4,517± square feet with 5 bedrooms and 5.5 bathrooms. Originally built in 1989 as a 3-bedroom, 2-bath home, the residence underwent a substantial expansion and renovation in 2015, resulting in a thoughtfully updated layout that blends rustic character with modern convenience. Pine wood walls throughout the home create a warm and inviting atmosphere, while the recently remodeled kitchen features stainless steel appliances, a gas-burning stove, and generous cabinet and counter space. Designed for comfortable everyday living, the home includes walk-in showers, walk-in closets, and a separate laundry room with a utility sink. A Generac generator, fiber internet service, and a recently rebuilt well with a new tank and pump provide reliability and convenience. The attached three-car garage includes a radiant floor heating system supplied by a wood stove located behind the residence, creating an efficient supplemental heat source during cooler months. In addition to the main residence, the property includes multiple additional living spaces that provide flexibility for guests, extended family, caretakers, or potential rental opportunities. A large multi-use barn includes a comfortable 2-bedroom, 1-bath apartment, meeting area, attached garage, and additional storage and utility space. Another detached garage building includes a 1-bedroom, 1-bath apartment featuring tongue-and-groove walls, hardwood flooring, and high UV-rated automatic garage doors. The acreage offers an attractive blend of mature timber, open clearings, rolling terrain, and established trail systems throughout the property. Extensive side-by-side trails create easy access across the land for riding, hiking, recreation, and property maintenance. Open areas provide space for gardening, recreation, equipment storage, or hobby farm use, while the mature wooded sections create excellent wildlife habitat and scenic natural surroundings. Additional improvements include four hen houses, adjoining carports for equipment storage, and an enclosed metal hay storage building located within a small pasture area. Portions of the property are fenced with durable post-and-rail fencing and reinforced cross-bracing. A gated entrance enhances both privacy and security while creating an attractive approach to the property. Whether you are searching for a private Tennessee homestead, recreational getaway, hunting property, multi-generational living setup, or a property with future income potential, this Monroe County tract offers the flexibility and infrastructure to support a wide variety of uses. Owner financing is available, and all utilities are already in place, including fiber internet access. Conveniently located near the foothills of the Smoky Mountains, this property provides the benefit of rural seclusion while remaining within reasonable driving distance of nearby towns and outdoor destinations throughout East Tennessee.