The Uptown Community lies just north of the Centre City area. It is bounded on the north by the steep hillsides of Mission Valley, on the east by Park Boulevard and on the west and south by Old San Diego and Interstate 5.

The Uptown Community is located on a level mesa that is divided by numerous canyons and bordered by two major parks, Presidio and Balboa. The Uptown community contains some of the oldest neighborhoods in San Diego exhibiting a variety of historic architectural types and a heavily traveled pedestrian mixed-use retail commercial area. The area also features a wide range of residential opportunities and a diverse mixture of people within a distinctly urban setting. The area includes the neighborhoods of Mission Hills, Middletown, Hillcrest, the Medical Complex, University Heights, and Park West. Located in Hillcrest is the nationally recognized Uptown District, a model of mixed-use infill development that includes housing, a retail core, offices, live-work spaces and a community center.

The Uptown District is a pedestrian-oriented, mixed-use retail center and residential development. The redevelopment of a 14 acre site known as the "Sears site" was completed in 1990, following a complex planning process with extensive community involvement. The project has attracted national attention as a model for the redevelopment of low-density, obsolete commercial sites for new housing and community uses. Its significance lies in its success in repairing an older city fabric that was damaged by 1950s commercial development. Uptown District has greatly spurred development in the surrounding Hillcrest neighborhood, especially adjacent to the site along University Avenue, which is the main arterial road, according to the San Diego Daily Transcript. The National Association of Home Builders named Uptown District the Project of the Year in October 1991. It was awarded the Urban Design Award by the California Council of the American Institute of Architects the following month.