Winter Park proper, and particularly Park Avenue by Rollins College, can be outrageously expensive.
Downtown is a trip worth taking just to mix things up. You can walk Lake Eola in the heart of downtown, take in a meal, and shoot some pool as well. Downtown is laid back compared to "The Attractions" area of International Dr. It is a safe area even at night.
There used to be a sign across from Rollins which read, "Welcome to Winter Park. Please drive with extraordinary care." The college kids painted out the letter "e" in care.
"Welcome to Winter Park. Please drive with extraordinary car."..:wink: Lots of "Old Money"...