One of the most heavily followed celebrity homes in all of Hollywood, Farralone was built by wealthy socialite Dora Hutchinson as a party pad for the rich and famous. Famous guests have included Lucille Ball, Ava Gardner, Judy Garland and others, but the spot is primarily known as the main hangout for Frank Sinatra, who rented the location for nearly a decade during the "Rat Pack" years.
Most interesting of all is that Sinatra subletted the 1,000-square-foot guesthouse to a certain star by the name of Marilyn Monroe, who used the home as a meeting spot during her alleged affair with President Kennedy.
The 10,000-square-foot main house features 4 bedrooms/5.5 baths, a grand gallery, three lower level private offices, and 16-foot glass walls that provide stunning natural light. Outside, it's all about location, location, location — and Farralone has it made. Besides the winding private road leading to the main residence at the top of a hill, there are also 14 acres of vineyards, horse riding trails, and immense privacy thanks to a surrounding 3,000-acre wildlife preserve. “You would have to be in a helicopter to see the house,” the listing agent tells Forbes
Of course, despite its seclusion, you've likely seen Farralone before. The home and its setting has been used in films and music videos such as "Mad Men," "Californication," "Swordfish," "Dream Girls" and "Ali." According to the listing, anywhere from $500,000 to $2 million can be made annually, just from renting to film productions.