361 South Upper Street
Lexington, Kentucky 40508
Add your chapter to the story of this iconic c. 1805 log cabin, 220 years after its construction.
Thought to be the oldest surviving log residence in Lexington still on its original site, this two-story, two-bay clapboard-wrapped home offers a blend of early Kentucky heritage and downtown convenience.
Originally located in one of Lexington’s first “suburbs,” the cabin now enjoys a central location in the heart of Downtown. Wagonmaker John Stilfield purchased the original lot from hemp manufacturer David Dodge; Stilfield’s descendants occupied the home until 1913.
In 1994, the Blue Grass Trust for Historic Preservation saved the structure from demolition, undertaking a careful restoration that preserved its integrity. Later occupants further enhanced the home with sensitive renovations. Today, its rich character endures through hand-hewn logs, exposed beams, very old hardwoods, two brick fireplaces, and historic cabinetry including linen “presses.”
Downstairs, the home’s heritage is on display with exposed logs and beams and built-ins for books or collections. The updated adjoining kitchen and bath retain traditional charm. Upstairs, a sunlit bedroom provides ample space for a sitting area beside the fireplace.
French doors and limestone slab steps lead to the spacious rear greenspace – a coveted & rare feature for a downtown property. A stone pathway leads to a generous, private off-street parking area accessible from Mack’s Alley.
Recent enhancements include a remodeled bathroom with walk-in shower, full exterior painting, a new heat pump, a new Bosch dishwasher and a handcrafted storm door by Bourbon Millworks.
Preservation guidelines ensure the home will retain its distinctive authenticity. Board of Architectural Review approval is required for changes to the exteriors of homes within the South Hill Historic Overlay. We are pleased to provide further materials and guidance to interested parties.
