When Paramount Pictures chairman and CEO Brad Grey bought Frank Sinatra’s former Los Angeles house in November 2010 for $18,500,000, the famous Hollywood producer had big plans to restore and renovate the brick ranch that sits on a park-like 2.3 acres.

Frank Sinatra. Source: IMDb

It was the kind of project that could only happen in Hollywood: Deep-pocketed movie mogul acts on inspiration to retain a connection with one of the world’s greatest entertainers.

According to The Hollywood Reporter, Grey was 18 years old when he first met the “New York, New York” crooner while Grey promoting a concert in Buffalo, NY. Flash forward about 40 years, over which time Grey kept in touch with Sinatra over using his music during production of “The Sopranos,” and we wind up with a new twist on the old storyline of starry-eyed fan running smack dab into harsh reality.

Turns out that, in the end, the Sinatra house that inspired Grey’s dreams was merely a nice set for Grey’s wedding in April 2011 to his new wife, Cassandra. The wedding was called lavish, and attended by the likes of Tom Cruise, Brad Pitt and Jennifer Lopez. The couple has since moved to Bel Air, making Grey’s ownership stint a lot like Sinatra’s.

Brad Grey and his new wife, Cassandra, won't live in Sinatra-land after all. SOURCE:

“My client still owns (the Sinatra house) but I sold him another property. He didn’t want to go through the process of renovating the house,” said Stephen Shapiro, who holds the listing at Westside Estate Agency.

The property has been back on the market since last September, when Grey listed the Holmby Hills residence for $23.5 million. After a price drop on March 15, the former Sinatra home at 320 N. Carolwood Dr. was re-listed for its current list price of $19,995,000.

“I can never tell when I show it whether someone is interested in tearing it down or renovating,” Shapiro said. “I showed it yesterday to a client who loved the house and is considering remodeling, but the overwhelming value is in the land.”

Maybe it was meant for Grey to mirror Sinatra’s own quixotic habitation of the serene estate that, in the end, proved more of a headache. According to the Sinatra biography “The Voice,” by James Kaplan, Sinatra bought the house in 1948 for $250,000 at a time when his career was at a low ebb. Sinatra had built a dream home in Palm Springs, and was strapped for cash and on the verge of divorce.

It was a fortune in 1948, and he couldn’t afford it. He wasn’t selling records anymore and he had just built this extravagant place in Palm Springs,” Kaplan says. “A lot of it was being closer to MGM and being in this classy neighborhood, closer to Humphrey Bogart and Walt Disney and people like that.”

Kaplan said that in February 1950, Sinatra’s soon-to-be ex-wife Nancy Barbato Sinatra changed the locks at the Carolwood home.“This was the beginning of the very end of their marriage,” he says. They divorced in 1951.

Like Sinatra’s marital hiccups during the time of his Carolwood Drive ownership, Grey had also just gone through a divorce of his wife of 21 years, Jill Grey, the year before he purchased the Sinatra estate, which had been in the hands of the previous undisclosed owner for 50 years. That means the Sinatra house was part and parcel to a stage of marital change for the celebrated producer. Grey’s list of credits for movies and TV productions is studded with some of the most popular shows of this generation.

Fitting, perhaps, that his own real-life episode in Hollywood real estate should contain some interesting drama, too.

As for how the Sinatra angle helps market the 8,600-square-foot home? Listing agent Shapiro said “it’s interesting that Frank Sinatra owned the house but they don’t buy it because Frank Sinatra owned it.”

Unless you are Brad Grey, that is.


Stephen Shapiro of Westside Estate Agency holds the listing. [Westside Estate Agency]
Paramount Exec Brad Grey Buys Sinatra Home  [The Hollywood Reporter]
Brad Grey’s New Wife Cassandra’s Video Goes Viral [Los Angeles Times Blog]
Brad Grey CEO & chairman Paramount Pictures  []


Frank Sinatra bought this brick ranch for $250K in 1948. It's back on the market. Source: Westside Estate Agency

About the Author

Laura Vecsey is a former sports columnist, news reporter and politics writer and has worked for the Seattle Post-Intelligencer, Baltimore Sun, Albany (N.Y.) Times-Union and Harrisburg Patriot-News. She was also a regional editor with She is a graduate of Sarah Lawrence College.

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