It’s hard to believe it’s been nearly three decades since Matt Damon completely disrupted Hollywood. He famously exploded onto the scene back in 1997 with Good Will Hunting, the movie he co-wrote alongside childhood friend Ben Affleck. That film didn’t just win the duo an Oscar—it instantly launched Damon into the industry’s upper echelon. Since then, he’s anchored massive franchises like Bourne and Ocean’s, while delivering standout performances in everything from The Departed to Oppenheimer. Now, Damon is gearing up for one of the absolute biggest projects of his career. He’s reunited with director Christopher Nolan to star in The Odyssey, a massive US$250 million mythic action epic featuring Tom Holland and Zendaya.
Off-screen, Damon is just as busy. He’s entrenched in the business side of showbiz through Artists Equity, the production company he and Affleck launched in 2022. When he’s not on a movie set or running a studio, he’s focusing on his philanthropic work as the cofounder of Water.org, a nonprofit dedicated to expanding access to safe drinking water worldwide. Through it all, he keeps his personal life relatively low-key, splitting his time with his wife, Luciana Barroso, and their four daughters.
With a massive career comes an equally impressive net worth—estimated around US$55 million—and Damon has reportedly invested in some seriously high-flying assets, including a Bombardier Global 7500 private jet. But his eye for luxury is perhaps most obvious in his real estate. Over the years, he’s assembled a collection of trophy properties spanning from Los Angeles to New York. Here, we’re taking a look inside the property portfolio of one of Hollywood’s most enduring leading men.
In the early 2000s, Damon combined two neighbouring North Bay Road parcels to create a sprawling waterfront compound in Miami Beach’s ultra-exclusive La Gorce area. Purchased separately in 2005 for a combined US$14.5 million, the Mediterranean-style estate ultimately grew into a roughly 12,700-square-foot property with a main residence, guesthouse, pool house, wine cellar, summer kitchen, and 170 feet of Biscayne Bay frontage. Damon eventually sold the compound in 2014 for around US$15 million after initially listing it for nearly US$19 million.
For nearly a decade, Damon and his wife owned a sprawling Pacific Palisades estate that served as their primary West Coast base. The actor purchased the home in 2012 for US$15 million before selling it in 2021 for US$18 million after a brief stint on the market. Spanning more than 13,500 square feet, the seven-bedroom residence showcased soaring mahogany ceilings, walls of glass, natural stone finishes, and a central atrium that filled the home with light. Resort-style amenities included a koi pond, waterfall pool, spa, wine-tasting room, gym, and expansive indoor-outdoor entertaining spaces. The buyers were former Warner Bros. CEO Ann Sarnoff and private equity executive Richard Sarnoff.
Damon made headlines in 2018 when he shelled out US$16.7 million for a triplex penthouse in Brooklyn Heights, setting a record at the time for the borough’s most expensive residential sale. The sprawling 6,200-square-foot residence includes six bedrooms and a massive private rooftop terrace with sweeping views of Manhattan and New York Harbor. Fellow actors Emily Blunt and John Krasinski also bought a full-floor apartment in the building for US$11 million in 2019.
In 2022, Damon picked up a sprawling 13-acre property in Bedford, a leafy enclave in Westchester County, for US$8.5 million. The estate centres around a 7,190-square-foot home built in 2004 with four bedrooms and five-and-a-half bathrooms, alongside a long list of amenities including a saltwater pool, tennis court, greenhouse, antique barn, treehouse, and spring-fed pond. Records show the residence previously traded for US$6.25 million in 2011. Damon reportedly acquired the property through an LLC tied to Pearl Street Films, the production company he cofounded with Affleck.
Damon expanded his California real estate holdings in 2024, with the purchase of a US$8.5 million condo in West Hollywood. Designed by acclaimed architecture firm Olson Kundig, the sleek fourth-floor pied-à-terre spans roughly 2,900 square feet with two bedrooms, two-and-a-half bathrooms, walls of glass, and sweeping views of the Hollywood Hills. One of the residence’s standout features is its enormous 1,600-square-foot private terrace, among the largest outdoor spaces in the building. The high-design condo also includes custom finishes and a chef’s kitchen outfitted with Sub-Zero, Miele, and Gaggenau appliances.
This article was originally published on Robb Report USA.
Cover photo: Weiss Eubanks/NBCUniversal via Getty Images