Winter Park is mourning the loss of a beloved philanthropist, entrepreneur, and friend with the passing of Michael (Mike) Winn at the age of 82. A longtime realtor and resident, Winn, along with his wife, Gail, are known by friends and associates for their involvement in local organizations and efforts to make the city a better place.
“Part of what absolutely drove him was the community he lived in,” said Alan Manning Chambers, vice president of operations at John Craig Clothier and Park Avenue District president. “He and Gail didn’t have children, so Winter Park is really like their child.” Chambers worked with the Winns on events that included fundraisers, social gatherings, and popular Christmas parties at the garage of local automobile enthusiast, Rick Vimmerstedt. “They were extremely generous with people who were in need and a with the city that Mike loved,” Chambers said.
A native Central Floridian, Winn attended Killarney Elementary School and Edgewater High School, and studied at the University of South Florida. He and Gail resided on Mayfield Avenue and were active in the arts community. Their involvement included supporting the Winter Park Sidewalk Art Festival Patrons Program. Mike also held a seat on the Orlando Museum of Art Board of Trustees and he and Gail funded its 2024 Florida Prize in Contemporary Art Award.
Winn founded several businesses with friend and business partner Lief Erickson, among them were Winter Park Land Commercial and RealCom Real Estate Services, Inc. Winn completed more than 100 transactions and was known by many as “Mr. Winter Park.”
“We worked on about seven companies over the years,” said Erickson, who first met Winn after moving to Winter Park in 1972. Their business relationship began the following year and spanned more than 50 years. “He’s one of the kindest, most giving people I ever knew. We had a wonderful relationship and I enjoyed every minute of it.”
Among Winn’s holdings is the building at 400 W. New England Ave. in Hannibal Square. According to Winter Park Planning Director Emeritus Jeff Briggs, Winn commissioned the mural on the side facing Shady Park as a means of spotlighting the community. “He always thought that commercial area didn’t get the recognition it deserves,” said Briggs. Of Winn’s gifts to the city, the most well-known is the clock and Park Avenue historic marker installed next to Central Park and dedicated in 2023.
“Mike was a lifelong acquaintance but a friend in the last few years,” said Briggs, who worked with the Winns on the clock installation and another major project currently in progress.
The proposal for twin archway signs bookending the Park Avenue district was approved this year and scheduled for installation next year. Briggs brought the concept before City Commission and after funding for one arch was approved through the Community Redevelopment Agency, the decision to fundraise for a second sign moved forward with Winn’s assistance. “It was the easiest thing I’ve ever done,” said Briggs. “We approached eight people for $25,000 each and all eight said yes – and Mike was one of the donors.”
A public memorial will be held on Thursday, Oct. 24, at First United Methodist Church of Winter Park, 125 N. Interlachen Ave. Erickson says there will be many memories to share and many friends to share them with. “The pastor of the church asked how many people we can expect. My wife told him, ‘The entire city of Winter Park.’”