Global Real Estate Elite: The World's Most Expensive Private Islands and Their Ultra-Wealthy Owners

What do billionaire tech founders, music superstars, and business magnates have in common? They’re not just collecting wealth—they’re collecting entire islands. The luxury real estate market has reached stratospheric levels, with ultra-high-net-worth individuals spending hundreds of millions on exclusive private islands. These acquisitions represent far more than vacation retreats; they’re strategic asset allocations that combine lifestyle prestige with tangible investment potential. Here’s a closer look at the most expensive island properties in the world that have changed hands in recent years, and the visionary billionaires behind these extraordinary purchases.

Skorpios Island, Greece: $150 Million — When Prestige Meets Geopolitical Status

The crown jewel of recent ultra-luxury island acquisitions is Skorpios Island in Greece, purchased for a staggering $150 million. The 74-acre Mediterranean paradise was snapped up by Ekaterina Rybolovlev, daughter of Russian billionaire Dmitry Rybolovlev, who outbid some of the world’s most recognizable names. When Bill Gates, Giorgio Armani, and Madonna set their sights on this property—a historically significant location where shipping magnate Aristotle Onassis once married Jackie Kennedy—they eventually stepped aside. The acquisition, which also included the neighboring islet Sparti, represents a masterclass in ultra-luxury real estate positioning, combining historical pedigree with Mediterranean lifestyle appeal.

Lanai, Hawaii: $500 Million — Oracle’s Tech Billionaire Reshapes an Entire Community

Larry Ellison, co-founder of Oracle, didn’t simply purchase 98% of Lanai as a personal playground—this $500 million investment demonstrates a different investment philosophy. Ellison’s acquisition of this 141-square-mile Hawaiian island reflects a commitment to infrastructure development and community enhancement for its 3,000+ residents. The island, believed to be the largest privately-held island in the United States with nearly 50 miles of pristine coastline, now hosts luxury Four Seasons resorts that generate revenue streams while maintaining the island’s ecological balance. This model demonstrates how the world’s most expensive islands can serve dual purposes: personal sanctuary and operational asset.

Cayo Norte, Puerto Rico: $32 Million — Google Founder’s Caribbean Conquest

Larry Page, Google’s co-founder, shares a particular affinity for private island ownership. In 2018, through an LLC named U.S. Virgin Island Properties, Page acquired Cayo Norte for $32 million—the largest privately-owned island in Puerto Rico. This tropical acquisition boasts glittering white-sand beaches, thriving coral reef ecosystems, and wildlife habitats for endangered sea turtles. The strategic Puerto Rico location provides both tax advantages and geographical proximity to North American markets, exemplifying how contemporary billionaires blend lifestyle aspirations with financial optimization.

Île Gagnon, Quebec: $25.5 Million — European Architecture Meets North American Exclusivity

Celine Dion’s private island residence on the Rivière des Mille Îles in Quebec showcases how luxury island investments extend beyond tropical paradises. Built as a French Norman château-style mansion, accessible via a private gated bridge, the property embodied fairy-tale residential prestige. Though Dion sold this $25.5 million estate in 2016, the transaction illustrates how non-tropical islands attract premium valuations based on architectural sophistication and historical aesthetics. Dion’s decision to divest reveals that even ultra-luxury island properties remain subject to changing personal priorities and market dynamics.

Bonds Cay, Bahamas: $16 Million — Celebrity Collaboration Meets Eco-Tourism Investment

Shakira partnered with Pink Floyd’s Roger Waters and Spanish singer Alejandro Sanz to collectively acquire Bonds Cay in the Bahamas for $16 million—one of the most expensive island purchases driven by creative collaboration. Located 120 miles off Florida’s eastern coast, this 700-acre property boasts immaculate white-sand beaches, five distinct beach areas, and three natural salt pond lakes. The ownership trio’s strategic vision focused on transforming the island into an eco-friendly luxury destination and artists’ retreat, combining environmental stewardship with cultural asset development.

The Investment Thesis Behind Ultra-Luxury Island Acquisitions

The pattern emerging from these transactions reveals that the world’s most expensive islands serve multiple functions simultaneously: personal wealth expression, operational commercial assets, tax-optimization vehicles, and long-term equity stores. Billionaires and ultra-high-net-worth individuals view premium private island ownership not merely as consumption, but as sophisticated portfolio diversification. Whether serving as luxury hospitality operations, environmental preserves, or architectural showcases, these acquisitions represent the ultimate convergence of lifestyle luxury and financial engineering at the highest echelons of global wealth.