What's Changing Along North Roosevelt: A New Town Guide To The Searstown And Key Plaza Rebuilds

The fence around the old Sears went up this summer, and by the last week of June the front wall was already a crater. If you live in New Town, you probably drove past it on the way to Publix and did the mental math the rest of us did: five years of this, minimum, on the one road every errand in the neighborhood runs through.

Here is the part that has not been said clearly enough in one place. The Searstown teardown and the newly proposed Key Plaza rebuild are not two separate renovations happening to look similar. They are the same developer story, told by the same law firm, on behalf of the same grocery chain, staggered by roughly a year and a half. The sequence is the story. Renderings will come and go. What matters for anyone who already lives here is which errand moves where, and when.

The two projects, side by side

Both are being shepherded through city approvals by Key West attorney Bart Smith of Smith Hawks. Both were reviewed under city planner Taylor Brown's Development Review Committee. Both replace 1960s-era strip malls that sit low in the flood plain. And both were designed with parking lots facing the boulevard, which has already become the loudest local complaint about the plans.

The Searstown sequence, in the order you will feel it

The commission approved a major development plan in April 2025 to rebuild the shopping center in a multiyear, phased approach. Publix will move back into its original location after work begins with the demolition and replacement of the old Sears space. The project will be completed in four phases to minimize interruptions for tenant businesses, with the first phase expected to be completed and open by fall 2028, and the final phase expected to be finished by 2031.

Translated into New Town errands:

1. The Sears end comes down first. That is what you are watching now.
2. A brand-new Publix rises in the Sears footprint, elevated a full story above base flood.
3. The current Publix at the far end closes. Groceries shift to the new store at the opposite corner of the plaza.
4. The old Publix, plus the middle of the plaza, comes down in sections. TJ Maxx, Outback Steakhouse, Royal Furniture, Imagination Station, the medical offices, and the Monroe County Tax Collector's driver license office are all in the middle of that runway.
5. Somewhere in 2031, the last phase wraps and everyone who stayed is under a new roof.

The tenant list matters because the plaza is where non-tourist Key West does its errands. Publix bought the whole plaza in January 2022, which includes Royal Furniture, TJ Maxx, Outback Steakhouse, Imagination Station toy store, medical offices and the local driver license office, operated by the Monroe County Tax Collector. None of those businesses is going anywhere in the short term, but each will have a window during phases two through four when its current storefront is inside a construction fence.

Key Plaza is one plaza behind

If Searstown is the plaza you can already see changing, Key Plaza is the one you should be watching for the paperwork. A proposal to demolish and rebuild nearly all of Key Plaza, the 60-year-old, Publix-anchored shopping center at North Roosevelt Boulevard and Kennedy Drive, got its first formal review by city staff on June 26, the opening step in what the developer's attorney said could be six months to a year-and-a-half trip through city approvals.

The scale is worth sitting with. The roughly 19-acre center, which once housed a Kmart that closed in 2022, would be rebuilt in four phases under the plan. Total commercial space would shrink from about 256,000 square feet to 190,925, a reduction of roughly 64,000 square feet. The Kmart box has sat vacant since March 2022, so a chunk of that "reduction" is space no one has used in years. What the drawings do add is structures built to current flood codes, including a new Publix raised a full story with parking tucked beneath it, plus new landscaping, reduced paved surface to improve drainage, and a reworked stormwater system.

The critical detail for daily life: Key Plaza's Publix and Searstown's Publix are less than a mile apart, and both are owned by the same company. If the phasing on the two projects ever overlaps in a way that pulls both stores offline at once, that is a New Town problem, not a downtown one. Nothing in the current schedule suggests that will happen, but it is worth asking at the next Planning Board hearing.

What actually changes about your week

Strip away the site plans and the tenant list turns into a running list of small logistical questions.

