Outpost Estates is located in the Hollywood Hills east of Runyon Canyon Park, north of Franklin Ave and is centered around Outpost Drive. Developed by Charles E. Toberman, it is one of the original 1920s Hollywood luxury residential neighborhoods in the heart of Old Hollywood.

Most of the original houses have been preserved, and Lower Outpost looks much like it did in the 1920s. The origin of the name "Outpost" derives from an early building on the site. The Outpost Estates development was also one of the first neighborhoods in the country to offer all underground utilities.

A little bit of Outpost Estates history... The first ten and a half acres of the Charles E. Toberman luxury subdivision in Hollywood known as Outpost Estates, received its name from its previous owner, General Harrison Gray Otis, the founder of the Los Angeles Times and the Chandler dynasty.

General Otis, a veteran of the Spanish American War purchased the acreage from Don Tomas Urquidez who in 1853 had built the first adobe home “in the valley” on an Indian burial ground at the northwest corner of what is now Franklin and Sycamore. General Otis re-named the adobe “The Outpost” and it became a clubhouse of sorts for his buddies from his military days. This piece of real estate would change hands a number of times before becoming part of the Out-post Estates.

The streets in and around Outpost Estates are as follows; Cantata Dr, Carman Crest Dr, Castilian Dr, Chelan Dr, Chelan Pl, Chelan Way, Hillside Ave, La Presa Dr, Larmar Dr, Los Altos Pl, Los Tilos Rd, Malaga Dr, Maravilla Dr, Oporto Dr, N Orchid Ave, Outpost Cir, Outpost Cove Dr, Outpost Dr & Senalda Rd.