Orlando’s quintessential ‘old money’ neighborhood, Winter Park is characterized by nice homes, cobblestone streets and oak trees covered in Spanish moss. Claudia Zequeira
An independent city created for northern snow birds, Winter Park is Orlando’s quintessential “old money” neighborhood. Posh boutiques and museums dot this charming enclave where the women are just a little bit blonder and a little bit thinner than anywhere else. Cobblestone streets are the norm here, as are wonderfully old oak trees covered in Spanish moss. Rollins College is the town’s cultural center, with its chapel serving as the backdrop of a popular classical musical series.
Neighborhood residents — largely well-to-do families — have more than a few cultural gems in their own backyard, such as the intimate but stunning Charles Hosmer Museum of American Art, which holds a respectable collection of works by Louis Comfort Tiffany. Fine dining options and specialty shops are abundant here, particularly along well frequented Park Avenue, but residents may also enjoy less expensive fare: a Saturday farmers market at 200 W. New England Ave. offers fresh produce, exotic spices, baked pies and homemade jellies, among other treats. Wonderful ethnic options are also available, such as Sazon436 on Semoran Boulevard (State Road 436), which was voted Orlando’s Best Puerto Rican restaurant in a recent Orlando Sentinel survey.