Anticipation high for $15M Naples mixed-use project, even amid permitting delays

When Wynn’s Downtown broke ground at the end of May, developer Jeff Wynn was hopeful he’d have the certificate of occupancy in hand by the fourth quarter of 2026. But as often happens with construction projects, permitting delays have pushed that date back to the end of January 2027.

“We’re still planning about a 15-month build,” says Wynn, president of Downtown Naples (a development company run by the Wynn family overseeing the project and Wynn Properties.) The project went vertical in November, Wynn says, adding “the first floor is going up, and there’s a lot of cement going down. So overall, we’re moving forward.”

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No one is likely anticipating the completion of the $15-million, 45,000-square-foot, three-story mixed-use building on First Avenue South near Goodlette-Frank Road in Naples more than Kristen Coury, founder, CEO, and producing artistic director of Gulfshore Playhouse. That’s because the theater, which opened its new performance home next door in fall 2024, will be moving its administrative offices to the second floor of Wynn’s Downtown and leasing the 17 studio apartments on the third level for housing the theater’s visiting actors.

“We’ve got the biggest show on stage we’ve ever done right now — “White Christmas” — and we really had to compete with all the big theaters around the country that are also doing this with professional actors,” says Coury. “It would have been wonderful to have an additional ace up our sleeve in terms of being able to offer them walkable private housing. So we cannot wait for it to be done; we’re waiting with bated breath.”

The first floor of Wynn’s Downtown will include an 8,000-square-foot restaurant space along with additional space for retail shops. Jeff Wynn is getting interest in the restaurant space, especially since the project has started going vertical and people can better conceptualize the possibilities.

“We’ve gone kind of zero to 60 as far as people looking,” he says in a November interview. “In terms of what we could have there, we’re going through our due diligence.”

He confirms a women’s apparel shop will take one of the smaller retail spaces. And he’s also gotten a lot of interest in the available office space on the second floor. Gulfshore Playhouse will be occupying half of that office space, with the remaining space available for lease.

Coury is looking forward to getting set up there, as Gulfshore Playhouse’s administrative offices are about 15 minutes away on Golden Gate Parkway. “We’re having meetings about what that is going to look like,” she says. “The office will be brand new and built to our requirements, so it will be an absolute upgrade. 

Photo by Matthew A. Schipper

“But what will be a real game changer for us is going to be that they’re right next door [to the theater],” she continues. “One of the things we hadn’t anticipated is how much of our lives take place at the theater now. We’re giving tours and having meetings — there are all kinds of things going on. Juggling the back and forth has become a little project all its own.”

Wynn’s watching other development projects nearby in the Naples Design District, and he’s looking forward to seeing everything coalesce. “It’s going to be an amazing First Avenue South when all these pieces come together,” he says. “I’m excited for Wynn’s Downtown to be done in the middle of the 2027 season. It’s going to be a great project, and I’m just glad to see concrete and columns up in the air at this point”