When it came to real estate, Frank Sinatra did things his way. Although the New Jersey-born music icon bounced around from one eye-popping estate to another, Sinatra’s Twin Palms pad epitomized his party lifestyle. Seeing everything from legendary spats with onetime wife Ava Gardner to a revolving door of mega-famous celebrity guests, Ol’ Blue Eyes’ time in the desert was anything but ordinary.
Frank Sinatra paid only $150,000 for his Twin Palms estate
As the story goes, a 31-year-old Frank Sinatra walked into architect E. Stewart Williams’ office in May 1947 with a huge opportunity — and a potential calamity.
According to Visit Palm Springs, the crooner expected the well-known homebuilder to accept a litany of personal designs, which Williams privately believed would be a disaster for his firm’s reputation. But instead of Sinatra’s lavish, Georgian-style abode, Williams persuaded the singer to accept a more practical and modern design.
In the end, Williams built Sinatra his dream desert escape at unbelievable speed, wrapping it up in time for Ol’ Blue Eyes to throw a New Year’s Eve party featuring the tip-top of the Hollywood A-list. With a piano-shaped pool, an outdoor kitchenette, and the best sound system money could buy, Sinatra’s house suddenly became the place to be in Palm Springs. Cary Grant, Bing Crosby, and Bob Hope were just a few of the other stars who had similar desert getaways at the time.
Although $150,000 in 1947 wasn’t cheap, it would prove to be one of the more subdued real-estate transactions Sinatra undertook. With its 4,500 square feet of living space, custom-built cabana, and panoramic views, Sinatra’s Twin Palms estate was a steal. Buying a similar property in Palm Springs today runs between $3 million and $5 million (per Redfin), though Sinatra paid an inflation-adjusted $1.9 million.
Frank Sinatra’s Twin Palms estate saw plenty of drama
Though Frank Sinatra was known for recording music and movies at a breakneck pace, he believed in the second part of the “work hard, play hard” mantra. And when a Jack Daniel’s flag flew above the house, that typically meant one thing: Sinatra was home and ready to party (per Country Living).
But the hard-partying lifestyle took a toll on Sinatra. After he split with his first wife, Nancy Barbato, in 1951, the singer got hitched to movie star Ava Gardner in what would turn out to be an incredibly tumultuous marriage. By 1953, Sinatra and Gardner were on the outs — apparently over his fling with Lana Turner — and the couple separated for years.
According to the Desert Sun, the Jack Daniel’s flag came down for the last time in April 1953, when the Rat Pack member sold his estate for an undisclosed sum.
By the time Sinatra and Gardner officially divorced in 1957, he had settled into another spectacular home in the Palm Springs area. Technically in Rancho Mirage, the property would be his primary home for nearly the rest of his life, although Sinatra had acquired a wandering eye for real estate that led to a stunning accumulation of opulent properties.
The crooner bounced around from Manhattan to Malibu
Frank Sinatra loved entertaining high-profile guests in his main Palm Springs home, which he expanded into a larger and more guest-friendly version of his Twin Palms estate. Anticipating a second visit from John F. Kennedy, Sinatra even added a detached bungalow and a second pool for additional privacy.
Eventually, he also bought a spectacular hideaway in nearby Palm Desert. Known as Villa Maggio after his From Here to Eternity character (per the New York Post), the estate has a helipad, more than 6,000 square feet of living space, and majestic views of the Coachella Valley.
When he wasn’t at Villa Maggio or his Palm Springs abode, the Chairman of the Board could often be found at the legendary LA estate Byrdview, as detailed in Architectural Digest. Sinatra regularly leased the luxurious seven-bedroom home throughout the ’50s and ’60s and welcomed an array of famous visitors; at one point, Marilyn Monroe even lived in his guest house. The luxurious home has appeared in various TV shows and movies, including Mad Men and Dreamgirls.
Sinatra also lived in a spectacular Manhattan penthouse overlooking the East River. During his short-lived marriage to Mia Farrow in the late ’60s, the apartment was such a hot spot that Andy Warhol named it the “glittering grotto,” Business Insider reports. And when Sinatra eventually looked to enjoy a quiet retirement, he and his wife Barbara built a beautiful oceanfront house in Malibu. Though it was listed just shy of $13 million in 2018, actor/comedian Mindy Kaling scooped it up for $9.55 million in 2020, according to the Los Angeles Times.
Though the list of properties might seem staggering, the iconic entertainer lived well within his means. According to Celebrity Net Worth, Sinatra still had a $200 million fortune at the time of his 1998 death, equivalent to roughly $350 million in 2022 dollars (per the U.S. Inflation Calculator). Loftier estimates put his net worth around $600 million when he died.
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