For most of the last decade, if you lived in Clearwater and someone asked what was happening downtown, the honest answer was "not much." Cleveland Street had bones, a few holdout businesses, and a reputation the city's own vice mayor recently summed up in one word: for decades, downtown Clearwater has been known as a ghost town, and now signs of life can be seen in the 400 to 600 blocks of Cleveland.
That framing is outdated by about six months. Between April and mid-July of 2026, the corridor between Osceola and Myrtle picked up a Michelin-pedigree restaurant announcement, a European café, a public showroom, a completed demolition on a $50 million anchor site, and three finished historic restorations. If you live here, the practical shift is this: Cleveland Street is now a place you can plan a Saturday around, not a place you drive through on the way to Coachman Park.
The Telephone Building Finally Has a Tenant
The corner to know is 534 Cleveland. Rippers, a new American-style restaurant from the team behind Michelin-starred Rocca, is moving into Clearwater's historic Telephone Building on Cleveland Street. Located on the ground floor at 534 Cleveland St., Rippers will be Tastes Pretty Good Hospitality Group's first Pinellas County concept, and is also the first to move into the Telephone Building, which was built in 1914 and is the first fully-restored historic landmark completed by the Cleveland Street Alliance's coordinated restoration initiative.
The pedigree matters because Tastes Pretty Good is not a chain testing a suburban market. Besides Rocca, the group also operates Michelin-recognized Bar Terroir and Michelin Bib Gourmand Streetlight Taco. Culinary director Bryce Bonsack said the space itself shaped the concept:
"When we walked into that space, we were immediately drawn to it. It's historic, it has incredible character and there's so much history behind it."
Read that as a data point about how the corridor is being programmed. The restored buildings are pulling operators who could open anywhere in the Bay area and are choosing this block on purpose.
Three Restorations, Three Addresses
If you have been away from downtown for even a year, the storefronts read differently now. Three of the corridor's most recognizable historic buildings finished restoration in the last cycle, and a city presentation in late May put them on the map in one sentence.
| Building | Address | Original build | Status as of May 2026 |
|---|---|---|---|
| Peoples Bank | 432 Cleveland | 1910, remade 1920s Mediterranean Revival | Restoration complete |
| F.W. Woolworth | 519 Cleveland | 1910, Woolworth store from 1928 | Restoration complete |
| Telephone Building | 534 Cleveland | 1914 | Restoration complete; Rippers incoming |
Sources: historic renovations to the Peoples Bank building at 432 Cleveland, the F.W. Woolworth Co. building at 519 Cleveland, and the Telephone Building at 534 Cleveland are complete, per the city's economic development director. Architecture firm Halflants + Pichette led two of them, and the Woolworth work is worth pausing on. Constructed in 1910, the building became a Woolworth store in 1928, and at the time, Clearwater was the smallest city in the country to host one of the more than 1,000 Woolworth locations nationwide. The restoration stripped decades of paint and stucco off the facade to expose the original brick.
For residents, the visible change is not a plaque. It is a legible streetwall between Osceola and Myrtle where three of the tallest, oldest structures now look like themselves again.
The Good Life Showroom Is Actually Useful
Most "vision centers" for downtown redevelopment are polite fictions with a scale model in the corner. The one that opened on April 18 at 331 Cleveland is more interesting because it is doing a job residents can use. Developed by the Cleveland Street Alliance, the showroom is located on the ground floor of the Water's Edge building at 331 Cleveland Street. It is designed to guide visitors through the district's evolution, connecting historic context, current activity and future development within a single environment. The 1,400-square-foot showroom combines large-scale digital media, a detailed downtown model and guided presentation spaces into a single immersive experience. At its center, a 56-foot LED ribbon wraps the interior, presenting a continuous visual narrative of Clearwater's past, present and future.
Skip the marketing framing and use it as a reference. If you want to see which storefronts are next, or where the entertainment anchor is going, the model on the floor is the fastest way to get oriented. Admission is free.
