Cleveland Street's Quiet Takeover: What's Actually Opening in Downtown Clearwater

Three thousand people showed up at the corner of Cleveland Street and Fort Harrison Avenue in July to watch a clock get turned back on. The occasion was the reopening of the Peoples Bank Building, restored down to its original brick and storefront glass, and the crowd came for the clock tower ceremony as much as anything else. Within days, the news that followed the celebration wasn't about the building. It was about who was moving into it.

That's the part worth paying attention to if you live anywhere near downtown Clearwater. The story isn't just that empty buildings are filling up. It's that one restaurant group keeps being the one to fill them, and understanding why tells you more about what's coming next than any single opening does on its own.

One Group, Two Buildings, Same Month

Tastes Pretty Good Hospitality, the group behind Tampa's Rocca, Bar Terroir, Lumbre and the Michelin Bib Gourmand recipient Streetlight Taco, announced two Clearwater projects within the same few weeks this past July. First came Rippers, a deep-fried hot dog and burger concept moving into the ground floor of the historic Telephone Building at 534 Cleveland Street, a structure built in 1914 and now the first landmark completed under the Cleveland Street Alliance's restoration push. Then came the bigger announcement: Streetlight Taco's second location ever, and its first outside Tampa, taking the ground floor of the newly restored Peoples Bank Building at Cleveland and Fort Harrison.

Tastes Pretty Good CEO Nick Reader framed the move as a homecoming of sorts.

"We started in Tampa as a love letter to the city we grew up in. When this opportunity arose to come to Clearwater, we saw something very familiar. We understood the vision, we understood where it could go and we knew we wanted to be part of it."

That's not a group testing the waters with one small storefront. That's a single operator claiming two of the corridor's three fully restored buildings inside the same month, with a brand that already carries Michelin recognition from its January 2024 South Tampa opening. If you're wondering what downtown Clearwater is going to feel like a year from now, the answer starts with the fact that one company is currently setting the tone for it.

The Nine Buildings Behind the Boom

The two Tastes Pretty Good buildings are part of a longer list. At a city council work session in late May, the Cleveland Street Alliance laid out the full scope: nine properties along Cleveland Street between Osceola and Myrtle avenues are either finished or in progress.

City Councilman Michael Mannino, who requested the work session, described downtown Clearwater's recent history bluntly: for decades it had been known as a ghost town, and only now are the 400 and 600 blocks of Cleveland showing signs of life. The Cleveland Street Alliance told council members the full project is expected to generate $200 million in private investment for the district.

Where the Money Comes From

This is the part most coverage glosses over, and it matters if you're trying to understand why this particular stretch of downtown is moving so fast while so much of Florida's small-city downtowns stay stuck in planning purgatory. At that same May work session, city officials confirmed the restoration effort is being funded by members of the Church of Scientology, working through the Cleveland Street Alliance. It's a matter of public record, discussed openly at a public council meeting, and it helps explain the pace: this isn't nine different landlords moving at nine different speeds. It's one coordinated funding source moving through a punch list, building by building.

Beyond Cleveland Street

The activity isn't confined to the historic core. Over on East Bay Drive, a former Boston Market at 4001 E. Bay Drive is becoming Dank Burrito this fall, a North Carolina-born chain making its second Florida stop after a spring opening in Ponte Vedra. Franchise owners Bryan and Lambdin Hill, along with general manager Jackie Garcia, are turning the space into a 3,100-square-foot spot with custom graffiti honoring Bay Area icons like the Buccaneers, the Sunshine Skyway Bridge and local beach scenes, painted by an artist known as Pause who's scheduled to install the work in early September.

"Clearwater has had enough of cookie-cutter chains and deserves more," Hill said in announcing the opening. "Dank brings the flavor, the vibe, and the experience you can't get anywhere else."

It's a small data point, but it lines up with the Cleveland Street pattern: independent, personality-driven concepts choosing Clearwater specifically, not just picking it because a strip mall had a vacancy.

The Gateway Anchor Still on Paper

The most ambitious piece of the downtown plan hasn't broken ground yet. EVO Entertainment is slated to build an 83,000-square-foot, $50 million family entertainment complex at the corner of Cleveland Street and Myrtle Avenue, the literal gateway into downtown. Plans call for a seven-screen multiplex anchored by a screen described as more than 130 feet wide, billed as the largest in the world, with Dolby Vision and Dolby Atmos in every auditorium, plus 16 lanes of bowling, laser tag and rock climbing.

Worth being straight about: as of the April 2026 reporting on the project, no construction timeline or permit schedule had been finalized, and organizers said design work, permitting and traffic and parking plans still needed to be worked out before anyone breaks ground. It's real, and it's the intended anchor for the whole corridor, but it's further out than the restaurants already moving into finished buildings.

The Bigger Bet Two Blocks Over

On the site of the old City Hall, developers the Gotham Organization and the DeNunzio Group held a ceremonial groundbreaking on April 6, 2026 for The Bluffs, a 630,000-square-foot mixed-use project with a 400-unit luxury rental building, more than 10,000 square feet of retail and 440 parking spaces. It's described locally as the second and more prominent piece of a two-project development from the same developers.

A few blocks away, the city's new $31.6 million City Hall at 200 S. Myrtle Avenue, a two-story, 40,000-square-foot building that broke ground in 2024, is in the middle of phased move-ins scheduled for August and September of this year. If you've driven past Myrtle Avenue recently and noticed moving trucks, that's what you're seeing.

What's Actually Booked This Month

For residents, the most immediate way to feel the shift is at The BayCare Sound, the amphitheater inside Coachman Park. Deep Purple plays there tonight. Blues Traveler, the Gin Blossoms and the Spin Doctors follow on August 31. John Fogerty and Steve Winwood are booked for September 19, and Freedom Rocks, featuring 38 Special, the Marshall Tucker Band and Don Felder, rounds out the fall lineup on October 11. Whatever downtown Clearwater becomes over the next few years, right now it already has a concert calendar that would have been hard to imagine when Cleveland Street was still mostly boarded storefronts.

What This Means If You Already Live Here

The generic version of this story says downtown Clearwater is having a moment. The more useful version says the moment has a shape you can actually track. Three buildings are done. Six more on the same block are next, expected to finish late this year or in 2027. One hospitality group is choosing where its flagships go first. One funding structure is paying for the historic restoration underneath all of it. And two much larger projects, the EVO complex and The Bluffs, are set to bookend the corridor once they catch up to the pace the restaurants have already set.

If you're already spending your Friday nights on this stretch of Clearwater, the next building to watch is the Brown Brothers Building at 615-621 Cleveland and its five neighboring storefronts. That's the next domino, and given how quickly Rippers and Streetlight Taco went from announcement to opening, it's worth keeping an eye on before it's suddenly finished too.

For more on how this part of the city fits into the bigger picture of living in Clearwater, our Clearwater neighborhood guide has additional local context worth bookmarking. And if downtown's momentum has you thinking about what your own Clearwater property might be worth in this market, Khristian Marcotrigiano and the SoldByKhris team are always glad to talk it through, starting with a free instant home valuation.