Up to Eight Billboards in Winter Park to be Removed

The concept of a deal approved by the City Commission calls for four new billboards along I-4 while eight billboards along surface roads come down

Dec. 11, 2025

By Beth Kassab

For years, Winter Park officials have wanted to rid the city of billboards — considered by some to be analog roadside spam — and this week brought the first step in taking down as many as two billboards on Fairbanks Avenue, four of the structures on Aloma Avenue, one on Lee Road and one on Interstate 4.

City commissioners voted 5-0 to approve the concept of a deal that will require a series of land swaps and annexations and the permitting of four new billboards along I-4 in exchange for the eight other signs coming own.

“We’ve been working for many, many many years to try to eliminate as many billboards in the core of the city,” City Manager Randy Knight told the commission.

The terms call for:

• Clear Channel Outdoor will remove two billboards at 1873 and 2095 Fairbanks Avenue and one at 2522 Aloma Avenue. All three of those signs are double-sided. In exchange, Winter Park will issue a permit for Clear Channel to construct a new billboard at 2600 W. Fairbanks with a digital sign facing westbound I-4 traffic and a static sign facing eastbound traffic. Clear Channel would also remove a three-sided billboard at the southeast corner of I-4 and Lee Road. It would be replaced by a new billboard about 300 feet to the south, which will require a property swap with the city. The property swap could come before the commission as early as January.
• The Lamar Company will remove a digital billboard at 1621 Lee Road and the city will permit a new digital billboard at 909 N. Wymore Road. This means the city will also need to annex a portion of land for the structure.
• Outfront Media will remove three billboards at 2090, 2145 and 2431 Aloma Avenue. The city will issue a permit for a new digital billboard at 1885 Dartmouth Avenue. The city must annex several properties on Dartmouth to make that portion of the deal happen.

Mayor Sheila DeCiccio asked if Clear Channel could also remove a billboard on U.S. 17-92 and Gay Road. The company would not agree to remove it but said it would replace the digital side of that billboard with a newer technology that creates less light pollution.

“We definitely want that,” DeCiccio said of the upgraded features.

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