
Whether you want a beachy retreat or a swank pad you can pick out in episodes of Mad Men, Frank Sinatra hung his hat in two homes that are on the market at the same time, for nearly identical price points.
If Malibu is your bag, one estate was designed by architect Ted Grenzbach and Sinatra and his wife, Barbara in 1992. When the Sinatras lived there, a veritable who’s who of Rat Pack era celebrities visited, from Dick Martin, Jack Lemmon, Gregory Peck, and Dick Van Dyke, and more.
And it’s a beautiful home designed to showcase the ocean views, with an open floor plan and floor-to-ceiling windows. The 5,800 square foot house has seven bedrooms and nine bathrooms.

But if you’re wanting a swinging pad from the Midcentury Modern era, you may want to scoot into the Chatsworth neighborhood of Los Angeles.
While Sinatra didn’t actually own this home located at that overlooks the Chatsworth Nature Preserve, he did lease the property for about 10 years. Designed by William Pereira in 1949, the home has all the expected features of a Midcentury Modern home, from 16-foot walls of glass, a wet bar ready to make Manhattans, an office, and more.
Want to know what late actress was rumored to be leasing the guest house from Sinatra for a time? Check out the whole story at SecondShelters.com.