"I'm excited for Wynn's Downtown to be done in the middle of the 2027 season," developer Jeff Wynn told the Business Observer last December. He said it the way you'd talk about a project that had already slipped once and was about to slip again, hopeful but hedged.
If you live in Naples Square or Eleven Eleven Central, you've probably clocked the same thing on your own walks down First Avenue South. The theater is finished. The garage is finished. The building that's supposed to connect them, the one with the restaurant everyone assumed would be open by now, is still wrapped in construction fencing. That gap between what's done and what's promised is the actual story of the Design District this fall, and it's worth understanding exactly where the gap sits before you plan your next few months around it.
What "finished" actually looks like on First Avenue South
Two pieces of this corner have been open long enough that they've stopped feeling new. Gulfshore Playhouse's home, with its 368-seat Moran Mainstage and the smaller Struthers Studio, opened in fall 2024. The city's 355-space municipal garage next door followed in spring 2025. Together they solved the two problems that used to make this stretch of downtown feel like an afterthought: nowhere to see a show, nowhere to park if you did.
What they didn't solve is what happens between parking and curtain. A garage and a theater get you to your seat. They don't get you dinner first.
The corner that's still wrapped in construction
That's the job Wynn's Downtown was built to do, and it's the piece still going up. The Wynn family broke ground on the 45,000-square-foot, three-story building on May 30, 2025, at 1090 First Ave. S., near the corner of First Avenue South and Goodlette-Frank Road. The plan called for a 15 to 16 month build with a certificate of occupancy by the fourth quarter of 2026.
Permitting delays pushed that back. As of the most recent public update, the target has moved to the end of January 2027, and Wynn's own language about the "middle of the 2027 season" suggests even that date carries some slack. Construction went vertical in November 2025. By December 2025, Wynn described it as concrete and columns going up on the first floor, moving forward but not fast.
Here's the timeline laid out plainly:
| Piece of the project | Status |
|---|---|
| Gulfshore Playhouse (368-seat Moran Mainstage, Struthers Studio) | Open since fall 2024 |
| Municipal parking garage (355 spaces) | Open since spring 2025 |
| Wynn's Downtown groundbreaking | May 30, 2025 |
| Original certificate of occupancy target | Fourth quarter of 2026 |
| Revised certificate of occupancy target | End of January 2027 |
More than two years will have passed between the first piece opening and the last piece even reaching its revised target. That's not a delay measured in weeks. It's a delay measured in an entire theater season.
Why the empty restaurant is the real story
The building itself isn't the interesting part. The restaurant space inside it is, because it's the single piece of this project that turns a theater-and-garage combo into an actual neighborhood.
The first floor is built around 7,963 square feet of interior restaurant space plus 1,700 square feet of covered outdoor dining, positioned at the ground level facing the Playhouse. As of the most recent leasing update last December, one small retail bay had a confirmed tenant, a women's apparel shop. The restaurant space did not. Wynn described leasing interest going from nothing to a flood once the building started rising above grade, but said the restaurant decision was still in due diligence, no operator named.
That gap matters more than the square footage does. A vacant retail bay is a minor inconvenience. A vacant restaurant space on the ground floor of the building meant to anchor the district's dining scene is the reason the promise of "walk out of the theater and grab dinner" still doesn't work here.
Kristen Coury, Gulfshore Playhouse's founder and CEO, is counting on the building for more than dinner. The second floor is meant to house the Playhouse's administrative offices, currently about fifteen minutes away on Golden Gate Parkway, and the third floor holds 17 studio apartments earmarked for visiting actors and theatrical crew. Last December, with one of the company's largest productions on stage, Coury described competing for professional talent against theaters nationwide that could already offer walkable housing to visiting actors. Her read on the wait was direct.
"We cannot wait for it to be done. We're waiting with bated breath."
More neighbors before more amenities
While the restaurant question sits unresolved, the block is adding residents on a faster clock. On November 21, 2025, the Naples Design Review Board gave final approval to a three-story, 30-unit condo and townhome project on the parcel immediately next to Wynn's Downtown. The 2.46-acre site is bordered by The Collective, the design showroom to the west, Naples Square I and III to the south, and the new parking garage and the Wynn parcel to the east. It's the last piece on that side of the avenue to clear redevelopment approval, replacing four single-story metal storage buildings that had stood there since 1979 and 1982.
The project, backed by Texas-based GeoSouthern Intermediate Holdings under George Bishop and Margaret Molleston of GeoSouthern Energy, will include a resort-style pool deck, a dog park, and a fitness center, with homes spread across three floors and private terraces on the upper units.
Put the two projects side by side and the sequencing tells you something. The building most likely to bring new full-time neighbors to this stretch of First Avenue South is moving through approvals faster than the building meant to feed them. Density is arriving before amenity does, which is a pattern worth watching if you're trying to guess what this corner actually feels like a year from now versus what it feels like today.
What this means for your fall and winter routine
If you're timing dinner around a show at the Playhouse this season, the math hasn't changed yet. The corner across the street is still a construction site, not a dining room, and even the developer's own language about a mid-2027 finish suggests that won't flip quickly once the shell is done. Restaurant buildouts, permitting for a commercial kitchen, and hiring a staff all happen after a certificate of occupancy, not before it. A January 2027 CO realistically points to a spring or summer 2027 opening for whatever concept eventually signs the lease, if the timeline holds at all.
For now, the honest read is that the Design District has expanded its footprint without yet expanding its dinner options. Fifth Avenue South, a block or two south, remains the fallback for a pre-show meal, the same role it's played since Wynn's Downtown was still a concrete plant and a catering kitchen. That's not a knock on the project. It's just where things actually stand on the ground this September, which is worth knowing before you build your season around a restaurant that hasn't opened yet.
What has changed, permanently, is the shape of the corner itself. A theater that used to be a parking lot. A garage that used to be a negotiation. A restaurant space that's still just framing and rebar, with one confirmed tenant next door and thirty new neighbors on the way regardless of when the kitchen opens. The Design District is being built in the order the partners could build it, not the order a resident would have chosen. Knowing which pieces are actually finished, and which ones are still six months to a year out no matter how the framing looks from the sidewalk, is the difference between planning around this block and being surprised by it.
If you're weighing how a corner like this one shapes value for a condo at Naples Square, Eleven Eleven Central, or elsewhere downtown, that's the kind of on-the-ground read Maureen Sexson tracks block by block. Reach out to talk through what's actually finished, what's still framing, and what that means for your next move in central Naples.
