The Wynn family plans a new three-story mixed-use development adjacent to the future Gulfshore Playhouse and city parking garage on First Avenue South in the Naples Design District. 

The Wynns, best known for their longtime Wynn’s Market in Naples, propose a 45,000-square-foot building with a large restaurant and retail spaces on the ground floor, office spaces on the second floor and an apartment and 18 transient lodging units on the top floor. The fully furnished lodging units will be strictly for actors and other theatrical personnel in town for performances at the Gulfshore Playhouse. 

The project on slightly less than an acre at 1090 First Ave. S., near the southwest corner of First Avenue South and Goodlette-Frank Road, stems from a public-private partnership between the city of Naples, the Gulfshore Playhouse and the Wynn family. Jeff Wynn, president of Wynn Properties and the manager of Downtown Naples LLC, the family company behind the redevelopment project, said he has been working on the deal for about five years with Kristen Coury, CEO of Gulfshore Playhouse. 

“It’s a neat project and I think perfect for that area, and I think it’s something needed,” Wynn said. “I think with the garage, and then the Playhouse and all that it’s really going to jumpstart that area.” 

Since 1985, the Wynn’s family has owned part of that property, which previously was home to Krehling Industries concrete business. 

“It used to be our old mower and bike shop, and then it housed our Wynn’s catering operation from about the mid ‘90s. So that’s where Wynn’s Catering was at with a large commercial kitchen,” Wynn said. “Our parcel used to be an old concrete plant. That area used to be the industrial area. And now you look at it from the industrial area to, in five to 10 years, I say you won’t even recognize how that area’s changed over the last 10 to 15 years. And we’re just excited to be part of it.” 

The Wynn building was razed and additional kitchen space was built last year at Wynn’s Market. “We contributed some land to the public garage and then we we’re able to do a partial land swap with Gulfshore Playhouse and kind of allowed us to get the parcel that we have now,” Wynn said. 

That parcel on the southwest corner of 12th Street and First Avenue South is in front of where the next municipal parking garage will be built this year. The Gulfshore Playhouse and the city parking garage will use the Wynn parcel as a staging area while they are under construction. 

“We’re hoping we can break ground the end of the first quarter of 2025,” said Wynn, noting that the project is targeted for completion by the end of 2025 or the beginning of 2026. 

The parking garage is expected to be completed at the end of January 2025.  

“We can’t break ground till the garage is completed, or until the construction firm is off of our property,” Wynn said. “Things take longer than expected, but we still have a long way to go with our approvals. So, we hope the garage will be done and then we’ll start building.” 

The Wynns’ parcel is the last piece to be considered within the Naples Square planned development. The submitted site plan has been undergoing staff review, so all city departments are taking a look at it, said Leslee Dulmer, the city’s deputy planner director. 

“Once the site plan is found sufficient, because this is a project within a planned development, City Council has final review and approval authority of the site plan,” Dulmer told the Naples Design Review Board at its Jan. 25 meeting. “Additionally, the transient lodging use on the third floor will require a conditional-use approval as well from City Council. Those two petitions will be packaged together and heard together as a full complement of development.” 

Once approved by Council, the project will return to the DRB for final review. At the January meeting, the DRB granted a continuance for the petitioner to come back for another preliminary design review with some more details and information before the final design review. 

“This is becoming a destination spot. This area is as vibrant as Fifth Avenue, and if we don’t get it right, the relationship of these buildings right, then it’s going to be unfortunate,” said DRB chair Stephen Hruby. 

Project architect Robert Vadya of Naples-based Beck Architectural Group told the DRB that his firm worked hard to create a useful, vibrant building. 

“We tried to create a very strong draw for the people who are parking in the garage, exiting the garage and headed to First Ave South or over to the Gulfshore Playhouse,” Vadya said. 

Architectural plans show a pedestrian via cutting through the building with brick pavers, potted plants and seating, including possible outdoor seating for the proposed restaurant. 

“We’re going to have about a 7,000- to 8000-square-foot restaurant right on 12th and First where patrons of Gulfshore Playhouse can have dinner there before they go to a great off-Broadway show,” Wynn said. “We’ve had a couple of nationals that have looked at it and two locals. We don’t have a real concept yet.” 

In addition to the restaurant, retail space will be available to lease on the western end of the building’s ground floor. The Playhouse will lease about 13,000 to 14,000 square feet of space for its offices on the second floor above the ground-floor restaurant, and about 6,000 to 7,000 square feet of leasable space is expected to be left on the second floor. 

“I’ve already had two or three potential tenants that have already asked about it and want to know more about the office space,” Wynn said. 

In addition to the transient units, a large apartment on the third floor will be available for use by the Wynn family. 

“I think that this is going to be a great project and I think it’s going be very popular,” Wynn said. “With the restaurant space there, it’s going to be amazing.” 

The “Tim Aten Knows” weekly column answers local questions from readers. Email Tim at tim.aten@naplespress.com.