The World's Most Expensive Private Islands: A Decade of Ultra-Luxury Real Estate Transactions

For those seeking the ultimate escape from urban life, private islands represent the pinnacle of luxury real estate investment. Over the past decade, some of the world’s wealthiest individuals and celebrities have acquired spectacular private properties across tropical and temperate locations, establishing benchmark prices for the most exclusive island market segment globally.

Understanding who owns these most expensive islands in the world and why they command such astronomical valuations provides insight into ultra-premium real estate trends and the aspirations of the global elite.

Larry Ellison’s Vision for Lanai, Hawaii

Oracle co-founder Larry Ellison acquired approximately 98% of Lanai, a 141-square-mile Hawaiian island, in a transaction valued near $500 million. Rather than treating the property solely as a personal retreat, Ellison has directed substantial capital toward infrastructure development and community enhancement initiatives benefiting the island’s 3,000+ residents.

The island stands as America’s largest privately held landmass, featuring nearly 50 miles of pristine coastline. Recognizing its tourism potential, the property now hosts multiple Four Seasons luxury resorts, positioning it as an exclusive destination combining natural beauty with world-class hospitality amenities.

The Rybolovlev Record at Skorpios Island, Greece

Among the most expensive islands ever acquired, Skorpios Island commands particular attention following its $150 million purchase. Ekaterina Rybolovlev, daughter of Russian billionaire Dmitry Rybolovlev, secured this 74-acre Grecian property along with neighboring islet Sparti, outbidding several high-profile competitors including Microsoft founder Bill Gates, fashion icon Giorgio Armani, and pop legend Madonna.

The island’s commanding price reflects both its storied past—serving as the wedding venue for shipping magnate Aristotle Onassis and former First Lady Jackie Kennedy—and its exceptional natural characteristics. Its rare combination of historical significance and pristine Mediterranean landscapes justified the premium valuation.

Larry Page’s Puerto Rican Acquisition at Cayo Norte

Google co-founder Larry Page demonstrated comparable appetite for island properties through his 2018 acquisition of Cayo Norte, Puerto Rico’s largest privately owned island. Executed via investment vehicle U.S. Virgin Island Properties, the $32 million purchase secured an undeveloped tropical sanctuary renowned for white-sand beaches, vibrant coral ecosystems, and wildlife populations including endangered sea turtles.

The property’s ecological significance and development potential enhanced its appeal to technology sector investors seeking alternative portfolio diversification.

The Celebrity Collaboration: Bonds Cay, Bahamas

Located 120 miles offshore from Florida’s east coast, Bonds Cay attracted an unusual consortium of creative industry figures. Shakira partnered with Pink Floyd founding member Roger Waters and Spanish recording artist Alejandro Sanz to jointly acquire the 700-acre property for $16 million.

This five-beach, three-salt-pond composition provides the foundation for an ambitious project—transforming the island into an eco-conscious luxury destination and artists’ retreat that merges residential exclusivity with environmental stewardship.

Celine Dion’s Rivière des Mille Îles Estate

Quebec’s Île Gagnon gained prominence through Canadian music icon Celine Dion’s acquisition of this private island sanctuary on Rivière des Mille Îles. Dion commissioned construction of a French Norman chateau-inspired mansion, accessible exclusively via private gated bridge—a design choice that enhanced the property’s secluded, fairy-tale ambiance.

The 2016 sale at $25.5 million reflected strong demand within North America’s ultra-high-net-worth residential market, demonstrating sustained valuation strength despite the property’s subsequent market reentry.

Market Insights: Understanding Premium Island Valuations

These transactions collectively illustrate several key market dynamics shaping the world’s most expensive islands. Pricing premiums reflect multiple factors: geographic exclusivity, development potential, natural features, accessibility to major markets, and ownership prestige. The diversity of buyers—from technology entrepreneurs to international celebrities—underscores the universal appeal of private island ownership among ultra-wealthy investors and cultural figures globally.