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Location: Chatsworth, California

Price: $12,000,000

It might be just 60 years old, but the Fox Residence has many lifetimes worth of history attached to it. Designed by the modernist duo of Pereira & Luckman, the sleek midcentury manse was -- and all of this is according to the brokerbabble so please take it with a grain of salt -- built for Dora Hutchinson, heiress to the Chase Manhattan Bank fortune, who threw lavish parties and hosted the likes of Ava Gardner and Lucille Ball. Judy Garland and Vicente Minnelli are said to have married on the property before Hutchinson returned to New York and began renting the place to Frank Sinatra. Sinatra then sublet the guest house to the one and only Marilyn Monroe, who supposedly had a tryst with John F. Kennedy here. With all that history, it's no wonder that the place served as the setting for the Mad Men episode "The Jet Set." The 10,000-square-foot glass-and-steel house sits on 14 acres and enjoys downslope views. It's priced at a heady $12,000,000.

• Farralone Estate [Official Site]
• Frank Sinatra Fox Residence For Sale in Chatsworth [Curbed LA]
• The Complete House of the Day Archive [The Atlantic Life]