Dominating the courthouse square, the two-story red brick courthouse (1894, Walter Chamberlin and Company) boasts a tall central clock tower with a cupola and windvane. Undertaken after fire destroyed the 1852 courthouse by William Nichols, the building has the eclectic styling of its era, including round arches, decorative brickwork, and columned porticos (not identical) on all four facades, although a 1950s addition covered the south entrance. This is one of several courthouses in the South designed by the Chamberlin firm of Nashville. The adjacent one-story buff brick chancery building (1930) has a hard-edged Art Deco style.
Nine streets intersect at the square, creating a large traffic circle. The oldest building on the square is the side-gabled former Bank of Commerce (c. 1885; 116 Court Square), with an ornate parapet finished with decorative metal coping. The Classical Revival Masonic Temple (1910, P. J. Krouse; 126 Court) and the stout Rayner Building (1915; 404 Court) are the tallest at three stories and anchor their west and north blocks.
The square reflects the strong Jewish presence in Lexington’s merchant class. The Sontheimers built their dry goods store (1892; 118 Court) on the west side, now with a heavily stuccoed front. The one-story, four-store block (c. 1900) at 218–224 Court included the Rosenthal and Cohen clothing stores. The I. Flower Store (c. 1905) at 226 E. China Street was later used as the Strand Theater. On the square’s east side, the Applebaum Brothers Clothing Store (c. 1915; 304 Court) and the adjacent Flowers Department Store (1920) at number 306 were downtown mainstays.