WINTER PARK — No matter how many seasons you’ve been attending the Winter Park Playhouse, the look, feel, and even the new vibes inside their newly renovated property will wow you.

Trust us.

In fact, the more familiar you are with the Playhouse’s longtime building at 711 N. Orange Ave. in Winter Park, the more surprised you’re likely to be once it reopens on Friday, Aug. 7 for the start of its 2026-2027 season with the production, Never Can Say Goodbye. The property now combines a far more spacious lobby with a new cabaret room, two bars, a much larger theater and stage, expanded restrooms, and even two floors of office space. It is literally a new beginning for the theater known for specializing in new and innovative musicals.

Freeline Media got an early tour of the property on Tuesday. For those longtime fans of the Playhouse, and any newcomers curious about their building, here’s a tour of what to expect.

What Got Renovated at The Winter Park Playhouse?

With the theater company’s name prominently displayed above the main entrance, there’s no problem finding this landmark building that now has the sophisticated look of a theater located Off-Broadway, eager to compete with the big boys of musical theater.

“After 10 months of hard work and anticipation, The Winter Park Playhouse unveiled its newly renovated theatre home at a celebratory ribbon-cutting on July 7,” the Playhouse notes in a news release. With Orange County Mayor Jerry Demings and Winter Park Mayor Sheila DiCiccio on hand for the ceremony, the theatre officially opened its doors to this renovated and dramatically-altered building.

The main, L-shaped lobby is now considerable more spacious, and with fewer small tables and chairs for patrons who want to relax before the theater opens. There is good reason for that: a new cabaret room has been created, complete with plenty of seating and even a new bar.

This will be where the Playhouse stages its popular Spotlight Cabaret series, and where patrons can relax before the theater opens for the show they’re attending.

A second bar is available in the main lobby, and there are much larger rest rooms for both men and women. The theater itself has a considerably larger stage, as well as expanded seating that includes two pathways leading up to the seats, and a third one separating the front and back rows. More people can fit into the theater, and its much easier for them to move around now.

Another significant change: there is a balcony above the stage where the musicians, led by musical director Christopher Leavy, will be performing. An elevator was installed to enable the crew to transport the musical instruments onto the balcony, which is spacious enough for the actors to perform on occasion.

The Playhouse staff also has two floors for office space, including a front entrance where patrons can stop by during the day to purchase tickets to upcoming shows. It’s literally an entirely new theater.

Why Did Winter Park Playhouse Renovate its Building?

When the building’s owner decided to sell the property in 2024, the City of Winter Park and the Playhouse partnered to apply for an $8 million Tourist Development Tax. It was awarded in October 2024, providing the funds to acquire, enlarge, remodel and improve the theatre’s building. Construction began in November 2025.

“This generous TDT grant from Orange County ensures the survival of a beloved cultural cornerstone that attracts visitors from around the world and makes a $2.3 million-dollar economic impact on the region,” the Playhouse notes, while adding that the July soft opening is just in time to kick off the new 2026-2027 Series of Professional Musicals in August.  

The theater will be leased exclusively to Winter Park Playhouse.

How Can I Get Tickets for the New Season?

The Winter Park Playhouse’s new 2026/2027 season kicks off on Aug. 7 with six new musical productions, starting with the 1970s musical Never Can Say Goodbye.

The Playhouse is offering 6-Show Series subscriptions at a discount off the established single ticket price, with all 6 musicals available for $282 for adults and $258 for senior adults (62 years and older). A “You Pick 3” Series subscription is also available for $153 for adults and $141 for senior adults. Individually tickets range from $20 to $52. Two preview performances will be performed prior to opening night at $25 per ticket.

6-Show Series subscriptions are on sale now, while “You Pick 3” Series subscriptions are now on sale, available by calling the Playhouse Box Office at 407-645-0145. 

Michael Freeman is an Orlando journalist, playwright, and author of the book “Bloody Rabbit”. Contact him at Freelineorlando@gmail.com.