What Broke Ground, and What's Next
The next milestone is the block that has been fenced for months. One of the major upcoming attractions is the proposed EVO Entertainment Clearwater center, an 83,000-square-foot family-oriented entertainment venue. On June 29, the Alliance announced that site demolition had been completed, which is the first construction milestone rather than a symbolic one. The renderings pitch an unusually large cinema component, described in local reporting as a screen 131 feet wide and seven stories tall.
That is the anchor. The connective tissue is the rest of the 600 block. Work on the Brown Brothers Building at 615-621 Cleveland, as well as properties at 623 Cleveland, 629 Cleveland, 635 Cleveland, 639 Cleveland, and 645 Cleveland is expected to wrap up later this year or in 2027. That is a run of six adjacent addresses in active work at the same time, which is why the walk between Osceola and Myrtle is going to look meaningfully different every quarter through 2027.
The dollar figure people keep asking about: the overall downtown Clearwater redevelopment effort is projected to total about $350 million, with nearly $100 million invested in the Cleveland Street projects. The Alliance's own presentation to city council in late May put the private-investment figure specifically at $200 million for the district. Both numbers are large, and both are useful mostly as a way to gauge whether the pace holds.
The Cafés Filling In Between
The corridor is not waiting for the anchor to open before it starts eating. The Alliance's own July release cycle points to Nourish & Nosh Bakery Bistro, a European café bringing fresh, made-from-scratch dining to downtown Clearwater, and press notes have flagged a modern Japanese gathering concept to open at 635 Cleveland Street within the emerging entertainment district.
A block over on East Bay Drive, another operator is taking the same bet on Clearwater's appetite for something other than a chain. Dank Burrito's new Clearwater eatery will open this fall at 4001 E. Bay Drive, serving what the company calls a bold fusion of global street-food inspired flavors in burritos, tacos and bowls. The owner is transforming a former Boston Market into a 3,100-square-foot hangout with custom graffiti that honors Bay Area icons like the Buccaneers, the Sunshine Skyway Bridge and native beach scenes.
None of these are destination restaurants for out-of-town visitors. They are neighborhood rooms designed to be used on a Tuesday.
Coachman Park Is Doing the Programming Work
The reason the Cleveland Street math pencils is three blocks west, at 300 Cleveland St. Coachman Park's redevelopment gave the corridor a reason to fill up on weekends before any of the restored buildings had tenants, and the 2026 schedule kept that pattern going.
- Sea-Blues Festival ran Feb. 28 through March 1 with general admission free, at Coachman Park, 300 Cleveland St., with free downtown parking all day Saturday and Sunday and cashless event operations.
- Clearwater Celebrates America returned July 3-4. The event brings two nights of live entertainment, food vendors, family activities, dazzling light shows and a spectacular fireworks display over Clearwater Harbor.
- The Ginormous Easter Egg Hunt in April and a run of concerts at The Sound have kept the park in weekly rotation.
The practical resident read: Coachman Park is the demand generator, and Cleveland Street is finally converting that foot traffic into places to eat and browse before or after a show.
A Saturday on Cleveland Street, Right Now
If a friend asks how to spend an afternoon downtown this month without leaving a two-block radius, the itinerary is short enough to actually follow:
- Start at 331 Cleveland at the Good Life Showroom to see what is under construction on which block. Fifteen minutes is enough.
- Walk east and read the facades at 432, 519, and 534 Cleveland. The Woolworth brick and the Peoples Bank corner reward a slow pass.
- Continue to the 600 block to see the Brown Brothers work in progress at 615-621 and the EVO site.
- Loop back toward Coachman Park at 300 Cleveland St. for whatever is on the calendar that evening.
- Add Rippers to your list for when it opens, and keep an eye on the 635 Cleveland Japanese concept and Nourish & Nosh.
This is a different downtown than the one Clearwater residents got used to ignoring. It is not finished, and the ownership questions the city council raised on May 28 are not settled. What has changed is that the corridor now has enough dated openings, completed restorations, and scheduled programming to plan around instead of wait on.
If you have been curious what the downtown momentum means for the surrounding neighborhoods, from the waterfront blocks near Coachman Park to the older streets north of Drew, that is the conversation to have with an advisor who watches this market weekly. Reach out to Maria Azuaje to schedule a consultation and get a straight read on where Clearwater is heading next.
