On April 5, 1865, during the final days of the Civil War, as General Robert E. Lee and his army continued their westward retreat, Union troops attacked and destroyed a Confederate wagon train near Paineville.

[5] The engagement was one of the few, if not the only one, to involve Black Confederate troops,[6] and was among a number of skirmishes in the last week before the surrender to Ulysses S. Grant at Appomattox Court House on April 9, 1865.

In the 1960s, after desegregation, the property of historic Paineville School, on Route 616, was put up for auction along with several other small schoolhouses in Amelia County.

During the early 20th century, the Rosenwald School project constructed thousands of facilities across the South primarily for the education of African American children.

As of 2023 the original Paineville structure was still intact, serving as an outbuilding for an adjacent house, and the property was again listed for sale.