Originally, a four-room schoolhouse was built to accommodate the south side of Lexington to meet the city’s expanding enrollment. The building was demolished to make way for the new Dudley school that was built in 1881. According to the Lexington History Museum, “In 1881, the Dudley School was rebuilt with twelve classrooms, to consolidate the old Dudley and Annex (on Bolivar Street). In 1886, a four-room annex was built to meet expanding enrollment. During the 1891-92 school year, enrollment exceeded 600 pupils. The Annex was again opened to alleviate overcrowding”. Due to increased enrollment, the size of the building would go through one more addition.
The school was named the “Dudley school” after the doctor Benjamin Dudley, the first chairman of the surgical department at the Transylvania Medical School. Dr. Dudley was a huge supporter of local education and strived for higher learning among the community of Lexington during his career and life in the city. Teacher Mary Desha contributed to the historical significance of the building as one of the four founders of the Daughters of the American Revolution, making the school an historic landmark for Lexington, Kentucky. Mary’s story is noted on a plaque outside the south-facing side of the building.
The Dudley school remained active in the Lexington school system until 1932 when it was finally closed to students. In 1934, the building was operated by the Fayette County Relief Association, and their residency at the Dudley school lasted for a decade. With the second and final addition to the building finished in 1944, the Agricultural Adjustment Administration took over the building and occupied it until 1970. The Dudley schoolhouse then operated as a youth center again for a brief period. The property then sat vacant until 1979, undergoing deterioration from lack of maintenance.
In 1978, the schoolhouse was incorporated in the South Hill Historic District. It was in disarray and in need of rehabilitation. It was renovated in 1979 as commercial space, dining, retail, and local housing all under one roof. This change from the old schoolhouse into a renovated shopping center led to a new life for the building. From the early 1980s to present day, this building remains a prominent building in design that stands out from the surrounding buildings in the South Hill neighborhood.