In the 19th century this area was home to cotton fields. The development of the Winnetka Heights subdivision around 1910 marked the beginnings of Kings Highway. It started with the construction of numerous apartment buildings for the residents awaiting completion of their new homes in Winnetka Heights. Platted as Oak Cliff Annex, the area was designed along the unique diagonal thoroughfare of Kings Highway. During its existence, the trolley stopped at the eastern entrance, where a brick archway once stood, marking the gateway to the neighborhood.
The development did not cease when Winnetka Heights was finished. Many of the original 1910 apartments remain, but it is the diversity of the area that is so appealing. While much of the neighborhood has a 1920s middle class feel with single family Craftsman bungalows, Kings Highway is lined with examples of Tudor, late Queen Anne, Neoclassical and Prairie-style homes. Many of the smaller houses have been restored, as have many of the larger two story homes. However, there are still homes that await creative hands to bring them back to their original splendor.
The Kings Highway Conservation District is the second of its kind in Texas and the first in Dallas. A group of residents banded together in the mid-1980s to save this historic neighborhood. The Conservation District was created, and a specific city-enforceable ordinance was written by the neighborhood to direct such topics as zoning, setback, renovation, and general appearance of the exteriors. Conservation Districts are not a strict as Historical Districts.