At the turn of the 20th century, the area within the present day Highlands-Douglass neighborhood was home to rolling farmland and scattered family farms and estates.  In 1912, the extension of the streetcar line along Bardstown Road to Douglass Boulevard (Douglass Loop) brought development with it, and over time the land was divided into what became the subdivisions of today.  At the turn of the century, part of the Woodbourne Estate  property, including Big Rock, was donated to Cherokee Park. The remainder of the property was subdivided as Douglass Park subdivision.

The western portion of Highlands-Douglass developed more quickly than the eastern portion. In addition to being on more level terrain than the eastern portion, the extension of the Bardstown Road streetcar line in the early 20th century was the largest factor behind this growth in development.  The original Douglass Park subdivision was carved into several smaller subdivisions prior to World War I, when development of the area slowed. The 1920’s, however, saw a building boom in which more than a dozen new subdivisions were platted. The names of the subdivisions and their developers are reflected today in the familiar street names of the neighborhood: Lauderdale, Woodbourne, Kenilworth, Weber, and Kaelin. The  housing styles in these subdivisions most likely reflect the socio-economic status of the original residents and the people to whom the new homes were marketed. Large historical revival homes (colonial, Tudor, etc.) in the western portion suggest an affluent upper-middle class population; while the bungalows of the southern portion, near the intersection with Taylorsville Road, indicate a more middle class population.