Downtown Windermere's Empty Corner Just Filled In, and Not One New Tenant Is a Chain

For years, the corner of Main Street and East Sixth Avenue was the one thing in downtown Windermere that never seemed to move. Chain-link fencing around two aging single-family lots, a hair salon and a coffee shop that had clearly been there since before most current residents arrived, and a lot of speculation every time a new rendering showed up at a Town Council meeting. Anyone who has driven through downtown on the way to Publix or the Lake Butler boat ramp has watched that corner sit half-built for what felt like a decade.

It took sixteen years from the day the land was bought to the day the first customer walked in. And what finally filled that corner in is not what most small towns get once a developer clears the approvals. No drive-through, no recognizable national logo on the sign. Nearly every business now open or opening on that stretch of Main Street is run by someone who already lives in Windermere or grew up close enough to walk there. That was a choice, not a coincidence, and it explains more about how this town actually operates than a simple list of new restaurant names would.

Sixteen years from purchase to first customer

Jim Gissy and Jim Karr, longtime business partners, bought most of the properties on that corner back in 2009 for $500,000. The rezoning request didn't reach Windermere's Development Review Board until February 2021, and the Town Council didn't approve a final development plan for the 2.17-acre parcel until August 2023. Construction, led by local general contractor Hembree Construction and brothers Jay and John Hembree, who both grew up in town, took roughly two more years after that. The first tenant didn't open its doors until December 1, 2025.

That is what "revitalizing downtown" looks like in a town small enough that every rezoning gets debated by name in a public meeting, not by a planning commission most residents have never heard of.

What's actually open right now, and what's still filling in

Fresco Pizzeria is the one most residents will recognize first. It's the Scialoia family's second location, nineteen years after they opened Fresco Cucina Italiana as a small deli in Dr. Phillips back in 2006. The Windermere spot leans grab-and-go, with sandwiches, wood-fired pizza, and Italian baked goods built for people picking up dinner between school drop-off and practice, plus a wine-dinner side for slower nights. Windermere Brewing, which has operated downtown since July 2022, brews a custom Italian-style beer specifically for the new location. Achille Scialoia, who runs front of house while his mother Teresa and brother Luigi cook, put the appeal in plain terms: "a lot of people are excited, because they can walk."

Jim Karr was blunt about why the tenant list looks the way it does:

"We never wanted a big corporate brand in here."

That single line explains the whole roster. Karr's family has held at least one property on this block since 1989, and he lived most of his life in Windermere before moving to a home on the west side of Lake Butler. Gissy, an executive at Westgate Resorts, has his own long-standing ties to the town. The businesses they leased to are, almost to a one, run by people with a personal stake in Main Street rather than a regional expansion plan.

The wine bar you can't just walk into

Solvino is the tenant with the most complicated story, and the one most likely to catch a resident off guard. It started as a straightforward wine bar concept from Arjun and Sara Kumar, Windermere residents themselves. The plan hit a wall when the Town Council denied the conditional-use permit Solvino needed to serve alcohol as a stand-alone wine bar. Rather than fight that decision, the Kumars redesigned the business into a full restaurant, since a restaurant serving food doesn't trigger the same permitting requirement. Arjun Kumar described the shift plainly: "We always wanted to be a restaurant; it was just we were limited based on this development."

The redesign turned out to expand the concept rather than shrink it. When another business pulled out of the project, Solvino picked up the extra square footage and used it to build a full commercial kitchen. What opened is not a walk-in wine bar. It's a private membership club with a retail storefront attached, one that prioritizes Windermere residents in its membership rollout and stocks products from a Windermere-based chocolatier, Maison Des Rêves, alongside a local sourdough bakery.

A few things worth knowing before you plan an evening around it:

• Solvino operates as a members-only club, not a walk-in restaurant, so a membership is the entry point, not a reservation.
• Fresco's grab-and-go counter and its slower wine-dinner service run as two different experiences inside the same space.
• Revel Realty is a rebrand of an existing, decades-old firm, not a new company setting up shop.
• Ace Hardware, Allstate, Elysium Interiors, and Victoria Jewelers are largely returning tenants from the original downtown footprint, not new arrivals.

The road work outside is a different project entirely

If you've spent 2026 rerouting around downtown, that's not the Main Street redevelopment. It's a separate town capital improvement project. Crews have worked through storm drainage, swale grading, and park cleanup on Second Avenue, Third Avenue, Bessie Street, and Butler and Forest streets nearly continuously since February, with work still ongoing in July at Eighth Avenue and Magnolia Street. Fernwood Park and Palmer Park have both seen swale and rain garden work as part of the same effort. None of it is connected to the Gissy and Karr project, but the two have overlapped enough this year that it's easy to assume one caused the other.

What to watch before the year is out

The corner that sat empty for sixteen years is finally doing what a downtown corner is supposed to do, which is give people a reason to park the car and walk somewhere. Whether that reason is a slice from Fresco, a membership at Solvino, or just watching who else signs a lease next, the pattern so far has held. Every name on that roster has a personal address in or near Windermere attached to it. For a town this size, that is the actual story, not the storefronts themselves.

If you're curious how a small downtown's changes like this tend to ripple into home values and buyer interest in Windermere, that's exactly the kind of local read the Mary Rossi Team tracks closely. Get in Touch if you'd like to talk through what's happening in your corner of Central Florida.