A courthouse has existed in Leonardtown since 1710. In 1736, the General Assembly authorized the justices of St. Mary's to build a new courthouse to replace the original wooden structure. This building survived until 1831, when it accidentally burned, destroying valuable records. A new courthouse was reconstructed on the site by 1832. For nearly 100 years, the courthouse was the scene of civic gatherings and meetings. Because of concern for the stability of the 1832 structure, another courthouse was constructed on the site in 1901. In 1957, the courthouse underwent extensive remodeling. The exterior red bricks replaced the yellow bricks used in 1901 and a more unified, pediment facade was incorporated. The most recent renovation and addition, completed in 2001, houses three circuit courts and related judicial offices.