Charles City County was formed in 1634 as one of Virginia's eight original shires. The present Charles City County Courthouse was once very similar to surviving courthouses in Isle of Wight, King William, and Hanover counties. It was built between 1749, when Charles City justices finished raising money to finance the construction of a new building, and 1757, when they made a final payment to Colonel Richard Bland of neighboring Prince George County for completing the work. As originally built, the courthouse had a five-bay arcade, or piazza, fronting a central courtroom flanked by two jury rooms. In the early nineteenth century, a chimney was added in the south wall behind the magistrates' platform, a doorway was cut through one of the flanking courtroom windows to provide access to a small brick clerk's office erected to the west, and windows were punched into the south wall to provide better light for the bench.
Following heavy damage during the Civil War, most, but not all, of the sash were replaced (an original, wide-muntin sash window survives in the south wall window of the east jury room). Between 1880 and 1893 the courthouse was radically altered to provide more courtroom space. The orientation of the building was reversed. The chimney on the south end was removed, the flanking windows were blocked, and an entrance door was constructed. At the north end of the building, the wall dividing the courtroom from the arcade was removed, the arched openings of the piazza were enclosed, and the judge's bench and bar were erected in the former center bays of the piazza. The building has undergone a number of renovations over the past hundred years, including a major reworking following an arsonist's attempt to burn the courthouse down in 1989. The effort fell short, unlike many in the colonial days, when public buildings were all too often torched by rogues and disgruntled criminals.