Drive west on State Road 434 past the entrance to The Springs and you will pass two signs that tell opposite stories about the same half mile of road.
One belongs to a Jack in the Box that opened this year inside the shell of a Wendy's that sat empty for months. The other belongs to nothing at all, because the Chick-fil-A that was supposed to go up on a former bank site a few blocks away never broke ground. Both projects looked at the same stretch of Longwood commercial frontage in the same window of time. One moved forward. One walked away. The difference between them is not about whether people want fast food on 434. It is about whether a building already exists to put it in.
That distinction, once you notice it, explains a lot of what has changed and hasn't changed along the corridor outside The Springs' gate this year.
The Same Stretch of 434, Two Different Outcomes
The Jack in the Box at 815 West State Road 434 sits in a building that used to be a Wendy's, and according to the franchisee behind the project, the chain had not operated in Florida in roughly three decades before this location. The City of Longwood's development tracker now lists the site as open, and the company has said publicly that it plans to use this Longwood store as the first of ten new locations it intends to open across greater Orlando.
A few blocks away, a different national chain hit every checkpoint a city government can offer and still didn't build. The Chick-fil-A project on a former Fifth Third Bank site was fully approved and fully permitted, according to the city's own development update, before the developer pulled out. The city's notice to residents put it plainly: the developer cancelled the project "citing unexpectedly high costs." The bank building has since changed hands to a commercial developer who is now exploring other uses for the site.
Same corridor. Same year. One chain took over four walls that already existed. The other needed to build from scratch, and the math didn't work.
Reuse Is Winning, Ground-Up Is Stalling
Once you see the Jack in the Box and Chick-fil-A story, a pattern shows up everywhere else on the map.
Trustco Bank is opening a 16,000-square-foot regional headquarters at 225 West State Road 434 this year, and the project is a renovation of existing medical office space rather than new construction. EōS Fitness has told the city it plans to move into the old LA Fitness building, which closed in March 2026, with a tentative opening window of September. As of the city's most recent update to its development map, that project was still listed as an anticipated permit submittal rather than a confirmed date, which is worth knowing if you were planning to time a membership around it.
Here's how the active projects on the corridor break down:
| Site | What's happening | Reuse or new build |
|---|---|---|
| 815 W. SR 434 (former Wendy's) | Jack in the Box, now open | Reuse |
| Former LA Fitness building | EōS Fitness, tentative September 2026 | Reuse (permit pending) |
| 225 W. SR 434 (former medical office) | Trustco Bank regional HQ | Reuse |
| Former Fifth Third Bank site | Chick-fil-A, cancelled | New build, stalled |
| Oak Reserve | New 16,000+ sq. ft. office building | New build, underway |
The one true exception on that list is Oak Reserve's new office building, which shows the corridor isn't frozen on ground-up construction across the board. But among the retail and restaurant projects specifically, the pattern holds. Vacant buildings are filling. Vacant lots that need a full retail build from the ground up are the ones running into trouble.
The residential side of the ledger tells a slightly different story. The city has a 3-unit townhome project under review and a 4-unit townhome project already approved, developed by Oakwood Construction. A 50-unit, three-story multi-family building cleared through administrative, staff-level approval rather than a public hearing, because the use fit the property's existing zoning outright. Small-scale residential infill is still moving even while large ground-up retail construction stalls out. It's a useful thing to know if you've wondered why a new restaurant seems to show up in an old strip mall faster than a new building goes up from bare dirt.
Fire Station 15 Is the One Public Project Actually Under Construction
Not everything on this stretch is retail. The city signed a demolition contract for the old fire station adjacent to Reiter Park, with architectural plans for its replacement already complete and demolition originally targeted for the second quarter of this year. That puts the project either mid-build or just past the demolition phase by now, depending on how closely the contractor held to schedule. It's a slower-moving project than a restaurant build-out, but it's one of the only public infrastructure projects actually breaking ground on this side of town, which puts it in the same category as Oak Reserve: real new construction, just not retail.
Reiter Park Still Runs the Saturday Morning Clock
Whatever changes around it, Reiter Park at 311 West Warren Avenue keeps its own schedule. The Longwood Farmers Market runs every Saturday from 9 a.m. to 1:30 p.m., rain or shine, according to the city's own calendar, and it's the kind of fixture that doesn't care what's happening two blocks over on 434. Produce, baked goods, local vendors, the same rhythm week after week. If you live inside The Springs and want a reason to be out the gate before the day heats up, that market is still the most reliable one on the calendar, fire station construction or not.
What the Corridor Is Actually Telling You
None of this changes what it feels like to live behind The Springs' gate, spend a Saturday at the community pool, or walk the trails along the Wekiva River Conservation Area edge. But it does explain something that might otherwise look random: why a new tenant seems to show up in an old building faster than a new one gets built from the ground up nearby. Vacant space with existing walls, existing parking, and existing utility hookups is a much easier and cheaper project to greenlight than a full retail build on an empty lot, especially with construction costs where they've been. That's the actual mechanism behind the Jack in the Box opening while the Chick-fil-A stalled, and it's likely to keep playing out the same way as more of the corridor's older buildings turn over.
If you're the kind of resident who notices these things while you're driving to the farmers market or dropping off dry cleaning, keep an eye on the old LA Fitness building this fall. Whether EōS actually opens on schedule, or slips the way a lot of "tentative" dates on a city permit tracker tend to, will tell you something real about how fast this particular stretch of Longwood is willing to move.
Curious what any of this means for your home's value inside The Springs, or just want a second opinion from someone who watches this corridor closely? Holt Real Estate is happy to talk through it. Get a Free Home Valuation whenever you're ready.
