13. Pumpkin Key — $95 million

Key Largo, here we come. This 26-acre, 5,000-square-foot home actually sits on its own private island in the Florida Keys. It features one main home with three bedrooms, several cottages, a dock master’s apartment, a 20-slip marina that can easily accommodate a mega yahct, as well as plenty of lots available for new development. Plus, golf cart paths circle the island. Oh yeah, and in the middle of the island, you’ll find tennis courts that also serve as a helipad. No big deal, right?