Meet the Billionaire Buying Up Trophy Homes Across the U.S. (Including the Playboy Mansion)—to the Tune of $326 Million

Daren Metropoulos might not be a name you’ve heard before—but there’s no doubt you will be familiar with some of the billionaire businessman’s incredible real estate holdings.

In the past 18 years, the 41-year-old son of a private-equity billionaire has spent around $326 million buying up iconic, and arguably priceless, properties. They include Hugh Hefner‘s Playboy Mansion in L.A., a “hurricane-proof” bunker mansion in Miami Beach, FL, and a $148 million “architectural gem” in Palm Beach, FL.

But these are just a handful of conquests in Metropoulos’ ongoing hunt for trophy homes. He’s amassed quite a spectacular real estate portfolio through family connections and his own interest in the market.

The entrepreneur boasts a treasure chest of incomparable homes he plans to both “preserve” and “reimagine,” he told the Wall Street Journal.

So how does Metropoulos go about finding these rare real estate investments?

“My general approach is very measured and tactical and I am particularly interested in hidden jewel properties that rarely come to market,” he told the Journal. “In any business dealing, it’s paramount to remove one’s emotions. You have to stay disciplined with your terms and expectations.”

As for how he funds this extravagant hobby, Metropoulos concedes that he had the benefit of a privileged upbringing, courtesy of his father, private-equity investor C. Dean Metropoulos.

The elder Metropoulos is credited with reviving brands such as Hostess, Bumble Bee Tuna, and Ghirardelli Chocolate, while also building his own real estate empire. The businessman passed down his prowess to his youngest son, who began working for the family business when he was 15, learning how, when, and where to purchase the perfect investment property.

Here’s a look at the impressive real estate portfolio the younger Metropoulos has spent the past 18 years building.

$148 million Palm Beach, FL, estate

The Mediterranean Revival-style home is considered one of the area’s “architectural treasures,” according to the Journal. It was built in 1919 and completely renovated.

“I’m an old soul at heart,” Metropoulos said about the property.

Cow Bay Road, Martha’s Vineyard, MA

In 2007, Metropoulos and his brother, Evan, paid $20 million for a 13.5-acre property they plan on making a family compound. The brothers are 50-50 owners of the beachfront property that will feature two new homes at 6,500 square feet each. There will also be a gym, pool, and tennis court.

Residences at Mandarin Oriental, New York City

Metropoulos purchased two condominiums on the 69th floor at the Residences at Mandarin Oriental in Columbus Circle. One unit is 2,300 square feet and was bought for $6.9 million in 2006. He later bought a 1,900-square-foot condo there for $10.4 million.

Playboy Mansion and mini Playboy Mansion

Before buying the actual Playboy Mansion, Metropoulos purchased a “miniature version” of the house, located next door, for $18 million.

He bought the 10,600-square-foot house on South Mapleton Drive from Hefner. He upgraded the pool, basement, and kitchen, but left some of the original charm to the house. The house is worth around $60 million today.

As for the Playboy Mansion in Los Angeles, Metropoulos bought the 20,000-square-foot property for $100 million in 2016 and joined the two properties to make one estate.

Altos del Mar, Miami Beach, FL

Metropoulos bought this “hurricane-proof” home in 2021 for $18 million. The 6,000-square-foot oceanfront property is in the gated Altos del Mar community.

The house stands out with its full-house generator and floor-to-ceiling windows that can withstand winds of up to 257 mph.

Kauai, HI

Metropoulos dropped a cool $11.4 million in 2016 for a home on 7.3 acres on the north shore of Kauai. Designed by Hawaii architect Gary Tobey, it features custom guest pods, a main house that overlooks the ocean, and a 100-foot Olympic-size pool. He is adding a spa and has plans to restore the zoo for rescue animals.

Today, the property is worth about $18 million.

Indian Creek, Miami Beach, FL

More Miami Beach for Metropoulos. In 2022, he purchased a $1.8 million condo at the Monaco Yacht Club & Residences in North Beach. The building has its own private marina.

Casa Amado, Palm Beach, FL

He didn’t forget about Palm Beach. In June, Metropoulos purchased the oceanfront Casa Amado. The estate features 10 bedrooms, a gym, and a home theater. It also has its own beach cabanas and pool cabanas.

When he purchased the property Metropoulos called it a “true sanctuary.”

Aren’t they all?