The most visible sign of the Searstown rebuild is the hole in the front of the old Sears building on North Roosevelt Boulevard. Demolition crews had opened it up by June 30, 2026, behind a construction fence that also surrounds the separate building that used to be Sears Auto Center, according to Keys Weekly. For many New Town and Midtown households, though, the first change they actually felt came a few weeks later at the driver license counter. That counter is no longer in the plaza.
The whole project is built around one idea. Searstown is being replaced in pieces while it keeps operating, and its Publix will move twice so the grocery store never has to close. That design keeps the parts people use most open. It also means the plaza will keep changing for roughly five years, with only a handful of firm dates along the way.
The first thing to leave was the license office
The Monroe County Tax Collector's Searstown Driver License Office stayed open through Friday, August 7, 2026. The Key West Main Office then closed August 10 to 12 so the state could install new driver license equipment, and it was scheduled to reopen for consolidated service on Thursday, August 13, at noon, according to the office's July 30 announcement.
Key West driver license service is now at 1200 Truman Avenue, Suite 101, in the Harvey Government Center. The Tax Collector's office directory lists it there. The announcement says the same driver license services offered at Searstown are available at the Main Office, along with the office's other services, and that the lobby counter was expanded with more customer service and supervisor workstations.
The Tax Collector gave its own reasons for the move, and wait times were one of them. The office's review found that Searstown customers generally waited longer than customers at the Main Office, and peak waits at Searstown sometimes reached two hours. Constitutional Tax Collector Sam Steele put the consolidation this way:
"This project is about better service and responsible use of public resources. By consolidating our Key West operations into one location, we can make services more convenient for the public, improve efficiency, reduce wait times and eliminate approximately $136,000 in annual recurring costs."
One detail matters to people who live near Truman Avenue. As part of the consolidation, the announcement says, the state approved a new driving test route designed to limit the impact on nearby residential streets.
The Searstown license office was a separate leased location, so it could leave on its own schedule. The plaza's anchor tenant can't simply leave, and that's why the rest of the project is sequenced the way it is.
How Publix stays open while it gets replaced
Publix has anchored one end of Searstown for more than 40 years. Keys Weekly reports that the company bought the whole plaza in January 2022. The Keys Citizen dated Publix's purchase of the shuttered Sears property to late 2021, after the department store closed in August 2020. The approved development plan sets out the order of work:
- The old Sears space at the far end of the plaza is demolished and rebuilt.
- Publix moves into a temporary store in that rebuilt space.
- A new supermarket goes up at the opposite end, on the site of the current store.
- Publix moves back into its original location.
- The remaining spaces are replaced section by section.
The project is split into four phases to keep interruptions for tenant businesses as small as possible. Bart Smith, the Key West attorney who represents the developers, told the City Commission that in April 2025. Under that plan, the rest of the center keeps running while one end is torn down and rebuilt.
That's why the tenant list looks the same as it did last spring. Keys Weekly's July report listed Royal Furniture, TJ Maxx, Outback Steakhouse, the Imagination Station toy store and medical offices as plaza tenants. We found no announcement that any of them had moved or closed as of early October 2026. The license office is the only departure we could confirm.
What the finished center is planned to include
The Planning Commission approved the major development plan unanimously at its February meeting. The applicant was Smith, Hawks, P.I., on behalf of Publix/Real Sub, LLC, for 3200 N. Roosevelt Blvd., the Keys Citizen reported. The City Commission followed with a 6-1 vote in April 2025. The plan as the Citizen described it:
| Element | Planned figure |
|---|---|
| Total commercial retail space | Almost 180,000 square feet |
| Grocery store | 66,854 square feet, built over a covered parking deck |
| Additional retail | 56,166 square feet |
| Restaurant | One, plus multiple new retail spaces |
| Estimated daily vehicle trips | 7,789, classified as low-intensity commercial retail |
| Trees | 129 removed, 575 planted |
| Palms | 82 removed, 205 planted, 18 kept |
The redevelopment also brings the center up to current building codes by raising its structures above base flood elevation. For drivers on North Roosevelt, the Citizen reported that the 7,789-trip estimate falls well below the threshold for a higher traffic impact classification. The plan also calls for better pedestrian pathways and more green space at a plaza that dates to 1965.
The plan does not include housing. City officials have discussed workforce apartments above Searstown, Overseas Market and Key Plaza for decades, and the city once approved a density increase of 40 units per acre to encourage shopping centers to add homes. The commission approved this plan without requiring housing, and the one dissenting vote was cast over that omission, Keys Weekly reported in 2025. That means the debate over housing on North Roosevelt will now come down to the other two original strip malls.
The calendar, known and unknown
Searstown is one of Key West's three original strip malls. Here is its history and the forecast schedule in one place:
| Date | Milestone |
|---|---|
| 1965 | Searstown Plaza built on North Roosevelt Boulevard |
| August 2020 | Sears closes |
| Late 2021 to January 2022 | Publix buys the Sears property, then the full plaza |
| April 2025 | City Commission approves the major development plan, 6-1 |
| By June 30, 2026 | Demolition opens up the front of the Sears building |
| August 7, 2026 | Searstown driver license office's last day |
| August 13, 2026 | Consolidated license service set to open at 1200 Truman Ave. |
| Fall 2028 | Forecast opening of phase one |
| 2031 | Forecast completion of the final phase |
The 2028 and 2031 dates are forecasts the developer's attorney gave the commission. They are not completion guarantees. Several things people will want to know had not been publicly reported as of early October 2026:
- When Publix will open its temporary store on the old Sears site
- Any construction update after the July demolition report
- Any changes to parking, entrances or traffic lanes on North Roosevelt
- Whether any current tenant plans to move, and if so, where
The site plan and the video of the Planning Board meeting are posted on the City of Key West website. The city's commission agendas are where the next official milestone is most likely to appear.
Our agents live and work in New Town and Midtown, and we follow the North Roosevelt corridor closely. If you own property near Searstown and want to talk through how a five-year rebuild could affect your plans, the team at BHHS Knight & Gardner Realty is glad to help. Contact Us.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
