The southern portion of Whitfield Estates was developed on land originally owned from 1876 to 1912 by Fannie and General John Riggin Jr., an aide-de-camp of General Ulysses S. Grant during the Civil War. In 1924, a corporation led by Louis Broughton Whitfield of Montgomery, Alabama, assembled 682 acres that included the 218-acre bayfront estate of the late Alfred Ringling. Planned as a town to rival Coral Gables, Whitfield Estates was designed with a tourist hotel overlooking the bay, an 18-hole golf course, a business district, a yacht club, and man-made islands in the bay. Construction began in October 1924, lots in the first unit south of Whitfield Avenue went on sale in January 1925, the phase north of Whitfield Avenue was platted in October 1925, and units east of the Tamiami Trail and the Donald Ross-designed golf course, now Sara Bay Country Club, were added in 1926. Promoted as "the Jewel of the West Coast," it became one of the most highly regarded development ventures of Florida's 1920s Land Boom. Bobby Jones served as assistant sales manager, and builders and architects included T.A. Monk and Ralph Twitchell. By the summer of 1926, an apartment building, 61 homes, a retail store, and the country club were completed or under construction. Whitfield Estates incorporated as a town in June 1926 and elected its own mayor, but the Land Boom had already begun to collapse, and the developer filed for bankruptcy in March 1927. Development halted and did not resume until the 1940s during the post-World War Two housing boom. In 1949, Whitfield Estates established its own zoning district, which lasted until 1981 and ultimately led to the creation of the Whitfield Residential Overlay District. Its special character is distinguished by a century of architectural styles, including many vintage homes built during one of Florida's most exciting eras.