Billionaires and Icons: The World's Most Expensive Island Properties Unveiled

When the world’s wealthiest individuals and most celebrated figures seek refuge from the ordinary, they don’t settle for ordinary real estate. Instead, they invest in some of the planet’s most exclusive and most expensive island properties. From Caribbean havens to Mediterranean hideaways, these ultra-luxury acquisitions tell a fascinating story about how global elites choose to spend their vast fortunes—and reimagine entire communities in the process.

The Art of Island Investment

Over the past decade, some of Earth’s most desirable private islands have changed hands for staggering sums, reshaping both landscapes and local economies. These weren’t impulse purchases or simple vacation homes; they represent strategic real estate plays by billionaires and celebrities who view island ownership as the ultimate status symbol and long-term investment. The prices tell the story: ranging from $16 million to $150 million, these acquisitions have made waves in the luxury real estate world and demonstrated that for the ultra-wealthy, geography truly is destiny.

Hawaii’s Largest Private Island: Lanai’s Transformation

When Oracle co-founder Larry Ellison purchased nearly 98% of Lanai—a sprawling 141-square-mile Hawaiian island—the reported price tag hovered around $500 million. Unlike typical billionaire island purchases driven purely by ego, Ellison’s vision extended beyond personal luxury. He committed to developing the island’s infrastructure and enhancing quality of life for its 3,000+ residents, transforming Lanai into a model of sustainable island development. Today, the island boasts nearly 50 miles of pristine coastline and serves as home to elegant Four Seasons resorts, making it accessible to travelers who want to experience the island’s stunning beaches and lush landscapes without needing Ellison’s contact information.

Bahamas’ Artistic Collaboration: Bonds Cay

Not to be outdone, global music sensation Shakira teamed up with unlikely collaborators—including Pink Floyd’s Roger Waters and Spanish artist Alejandro Sanz—to acquire Bonds Cay in the Bahamas. Their combined investment of $16 million secured a 700-acre paradise featuring five pristine beaches, immaculate white sands, and three salt-fed lakes. Located 120 miles off Florida’s coast, the trio’s ambition centered on transforming their acquisition into an eco-conscious luxury retreat and creative sanctuary where artists could find inspiration. This collaboration between music industry titans demonstrates how modern island ownership often reflects shared vision rather than individual whim.

Quebec’s Enchanted Estate: Île Gagnon’s Legacy

Canadian songstress Celine Dion’s contribution to the world’s most expensive island club came through her Quebec property on the Rivière des Mille Îles. She constructed an elaborate mansion styled after a French Norman chateau, accessible via a private gated bridge that enhanced the property’s fairy-tale mystique. However, Dion eventually decided island life wasn’t her permanent calling. She divested the property in 2016, selling it for $25.5 million—a transaction that underscored how even elite island investments can lose their allure over time.

Greece’s Most Coveted Prize: Skorpios Island’s Record-Breaking Sale

Few properties have attracted as much elite attention as Skorpios Island—the 74-acre Greek sanctuary famous for its natural splendor and historical significance as the wedding venue where shipping magnate Aristotle Onassis married Jackie Kennedy. The island had long been coveted by A-listers including Bill Gates, Giorgio Armani, and Madonna, each presumably imagining themselves as custodians of this Aegean treasure. Yet when the opportunity arose, it was Ekaterina Rybolovlev, daughter of Russian billionaire Dmitry Rybolovlev, who secured both Skorpios and its neighboring islet Sparti for a breathtaking $150 million. This transaction set a new benchmark for most expensive island acquisitions and signaled that ultra-prime Mediterranean real estate commanded stratospheric valuations.

Puerto Rico’s Largest Private Holding: Cayo Norte

Google co-founder Larry Page evidently shared Ellison’s appreciation for private islands, demonstrating that Silicon Valley titans frequently allocate capital toward exclusive island properties. In 2018, Page orchestrated the purchase of Cayo Norte—Puerto Rico’s largest privately-held island—through an LLC called U.S. Virgin Island Properties, paying $32 million for the privilege. The island showcases everything tropical paradise promises: glittering white-sand beaches, vibrant coral reefs, and diverse wildlife including endangered sea turtles. For Page, the acquisition represented not just a retreat from technology’s demands, but tangible ownership of one of the Caribbean’s most exceptional landscapes.

The Billionaire Island Phenomenon

These five acquisitions collectively represent over $750 million in ultra-luxury real estate spending and reflect a broader trend among global elites: the most expensive island properties serve as repositories of wealth, status, and personal vision. Whether transformed into community assets like Lanai, artistic sanctuaries like Bonds Cay, or preserved as private retreats, these islands demonstrate that for those with sufficient capital, paradise isn’t merely a destination—it’s an asset class. As climate concerns and changing lifestyles reshape luxury preferences, these most expensive island purchases will likely remain among the most significant real estate transactions of the era, each telling a unique story about ambition, wealth, and the endless human desire to own a piece of paradise.