The area was inhabited for approximately 8,000 years by Native Americans of the Fernandeño-Tataviam and Chumash-Venturaño tribes that lived in the Santa Monica Mountains and Simi Hills and close to the Arroyo Calabasas (Calabasas Creek) tributary of the Los Angeles River in present-day Woodland Hills. The first Europeans to enter the San Fernando Valley were the Portola Expedition in 1769, exploring 'Alta California' for Spanish missions and settlements locations. Seeing it from present-day Sepulveda Pass, the oak savanna inspired them to call the area Santa Catalina de Bononia de Los Encinos (Valley of the Oaks). The Mission San Fernando Rey de España (Mission San Fernando) was established in 1797 and given the Valley's land, including future Woodland Hills. After the Mexican War of Independence the secularized Mission lands became the Rancho Ex-Mission San Fernando.
Ownership of the southern half of the Valley, south of present-day Roscoe Boulevard from Toluca Lake to Woodland Hills, by Americans began in the 1860s. First Isaac Lankershim (as the "San Fernando Farm Homestead Association") in 1869, then Isaac Lankershim's son, James Boon Lankershim, and Isaac Newton Van Nuys (as the "Los Angeles Farm & Milling Company") in 1873, and finally in the "biggest land transaction ever recorded in Los Angeles County" a syndicate led by Harry Chandler of the Los Angeles Times with Hobart Johnstone Whitley, Gen. Moses Sherman and others (as the Los Angeles Suburban Homes Company) in 1910. The area was so big that 12 years passed—Van Nuys and Canoga Park were founded—before anyone would get around to the Woodland Hills area.
In 1941 the community was renamed Woodland Hills. Harry Warner, of the Warner Bros. Studio, bought 1,100 acres (4.5 km2) in the area in the 1940s for a horse ranch, named Warner Ranch. The modern Warner Center commercial zone is named for Harry and features high-rise buildings, hotels, and shopping centers. A major transit hub — the western end of the LACMTA Orange Line — opened here in October 2005.
The population of Woodland Hills is approximately 70,000. The region is recognized for having the warmest weather in the City of Los Angeles.