Key Plaza Could Be Key West. They’re Giving Us Boca.

Streets for People  |  Friends of Car-Free Key West & Duval Street/Historic Downtown  |  Chris Hamilton  |  June 27, 2026

Drive into Key West on North Roosevelt Boulevard and tell me you have any indication you’ve arrived in paradise.

Four lanes, a turn lane, traffic moving like it’s got somewhere better to be. McDonald’s, Walgreens, Home Depot, multiple car dealers, a Wendy’s, Dunkin Donuts and more. Big signs shouting at you because the stores sit a football field back behind their parking lots and need the help. Save for the palms along the water, you could be on US-1 outside Boca or US-41 outside Naples or any stretch of asphalt on the mainland. We built the one ugly mile in America’s prettiest island town, and we built it to look like everywhere else.

Now we’re slowly rebuilding it. And you know what – yea, it’s going to look refreshed and better, and it’s going to be exactly the same.

Couple years back, the Overseas Market got a facelift — new parking lot, more trees, a roundabout people actually talked about for a minute. But still the exact same auto-oriented strip mall. Fencing just went up at Searstown as it’s about to be torn down and rebuilt. Same massive parking lots fronting the Boulevard and indistinguishable from what’s there now, save that it will be prettier. And this Thursday, the city’s Development Review Committee took its first look at a development proposal to totally rebuild Key Plaza, the Publix-anchored center at Roosevelt and Kennedy that used to have a Kmart. Guess what? Surprise surprise. They’ve proposed another glorified and gussied up asphalt wonderland.

Three shopping centers, three rebuilds, and every one of them a nicer, hardened, better-drained version of the same old mainland strip mall. And not one of these projects chose to build any housing. Win the engineering, lose the heart and soul of the island.

Yes, there’s some good happening with these redevelopments — and we’ll get to it. But let’s walk through what we keep getting wrong, why it matters way past N. Roosevelt Boulevard, and consider what if anything the city can still do about it. Come explore with me.

A Better Version of the Same Thing

The Key Plaza plan is, by almost any measure, better than the sad, flood-prone asphalt lake sitting there now. The 1970s buildings come down and go back up to current flood code. The new Publix gets lifted a full story with parking tucked underneath — exactly the kind of smart, elevated design this island needs more of. Total retail actually shrinks by about 64,000 square feet, the stormwater gets fixed so the lot stops flooding every time it rains, and the plans add roughly 130,000 square feet of new landscaping. You can read the full rundown of what’s proposed in in today’s Key West Citizen paper.

All real. All better. But better is not the same as different. This is a better version of the same thing — but better than terrible isn’t the bar. Not here in Paradise.

Makeup on a Parking Lot

So here’s what bugs me.

There is nothing — not one thing — about this design that says Key West. Drop these site plans on a desk in Boca, in Naples, in Fort Myers, in any one of a thousand mainland Florida suburbs, and nobody would blink. The anchor sits at the back of the lot. The parking sits out front, fronting both North Roosevelt and Kennedy Drive. A few small retail pods float near the street so you can see clear through them to the big boxes behind. Cars first, buildings second. It’s the formula every strip mall in America has followed since about 1975, and we’re about to pour it fresh on the most valuable two-by-four-mile patch of island in America.

The city’s own slide shows the plan builds 704 parking spaces — and notes, right there on screen, that it still exceeds code. Nobody required all that asphalt. The code asked for less (636) – which to us still seems excessive. And that asphalt takes up almost 60% of the entire 19 acres with 22% accounted for in buildings and 20% for so called “open space/landscaping.” 

The plan dresses this up promising much more “green space” – going from 5% to 20% and noted as “open space/landscaping” in the data table. That’s got to be good, right? But look at where that “green” actually ends up. It’s the skinny islands between parking rows. It’s the landscaped strips around the edges. The application gives away the bias as the buffers along North Roosevelt are there to “screen the commercial activity and present a more attractive appearance to passing drivers.” Are you kidding me, more attractive for people in cars on the highway – insert eyeroll emoji here. The landscaping isn’t a park, or a plaza, or a place. It’s makeup on a parking lot — greenery whose job is to hide the asphalt from people driving past. That’s not open space. That’s a nicer-looking windshield view.

