Harbor Oaks was Clearwater's first planned residential development. Dean Alvord, a major developer in New York state, opened Harbor Oaks in 1914. Bringing modern planning concepts to the Pinellas County area, the development offered innovative features such as underground utilities, paved streets, curbs and sidewalks, a sewer system, and tree lined parkways. Deed restrictions ensured a rich architectural mix of mostly two story homes including fine examples of Mediterranean Revival, Colonial Revival, Tudor Revival, Mission and Bungalow styles. Local newspapers called Harbor Oaks "the Riviera of the Sunny South" and "the finest shore development on the West coast of Florida". The development was essentially completed by 1930. Harbor Oaks has been the home of such prominent persons as author Rex Beach, Brooklyn Dodgers owner Charles Ebbett, inventor Donald Roebling, industrialist Robert Ingersoll, and members of the Studebaker and Proctor and Gamble families. The Harbor Oaks Historic District was listed in the National Register of Historic Places in 1988.

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