Winter Park, Florida has some great features. Park Avenue in the heart of WInter Park is first. This is near Rollins College and is the quintessential Winter Park experience.  Park Avenue has a long park in the middle of the street and has restaurants, spas, retail, specialty shops all down about 1-2 miles.  This Avenue has restaurants from the Briar Patch - upscale family style restaurant to Italian and French, very upscale. The shops include Banana Republic to art stores.  Many places to see - all along a tree shaded brick road.  This is the Avenue that WiInter Park hosts it's famous Art Festival on each year.

Parke Avenue has a rival at this time with Winter Park Village. This is a newer shopping center that includes resteraunts and a movie theater. Park Avenue has it's charm but Winter Park Village seems to have something for everyone too. Cheesecake Factory to Ruth's Chris for eateries. Shopping from jewelry and specialty shops to Pier One and Borders bookstore.  This is not as walkable as Park Ave but does feature very nice and updated retail space.

Museums and points of interest in Winter Park are:

The Cornell Museum of Fine Arts (Rollins College)

Polasek Museum and Sculpture Garden

Morse Museum

The dining in Winter Park is vast from Fiddler's Green (authentic Irish cuisine and live music) to posh French cuisine and Siam Garden. Winter Park has it all for food.