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Park Avenue - Downtown

Rollins College

Sidewalk Art Festival

Morse Art Museum

Scenic Boat Tour

Once a haven for artists, writers and some of the most influential families in the country, Winter Park was promoted in the late 1800s as a refuge for “the cultured and wealthy.” Those early boosters would almost certainly be pleased to see how it all turned out.

Today, the city is home to 70 parks and nearly as many oak trees (20,000) as residents (24,090). Its eight square miles encompasses lovely old homes, an upscale shopping district, a prestigious liberal arts college, a plethora of galleries and museums and street signs that admonish motorists to “drive with extraordinary care.”

The heart of Winter Park is Park Avenue, stretching 10 blocks and boasting more than 100 shops, from upscale national retailers to one-of-a-kind boutiques. The Avenue, as locals call it, is a European-inspired thoroughfare featuring hidden courtyards, sidewalk cafés and a charming Central Park facing the storefronts.

In addition, the downtown shopping district has begun to spread west on New England Avenue as developer Dan Bellows builds posh apartments and retail stores in previously blighted areas.

On the south end of Park Avenue is the Charles Hosmer Morse Museum of American Art, showcasing the world’s largest collection of Tiffany glass. Each Christmas a set of priceless, holiday-themed Tiffany windows are moved to Central Park, where they are displayed as part of the city’s seasonal festivities.

Several blocks farther west is Winter Park Village, a red-hot retail and entertainment center on U.S. 17-92. New condominiums are available in the Village, which attracts a generally younger crowd than Park Avenue and has emerged as one of Central Florida’s most popular see-and-be-seen destinations.

Year-round the city is alive with festivals and special events, from the Sidewalk Art Festival, drawing more than 250,000 guests each spring, to the Exotic Car Show and assorted celebrations in Central Park.

On the shores of Lake Virginia, beautiful Rollins College, the oldest institution of higher education in Florida and one of the top-rated private liberal arts colleges in the country, is home to the Cornell Fine Arts Museum and the internationally renowned Bach Festival Choir.

Incongruous as it may sound, Winter Park also hosts a Saturday morning farmers’ market, where visitors can buy everything from fresh produce to houseplants and crafts.

High-end condos account for most new residential construction in Winter Park. More than 500 apartments, condos and hotel rooms are either under construction or moving through the approval process.

To see Winter Park as it should be seen, shell out five bucks and take a guided tour along the Winter Park Chain of Lakes. Scenic Boat Tours, headquartered at Dinky Dock near Rollins College, has been cruising these canals since 1938, offering regular folks a chance to peek into the backyards of the rich and occasionally famous.