526 Old Middlesboro Hwy Historic charm meets contemporary living standards in this 1850's-era home and guesthouse with views of McCloud Mountain! Preserved architectural character and timeless countryside charm grace this home as you pull up to discover historical details including a charming covered front porch with flagstone floors and brick columns, along with an earthen root cellar with arched stone ceilings and a former smokehouse in the backyard. The home's leaded glass front door and sidelights with transom leads into a storybook layout steeped in a romantic Old World provenance with preserved details that include ornate tile ceilings, period millwork, decorative fireplaces and original hardwood floors. This statuesque traditional offers gracious living spaces that transport you to peaceful times of a bygone era, from the large light-filled living room to the elegant formal dining room with classic built-ins. The updated kitchen serves up modern functionality with gorgeous upgrades, all while conserving a historic allure. Light spills in from large windows, illuminating the center island, staggered cabinets, custom tilework, chalkboard feature wall and tall coffered tile ceilings. A large laundry room is stationed around the corner with storage cabinets, as is the updated bathroom with clawfoot tub. A main floor bedroom exudes a timeless aesthetic along with two additional bedrooms upstairs, all with decorative fireplaces. The partially fenced yard reveals a deck as well as a flagstone path and patio with firepit, along with a detached garage and shed. An additional highlight is the SECOND HOME located on the property offering 1 bedroom, 1 bath, and approximately 1, 629 additional square feet--perfect for a mother-in-law residence, guest quarters, or investment income opportunity. The spacious guesthouse is a flexible building that can serve as a office or other purpose, complete with heat and air in an open-style layout with full kitchen and bathroom. Located just a few miles from Norris Lake (approximately a 10-15 minute drive), this property is also convenient to Royal Blue riding trails, with access to extended mountain adventures that can take you all the way to Windrock. This home's unique history and country-contemporary appeal will capture your heart. Don't miss out! Buyer to verify all information.