The World's Most Expensive Island Acquisitions: Inside the Billionaire's Real Estate Game

When ultra-wealthy individuals aren’t just buying property—they’re buying entire islands. Over the past decade, some of the globe’s most prestigious private islands have changed hands, revealing fascinating insights into how the world’s elite spend their fortunes. From tech moguls to entertainment superstars, these purchases tell a story of exclusive luxury and ambitious development visions.

Google Co-Founder’s Caribbean Crown Jewel

Larry Page didn’t hesitate when Cayo Norte came on the market. In 2018, the Google co-founder’s investment vehicle, U.S. Virgin Island Properties, secured Puerto Rico’s largest privately-owned island for $32 million. This tropical haven features pristine white-sand beaches, thriving coral ecosystems, and serves as a sanctuary for endangered sea turtles. For those dreaming of the ultimate island vacation escape, Cayo Norte represents the pinnacle of Caribbean exclusivity—though the price tag certainly matches the prestige.

Russian Heiress Claims Greek Treasure

Not even global superstars like Bill Gates, Giorgio Armani, and Madonna could outbid Ekaterina Rybolovlev for Skorpios Island. The Russian billionaire’s daughter made waves with a staggering $150 million purchase of this 74-acre Greek jewel in 2018. Skorpios carries legendary status: it’s where shipping magnate Aristotle Onassis married Jackie Kennedy. Paired with its neighboring islet Sparti, this property became one of the decade’s most jaw-dropping real estate moves.

The Canadian Château Dream

Singer Celine Dion understood the allure of owning an island oasis. Her private retreat on the Rivière des Mille Îles in Québec featured a mansion designed in French Norman chateau style, accessed exclusively via a private gated bridge—pure fairy-tale living. However, Dion eventually parted with this enchanting property in 2016, selling it for $25.5 million. The sale reminded the world that even dream island vacations sometimes lose their magic.

Bahamas Collective Vision

Music transcended boundaries when Shakira partnered with Pink Floyd’s Roger Waters and Spanish artist Alejandro Sanz to acquire Bonds Cay in the Bahamas. Their $16 million investment covers 700 acres of pristine beauty: immaculate white sands, five distinct beaches, and three salt pond lakes. Positioned 120 miles off Florida’s coast, this trio envisioned transforming their island into an eco-conscious luxury retreat and creative artists’ sanctuary—blending commerce with artistic inspiration.

Oracle’s Hawaiian Development

Larry Ellison’s approach to island ownership differs dramatically from most billionaires. Rather than building a personal playground, the Oracle co-founder acquired 98% of Lanai, a 141-square-mile Hawaiian island, for approximately $500 million. His strategy prioritized community development—supporting infrastructure improvements for the island’s 3,000+ residents. Lanai holds the distinction of being America’s largest privately-held island, boasting nearly 50 miles of pristine coastline. The silver lining for non-billionaires? Four Seasons resorts offer access to those stunning beaches and lush landscapes, making an island vacation experience possible without unlimited wealth.

These transactions underscore a compelling reality: the most expensive island acquisitions reflect personal ambitions spanning from pure luxury retreats to transformative community projects. Whether purchased for vacation havens or long-term investments, these properties represent some of the world’s most exclusive real estate achievements.