The majority of present day Kenwood was platted in 1903 and 1907. The 1903 plat was known as the Kenwood Addition to Laurel Heights (Monte Vista) and was owned by Joe Zeniner. It was bounded by Olmos Drive on the south, Rex on the north, between San Pedro and McCullough. The 1907 section, Lynwood Addition to Laurel Heights, was platted by JB Callahan and bounded by Mariposa and Zilla between McCullough and Howard. The area remained the north-central terminus of the city subdivision plat until the 1930s when Olmos Park Terrace was platted directly north.
After decades of decline, in 1973, the neighborhood was designated as an Urban Renewal Area by the San Antonio Development Agency (SADA). With funding from the US Department of Housing and Urban Development (HUD), SADA constructed single-family homes, duplexes, and an elderly senior living center in the neighborhood. Additionally, a community center and health clinic were constructed near Kenwood Park.
Today, the neighborhood is characterized by its mix of housing types, churches, and active commercial street corridors. Kenwood serves as the confluence of the central north-side and bridges the pre-WW2 streetcar neighborhoods to suburban-style developments nearby.