It has been 24 years since the song-and-dance team of Roy Alan and Heather Alexander brought some show-biz sizzle to town when they co-founded The Winter Park Playhouse. But last season, for the first time, the theater’s famously frolicsome mainstage musicals weren’t held at its familiar venue on Orange Avenue.
Now they’re back, baby! Using an $8 million grant via the Orange County Tourist Development Tax (TDT), the City of Winter Park bought the cozy venue for $3.875 million and spent the rest on a massive renovation project. A range of other donors participated as well, bringing the project’s total cost to $10,063,727. In the meantime, though, the show had to go on elsewhere.
Was it worth the inconvenience? Fans sure think so. Crews finished earlier than expected—getting the job done in an extraordinarily tight eight-month period. The city leased the renewed, reimagined and expanded venue back to the theater for a nominal fee. Now, for the 2026–27 season, it’s business as usual—only in a much nicer and more tech-forward setting.
The new Winter Park Playhouse—the region’s only year-round professional musical theater—boasts a spruced up exterior with two large double-door entrances, a permanent canopy and a prominent marquee that better suits its upscale 32789 address.
But it’s inside where the magic really becomes apparent. The theater now has a more expansive (and easier to navigate) lobby, a more readily accessible box office and, of paramount importance, expanded restrooms.
In addition to updated tile and brass faucets and mirrors, there are—count ’em—eight toilets in the ladies’ room. The refined gentlemen’s facilities sport similar brass fixtures and mirrors with black tiles on the walls and white tiles on the floors. Classy!
Speaking of comfort, playgoers will now occupy plush chairs—five inches wider than those cramped ones they replaced—that sport shiny brass row-and-number markers. The chairs are custom made, upholstered in burgundy velvet with mahogany frames and cast-iron end panels decorated with gold filigree on the aisles. The arms have sturdy, built-in cupholders. (Capacity has also increased, from 124 to 172.)
There’s plenty to love for actors, too. Backstage, there are two expanded dressing rooms—that can accommodate 14 rather than 7 at a time—with restrooms and showers, no less. Plus, there’s a dedicated green room/rehearsal space with large mirrors and a “sprung” floor—a flexible surface that’s safer for dancers.
The auditorium is reconfigured with a stage that’s just as wide but twice as deep as the previous space—which makes mounting larger and more elaborate productions possible. A musicians’ loft keeps the players from taking up real estate alongside the actors, while a large booth in the back has been built from which sound and light techs will operate upgraded systems.
And there’s now a 72-seat room dedicated to the theater’s ever-popular monthly Cabaret Spotlight Series. The space has its own bar, 17 tables, 72 seats plus bar stools—providing an ideal intimate ambiance for watching solo concert-style performances. At least two fans really liked the idea and offered their support.
Frank Santos, president and CEO of Rosen Resorts & Hotels, and Corbett Compel, course director for the Sports Production Broadcast Program at Full Sail University, gave the theater a $500,000 gift (the largest in its history). The cabaret room has, as a result of that donation, been named the Santos-Compel Cabaret Lounge.
Still, Alan (artistic director) and Alexander (executive director) are equally excited about the decidedly less sexy new laundry room. Says Alexander: “I remember when my husband and I used to take costumes home to clean them.” Administrative offices were moved to a two-story space connected to the building and are still accessible via the lobby.
Looking back, Alexander says that if the renovation process had a theme song, if might be “Looks Like We Made It.” (Or maybe “The Impossible Dream.”) She adds: “It took so long, and it was so much work, but it’s a legacy, right? The community deserves to have a theater to inspire and entertain the thousands of residents and visitors we serve.”
So you can see why everyone was so excited about the 2026-27 season—which got underway in August with Never Can Say Goodbye: The 70s Beehive Musical.
Up next will be The Rat Pack Lounge (September 25 to October 18), A Christmas Survival Guide (November 20 to December 20), Now Comes the Fun Part: The “How the #@&! Did I Get This Old” Musical (January 22 to February 14, 2027); All Hands on Deck (March 12 to April 11, 2027); Sister Amnesia’s Country Western Nunsense Jamboree (May 7 to May 30, 2027).
If you sense a theme here, it’s that The Winter Park Playhouse is all about sheer, unapologetic entertainment with fun and frothy musicals that are meant to be enjoyed. That’s been its formula for success since the very beginning—and more than 30,000 tickets are sold annually—so don’t expect the fancy new digs to portend any changes in terms of content.
The theater is also a solid corporate citizen with a history of giving back. Its REACH (Relevant Educational Arts for Children) program offers in-school performances and sends teaching artists to work with kids at no cost. Another program, SHARE (Senior Health through Arts Enrichment) takes musical theater to mobility-limited seniors who live in full-service care communities.
And the theater’s annual Florida Festival of New Musicals, held during the summer, is a four-day event that spotlights six never-before-produced musical works. Attendees experience concert-style readings and participate in talkback sessions with the writers and composers.
The Winter Park Playhouse is located (again!) at 711 North Orange Avenue, Winter Park. For more information, visit winterparkplayhouse.org or call 407.654.0145.
