Playhouse gets lease and city looks for Seven Oaks Park developer
The City Commission also took steps to limit residential pickleball courts
Aug. 14, 2025
By Beth Kassab
The Winter Park Playhouse is closer to its goal of starting a $10 million renovation of the professional musical theater, which includes the purchase of the building by the city.
On Wednesday, the City Commission approved two critical steps — the funding agreement for Orange County to provide $8 million through a grant of tourism tax dollars and a lease agreement with the city to rent the building for $1 a year.
The lease also allows the playhouse to request up to a $600,000 “bridge loan” if it has not met its private fundraising requirement of $1.6 million to receive the county dollars at the start of the project. The playhouse must show it’s raised at least $1 million to request the loan.
“A lot of faith there,” Commissioner Marty Sullivan said. “But I’ve got faith in the playhouse to make this work.”
Heather Alexander, co-founder and executive director, said the playhouse has already secured $1 million in private funds toward the goal and has pledges totaling more than $600,000 set to come in over the the next three to four years.
“We will be just fine … so don’t worry we won’t be able to pay it back,” Alexander told the commission. “It may not even be necessary, that’s my hope.”
The city will use $3.8 million of the county grant to purchase the property at 711 N. Orange Avenue. The remainder of the county grant will go toward refurbishing the theater, including expanding seating by 50%.
The future of the 23-year-old nonprofit theater was up in the air just a year ago when the owner of its building said its lease would end and the building would be sold. That left theater supporters scrambling for a new home until, ultimately, the city agreed to buy the property through the grant.
As part of the agreements, the playhouse will be required to provide a report on its performance metrics each year to the city.
City seeks developer for Seven Oaks Park
Tired of seeing little use of Seven Oaks Park, which opened in January, the city is inviting developers to submit ideas to build out a pad within the park that would potentially draw more people to the greenspace. (Red outline in above photo at top of page.)
Permitted concepts could include “bars, taverns, and cocktail lounges (with at least 51% of revenue derived from food sales); bicycle shops; breweries and distilleries (with food service); corner stores (excluding convenience stores); fine arts museums; instruction in fine arts, dance, and music; food halls; health and wellness studios; recreational facilities; restaurants (including fast-casual and fine dining); retail businesses; specialty food and beverage markets; and theaters for film, music, or performing arts.”
The city won’t be obligated to accept any of the ideas, but can use the “invitation to negotiate” as way to feel out interest in the project, City Manager Randy Knight said.
“The city expects this redevelopment will respect and grow the quality of the city’s unique attributes and special features of Winter Park while remaining relevant to today’s social gathering places like Foxtail Coffee Co. and Shady Park in Winter Park, Plant Street Market/Brewery in Winter Garden, East End Market in Orlando, and Boxi Park in Lake Nona,” the document reads.
Mayor Sheila DeCiccio said the neighbors and other businesses “desperately” want something to happen there.
Commissioner Craig Russell agreed, saying that despite the controversy related to the park, “I think the spirit of this park was deliberately designed for this process … it was what the plan was and I think it’s time.”
Commissioner Warren Lindsey suggested a shaded area might be a good component of whatever development plans take shape considering the Florida heat the years it will take for the park’s oaks to mature.
New limits on residential pickleball
Residents who are looking to build a pickleball court on their property will find it hard, or maybe impossible, to do so under new rules imposed by the City Commission.
The rules, which are designed to prevent noise complaints related to the game’s trademark near-constant ball whacks, will not affect commercial or public pickleball courts.
Planning Director Allison McGillis estimated there are fewer than five residential courts in the city, though some homeowners may seek to convert tennis courts to pickleball over time.
“I don’t foresee a lot of them popping up, but it’s becoming more popular,” she said.
McGillis proposed changing city code to require pickleball courts have 20-foot setbacks from the rear and side property lines, an increase from the required 10 feet for tennis courts.
But commissioners opted to increase the requirement to 150 feet, meaning new courts would be virtually impossible for now given the size of most lots.
One private pickleball court is expected to be built just off Park Avenue and Morse Boulevard as part of a private residence attached to a coffee shop. But that court would not be impacted by the new rules because of a special variance given to the project.
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Dear WPV- I write to point out the utterly charmless and wasteful boondoggle-7 Oaks Park.Most of the funds were used to construct 1) Expensive but useless brick structures that look like BUS DEPOT SEATS hard on Orange Ave.,right in the NOISE and CAR FUMES. 2)Which don’t even face the “Park.” 3)Which don’t even have ROOFS to keep off the rain, just a few wooden slats.
Our charming city built this thoughtless, pitiful thing- which now cries out for a 7-11 to be built in its center.Shame on ALL involved!!!
agree
You go Woody! Try and find a living breathing person in that park and you’ll be the first!
The money should have gone to Mead Gardens! Can you imagine what that gem of a park/sanctuary would look like with a $7 million investment!
Any type of shade would be welcome and is imperative to attract people to Seven Oaks Park. The Florida summers are just too hot without shade.
Why are we looking at an 8.9 % 2026 budget increase for Winter park??? $233 million for 30,000 residences!!!
