During the 1920s and 1930s Hillcrest was considered a suburban shopping area for downtown San Diego. Real estate development began in 1910 and the area was built out by 1920. George Hill, a wealthy railroad tycoon, then purchased the land. Choate, two real estate developers, obtained that property. In 1870, Mary Kearney obtained a deed from the city for the land that eventually became Hillcrest. Presidio Park in Mission Hills and Old Town just down the hill are a part of San Diego history. Spanish colonization brought the first of twenty-nine California missions with the founding of the nearby San Diego Mission.

Kumeyaay Indians inhabited numerous villages scattered throughout the San Diego region. Initially, Hillcrest was a chaparral-covered mesa. ( November 2011) ( Learn how and when to remove this template message) Unsourced material may be challenged and removed. Please help improve this article by adding citations to reliable sources. This section needs additional citations for verification.