Leonardo DiCaprio is no stranger to success. From taking home an Academy Award for Best Actor in 2016, to becoming an environmental activist and producer, DiCaprio is a role model for many. But did you know that he is also an incredibly successful real estate investor? He has built a diverse portfolio of properties around the world, including some high-profile purchases and renovations. DiCaprio has been making strategic moves in the real estate market from New York City to Los Angeles for years.

This article will look closely at DiCaprio’s real estate portfolio and some of his most significant purchases and renovations over the years.

Inside Leonardo DiCaprio’s Real Estate Portfolio

1994: Hollywood Hills Compound

DiCaprio’s smart investment strategy began with a savvy real estate purchase of two adjacent properties in the Hollywood Hills, one purchased from Madonna for $2 million and the other in 1994 for $2 million. He transformed the compound into a luxurious entertainment hub and even rented it out to A-list friends like Tobey Maguire. He also showcased his foresight by converting the property’s basketball court into a high-end election night viewing party venue, as reported by Vanity Fair.

1998: Malibu Bungalow

DiCaprio invested in a prime oceanfront property in Malibu after the success of Titanic. The 1950s bungalow boasts three bedrooms, two bathrooms, and 1,765 sq ft of living space. Inside, the kitchen boasts a herringbone backsplash and brass finishes, a marble fireplace in the living room, and blue patterned wallpaper on the stairwell. Outside, a private hot tub on a wooden deck leads directly to the beach. Despite trying to list the property for $10.95 million in 2016, DiCaprio ultimately decided to put it on the rental market for $25,000 a month in 2017.

1999: Silverlake Spanish-Style Hacienda

In 1999, DiCaprio added to his West Coast real estate portfolio with a Spanish-style hacienda in Silver Lake. He paid $769,000 for the four-bedroom, four-and-a-half-bathroom pad with exposed beam ceilings, hardwood floors, and an elevator connecting all three floors. The property also featured a covered loggia and a backyard swimming pool. DiCaprio held onto it for nearly 20 years before finally selling it for $1.56 million in 2018.

2005: An Entire Island near Belize

DiCaprio made a bold move in environmental preservation by buying Blackadore Caye, a 104-acre island off the coast of Belize, for $1.75 million. He’s teamed up with Delos CEO Paul Scialla to create a luxury resort that also restores the island. Architect Jean-Michel Gathy designed the resort to include 36 bungalows and 36 estate homes. DiCaprio’s goal was to open the island to the public in 2018, but it has yet to be realized.

2008 and 2014: Two NYC Eco-Conscious Apartments

In 2008, DiCaprio made a smart move, buying his first East Coast property for $3.67 million in Battery Park’s eco-friendly “The Riverhouse” high-rise. Six years later, he doubled down, snagging a neighboring unit for $8 million. Both still owned by him. The buildings are packed with amenities, including solar panels, a lap pool, a yoga studio, and a 24/7 concierge. Tyra Banks, Oliver Stone, and Cobie Smulders also call it home.

2014: The Dinah Shore Palm Springs Estate 

DiCaprio, like many celebrities, sought a vacation home outside the city and settled on a $5.2 million Palm Springs complex built by architect Donald Wexler for actress Dinah Shore in 1964. Spanning 7,100 sq ft with six bedrooms, 7.5 bathrooms, a guest house, a tennis court, a pool, and a gym, DiCaprio placed it on the rental market in 2016. He also invested in a $2.05 million 1930s ranch in Studio City, LA, which he sold for a profit two years later. In 2014, he bought a $10 million Greenwich Village condo but quickly flipped it for a loss in 2016.

2017: The Malibu Rebuild

In 2017, Leo DiCaprio invested in a $23 million beachfront property in Malibu’s affluent Paradise Cove community. Initially, the 1.76-acre lot featured a small 610 sq. ft. cottage, but the actor likely had plans to upgrade. Reports indicate that the previous owner, billionaire Vinnie Viola, had already received approval to demolish the cottage and construct a new two-story residence with a pool, deck, and private beach access.

2018: Moby’s Los Feliz Pad

DiCaprio’s savvy real estate game continues with a $4.91 million purchase in Los Feliz. The traditional-style mansion, previously owned by musician Moby, sits on a secluded quarter-acre lot with five bedrooms, eight bathrooms, and luxury amenities like a pool and hot tub. Custom renovations by Moby, including millwork and upgraded fireplaces, add to the appeal. A hidden passage connects a lower-level guest suite to a steam room, and a loft space is ripe for yoga or study.

2021: A-list Spanish Colonial in Los Feliz

In 2021, DiCaprio made a smart move by purchasing Jesse Tyler Ferguson’s Spanish Colonial in Los Feliz for $7.1 million. The property, previously owned by Gwen Stefani and Robert Pattinson, boasts a unique 1928 build with four bedrooms and almost 5,000 square feet of living space. The design and furnishings, created by Will & Grace set designer Peter Gurski, showcase an eclectic aesthetic with dark teal walls, a wrought-iron birdcage chandelier, and tweed wallpaper in the main suite.

2021: Beverly Hills Estate

The Oscar-winning actor invested in a 1930s Beverly Hills estate, snagging it for $300,000 less than the asking price. He’s now renting out the fully renovated property with white oak floors, a spiral staircase, and a chef’s kitchen outfitted with top-of-the-line appliances. The space boasts black Marquina granite and white Carrara marble and includes a breakfast nook with French doors leading to an al fresco dining terrace.

2022: Bird Streets Nest Neighboring Property

Leo DiCaprio expands his empire by strategically acquiring neighboring property in LA’s elite Bird Street community. The $10.5 million off-market purchase adds a 4-bedroom midcentury modern home to his existing 5-acre compound, featuring four houses and four pools, totaling 15,000 sq ft of living space.

Conclusion

In conclusion, DiCaprio’s portfolio is a testament to his real estate savviness. He has strategically acquired properties in some of the most exclusive neighborhoods for personal use and as smart investments. His latest acquisition in the Bird Street community adds yet another valuable asset to his growing portfolio. It’s clear that DiCaprio knows how to spot a good deal and make smart investments. His portfolio serves as inspiration for those looking to make smart real estate decisions and diversify their investments.