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1.
Beverly Hills of the East Coast. Ultimate prep town. Swarmed by rich kids, rich people, expensive stores, über-ridiculous cars, and whatnot.
People in Winter Park are so rich, they use $100 bills to wipe the windshields of their Hummers.
by KRHimself December 15, 2003
 
2.
Playground and resting place for Orlando's old money. 1.5$ million an acre, brick streets, big trees and lots of lakes. Home of the racquet club, Park Avenue, Concours de Elegance, and the country clubby Rollins College. Laid back as only a complete lack of financial concern could bring.
A guy on Winter Park Crew is hosting a party, tell everyone to get in their air nautiques and head over to his million dollar boathouse, and remember it's the one on the right, the one on the left is his dad's...
by the park July 21, 2005
 
3.
The compton of the east coast.
I got some ghetto booty in Winter Park.
by ac333334 December 06, 2006