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Winter Park was incorporated more than 125 years ago, but when you amble along its prime shopping street, drive its brick-paved residential streets beneath canopies of moss-draped oaks and stroll the grounds of its college, you’re going to think: Village
A village with money, to be sure, working to keep its genteel, upscale image. In mid-August, for instance, some of the movers and shakers were so horrified that a Firehouse Subs and a burger joint would soon open on tony Park Avenue that the Planning and Zoning Board passed an ordinance forbidding any more.
What would the original residents — citrus farmers and lumberjacks — have thought? Their ideas probably wouldn’t have concerned the handful of wealthy northerners who decided around 1880 to buy lakeside land and change the community name to something inviting as a vacation destination. Thus, in 1881 Osceola became Winter Park.
Those speculators got rich(er). City history notes land was selling for just $1.85 an acre before the first train tracks reached what would become the heart of the community, in November 1880. But then, plats along the rail line suddenly were selling for $300 an acre.
By 1891, the now-incorporated Winter Park boasted a train depot, post office, telegraph office, two public schools and the state’s first four-year college, Rollins College. And those financiers and industrialists who were now wintering here had enough clout to lure three U.S. presidents to vacation here.
The town is only 8.7 square miles, but it encompasses six spring-fed lakes, which became prime locations even before the 20th century hotels and private estates were created.
A grand way to see how the other half still lives is to take the hourlong Scenic Boat Tour. The pontoon boat putts along a 12-mile route through three of the city’s lakes, including the ones dubbed “Old Money” and “New Money.”
The driver points out impressive homes owned at one time by Henry Sinclair of Sinclair Oil (nine bedrooms, eight bathrooms, two kitchens), Mr. Rogers of PBS fame (while Fred was still a music student at Rollins, his parents bought him a brick mansion), and a relatively new estate said to measure 16,000 square feet.
You can’t see their place from the water, but newer part-time residents are Sir Paul and Lady Nancy McCartney. They purchased part of a condo building to stay in when visiting her son from her first marriage. That lad is one of the 1,901 students enrolled this year at the private Rollins College, where a year’s tuition, room, board and books are about $52,000.
Rollins, founded in 1885, is on a tree-shaded, 65-acre, lakeside — of course — campus. It’s a pleasing stroll, and by golly, you enter the campus at one end of Park Avenue.
At the other end of the avenue is the city’s other landmark, the Charles Hosmer Morse Museum of American Art. Morse was one of the 19th century industrialists who first vacationed in, then retired to, Winter Park. His granddaughter’s husband, Hugh F. McKean, would be president of Rollins College for 18 years, and it was there that the McKeans first displayed their remarkable collection of Louis Comfort Tiffany’s works.
The Morse Museum opened in 1995. It displays what is arguably the world’s foremost collection of one of the design geniuses of America at the turn of the 20th century. In 10 galleries and 6 rooms representing Tiffany’s own estate on Long Island are displayed hundreds of works from his New York City studios including delicate necklaces, floor-to-ceiling window panels, glass bowls and religious-themed stained-glass windows.
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