
The struggle for stable stage spaces is one of the most serious structural issues impacting Orlando’s performing arts community, so I’m thrilled this week to share an upbeat update about the revitalization of a vital area venue. Since opening their doors in 2002, the Winter Park Playhouse has firmly established itself as Central Florida’s best — and only — dedicated professional musical theater space by producing 135 main-stage musicals, 171 cabarets, 56 special events and eight editions of their internationally known Florida Festival of New Musicals. On the evening of July 7, after 10 months of extensive expansions and upgrades to the building that they now own, WPP raised the curtain on its freshly renovated home during a ribbon-cutting ceremony attended by community leaders and elected officials.
“What this place is all about is bringing joy to the world. And we all know that art, and specifically music, unites people. You come in the door and you forget all the things. It doesn’t matter what your political leanings are, it doesn’t matter how much money you have, it doesn’t matter the color of your skin, your gender, any of those things; you all come together and you escape, and that’s what this place is all about,” WPP executive director Heather Alexander said in her welcoming remarks. “We wanted it to be a home: a home for you all, a home for our artists, a home where you walk in and you just feel happy.”
The updates are evident from the instant you enter the expanded lobby, which leads to an entirely overhauled main stage offering 171 plush Broadway-style seats (nearly a 40% capacity increase) surrounding the substantially larger stage. The reconfiguration required moving staff offices to the second floor — where they overlook the Goodwill across the street — as well as making major money-sucking modifications to the circa-1948 building. “They found a fuel tank under this stage. We had asbestos, we had termites,” said Alexander, adding jokingly, “we did not find buckets of gold or dead bodies.”
“We believe the arts matter. They enrich our lives, inspire creativity, bring people together and help define the character of our city. Cities are remembered not only for the buildings they construct, but for the culture they choose to nurture. For nearly 25 years, the Winter Park Playhouse has done exactly that,” said Winter Park Mayor Sheila DiCiccio during the inaugural event. Noting the $2.3 million annual economic impact WPP brings to the city, she added, “The real impact is measured in standing ovations, sheer laughter, unforgettable performances and the memories families create together.”
WPP’s glow-up was made possible in large part by an $8 million Tourist Development Tax grant awarded in 2024, and outgoing Orange County Mayor Jerry Demings used the ribbon-cutting as an opportunity to tout his new citizen task force, which will advise on uses for the $385 million collected annually from the 6% “heads in beds” hotel tax.
“Rather than just centralize that decision-making with the board of county commissioners, we open it up to the citizens to give us recommendations. As long as I’m mayor, for these remaining five months, I’m going to continue to use the authority that I have in order to do that,” said Demings. “These are the types of amenities that I want to see in this community, for all of us; for my children, for my granddaughters. I have four of them, and they are all performers — they are ballet dancers — and so I want them to have the opportunity to live in that kind of community.”
In addition to the main theater, Winter Park Playhouse also now boasts a brand-new cabaret lounge, which will be christened Aug. 19-20 by celebrated singer Natalie Cordone, who has been performing at the Playhouse for over 22 years. She’ll be accompanied on piano by Christopher Leavy, another longtime WPP mainstay who tells me that he’s especially excited for the “sumptuous” balcony that the pit orchestra will now occupy.
“When I first walked in this spring and saw how it was coming together, I was giddy. I was bouncing off the floor. And tonight, walking in and seeing it with the piano on stage, and all the lighting and everything, we started our rehearsal and I just started to cry,” says Leavy. “In the 19 years I have spent here, every time something was less than desirable, we would say, ‘We’ll fix that in Playhouse 2.0,’ but I don’t know that I ever thought I would live to see it.”
Back on the main stage, artistic director Roy Allen is readying Never Can Say Goodbye for its regional premiere on Aug. 7, a title he calls “apropos” for the first production in their new theater.
“Bringing new works to Central Florida is what we’ve always wanted to do,” Allen says, adding that although “most of this was for the patrons, to give them better comfort and get more of them in here,” the new facilities could facilitate more ambitious offerings, like London’s recent musical adaptation of The Curious Case of Benjamin Button.
“With this new space, I think that the sky’s the limit.”
Winter Park Playhouse, 711 N. Orange Ave., Winter Park, winterparkplayhouse.org

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