At some point fiscal discipline must take hold and the City’s wish list of nonessential projects needs to be throttled back!
If not our taxes will continue to spiral out of control!
What if a seriously upscale dog park were created with a beverage component, something with a lovely fountain and doggie play structure. With a beverage component, it might invite dog owners (and those who enjoy watching romping dogs) to socialize with one another while relaxing with a (non-alcoholic) drink and snacks?
Fantastic idea! It would bring a lot of people to the area, add something unique to the town landscape and make a sense of a somewhat missed project
What are the annual ticket sales ($ amount) for the Winter Park Playhouse.? I’d certainly factor that into the mix before considering any $10 million investment. I know it’s “the Arts,” but the ROI has to be phenomenally miniscule. Just as a matter of history, remember the $1 a year rent to the Chamber, for 99 years? We need to carefully consider these giveaways/bailouts.
“The future of the 23-year-old nonprofit theater was up in the air just a year ago when the owner of its building said its lease would end and the building would be sold.”
Are there no other spaces in NE Orange county that could be leased for $150,000+ a year? (the current occupancy cost per Playhouse tax return)
I’m amused that patrons seem to have no problem driving to the current location but a new location would be the harbinger of the final curtain call.
“Playhouse” is appropriate. WP taxpayers have been played for the last 5 years. Add this to the list.
Well-meaning or not, this commission is on track to do for 7 Oaks Park what NIL and the transfer portal have done for college football. If they continue, this 2 plus acre parcel can no longer be a park. It will be a combination of hardscape overkill and the (over)built environment – a la Rollins College. Those spindly oak trees? Just a spidery reminder of what could have been: a shady, cooler, passive, green respite. WP is full of people who walk/stroll, run, and bike. Shade, not retail or food courts, can mean the difference between being able to tolerate the gruesome heat- or not. Just because a space is green doesn’t mean we have got to build something in it. This should be the Central Park of the highly commercial Orange Ave corridor, specially with the steady erosion of nearby MLK Park. Two major companies cited the park in deciding to relocate to Orange Ave. Guess we may have to call them suckers.
I speak for myself and several others who all agree with Woody Igou, especially the “Bus Station” appearance along the Orange Avenue entrance to Winter Park. That is uninviting, as is the complexity of the park. A simpler less expensive green space would be an inviting and pleasant appearance along Orange Avenue. I’d support even more spending to revise this abomination to mirror the Winter Park Golf Course landscape….less concrete, more grass, no obstructive bus stop structures.
I totally agree with Woody Igor, building that park was a totally waste of taxpayers money. Commercially developing a small portion of the park will not encourage the use of the poorly designed, and poorly placed park. The Winter Park Commission should reduce the tax rate in proportion to the increase in property values. They should also stop expanding the CRA both in size and length of time. Winter Park is not a blighted city. The CRA was first approved when I was in office and it was only to last 20 years not to be expanded and renewed.
Not sure why the Winter Park Playhouse pays only $1 a year in rent. The chamber is an umbrella for many commercial establishments so its $1 a year rental fee makes sense, at least a little more sense but the Winter Park Playhouse? Why does it get this perk?
Also, if the Playhouse is a nonprofit does that mean it’s exempt from paying taxes?
Please explain.
I said it then, and I’ll say it again: the Seven Oaks Park should’ve been workforce housing for people employed by the City of Winter Park and their families, surrounded by cooling trees.
All the complaining! Remember the “Welcome to Winter Park” building when you exited I4 at Lee Road? Be thankful what you got and build on it-that is trees, bushes, natural shade. Maybe put a few picnic style tables with tin roofs like they have at cady way. Let in a restaurant nearby but not on the park but let them put tables with umbrellas on a piece of the park (lease it out for $2 a year so you all don’t complain-that’s double the playhouse). Just be creative and look at other cities to see what they did that worked.
Hmm….be creative and look at other cities?
If you drive down Orange Avenue, take a right on Fairbanks, and then a left on Park Avenue, you will see a successful and thriving park that is the pride of this city. It’s surrounded by residences, businesses, and….density? Can we say ‘density’ on this site?
Go back to what was recommended by the Orange Avenue Steering Committee. Not the distortion and flat out lies that were told about the “massing studies” that were so misleading that apologies had to be issued by candidates. And not the OAO 2.0 that was commission /Land Trust led with minimal citizen input. Winter Park deserves better. And one more thing, please have a fair process, not one that is written to fail or generate a certain outcome, and please not one approved by someone who’s name rhymes with Dodd Beaver.
Holy Smokes! How did this honesty get posted on this “trusted nonprofit journalism” site? The editor is either on vaycay or is slipping. 🙂
“John Elliott”All of the worst massing studies were a direct lens into a very narrowly averted high density future for the Orange Ave corridor. The major landowners ? They would have if they could have. No one -especially a commission candidate-should ever apologize for showing those studies, over and over, under any circumstances to those who pretend that 25 -35+ dwelling units per acre at 300 to 400 FAR in 5 ( or more) story buildings is the cure for what ails that section of Orange Avenue. If the new McCraney building is not big enough to suit you, John Elliott, just what size office buildings or apartment buildings would be big enough to suit you there? Is there a limit?