The square is dominated by the courthouse, which began as a two-story Flemish bond brick structure (now the north wing) with modillioned cornice and perhaps an arcaded porch to the south, which has disappeared. The courthouse served several purposes, including a place of worship for four religious denominations. Thomas Jefferson in 1822 described it as a “common temple” where “all mix in society in perfect harmony.” William M. Pratt, an engineer who was the University of Virginia's first superintendent of buildings and grounds, designed a new entrance wing (1859–1860) incorporating
Gothic Revival details. Pratt placed his addition across the south end of the existing courthouse and stuccoed the entire structure. In 1875–1880 George W. Spooner, a local builder who sometimes acted as an architect, removed most of the Gothic touches and added the present Ionic portico. His work is evidence both of the incipient Colonial Revival and of the strong undercurrent of continuity with earlier Virginia architecture. In 1938 Milton Grigg with Floyd Johnson “restored” the courthouse and removed the yellow stucco finish and the remainder of Pratt's Gothic work.
Until it was removed in September 2020, a Confederate monument, a statue of an infantryman (1909, American Bronze Co.), stood in front of the courthouse; to the west, a mounted statue of Stonewall Jackson (1921, Charles Keck) was removed following prolonged legal challenges in July 2021.