14. Peter Thiel's South Maui sanctuary

Estimated home value: $25.5 million

Title: Cofounder, PayPal; investor and entrepreneur

Thiel made the biggest single-family real estate purchase in the history of Maui with his $27 million home on the island of Maui back in 2011. Today the Maui County public assessor's office evaluates the property and home at about $25.5 million.

Situated on the Makena waterfront, the beach home is made up of four interconnected pavilions wrapped around a courtyard and swimming pool.

The early Facebook investor also owns homes in the Marina District in San Francisco, Los Angeles, and New York City, according to Variety.