- December 13, 2025
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When Wynn’s Downtown held a groundbreaking ceremony recently, it marked the final portion of a public-private partnership years in the making.
And when the project is wrapped up, it will complete a transformation of another area within the up-and-coming Naples Design District.
Everything kicked off when Gulfshore Playhouse purchased three acres at the corner of First Avenue South and Goodlette-Frank Road in Naples at the end of 2017 for $5.15 million. Two acres would be used to build a new cultural campus for Gulfshore Playhouse, and the remaining acre was earmarked for a parking lot.
But building a parking lot on prime real estate along First Avenue South wasn’t the ideal move. So the theater’s owner’s rep (a former city manager in Ohio) came up with a solution.
The Wynn family — owners of Wynn’s Market and other properties and entities in Naples, including a hardware store chain — had a piece of land right next door to the Gulfshore Playhouse land, where their Wynn’s Catering operation was located. It was better suited for parking, so the owner’s rep suggested Gulfshore Playhouse approach the family about a land swap, which they’d be likely to agree to for access to a better parcel of property.
The Wynns were on board, and the remaining acreage after the swap (the bulk of which was owned by Gulfshore Playhouse but a portion of which belonged to the Wynns) was donated to the city of Naples for the construction of a public parking garage.
(An aside: Gulfshore Playhouse Founder, CEO and producing artistic director Kristen Coury is married to Michael Wynn, who, while not directly involved with Wynn’s Catering or this project, is a prominent civic and business leader in town and CEO of Sunshine Ace Hardware. Coury asked Michael Wynn to chair the East of 41 Coalition that supported construction of the parking garage, which is when the couple got to know each other.)
The new Gulfshore Playhouse site opened in fall 2024, and the 355-space municipal garage followed this past spring. Now construction is beginning on Wynn’s Downtown, a $15-million, 45,000-square-foot, three-story mixed-use building that will complete the site and provide a range of benefits to the area.
“There are so many positives to this project,” says Jeff Wynn, president of Downtown Naples — a development company run by the Wynn family that’s overseeing the project — and Wynn Properties. “This is an amazing location, and it’s just going to get bigger, brighter and more amazing as the Design District grows.” (Jeff Wynn and Michael Wynn are first cousins.)
Wynn’s Downtown will include an 8,000-square-foot restaurant space on the first floor, along with additional space for retail shops. Wynn, 42, says he’s already gotten a lot of interest in the spaces. Being next door to Gulfshore Playhouse would be an obvious benefit for a restaurant operator, and a slew of new residential units planned for the area only add to the appeal.
“I think that our audience is going to eat it up, no pun intended, because it’s just right there,” says Coury. “It’s going to be so convenient.”
Half of the second floor of Wynn’s Downtown will house Gulfshore Playhouse’s administrative offices, with the remaining office space available for lease. There’s not a lot of office space available in the popular Fifth Avenue South area, and Wynn thinks businesses are interested in the new space for the proximity to that corridor without the current Fifth Avenue prices.
The third floor of Wynn’s Downtown will have perhaps the biggest impact for Gulfshore Playhouse, with its 17 studio apartments for housing the theater’s visiting actors. Gulfshore Playhouse will enter into a 20-year lease with Downtown Naples for the apartments, which can only be used by the theater for temporary housing.
Right now, the theater rents two- and three-bedroom apartments along with Airbnbs and sometimes hotel rooms throughout the city to house actors who travel from New York and other cities. They also have to provide transportation to get everyone to and from the theater.
The new private apartments will offer close proximity to the theater and help it attract talent as its stature grows with its new, bigger performance space. The theater’s rating within the League of Resident Theatres (LORT) has been increasing with the new venue, which means it’s paying higher salaries and attracting actors of a higher caliber.
But that comes with challenges. “A lot of actors at that level, who are on Broadway today and at Gulfshore tomorrow, want their own housing, and Naples is not the kind of town that has one-bedroom apartments abounding,” says Coury.
Even a two-bedroom, two-bath apartment might not work for these actors. “It’s very hard sometimes on negotiations, and we lose people sometimes,” she says. “Having these studio apartments, even though they’re going to be relatively snug, people will be able to close the door and call it their own and nobody’s going to bother them.”
The number of actors the theater needs to house has also grown with its new space. “Before we maybe had 20 actors a year, maybe 22 if we were going to do a big show for us,” says Coury. “Now we have 22 people in just one show. So our actor numbers are over 100 a year, plus the people attached to each show, like the director, the stage manager and the costume, lighting, and sound designers.”
Wynn expects a 15- to 16-month build for Wynn’s Downtown, with the goal of having a certificate of occupancy by the fourth quarter of 2026. Beck Architectural Group designed the building and EnviroStruct is the project’s general contractor.
The Wynn family, which has been in Naples since 1939, has already been involved with the transformation of Fifth Avenue South that started in the 1990s. They’re excited to be part of the redevelopment of another sector of the city.
“It’s helping all of downtown Naples with more options and more things to do,” says Wynn. “It’s just great to see the city grow. And we care about Naples. We want growth, but done the right way. So it’s pretty neat to be part of this project.”
