The Court Square Historic District in Leitchfield, Kentucky was listed on the National Register of Historic Places in 1984. The initial listing included 29 contributing buildings, including the 1935 Grayson County Courthouse, on 10 acres (4.0 ha). The listing was expanded in 1988 to add two more contributing buildings and two contributing objects. The increase included 106 & 104 N. Main, which include Late Victorian architecture, on 0.5 acres (0.20 ha).