A family cools down on Memorial Day at Dinky Dock Park, on the Winter Park lakefront.

Winter Park, Orange County

Most residents own their homes, and the area draws everyone from young urban professionals to families to students (at Rollins College) to retirees. Its public schools are highly graded; Niche.com gives them a solid “A+” rating.

Florida’s Original “Wintering Destination”

Designed around a central park and its main street, Park Avenue, Winter Park was born as a “wintering” destination for wealthy Northerners and became the first planned community in Florida when it was chartered in 1887. That same year, construction began on the Orlando and Winter Park Railroad, which brought affluent tourists to Central Park, at the heart of Park Avenue. Among those first travelers to Winter Park were presidents Grover Cleveland and Benjamin Harrison.

Today, the Winter Park Station serves SunRail and Amtrak commuters, and the park is host to a popular farmers market. The expansive tree canopy, bricked streets and plentiful benches are but a few of the amenities you’ll find not only on Park Avenue, but throughout Winter Park.

The elegant feel of a stroll down Park Avenue is still a big draw today. Families, couples, groups of friends and singles can all be found taking a leisurely jaunt or bike ride through the mix of local and popular chain boutiques.

It’s also a great place to do business. John Washburn, founder of Washburn Imports, sings Winter Park’s praises.

“Winter Park has always been home for me—I was raised here and now run The Imperial on Park right in downtown,” he says. “There’s a timeless charm in this town, from the winding chain of lakes to the generations of families who’ve stayed or returned to raise their own. I’ve traveled the world, but there’s no place like Winter Park—where a great meal and familiar faces are always just steps away.”

A view of Winter Park’s Scenic Boat Tour.

The Winter Park Chain of Lakes

Six lakes span a total of 999 acres along Winter Park and its neighbor city, Maitland. As you’d imagine, recreation is popular here, particularly fishing and water-skiing, but for those looking for a more peaceful setting, Lake Baldwin has been designated as a “no motor boat lake.”

A great way to get out on the water is on a Scenic Boat Tour of Winter Park. Cruise along lakes Osceola, Virginia and Maitland on a pontoon boat and gaze at the most opulent homes in the area. Modern mansions sit alongside historic structures, and there is a mélange of architecture styles, sometimes in the same home. You’ll get an up-close view of some of these homes as the boat navigates through the lakes’ manmade canals; as you pass through them, look up to get a different perspective of the towering cypress trees draped with Spanish moss.

The boat tour affords the opportunity to view the works of James Gamble Rogers II, a legendary name in Winter Park. In 1928, Rogers opened a branch of his father’s architecture firm in Winter Park, just as the city was being developed by the Winter Park Land Company. His focus was on residential buildings; his elegant home designs are still sought after today.

Knowles Memorial Chapel at Rollins College;

The Rollins Connection

Located on the banks of Lake Virginia, Rollins is the oldest college in Florida and was founded in 1885 by New England Congregationalists who brought their style of liberal arts education to Florida. You can see the college on the boat tour, and also the lakeside dwelling where Fred Rogers lived as a student there before he became famous.

Other notable names who graduated from Rollins College include Alice and Pete Dye, Buddy Ebsen, NSYNC’s Chris Kirkpatrick, Anthony Perkins and our own Brendan O’Connor and Catherine Walters.

Rollins is consistently ranked as one of America’s best colleges by the U.S. News & World Report and has produced Rhodes, Fulbright, Goldwater and Truman scholars.

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