$15M Wynn’s Downtown Project Brings Offices, Studios & Actor Housing to Naples Design District

If you’ve walked through Naples' Design District lately, you might’ve seen signs of real growth—and, spoiler alert: it’s not just more filtered coffee shops.

Breaking ground in late May, Wynn’s Downtown is a new $15 million, three-story, 45,000-square-foot mixed-use development at 1090 First Avenue S. It’s set to become a cornerstone of the district, designed as a creative hub, home to offices, restaurants, retail, and—uniquely—studio apartments reserved for out-of-town actors with Gulfshore Playhouse.

Here’s how it all stars lined up:

From land swap to landmark
Back in 2017, Gulfshore Playhouse purchased three prime acres at First Avenue South and Goodlette‑Frank, but carving out a parking lot there felt like fast-forwarding into a downtown headache. A savvy owner’s rep suggested a strategic land swap with the Wynn family—owners of local staples including Wynn’s Market. That led to a better parking solution and the groundwork for today’s project.

What’s inside Wynn’s Downtown?

• Ground floor: An 8,000-square-foot restaurant (buzzing location there) plus space for retail tenants.

• Second floor: Office space split between Gulfshore Playhouse’s admin team and spots available for lease—something rare just off Fifth Avenue without the Fifth Avenue price tag.

• Third floor: Seventeen studio apartments—compact, but golden real estate for the actors Gulfshore brings in, now allowed to call their own space for the season.

Why the studios matter
Gulfshore Playhouse suddenly found itself booking scattered Airbnbs, traveling to reach housing—and losing talent along the way. Actors—and designers—today look for both convenience and privacy. A snug studio close to the theater means no Uber shuffle and better negotiating power in casting.

Timeline and vision
Construction is expected to last 15–16 months. Downtown Naples Development, led by the Wynn family, is aiming for occupancy by late 2026.