Here’s what really cheeses me, as someone who spent a career around this stuff. Nobody builds this way anymore — not if you’re thinking about people and community. Go look at what Publix itself is building on the mainland (we’ll get there). The whole industry has spent twenty years relearning what Duval Street never forgot: people want to walk, they want to stroll from store to store. They want the storefront at the sidewalk, the door right there, the parking tucked behind or below where it isn’t the first and last thing you see. Why is there no retail fronting the Boulevard? Why nothing built up to Kennedy with the parking pushed to the rear, main-street style, stitched into the neighborhood behind it? On an island this small, this walkable and bikable, this starved for the real thing — why did nobody reach for it?

So I asked them. After the meeting, I put it straight to the applicant’s team: did you consider a more urban, street-front layout — the massing toward Roosevelt and Kennedy, the parking behind, something less suburban? The answer, flat as the parking lot itself: “No. Didn’t consider urban or anything else.” Didn’t consider it. On nineteen acres. On this island. It never crossed the table.

And here’s the kicker — this isn’t a money problem. When I asked what the project will cost, they told me it’s well north of $20 million, comparable to the roughly $37 million going into Searstown. So we’re not talking about a developer pinching pennies and giving us what they can afford. We’re talking about a $37-million investment that couldn’t spare a single thought for whether this might look or work like Key West instead of Boca. It’s not the cheapest thing they could build. It’s the least they could be bothered to imagine.

I know the answer I’ll get. Everything around it looks like this, so this is what fits. But somebody, on some project, has to be the one that breaks the pattern instead of pouring it again. That’s how a trend starts. One developer, one site, one site plan that looks like a small city instead of a county road.

This matters way past Roosevelt Boulevard — because every time we hand someone another acre of free parking out front, we’re not just building a store. We’re training a habit. We teach people that the way you get anything in Key West is you drive to it and you park at the door. Then they take that expectation downtown — where the streets are narrow, the parking’s tight, and the whole magic of the place depends on people getting out of their cars. They circle Duval hunting for a Doris Day spot that was never coming. Or they just don’t go, because N. Roosevelt taught them parking is a right and downtown doesn’t deliver it. The walkable downtown is the product this island sells. N. Roosevelt keeps quietly undercutting it, one rebuilt parking lot at a time.

Housing: Publix Knows How. So Does the City.

Here’s the elephant in the room. We are a 4-by-2-mile island with the worst housing crisis in Florida. Our nurses commute from Homestead. Our line cooks sleep in their cars. And here sits 19 acres — nineteen! — getting demolished and rebuilt from the dirt up, a generational do-over on one of the biggest developable parcels in the city. And not one bedroom is part of the plan. Not one. I asked them that too — was housing ever considered? “No.” That was the whole answer.

Now, the easy thing is to dump this all on Publix, and Publix has earned some of it. But before we do, look at what this same company builds when somebody asks them to. In Charleston — a historic, flood-prone coastal city not unlike ours — Publix sits on the ground floor of a nine-story building with apartments stacked above it. [Link: WestEdge] In downtown Coral Gables, Publix is replacing an old single story store and building an 18-story residential tower on top of a new Publix. [LINK: Coral Gables] In Raleigh, there’s a Publix with 400-some apartments sitting right on top of it. [LINK: Publix at Peace] That’s just a sampling. This isn’t exotic. This is Publix’s own playbook, the one they run in any market where the locals expect more than a parking lot. 

And it’s not just a mainland thing. Drive up to Tavernier and watch a Publix get built right now with 86 units of workforce housing behind it. It took the developer three brutal years — staff said no, neighbors fought it, the state said no and then reversed — but it is happening, in the Keys, ROGO and all. So nobody gets to say it can’t be done here.

Which leaves two questions.

First: why does Publix think so little of Key West? In Charleston and Coral Gables and Raleigh they bring their A-game — street-fronting, housing on top, structured parking, the works. Here, on the most special island in America, they bring us the cheapest thing that clears the code. They lifted their own store a full floor and tucked parking underneath, so we know the talent was in the room. They just didn’t spend it on us. And here’s what makes it sting: back in 2021, when the City floated the idea of housing over these centers, Commissioner Sam Kaufman said the City had already heard Publix itself was interested in building employee housing. Interested. Five years ago. Somebody just had to pick up the phone and hold them to it.

Which is the second question, and the one that should keep all of us asking questions this election season: where was the City? This wasn’t a surprise that landed out of nowhere. Back in 2021, Commissioners Kaufman and Mary Lou Hoover did the work — they ran a community survey on the future of North Roosevelt and 770 people answered. Want to know what those people asked for? Bike and pedestrian-friendly design, 74%. Mixed-use residential and commercial, far up the list. Parking tucked behind or inside the buildings instead of fronting the road. The public told the City exactly what it wanted on this Boulevard — and the plans rolling through today deliver almost the precise opposite.

