A look into Leonardo DiCaprio's swish real estate portfolio

Award-winning actor, Leonardo DiCaprio, has had a long love affair with beautiful homes.

Since shooting to fame with his incredible performance in What’s Eating Gilbert Grape?, the climate-change activist has bought and sold a dozen or so properties – including a private island in Belize.

DiCaprio stands out from other celebrity homeowners (ahem, Ellen DeGeneres) because he doesn’t offload his buys swiftly or flip the homes. In fact, “[he] has retained most of his purchases, turning his less frequented homes into rental properties,” says Architectural Digest.

Keen to know what properties this notoriously private thespian has in his orbit? Here’s a round up of all the luxury digs DiCaprio has bought and sold since he rose to fame – including his latest purchase in Beverly Hills.

1994: Hollywood Hills compound – $6 million (US$4m)

Back in the ’90s, DiCaprio bought two side-by-side properties – one of which was sold to him by icon Madonna for US$2 million – and the other for the same price in 1994. Offering jetliner views of the entire LA city skyline, this remains DiCaprio’s main home to this day.

Perched high in the Hollywood Hills, the property has since been fully renovated by the star, who added a basketball court at one point. He’s also rented out the pad to various actor friends, including Tobey Maguire.

1998: Malibu bungalow – $15 million (US$10.3m)

Fresh off of his mammoth success in 1997’s Titanic, the young actor bought a 1950s two-storey bungalow in Malibu with incredible ocean views for US$1.775m.

DiCaprio tried to sell the three-bedroom, two-bathroom home in 2016 for nearly US$11 million, but the price was trimmed down significantly to the US$2 millions. The actor waited, and after 23 years of ownership, sold it in late 2021 for US$10.3 million.

1999: Silverlake Spanish-style hacienda – $2.4 million (US$1.56m)

Rounding out the ’90s, Leo bought a lovely three-storey Spanish-style home with loggia and pool in the hills of LA’s trendy Silverlake area for US$769,500 back in 1999.

The superstar held onto the four-bedroom, four-and-a-half-bathroom pad for nearly 20 years, selling it for $1.56 million in late 2018. It had been elegantly updated and featured exposed wooden beams, arches and a full chef’s kitchen.

2005: An entire Island near Belize – $2.5 million (US$1.75m)

Yep, nature-lover Leo bought an actual island behind the world’s second-largest barrier reef off the coast of Belize. Known as Blackadore Caye, DiCaprio plans to build an island resort that “show[s] how people can live in complete harmony with the natural word.”

Partnering with Paul Scialla of New York–based developer Delos, his vision is to create a “restorative island,” where the luxury eco-resort and its efforts helps to heal the endangered island itself. The aspirational project has been delayed and is not yet built.

2008 and 2014: Two NYC eco-conscious apartments – $2.6 and $11.5 million (US$3.67m and $8m)

In 2008, DiCaprio purchased his first East Coast property, a US$3.67 million apartment in Battery Park high rise ‘The Riverhouse’. Then in 2014, he bought the unit next door for US$8 million – and still owns both.

The eco-friendly building is brimming with amenities, including filtered water, double-filtered air, a 50-foot lap pool, solar panels, 24/7 concierge service, yoga studio, and its own water treatment facility. The high-rise has been home to celebs such as as Tyra Banks, Oliver Stone, and Cobie Smulders.

2014: The Dinah Shore Palm Springs estate – $7.5 million (US$5.2m)

Designed by architect Donald Wexler in 1964 for big-band singer Dinah Shore, the midcentury modern gem is built on a 1.3-acre desert oasis compound. DiCaprio bought the property for US$5.32 million back in 2014 and occasionally uses it as his own vacation home.

Leo put the six-bedroom and 7.5-bathroom home complete with guest house, tennis court, pool, and detached gym on the rental market in 2016.

In 2014, Leo also bought a US$2.05 million 1930s ranch in LA’s Studio City hood, which is sold just two years later for US$2.237 million. The actor also bought in NYC again, this time a US$10 million condo in Greenwich Village, which had bananas wellness inclusions like a custom-designed light therapy system, circadian rhythm lighting, a built-in juicing station, and in-duct aromatherapy. Less than two years later, he sold it at a US$2 million loss.

2017: The Malibu rebuild – $33 million (US$23m)

In the exclusive enclave of Paradise Cove, DiCaprio shelled out an eye-watering US$23 million on a tiny 610-square-foot shack. However, said shack happened to be perched within 1.76 acres of rare Malibu beachfront and the previous billionaire owner already received development approval to build a two-storey home.

The plans reportedly included a swimming pool, a cliffside deck, and a private beach. His neighbours include Courtney Cox.

2018: Moby’s Los Feliz pad – $7 million (US$4.91m)

In 2018, DiCaprio bought a gorgeous renovated English Traditional home in LA’s trendy Los Feliz neighbourhood from DJ, singer/songwriter and Musician, Moby, who renovated the property.

Set on a corner lot, the totally re-imagined 1926 sanctuary features five beds and eight baths. There are statement ceilings, custom millwork, a chef’s kitchen, pools and even a secret “speakeasy style” entrance that connects an office and guest suite to a bathroom and steam room.

However DiCaprio didn’t buy the home for himself – it was purchased for a family member (understood to be his father), and according to Trulia, Moby owns the home next door. He’s since listed it for sale in 2021 for US$5.75 million.

2021: A-list Spanish colonial in Los Feliz – (US$7.1m)

This time, mum get’s a Los Feliz home.

In 2021, DiCaprio reportedly snapped up a gorgeous Spanish colonial property from Modern Family star Jesse Tyler Ferguson for his mother, Irmelin Indenbirken. Other previous celebrity owners include Gwen Stefani and Robert Pattinson.

Built in 1928, the charming half-acre hillside property features four bedrooms and was given a total design transformation by Ferguson and former Will & Grace set designer Peter Gurski.

Think dark teal-coloured walls in the double-storey study, a massive wrought-iron birdcage in place of a chandelier in the front foyer, and tweed Philip Jeffries wallpaper in the main suite, according Architectural Digest.

2021: Beverly Hills estate – $14 million (US$9.9)

Before the year was out and after offloading his longtime Malibu home, the Oscar-winning actor nabbed a posh 1930s estate in Beverly Hills for US$9.9 million.

Recently renovated, the five-bed, 5.5-bath property features white oak floors, a spiral staircase and of course, and chef’s kitchen accented by black granite and white Carrara marble. Outside, there’s a stylish pool, landscaping that includes olive trees, outdoor seating with a fire pit and separate guest house.