Come Fly With Frank Sinatra: Inside Five of the Crooner’s Multi-Million Dollar Homes

The Rat Pack leader was also a real estate mogul.

Come Fly With Frank Sinatra: Inside Five of the Crooner’s Multi-Million Dollar Homes

Few people have accomplished more in their careers or are as recognizable as Frank Sinatra. Before the legendary crooner passed away in 1998, he had sold approximately 150 million albums worldwide, starred in dozens of movies and television shows, acquired a long list of famous lovers, and had strong ties to both world leaders and the mafia.

He was also a prolific buyer and builder of homes, having owned estates from coast to coast, from Manhattan to Malibu. To celebrate the career of Ol’ Blue Eyes, we’re taking an in-depth look at five of Sinatra’s most swoonful properties. Some of them are even available to buy or rent. And while they don’t come cheap, they’ll make you feel like you have the world on a string.

House No. 1: Twin Palms, Palm Springs, California

“I wanna house.”

That’s what Sinatra said when he walked into architect E. Stewart Williams’ family office in 1947, according to the Guardian. The singer, who was wearing a white sailor’s cap and eating ice cream, was looking to build a home in Palm Springs. It was May, but Sinatra demanded a house be built and live-in ready by Christmas so he could host a Christmas bash. Furthermore, Sinatra did not have a home like this midcentury modern in mind: He wanted a Georgian mansion, which would have been a huge mistake (and it probably would have ruined the WIlliams’ reputation).

Twin Palms

Instead, the Williams persuaded Sinatra with layouts of a single-story house with aluminum and steel siding, walls of glass and a long, sloping roof. Ol’ Blue Eyes reportedly paid $150,000 — about $1.72 million today — to have it built in time for the party. Pictured here is the piano-shaped swimming pool.

Twin Palms

It’s a good thing Sinatra wasn’t stubborn, at least when it came to his real estate visions. The house, which Sinatra named Twin Palms, is one of the best examples of desert modernism still standing. The house is 4,500 square feet with four bedrooms and seven bathrooms.

Twin Palms

The house was the stage for many fiery fights between Sinatra and his then-wife Ava Gardner. The two divorced in 1957, and Sinatra sold the home that same year. Today, the home is a luxury rental starting at $2,500 a night via Natural Retreats.

Twin Palms

According to SinatraHouse.com, one of the sinks in this bathroom "has a crack in the basin from a champagne bottle that Sinatra hurled at Gardner" before he tossed her belongings onto the driveway.

Twin Palms

The light blue kitchen appears to have an oven from the 1950s.

Twin Palms

A very green guest room.

Twin Palms

A bedroom with its own fireplace and pool access.

Twin Palms

Another look at the living room and dining area, which has vintage Valentino Electronics recording recording equipment.

Twin Palms

According to Evan Thomas in his biography of Robert Kennedy, John F. Kennedy was supposed to stop by Sinatra's place in Palm Springs, but the FBI was concerned about Sinatra's ties to the mob, and Kennedy spent the night at Bing Crosby's estate. Sinatra had built a helicopter pad specifically for the president, but when he learned of the snub, Thomas says Sinatra destroyed the landing pad with a sledgehammer. There is no landing pad on the property today.

House No. 2: Farralone, Chatsworth, California

Sinatra rented this 10,000-square-foot estate in Chatsworth, California during the 1950s and stayed there on and off for a decade. The mansion has a number of nicknames — Farralone, the Fox Residence, the Great Glass Mansion and Byrdview.

Farralone

Chase Manhattan Bank heiress Dora Hutchinson had the home built in 1949 as a party pad for the rich and famous. Judy Garland and Vincente Minnelli updated their vows here, and according to Forbes, Hutchinson would set off fireworks to announce Happy Hour. Which is both awesome and obnoxious.

Farralone

At some point during his tenure, Sinatra sublet the estate’s single-bedroom, 1,000-square foot guest house to Marilyn Monroe. It has been rumored that this is the place where Monroe had an alleged tryst with JFK; however, that late night affair most likely happened in Bing Crosby’s place in Rancho Mirage, where JFK certainly stayed.

Farralone

Inside the guest house where Monroe stayed.

Farralone

The estate is perched on seven acres of land overlooking both the 1,300-acre Chatsworth Reservoir nature preserve and its many low-lying neighbors.

Farralone

The mansion was designed by William Pereira, the architect who built the Transamerica Pyramid in San Francisco and the Los Angeles County Museum of Art.

Farralone

Over the years, Farralone has doubled as a shooting location for Hollywood movies and television shows. The home appears in “Mad Men” in the second season’s eleventh episode where Don Draper parties with some hedonists. It was Beyonce’s house in “Dreamgirls,” the shooting location for Halle Berry’s pool scene in “Swordfish” and a party scene in the 2005 “Bewitched.” It also appeared in Showtime’s “Californication” and Usher’s “Burn” music video.

Farralone

According to Forbes, the house can pull in as much as $2 million per year for film shoots.

Farralone

Sinatra's Chatsworth compound has been up for sale and relisted several times. It went on the market in 2011 for $12 million, then de-listed and came up for sale at a reduced price of $7.5 million in 2015. It didn't sell, and then was re-listed for an even higher price of $12.5 million in late 2018, before it was again taken off the market in 2019.

Farralone

A cozy place to grab a drink from the bar and sit by the fire on cold nights.

Farralone

The home features 16-foot ceilings and expansive glass walls. The estate has enough parking for 200 cars and the property comes with approved zoning for a vineyard.

