Beginning in 1910 as Boulevard Subdivision, Grand Boulevard and its side streets were laid out north of the Yazoo River. The subdivision was a separate incorporated town until annexed to Greenwood in 1922. Pin oaks line the boulevard, transplanted from nearby river banks under the direction of Sally Humphreys Gwin, wife of one of the developers. The white professionals, merchants, cotton factors, and planters who lived here could commute to downtown Greenwood across an iron bridge and, later, the steel Keesler Bridge, which opened in 1925. Houses in this leafy neighborhood reflect fashionable styles of the time, including Tudor Revival at 207 and 601 Grand, built c. 1920 and c. 1930, respectively, and the Classical Revival Provine House (1910, H. C. White) at 319 Grand. U.S. 49 ran along Grand from the 1930s until 1953, when it was redirected and thus not long enough in time to commercialize the street and decimate its housing stock.