Timeless Charm Meets Modern Luxury in the Heart of Historic Jonesborough Located at the heart of Jonesborough, Tennessee's oldest town, this extraordinary 1860s home captures the essence of Tennessee and America's rich history. Offering over 4,000 sq ft of meticulously restored living space, 4 bedrooms, 4.5 baths, and a 3/4-acre corner lot perched just high enough to enjoy sweeping views of Main Street, this property is the picture of small-town Americana. Just steps from theaters, cafés, shops and the National Storytelling Center, it's the kind of home that sparks the imagination—a true Main Street dream. Every inch has been thoughtfully restored from the ground up, preserving original hardwood floors, moldings, mantles, staircase, handrails, windows, and siding—while seamlessly integrating modern upgrades like thermopane windows, a whole-home generator, Rheem EcoNet HVAC, central vacuum(s), and top-tier construction. Enjoy over 1,100 sqft on four inviting porches: a sleeping porch with views of the historic courthouse, screened porch off the kitchen, a classic rocking chair front portico, and a serene garden veranda. Over 2,000 sqft of Terraced hardscape and patios stretch across the estate, and exquisitely maintained landscaping creates an outdoor sanctuary, that can only be created with TIME and a CARING hand, complete with landscape lighting, sprinkler system, Bearboard tongue-and-groove decking, and copper gutters. Two charming outbuildings—a smokehouse-turned-yard shed and potting shed—add to the historic character. A detached carriage house includes an 850 sq ft garage with a private suite above—an ideal space for hosting guests or operating a Bed & Breakfast, making this estate a true showcase of Southern hospitality. Only a handful of historic properties exist where you can sit on your front porch and watch the charm on a HISTORIC Main Street of one of America's oldest towns. Buyer/Buyer's agent to verify all MLS info