Fisher Island Club
If living there just isn't exclusive enough, residents also have access to the well-to-do Fisher Island Club. Admittedly chicer than Mar-A-Lago, it includes an 18-hole golf course, four tennis courts, a beach that's somehow even more private than the rest of the beaches on the private island, and plenty of luxury amenities. The cost of membership? Just a cool $250,000 (not including the over $20,000 in annual fees). Fun fact: the club is also home to the former Vanderbilt mansion on the island.
[Photo via @fisherislandclub]