Inside Leonardo DiCaprio’s $72 Million Property Portfolio

DiCaprio’s crown jewel is his Hollywood Hills compound, a continually expanding fortress that’s been nearly 30 years in the making. It started back in the ’90s when he paid about $4 million for two neighboring homes in the Bird Streets area above the Sunset Strip, one of them from the “Queen of Pop,” Madonna. 

He decked out the roughly 4,600-square-foot main house with a basketball court, a wine cellar, an infinity pool, and even an underground garage. Over the years, the estate has become more than just a home—it’s a full-blown playground for A-list gatherings, complete with a screening room, spa, and solar panel upgrades. Meanwhile, his Great Gatsby co-star Tobey Maguire once rented the 4,000-square-foot house next door.

In 2006, he quietly ponied up $4.35 million for a 3.44-acre sloping parcel below his main residence, extensively landscaping it with pathways, gardens, and a few small, mysterious structures. And in 2018, he added an adjacent property with a 3,100-square-foot abode for $4.85 million, and, in 2022, he expanded once again with a $10.5 million pad built in 1963. Altogether, his Bird Streets spread now spans about five acres over five parcels—a mega-compound of pools, privacy hedges, and celebrity lore.

The veteran actor’s real estate holdings are not limited to the West Coast. In 2008, he shelled out $3.67 million for an apartment at Riverhouse in Manhattan’s Battery Park City, one of the city’s most eco-forward buildings. Designed by architect David Rockwell, the complex features filtered air, solar panels, and its own water treatment system—plus a yoga studio, billiards room, lap pool, playroom, and even a dog spa. Clearly satisfied, DiCaprio expanded his footprint at Riverhouse in 2014 by dropping another $8 million on a neighboring unit, bringing his Lower Manhattan holdings to nearly 5,000 square feet plus another 1,000 square feet of outdoor space with Hudson River views.

IIn 2014, DiCaprio jumped on the midcentury modern bandwagon, buying a storied estate in Palm Springs for $5.23 million. Built in 1964 by starchitect Donald Wexler for singer-actress Dinah Shore, the 7,000-square-foot home is a low-slung masterclass in desert modernism. It features six bedrooms, eight bathrooms, a guest house, a pool, a tennis court, and a detached gym, all set on 1.3 acres framed by the San Jacinto Mountains.

DiCaprio is famously private, but he hasn’t exactly kept his Palm Springs getaway entirely to himself. Since 2016, the property has been available as a vacation rental—at roughly $3,750 a night. With its wood-paneled ceilings, floor-to-ceiling glass walls, and striking stone finishes, the estate embodies Palm Springs cool while doubling as an income-generating investment.

DiCaprio also has a flair for historic architecture. In May 2021, he snapped up Modern Family actor Jesse Tyler Ferguson’s Spanish Colonial in Los Feliz for $7.1 million. Built in 1928, the nearly 5,000-square-foot home has hosted its share of celebrity owners—including Gwen Stefani—and was given a bold design overhaul by Ferguson and his husband, producer Justin Mikita, with help from set designer Peter Gurski.

The result is a mix of vintage glamour and modern cool: dark teal walls in the double-height study, a birdcage chandelier in the foyer, tweed wallpaper in the main suite, and a terra-cotta staircase. Outside, arched doorways open to a courtyard strung with fairy lights, a teal-tiled pool, and Juliet balconies.

Few A-listers can resist the singular allure of Malibu, and DiCaprio is no exception. In July 2021, he shelled out $13.75 million in an off-market deal for a 3,300-square-foot beachfront property in a tiny, gated enclave of just four other homes. Originally built in 2005, the modern four-bedroom, five-bath residence offers multiple decks and private steps that lead directly to the sand.

Now, four years later, DiCaprio has the airy and light-filled multilevel home back up for sale at $23 million. Perched on a low bluff, the home has rare access to El Sol Beach, one of Malibu’s most private stretches of sand.

In December 2021, DiCaprio branched out into Beverly Hills, paying $9.9 million for a five-bedroom, six-bath traditional tucked behind gates on a street canopied by purple-flowered Jacaranda trees. Built in 1936, the 5,000-square-foot home exudes old Hollywood charm—cathedral ceilings, a wrought-iron spiral staircase, and a balcony overlooking the backyard pool—but it’s been tastefully modernized with marble finishes, a sleek gourmet kitchen, and contemporary lighting.

Manicured hedges provide privacy, a detached guesthouse has a grill station of its own, and multiple spaces for outdoor entertaining include a fire pit lounge and a terrace for alfresco dining. Despite his reputation as a ladies’ man, DiCaprio’s 90210 property feels more like a family estate than a bachelor pad. It is unclear whether he uses the house himself or bought it for family members, but it is his only property in the world-famous ZIP code.