From NYC to Palm Desert

America’s most famous crooner is known for his melody about “New York, New York,” but only one of Frank Sinatra’s six properties was in the Big Apple.

In fact, Sinatra started out in Hoboken, NJ, across the river, and the first house he owned was in suburban Hasbrouck Heights nearby.

But soon, Sinatra began commissioning custom homes in California — apparently, he wanted them “My way.”

All told, Sinatra owned at least six homes during his 82-year life and rented numerous others — almost all of them in California or New Jersey — plus his penthouse in Manhattan.

Most of his homes had pianos, state-of-the-art sound systems for the time and mid-century modern architecture. They hosted roaring parties with Sammy Davis Jr., explosive fights with Ava Gardner, helipads, guest houses and plenty of parking for his “Rat Pack” friends before he died in 1998.

“My way” at Twin Palms

Palm Springs, California | $150,000

Sinatra and his first wife Nancy Barbato commissioned Twin Palms in 1947 for $150,000 — which is about $1.9 million today, according to the Bureau of Labor Statistics.

The four-bedroom, seven-bathroom home has a piano-shaped swimming pool flanked by two palm trees, giving the Palm Springs, California, home its name, according to the home’s rental website.

During Sinatra’s residency, he used a flag pole to raise a Jack Daniels flag, signaling to neighbors and friends they should come over for a party, according to the website.

Appropriately, Sinatra was buried with a bottle of his favorite Jack Daniels and a pack of dimes “to call his friends” when he died, The Post reported.

He built the 4,500-square-foot home with Nancy, from whom he split in 1951 following public rumors of infidelity. But the home bears more permanent remembrances of his second wife, Ava Gardner, whom he married in 1951.

The motor court bears the memory of Sinatra throwing Gardner’s belongings onto the driveway when she tried to “catch him” with actress Lana Turner at home, and one chipped sink was damaged by a Champagne bottle during one of the couple’s infamous rows, according to the site.

Sinatra sold the home in April 1953, around the time he and Gardner split.

The house designed by architect E. Stewart Williams has its original sound and recording system, but the kitchen has been restored with modern amenities.

Today, the home is available for rent as a short-term rental or an event venue.

“The house I live in”

Rancho Mirage, California | $4.3 million

After leaving Twin Palms in 1953, Sinatra moved to this private compound in 1954, which was considered his primary residence until 1995, when his declining health caused his family to sell the estate for $4.3 million, according to Realtor.com.

He called the main house “The house I live in,” after his 1945 Oscar-winning film. Sinatra purchased two adjoining lots, creating a 2 ½-acre estate.

The home was designed by William F. Cody in 1952 for Austin H. Peterson, who never moved in. Sinatra commissioned Cody to complete an expansion and remodel for his own tastes, the Desert Sun reported.

The one-story house with clapboard siding had two bedrooms when he purchased it, but by the end of his residence had expanded to 18 bedrooms and 23 bathrooms.

It underwent significant renovations when his fourth wife Barbara Marx moved in and “wage[d] a gentle war on orange,” Sinatra’s favorite color, according to a 1998 feature by Architectural Digest.

The “tiny” kitchen grew to become “restaurant strength” with a commercial range, walk-in refrigerator and a wine closet. He also added a helipad, a painting studio and a real caboose outfitted with a sauna, massage table, barber’s chair and exercise bench, the Desert Sun reported.

The estate next to the Tamarisk Country Club gave Sinatra easy access to his golfing hobby, and his model trains got their own house on the property. The compound even had a home theater, according to Architectural Digest.

Since purchasing several lots on Wonder Palms Road, the street has been renamed to Frank Sinatra Drive in his honor. The property last sold for $4.6 million in 1996, according to Realtor.com.

“It was a place of the happiest times we ever had with him,” his youngest daughter Tina told Architectural Digest. “That was his home, and you could feel it. It was full of great times, I met the world in that house.”

A rental just like Twin Palms: Farralone

Chatsworth, California | $7.5 million to $12 million

It looks like Sinatra has a “type” — this mid-century modern house bears a striking resemblance to his “Twin Palms” estate.

Sinatra leased an 8,200-square-foot ranch house in Los Angeles in the late ’50s and early ’60s from Chase Manhattan Bank heiress Dora Hutchinson, according to the LA Times.

Known interchangeably as Farralone or Byrdview House, the seven-bed, seven-bath, two-half-bath home was designed in 1949 by Washington’s Kennedy Center architect William Pereira. It has 16-foot ceilings and floor-to-ceiling windows.

An L-shaped trellis couches a swimming pool, and a smaller dipping pool sits near the guest house, which at one time housed Marilyn Monroe, according to Architectural Digest.

The home was listed for sale four times since 2011 asking between $12 million and $7.5 million but has not sold.

Since Sinatra, it has also served as a set for AMC’s “Mad Men” and the 2006 film “Dreamgirls.”

