In 1926 a group of Los Angeles real estate men partnered with several locals to form the New University Syndicate, initial developers of Rolando.
- The name Rolando came from the “rolling land” of the various canyons and mesas of the area.
- The paving of University Avenue in 1925 helped interest the developers to purchase the land and develop Rolando between two new “highways.”
- Rolando’s initial sales motto was “City of Rolando: Where You’ll Love to Live.”
- Having worked on high-end subdivisions in Los Angeles, the developers brought in landscape architect Theodore Meyer to design the development with curving streets, decorative street lights, areas for commercial development (Rolando Boulevard near the Island Park), and distinctive pedestrian walkways connecting streets.
- The original Rolando is made up of 5 subdivisions, platted and developed with street improvements between 1926 and 1928.
- Rolando’s rural location hurt sales and by 1930 the tract was in foreclosure to the State for failure to pay Mattoon Act Improvement Bond assessments.
- In 1939 local real estate men Ben Margolis, Harry Arthur, and Joe Levikow established the new Rolando Village Company and re-opened the area for development.
- With San Diego entering the Boom triggered by World War II, the area’s empty streets and existing infrastructure helped it quickly fill-in, with many of the popular small, minimal-traditional style homes dating from 1939 to 1941.
- Home owners would buy a lot from the Village Company and then choose from the recommended list of contractors, or choose their own—helping create the unique mixture of housing styles.
- After World War II, another 17 small subdivisions, mostly of tract homes, duplexes, and apartments filled in the area west of the original 5 subdivisions up to western boundary College Avenue.
- Unincorporated Rolando and southern neighbor Rolando Park annexed into the City of San Diego in 1954 and the City School District in 1955.
- Henry Clay Elementary opened in 1957 and Clay Park in the 1970s.
- The family focused Rolando Street Fair is held the last Sunday in March annually.