Many of the original homes on and around Holly Mont Drive were built starting in 1912 as part of the Krotona Colony, a Theosophical community. These were often modest cottages or Moorish-style bungalows intended for spiritual seekers. Most of the single-family residences currently on the street were constructed throughout the 1920s in the popular Spanish Colonial Revival style. For example, 6215 Holly Mont Drive was built in 1925. Holly Mont Drive is historically significant as the upper terminus of the Krotona Flight Stairs. Circa 1914-15, architects Mead & Requa designed the stairs, they served as the southern entrance to the Krotona Colony. The flight was originally intended to rise northward behind a monumental gateway but was abandoned as the architects "simplified" the design.