Exploring the World's Most Expensive Private Islands and Their Elite Owners

The global ultra-wealthy market for private island properties has produced some of the most remarkable real estate transactions in recent decades. From tech billionaires to entertainment icons, the acquisition of exclusive island retreats reflects both investment strategy and lifestyle aspiration among the world’s richest individuals. These premium properties, commanding prices that rival entire cities, showcase the defining characteristics of modern luxury real estate.

Lanai and Oracle: Hawaii’s Largest Private Holding

Larry Ellison, Oracle’s co-founder, acquired approximately 98% of Lanai, a 141-square-mile Hawaiian island, in what remains one of the most significant private land acquisitions. The reported transaction value reached around $500 million, establishing Lanai as the largest privately-held island in the United States with nearly 50 miles of pristine coastline.

Ellison’s vision extended beyond personal use; his development strategy focused on enhancing the island’s infrastructure and improving living conditions for its 3,000+ residents. The island now hosts multiple Four Seasons resort properties, transforming it into an accessible luxury destination while maintaining its status as an exclusive private estate.

Caribbean Island Ventures: Bahamas and Puerto Rico Properties

Bonds Cay in the Bahamas emerged as a collaborative acquisition when Shakira, alongside musician Roger Waters from Pink Floyd and Spanish artist Alejandro Sanz, secured this 700-acre tropical property for approximately $16 million. The island features five distinct beaches, immaculate white sandy shores, and three salt pond lakes positioned 120 miles from Florida’s eastern coast.

The trio’s strategic vision targets transforming the property into an ecologically-conscious luxury retreat and creative sanctuary for artists. This represents a growing trend where the world’s most expensive private islands serve dual purposes: personal sanctuaries and commercial investment vehicles.

Puerto Rico’s Cayo Norte entered the high-end market when Google co-founder Larry Page acquired this largest privately-owned Puerto Rican island in 2018 through an LLC structure for $32 million. The tropical paradise distinguishes itself through glittering white-sand beaches, extensive coral reef systems, and significant wildlife populations including endangered sea turtles.

European Island Prestige: Greece and Canada

Île Gagnon on Quebec’s Rivière des Mille Îles represents a distinct category of private island ownership—the architectural showcase property. Celine Dion constructed an elaborate French Norman-style chateau accessible via private gated bridge on this exclusive retreat, creating a fairy-tale estate. The Canadian singer subsequently sold this distinctive property in 2016 for $25.5 million.

Skorpios Island in Greece commanded the highest price among recent private island transactions when Russian billionaire Dmitry Rybolovlev’s daughter, Ekaterina Rybolovlev, purchased this 74-acre property along with neighboring islet Sparti for a staggering $150 million. This acquisition represents the most expensive private island transaction on record, surpassing other ultra-luxury properties.

Skorpios holds legendary status due to its historical significance as the site where shipping magnate Aristotle Onassis married former First Lady Jackie Kennedy, adding cultural prestige to its natural beauty and exclusive location within Greek waters.

The Global Market for Ultra-Luxury Island Properties

The transactions surrounding these world’s most expensive private islands reveal several defining investment patterns among global elites. Purchase prices ranging from $16 million to $150 million demonstrate the extreme stratification within ultra-luxury real estate markets. Tech entrepreneurs, entertainment personalities, and international billionaires increasingly view private island acquisitions as diversified investments combining lifestyle enhancement with asset appreciation potential.

These exclusive properties transcend traditional real estate categories, functioning simultaneously as personal retreats, investment vehicles, architectural showcases, and symbols of global status. As the ultra-wealthy continue expanding their portfolios, private island markets maintain their position as the pinnacle of accessible luxury real estate worldwide.