The Oliver School was first opened to students in 1892 as a six-room school. It was the first school in Clark County dedicated to the education of the county's African American residents. In 1904, the building was expanded to include high school classes, and in 1928 a gymnasium was added. From 1892 through 1956 (Brown vs the Board of Education), it provided the greatest educational opportunities for African-American students in Winchester and Clark County. During that period, it was the only place in the community where African-Americans received education at the secondary level. The school continued to operate until 1969, well after the time that education in the United States was declared integrated.
At the time when education facilities in the South were segregated, education of African American students was marked by great challenges of funding for resources and adequate facilities. Often, schools for Blacks were not built in an enduring way. The Oliver Street School building, however, was well constructed, and the fact that it still stands is testament to its remarkably well-constructed edifice.
Located in a dense residential area, the main brick building dates back to 1938, with the "addition" having been added in the 1950's. Today the school building remains as the most prominent feature of its local landscape. It is also the only surviving historic community high school in the Winchester community, as both the Winchester High School and the original Clark County High School buildings have been demolished. The building is currently under private ownership, and after undergoing extensive renovation which was completed in 2009, serves as an affordable housing apartment facility.
Property is actively residential. Inside building not open for tours.