And we did this exact dance just last year with Searstown, a few blocks up the Boulevard — same attorney, same four-phase shuffle, renderings so alike you could swap them and not notice. When that one came through with zero housing, Kaufman cast the lone no vote, reminded everyone the city had already approved a density bonus of 40 units per acre specifically to get housing built over these very centers, and asked how many more times we were going to drop the ball. Commissioner Hoover agreed we’d dropped it — and then voted yes anyway along with Mayor Henriquez, Vice Mayor Carey, and Commissioners Castillo, Haskell and Lee. That was a lost opportunity. We can’t make the same mistake again.

I sat through that whole DRC meeting. Every department in the building had a representative at the table — Planning, Engineering, Fire, Utilities, Police, the bike-and-pedestrian folks, even the tree people and ADA. Smart, dedicated public servants, every one, and they asked good, hard questions about stormwater and hydrants and traffic signals and sidewalks. For forty minutes. And in all that time, on a generational redevelopment of nineteen acres in a housing emergency, not one person asked the question: where are the homes? 

Which makes me wonder. Housing is one of the City’s four stated strategic priorities. Every other discipline gets a seat at that table. So why isn’t there one for housing? When a 19-acre site comes up for its first review, shouldn’t somebody in that room have the job of asking whether it should include homes? I don’t know the answer. But it sure seems like a question worth asking out loud.

That’s the part that hurts. The tool exists. The City built the density incentive in 2019 to do exactly this, on exactly these parcels. The public asked for it in 2021. Publix was reportedly interested. We’ve even found the ROGO units when we wanted them — we found them for the Lofts at Trumbo, we found them for the Lofts at Bahama Village, both downtown, both recent, both for workers. Every piece was on the table. And on Searstown, the Commission looked right at it, named it, and approved the parking lot anyway. Now Key Plaza rolls up with the same empty space where the housing should be, and the only question that matters is whether anyone at the City does one thing differently this time.

It isn’t just me. Linda Grist Cunningham — my friend, a local writer, and something close to this island’s conscience — looked at the Searstown plan and said she’d be a lot happier if the city had required two or three floors of housing on top. She talked about it here too. And every time these projects come up on Facebook, there’s the same chorus: hey, why not put some housing up there? When the island’s conscience and the car-free crank and half the comment section all land in the same place, that’s not an agenda. That’s just the obvious thing, sitting there unbuilt.

It’s Not Too Late to Get This Right

It’s like déjà vu all over again as in 2022 we wrote this story: “Time to Reimagine Car-Centric, Mainland Style Searstown and Kmart Into Island-Friendly Centers with Housing.” And here we are again. And maybe this time we can get it right as Thursday was the first look, not the last. Nothing’s poured. Nothing’s approved. From here Key Plaza goes to the Planning Board, then the City Commission — the developer’s own attorney told me the whole process could run another year and a half. That’s not a closed door. It’s a wide-open window.

But a window only matters if somebody climbs through it. These projects sail through with no housing and no imagination not because anyone’s twirling a mustache, but because the room is quiet — the applicant brings what’s easiest, the process checks its boxes, and unless someone stands up and says we want more than this, more than this never gets asked for. Searstown sailed through that quiet. This one doesn’t have to. 

So if you’ve read this far, you’re the someone. Email your commissioners and the people running this summer. Show up when Key Plaza reaches the Planning Board and say it plain: buildings to the street, parking behind, and homes for the people who keep this island running. It’s a once-in-a-generation rebuild. We don’t get a do-over on the do-over.

We want to make that turn at the Triangle, head down the Boulevard, and know — in our bones, before you’ve read a sign — that we’re not on the mainland anymore. That we’re someplace that decided to be itself. We can build that. Or we can build a nicer place to park, indistinguishable from every place else. We can do better. Do we have the guts to reach for it?

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Chris Hamilton is the founder of Friends of Car-Free Key West & Duval Street/Historic Downtown, a local advocacy group championing sustainable mobility and vibrant public spaces. Subscribe to the blog and follow on Facebook, Twitter, and Substack for updates. All stories are cross posted at KONK Life News. Originally from Washington, D.C., Chris spent over two decades leading nationally acclaimed initiatives in transit, biking, walking, and smart growth for Arlington County, VA’s DOT. Since moving to Key West in 2015, he has embraced a car-free lifestyle downtown, dedicating his time to non-profits and community projects. Explore all Streets for People column articles here.