• Driver license renewals. The Monroe County Tax Collector's Key West driver license office sits inside Searstown. When its phase comes up, expect a temporary relocation notice. Renew early if yours lands in a demolition window.
• The Imagination Station block. A generation of Key West parents has done birthday shopping in the same 1,500-foot corridor. That corridor comes down in the middle phases.
• TJ Maxx and Outback. Both were called out specifically by the developer's attorney as tenants the plan is designed to preserve. Preserved does not mean uninterrupted. Expect at least one long closure window each.
• Publix loyalty. Once the new Sears-end store opens in 2028, the old store closes. If you have a preferred pharmacist, follow them across the parking lot.
• The Sears Auto Center pad. That standalone building at the Glynn Archer end is part of phase one. It disappears first and does not come back as auto service.

Nothing on that list is a crisis. Together, though, they explain why the project's four-phase design is the single most important detail in either set of drawings. A single-phase teardown would have wiped out New Town's everyday retail for two years. The four-phase design trades speed for continuity. That is the trade the neighborhood is making, whether it realizes it or not.

The housing argument you will keep hearing

There is a second conversation running in parallel, and it will keep surfacing every time either plaza returns to the commission. Commissioner Sam Kaufman reminded his fellow commissioners that officials have discussed for decades the possibility of construction workforce housing apartments above the Searstown Plaza, Overseas Market and Key Plaza. The city even approved a density increase of 40 units per acre to incentivize shopping centers to add housing.

Neither project includes any. Commissioner Mary Lou Hoover agreed with Kaufman, saying, "We have indeed dropped the ball," before voting in favor of the new Conch RePublix Shoppes as proposed. Kaufman cast the lone dissent on Searstown. Key Plaza is walking in with the same footprint choice. Asked whether the developer had considered a more urban, street-fronting design with buildings brought up to North Roosevelt and Kennedy and parking placed behind, the applicant's representative said no, that an urban layout had not been considered.

For a homeowner, the housing question is not academic. Two 19-acre-ish sites with approved density bonuses, chosen instead to stay one story, sets a precedent for what the next commercial rebuild on the boulevard will look like. If you own in New Town, that precedent affects the character of the street your property faces for the next generation.

Where the neighborhood still gathers while this drags on

Construction seasons will come and go through 2031. The parts of New Town that are not on North Roosevelt keep functioning normally, and it is worth naming them because they are what makes the neighborhood a neighborhood rather than a commercial corridor.

Cozumel Park handles the day-to-day. Its shaded playground, splash pad, artificial turf field, and half-court basketball setup absorb the after-school and weekend traffic that used to spill through Searstown's parking lot on cooler evenings. The Clayton Sterling baseball complex a block from the high school runs youth leagues on weekend mornings. The Blake Fernandez Skate Park along the same fields keeps the teen crowd off the boulevard. Bayview Park continues to host the community events and December's lighted bike ride that anchor the seasonal calendar.

None of that changes because Publix moves 800 feet across a parking lot. It is worth remembering when the construction dust makes the neighborhood feel smaller than it is.

What to watch through the next approval cycle

Three specific dockets are worth tracking. First, the phase-one completion certificate for the new Publix at the old Sears end, currently pointing at fall 2028. Second, Key Plaza's HARC and Planning Board hearings, which under the six-to-eighteen-month estimate would land somewhere between late 2026 and mid-2027. Third, any commission-level negotiation over whether the density bonus finally gets used, either on Key Plaza or on the third boulevard site, the Overseas Market, that has been mentioned in the same breath for twenty years.

If you own a home in New Town, none of these decisions require action on your part. They are worth knowing about because they are the closest thing this neighborhood has to a five-year plan, and because "what's happening across from Publix" is going to be the most frequent question a house guest asks you between now and 2031.

Thinking about what any of this means for the value of a specific address, or planning a move within Key West while the corridor is under construction? Lori Langton has watched New Town's rhythms for more than two decades and is happy to talk it through. Schedule a free consultation to compare notes.