A pair of penthouses in New York, New York

Manhattan | $5 million + $150,000/month

Sinatra bought a 3,200-square-foot penthouse at 530 E. 72nd St. in Manhattan in 1961, where he was known to sleep until 1:30 p.m.

Overlooking the East River and near his favorite clubs, the home had 18-foot ceilings and 2,000-square-feet of outdoor balcony space where Sammy Davis Jr. would throw Champagne glasses onto FDR Drive, according to legend.

He lived there with his third wife, Mia Farrow, beginning in 1966, but they divorced when she would not quit “Rosemary’s Baby” to be in his film “The Detective,” and he sold the apartment in 1972.

The penthouse has since been completely renovated with four bedrooms, six bathrooms, a putting green and a replica of the floating glass staircase in Midtown’s Apple Store, according to Top Ten Real Estate Deals.

It most recently sold for $5 million in a bidding war in 2015, The Post reported.

Later in his life, Sinatra moved into a penthouse at the Waldorf Astoria with his fourth wife Barbara, who liked to dine at Le Cirque — though Sinatra could only be persuaded to eat in his car outside.

The penthouse was most recently rented for $150,000 a month, The Post reported.

Villa Maggio

Near Palm Desert, California | $4.25 million

Sinatra commissioned the compound during his short marriage to Mia Farrow in 1967 as a guys’ group getaway in the Coachella Valley.

He named it “Villa Maggio” after his 1953 “From Here to Eternity” character, Angelo Maggio.

Located in the desert, this nine-bedroom, 13-bathroom compound served as a gambling lodge.

Spanning 6,428-square-feet of living space, the estate has a resort-style pool, a lighted tennis court, a helipad and parking for 24 cars. The lodge has expansive mountain views.

It has been on and off the market for 15 years, now asking $4.25 million but unable to secure a buyer due to its remote location, The Post reported.

Retirement beach house

Malibu, California | $9.5 million

Sinatra and his fourth wife, Barbara Marx, commissioned this seven-bedroom, nine-bathroom Malibu beach house in 1990. They renewed their vows at the beach house in 1996.

The architecture, created by Ted Grenzbach, deviates from his other California homes, with arched doorways and Art Deco influences. Grenzbach was part of Marx’s redesign of Sinatra’s Rancho Mirage house and their “war on orange.”

The 5,824-square-foot home has an indoor-outdoor bar, a patio with ocean views, a private terrace, a steam room and a hair salon, Page Six reported.

The home was purchased in March 2020 for $9.5 million by a then-pregnant Mindy Kaling, who is best known for her role writing, producing and acting in “The Office.”

Suburban paradise in “Warm Valley”

Bergen County, NJ | $714,300

One of Sinatra’s first homes was a Cape Cod-style house in suburban Hasbrouck Heights — though he was already famous enough that police had to break up crowds at the house, according to a 1998 Baltimore Sun feature.

He shared this 3,200-square-foot house called “Warm Valley” with his teenage sweetheart and first wife Nancy and his then-1-year-old daughter Nancy. He purchased it in 1941, the year it was built, and sold it in 1944, the year they had their second daughter, Tina.

It was last sold for $300,000 in 1999 and is estimated to be worth $714,300 today, according to Realtor.com.

NJ Beach House

Sunset Court, Brigantine (near Atlantic City) | $3.3 million

Sinatra rented this seven-bed, seven-and-a-half bath beach house for only a week in 1991 during a performance at the Sands Casino in Atlantic City. He requested Hershey’s Kisses and a case of Jack Daniels for his stay, according to Realtor.com.

The 5,900-square-foot beach mansion was owned by Atlantic City restaurateur Tony Pullella, who had just moved in with his family but vacated for Ol’ Blue Eyes. When Sinatra left, he left behind a wig, which is still displayed at the house, according to Realtor.com.

The home built by architect Robert Johnson in 1988 was listed for $5.2 million in 2015, including the piano Sinatra used during his stay. The price has since been reduced to $3.3 million.

On other occasions when he performed in Atlantic City, Sinatra stayed at the Golden Nugget hotel, where his “Chairman’s Suite” had golden toilets, The Post reported.

Childhood apartment

Hoboken, NJ |

Sinatra famously grew up in Hoboken. His family moved several times, but his parents became homeowners when they purchased this four-floor townhouse for $13,400 in 1932, according to a 1988 article in the Jersey Journal.

What the Sinatras paid is only about $250,000 today — since then, and in part because of its ties with Sinatra, Hoboken has become exponentially more expensive. Today, the home is worth about $1.85 million, according to Realtor.com.

The home built in 1901 has hardwood floors and a second-floor deck. Today, the 1,877-square-foot home with three bedrooms and two-and-a-half bathrooms is split from a one-bedroom, one-bathroom apartment, though it was one combined home when the Sinatras owned it.