House No. 3: Penthouse, Manhattan, New York City

After moving on from Gardner, Sinatra married 21-year-old Mia Farrow in 1966. Sinatra was 50, so it's no surprise that the marriage only lasted two years. But while they were married for that short time, Sinatra purchased this 3,200-square-foot penthouse in Manhattan.

Manhattan Penthouse

Sinatra helped design the three-story triplex located in Manhattan's Upper East Side when it was under construction in 1961. However, it has been completely renovated over the years. For example, that glass staircase is a replica of one from an Apple store.

Manhattan Penthouse

Andy Warhol called the penthouse a "glittering grotto," according to the listing, because of its 18-foot floor-to-ceiling windows.

Manhattan Penthouse

Sammy Davis Jr. would toss empty champagne glasses out of the penthouse's window down onto FDR Drive, according to Top Ten Real Estate Deals.

Manhattan Penthouse

The home has four bedrooms and four bathrooms. What was once Sinatra's party room on the third level has been turned into the master bedroom.

Manhattan Penthouse

Sinatra owned the apartment for 11 years, selling it off to Andy Warhol's doctor in 1972. Farrow and Sinatra divorced in 1968, while Farrow was filming "Rosemary's Baby." The film was taking more time than expected, and Sinatra kept nagging Farrow to quit the set so she could star in his movie, "The Detective." Farrow refused, and Sinatra had Farrow served with divorce papers on set.

Manhattan Penthouse

The penthouse went up for sale at $5.6 million in 2013 and sold in 2015 for $4.9 million.

House No. 4: Villa Maggio, Palm Desert, California

While Sinatra still had the triplex in New York City, he custom built this desert getaway in Palm Desert, California in 1970. The compound is perched 4,300 feet above ground on 7.5 acres of land.

Villa Maggio

Sinatra christened it Villa Maggio, after his role in the critically acclaimed 1953 drama "From Here to Eternity." His performance as Angelo Maggio won him an Academy Award and a Golden Globe.

Villa Maggio

The main house is a midcentury lodge-style cabin with five bedrooms and five-and-a-half bathrooms. There's also a two-bedroom pool house with two saunas and a guest house; in total, the compound as eight bedrooms, 12.5 bathrooms and 6,428 square feet of interior living space.

Villa Maggio

Sinatra once said that orange was the happiest color. The kitchen is original to the house and features orange tiling, wood cabinetry and three industrial-sized fridges.

Villa Maggio

While the house has been restored and renovated, the owners have preserved much of the home's original features. Like this secret doorway between two guest bedrooms, just in case two strangers in the night fancy one another.

Villa Maggio

The compound is stuffed with memorabilia and photos, like in this bathroom, whose walls are adorned in photos of Sinatra and the Rat Pack.

Villa Maggio

A closeup of some of those pictures.

Villa Maggio

The estate was not cheap. Sinatra plopped down $1.9 million to build it in 1970, the equivalent of $12.5 million in today's dollars. It's also up for sale at $4.5 million, although it's having trouble finding a buyer. The home has been on and off the market since 2015.

Villa Maggio

Sinatra lived here for about 12 years. He sold it sometime in the 1980s after he married Barbara Marx, but the two were together when Sinatra lived in this house. During a game of charades, Sinatra became so enraged that he couldn't figure out an answer, he threw a clock through a sliding glass door.

Villa Maggio

The house was built with locally sourced stone and hardwoods, and features to full kitchens in the main home, several decks, nine fireplaces, a huge pool, lighted tennis court and a helipad that has not been destroyed by an angry, sledgehammer-wielding Sinatra.

House No. 5: Malibu Retreat, California

Sinatra and Barbara built this Malibu retreat in 1992, and it was in all likelihood the last home Sinatra ever purchased. The 5,824 square foot beach property has recently been listed on the market for a staggering $12.9 million, and is being sold by one of Marx's sons. Barbara passed away in 2017.

Malibu

Two years before Sinatra died in 1998, he and Barbara renewed their vows here in 1996. Don Rickles and Bob Newhart attended the celebration and gave speeches, according to Top Ten Real Estate Deals.

Malibu

The seven-bedroom, nine-bathroom home was a beloved piece of real estate for the couple during their twilight years.

Malibu

Edward "Ted" Grenzbach designed the house. It includes indoor/outdoor living, with large sliding glass doors that open up to Malibu's gorgeous weather.

Malibu

The home has some midcentury modern touches throughout, like in the kitchen. Unlike some of Sinatra's other homes, there's no orange color.

Malibu

The leopard-print staircase is adorned with Sinatra posters, album covers and photos.

Malibu

The master bedroom, located on the second story, has its very own fireplace, sauna and hair salon.

Malibu

If you don't want to wade in Broad Beach, take a dip in the dipping pool, located in a shady courtyard.

Malibu

The home sits on half an acre of beachside land with immaculately gardened grounds.

Malibu

There's tons of outdoor space to drink some Jack Daniels (Sinatra's favorite) and relax.

Bonus House: Wonder Palms Compound, Rancho Mirage, California

We'd be remiss if we didn't mention Wonder Palms Compound, the Rancho Mirage estate that Sinatra purchased in 1957 and owned until 1996. Unfortunately, there are no recent interior photos of the house available. Records say the house sold in January of 1996 for $4.6 million.

Now that you've taken a tour of many of Sinatra's favorite homes, which one would you like to fly away to?