It’s A City of Homes, and So Much More

By Randy Noles

When the Winter Park Board of Trade became the Winter Park Chamber of Commerce in 1923, the group quickly released a promotional brochure debuting a new slogan: “City of Homes.”

Well, yes and no. Winter Park has never been a city of only homes. Its distinctive appeal comes from not only its homes, but from its iconic business district, its parks, its churches and its schools.

Today’s New Urbanists are hard-pressed to improve on Winter Park’s original town plan, conceived in the 1880s by an unheralded civil engineer named Samuel Robinson. Remarkably, the city today looks much like Robinson envisioned that it should, and remains a model for modern master-planned communities.

That’s no accident. Winter Park’s civic leaders and elected officials have a pretty solid track record of defending the unique character of the city—a task that wasn’t always been easy during the region’s boom years.

In the late 1950s, for example, Winter Parkers came together to fight a proposed Interstate 4 route that would have paralleled Orange Avenue and then crossed U.S. 17-92 before turning north toward Maitland. In fact, over the howls of Orlando movers and shakers who wanted the highway completed post haste, an additional route was also scuttled until a third, well west of the city, was finally adopted in 1963.

Winter Parkers were adamant that preserving the picture-postcard charm of their city was more important than facilitating easier commutes.

I remember heated debates over widening and expanding Lakemont Drive and extending Lee Road eastward in an effort to facilitate traffic flow. Winter Parkers were adamant that preserving the picture-postcard charm of their city was more important than facilitating easier commutes.

In 1980, the fortuitously named Hope Strong Jr. defeated longtime Mayor Jim Driver, perceived in some quarters as being too friendly to developers, using the slogan “Winter Park Isn’t As Much Like It Used to Be As It Ought To Be.” (Strong later came up with the city’s much-noticed traffic signs, which read “Please Drive With Extraordinary Care.”)

More recently, there was a dustup over a proposed expansion of the Winter Park YMCA, which was opposed by residents in the surrounding Phelps Park area. The Y’s last major expansion, in 1997, was approved in large part because the organization signed a development agreement promising not to expand again, and not to buy additional land for expansion purposes.

This time, however, the City Commission failed to side with homeowners and okayed the Y’s plans. Of course, a state-of-the-art YMCA is unquestionably a major community asset, and allowing a parking lot and a zero-entry pool at an existing recreational facility is hardly as egregious as, say, okaying a new Super Wal Mart. Indeed, most new master-planned communities covet YMCAs because they are considered to be attractive amenities.

Agree or disagree with the YMCA decision, I’m glad Winter Park is the kind of place where such a proposal sparks debate. All of which is a roundabout way of welcoming you to this issue of Winter Park Magazine, which, among other things, celebrates some of the city’s most important and intriguing homes.

As always, we invite your comments and suggestions. Email me at or call me at (407) 647-0225.

Randy Noles


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