The first courthouse, erected in 1837, was burned in 1862 during General Earl Van Dorn’s raid. Local architect-builder Spires Boling has been credited with designing the present Italianate brick building (1870–1872), but so has the Memphis firm of Willis, Sloan, and Trigg, and attribution remains unresolved. The building’s most prominent features are its north- and south-facing Corinthian porticos on arcaded bases and the domed clock tower. The one-story east and west wings were added in 1925 by N. W. Overstreet, along with Colonial Revival fenestration and patterned brick veneer.
The former Pythian Hall (c. 1860; 110 S. Memphis) is a handsome, two-story brick building with round-arched windows and crowning blind arcade. At 114 S. Memphis, the Beaux-Arts classical former Bank of Holly Springs (c. 1910) has a full entablature with a garlanded parapet above fluted Ionic columns, all in limestone. Toward the middle of the block, the stuccoed building at 118 S. Memphis dates to c. 1890 and that at number 122 to c. 1870, and both have floriated, pressed-metal window lintels. The metal canopies on buildings around the square were added in the 1960s.
The two-story brick buildings on E. College east of Center Street with corbeled brick cornices and parapets date to c. 1870. The fourteen bays farthest west at numbers 120–128 were built as a block and have pressed-metal lintels and hood molds, as does the c. 1865 building at 114 E. College. Most of E. Van Dorn Avenue’s buildings also postdate the Civil War, but those at numbers 109 and 127–131 were built in the late 1830s. The building south of the square at Gholson Avenue and Memphis Street was built in 1834 as the land office and was the first brick building in town.