The World's Most Expensive Private Islands: A Look at Elite Real Estate Investments

The ultra-wealthy have long been drawn to private islands as the ultimate symbols of exclusivity and power. In recent years, some of the world’s most expensive private island transactions have reshaped the luxury real estate market, with billionaires and celebrities acquiring these coveted properties for staggering sums. These exclusive island purchases reveal not only the astronomical wealth of their owners but also the strategic value these properties hold in the global real estate landscape.

Strategic Wealth Display: How Billionaires Are Reshaping Island Ownership

The acquisition of a most expensive private island has become a hallmark of billionaire status. Unlike typical real estate investments, these island properties represent both personal retreats and significant development opportunities. Oracle co-founder Larry Ellison’s acquisition of approximately 98% of Lanai in Hawaii exemplifies this trend. His reported $500 million investment wasn’t merely about personal enjoyment; Ellison focused on comprehensive infrastructure development to benefit the island’s 3,000+ residents and position Lanai as a premium destination. The island, spanning 141 square miles with nearly 50 miles of coastline, is recognized as the largest privately held island in the United States. Its Four Seasons resorts have transformed it into an accessible luxury destination despite its single owner status.

Collaborative Ventures: When Celebrities Partner on Island Projects

Not all most expensive private island purchases involve solo moguls. The $16 million acquisition of Bonds Cay in the Bahamas demonstrates how prominent figures collaborate on ambitious island development. A partnership between Colombian music sensation Shakira, Pink Floyd legend Roger Waters, and Spanish artist Alejandro Sanz secured this 700-acre property, featuring pristine white-sand beaches, five distinct beach areas, and three salt pond lakes. Located 120 miles off Florida’s coast, the trio envisioned transforming the island into an eco-friendly luxury retreat and creative sanctuary. This approach reflects a growing trend among wealthy individuals to share ownership stakes in premium properties.

Varied Expressions of Luxury: Private Islands Across Continents

The definition of an ideal expensive private island varies dramatically across geographies. Canadian icon Celine Dion purchased Île Gagnon on Quebec’s Rivière des Mille Îles, where she constructed a mansion inspired by French Norman architecture. Accessible exclusively through a private gated bridge, the property embodied European elegance in a North American setting. When Dion eventually sold the island in 2016 for $25.5 million, it exemplified how these elite properties maintain significant market value despite changing ownership preferences.

Greece’s Skorpios Island presents another compelling case study in expensive private island valuation. This 74-acre Mediterranean gem gained historical prominence as the wedding venue of shipping magnate Aristotle Onassis and American icon Jackie Kennedy. Despite considerable interest from global celebrities including Bill Gates, Giorgio Armani, and Madonna, the property was ultimately acquired by Ekaterina Rybolovlev, daughter of Russian billionaire Dmitry Rybolovlev, for a remarkable $150 million—making it one of the most expensive private island purchases on record.

Tech Titans and Island Acquisitions: Larry Page’s Caribbean Investment

Google co-founder Larry Page has demonstrated a particular affinity for private island ownership. In 2018, through an LLC designated U.S. Virgin Island Properties, Page secured Cayo Norte in Puerto Rico for $32 million. As the largest privately-owned island in Puerto Rico, Cayo Norte offers distinctive natural assets including white-sand beaches, vibrant coral reef ecosystems, and wildlife habitats—notably home to endangered sea turtle populations. The acquisition underscores how tech entrepreneurs are diversifying wealth into tangible, geographically-secure assets.

The most expensive private island market continues to attract ultra-high-net-worth individuals seeking both personal sanctuaries and investment vehicles. These transactions, ranging from $16 million to $150 million, demonstrate the premium valuations commanded by exclusive island properties in an increasingly competitive global real estate marketplace.