Outpost Estates was named by General Harrison Gray Otis in the 1800’s when he named the house at Franklin and Sycamore “The Outpost” and used it as a clubhouse for his military friends. Charles E. Toberman developed the land now known as Outpost Estates and had a dream for the neighborhood to be one of the most exclusive and beautiful “residential parks in the world” and known as the “jewel in the hills”.

The area became known as an affluent area with many rich and famous residents. Homes had to be designed in Spanish, Mediterranean or California modern style, have red tile roofs, plenty of patios for "outdoor living," and be approved by architectural committee before being built. Most of the original houses have been preserved, and ‘lower’ Outpost looks much like it did in the 1920s.

In the 1920s, in the hills above the development, a large sign spelled out "Outpost" in red neon letters 30 feet high. It was intended to compete with the Hollywoodland sign, (which later became the Hollywood sign). At the time, it was the largest neon sign in the United States. The Outpost sign was dismantled during World War II, and the wreckage of the sign was left in place, buried in the weeds. Even the original foundation and electrical junction boxes survived. Read more about the Outpost neon sign here.

The Outpost Estates development was one of the first neighborhoods in the country to offer all-underground utilities. Read more about the history here.

Today, Outpost Estates is still known as the ‘jewel in the hills’ and is a popular destination for tourist looking to get a glimpse of life in the Hollywood Hills. The homes are still mostly Spanish, Mediterranean or California modern style, most streets are lined with historic street lights and all utilities are underground. The land is lush with plants and wild deer, coyote, hummingbirds, owls, hawks, and other wildlife run freely. Outpost Estates is/was home to many current and former celebrities (e.g., Gore Vidal, Penny Marshall, Bob Barker, Dolores del Río, Bela Lugosi, Orlando Bloom, Johnny Galecki, Winona Ryder, Felicity Huffman, Russel Brand, Madelaine Petsch, Kevin Smith, and many more).

Outpost Estates' is conveniently located near some of Hollywood’s best attractions like the Hollywood Bowl, Runyon Canon Park, and the Magic Castle. It is ‘hidden away’ in the Hollywood Hills, so it feels like a nice reprieve from the hustle and bustle of the greater Los Angeles city.