Madonna’s Old Hollywood Home, a Former Mafia Gambling Den, for Sale

Posted on: February 17, 2023, 06:24h. 

Last updated on: February 17, 2023, 12:04h.

Erik Gibbs Read More
Expertise: Asia Pacific Gaming, Gaming Business, Global Gaming.

A home that once belonged to Madonna and reportedly was a gambling parlor for mobster Benjamin “Bugsy” Siegel just hit the market. It’s available for around $21 million.

Castillo del Lago sits secluded below the Hollywood sign
Castillo del Lago sits secluded below the Hollywood sign. The former home of Madonna, once a home belonging to mobster Bugsy Siegel, is for sale. (Image: Carolwood Estates)

The house was purchased by Madonna for $5 million in 1993, according to a diary kept by her brother, interior designer Christopher Ciccone. About three years later, she sold it. It has changed hands several times since then.

A listing on the website of real estate agency Carolwood Estates indicates Castillo del Lago sits below the famed Hollywood sign. The posting was on the website as of February 16 but is no longer available.

The 1920s-era estate in the Hollywood Hills was also the location for several scenes from 1984’s Beverly Hills Cop.

A Piece Of History

“Houses of Los Angeles,” a 2007 book about real estate in the area, explains that the home was built by the architect John DeLario in the 1920s. The Spanish-style house was one of the first in what would become Hollywoodland.

In his book about his sister, Ciccone explains how the pop star spent about $3 million renovating and decorating the building. On one trip to London, with Madonna’s approval, he spent a “fortune” buying furniture before shipping it back to Hollywood. In addition, a painting that once hung in the Palace of Versailles made it to Madonna’s living room.

In 2010, Madonna sold the house to business manager Joe Pytka, who then sold it back to fashion designer Leon Max of Max Studio for just $7 million. Max then began a project to restore much of the original atmosphere that had made Castillo del Lago attractive in the first place.

The Carolwood Estates listing indicated that the home is approximately 10,500 square feet and contains nine bedrooms. It offers views of downtown Los Angeles and Lake Hollywood from its two floors, and includes a spiral staircase and an elevator at the entrance.

A lounge is located on the second floor of the main building on the second floor. In addition to its central courtyard and outdoor fireplace, the two-story room boasts beautiful trees, a media room, a bar, several terraces, and an outdoor lap pool.

Mob Era

Siegel reportedly lived in the house after buying it in the late 1930s. He was a notorious gangster who’s still famous today for his background in the mafia and in Las Vegas.

At one point, Siegel ran a legitimate gambling operation at California’s Santa Anita Park. He got into sports betting in California, managing part of a business that was making as much as $500K a day. At the same time, he used Castillo del Lago as an illegal casino, according to historians.

He reportedly rubbed elbows with Gary Cooper, Cary Grant, and Frank Sinatra, who may have visited the property.

In the 1940s, Siegel spent much of his time at the Flamingo Hotel and Casino in Vegas. He regularly traveled between Sin City and Beverly Hills, where he still maintained a residence with gangster girlfriend, Virginia Hill.

On June 20, 1947, while relaxing at home in Beverly Hills, an unknown assailant shot and killed Siegel in a sniper attack. To this day, no one knows who it was or who may have ordered the assassination.