For most of the last decade, if you wanted a real dinner out on a Tuesday night, you drove past downtown Windermere, not into it. The four or five blocks around Main Street held a coffee house, a realty office, a couple of homes, and not much reason to park. Jim Karr, the developer who has owned property there since 1989, put it plainly back in 2021: the town had grown, but the commercial footprint hadn't moved with it.
That changed on paper starting in 2021, when Karr and his partner Jim Gissy, an executive vice president at Westgate Resorts, filed plans to demolish those aging buildings and put roughly 21,850 square feet of new commercial space in their place. It changed in practice much more recently. The last of the storefronts opened this past December, and the thing worth noticing isn't the square footage. It's who signed the leases.
The block that sat quiet for years
The parcel Karr and Gissy redeveloped sat at the main entrance to Windermere's town center, and before construction it held two single-family homes, the office of Keene's Pointe Realty, and Allen's Creamery & Coffee House, along with an interior design studio and a hair salon. None of it was derelict. It just wasn't much, for a town that had kept growing around it.
The plan that replaced it had to clear Windermere's Development Review Board and the Town Council, and it had to stay inside the requirements of the Town Center Overlay District, which controls how commercial space in this specific stretch relates to the residential streets around it. That's a slower path than a typical retail buildout, and it shows in the timeline: preliminary plans went to the review board in February 2021, and the first tenants weren't serving customers until late 2025.
The Hembree brothers, who grew up in Windermere, led the construction. That detail matters more than it might sound. This wasn't an out-of-town contractor parachuting in to hit a deadline. It was two guys who learned to ride bikes on these same streets, building the thing that would replace the buildings they grew up walking past.
What actually filled the block
The finished project didn't chase a national chain to anchor it. Karr was direct about that from the start. What moved in instead:
- Fresco Pizzeria, which opened at the corner of Main Street and 6th Avenue on December 1, 2025. It's the second location for the Scialoia family, who have run Fresco Cucina Italiana on Turkey Lake Road in Dr. Phillips for close to two decades. The Windermere spot serves wood-fired pizza made from 48-hour fermented dough, Italian sandwiches, cannoli, and morning cornetti and cappuccino, with a slightly more elegant wine-tasting side for evenings.
- A high-end wine bar and restaurant from Arjun and Sara Kumar, who live in Keene's Pointe, a few minutes from the storefront they now own.
- Ace Hardware, Allstate Insurance, Elysium Interiors, and Victoria Jewelers, rounding out the block with the kind of everyday stops a town this size usually has to drive somewhere else for.
Windermere Brewing, which has been open in downtown Windermere since July 2022, brews an Italian-style beer made specifically for Fresco Pizzeria. That's not a supplier relationship you get by chasing the highest bidder for a storefront. It's what happens when the businesses on a three-block stretch already know each other.
Achille Scialoia, who runs Fresco Pizzeria with his mother Teresa and brother Luigi, talked about the location less like a business decision and more like closing a loop. People in Windermere had been driving to his family's restaurant in Dr. Phillips for years. Now the walk works the other direction.
"That's also the most exciting thing for me, is to have people just walk from their houses that's just down the street, come grab a sandwich, grab a glass of wine, have a little salad or pasta, be happy and go home."
That's the sentence that separates this from a standard downtown refresh. He's not describing foot traffic. He's describing his own neighbors.
Why the tenant roster reads like a guest list
Karr said it more than once during the leasing process: Windermere didn't need a big corporate brand. What the town needed, in his words, was something where people know the owners and feel at home. The Kumars live in Keene's Pointe. The Scialoias built their reputation nearly two decades down the road in Dr. Phillips before bringing it here. The Hembrees grew up on these streets before they built on them.
None of that is required for a commercial redevelopment to work. Plenty of towns fill new storefronts with regional franchises and call it revitalization. Windermere's version reads differently because the people behind the counter are the same people you'd run into buying produce at the Friday market or picking up a hammer at Ace Hardware on a Saturday morning.
The Friday ritual that was already here
None of this replaced what downtown Windermere already had going for it. The Windermere Farmers Market has run on Fridays from 9 a.m. to 2 p.m., weather permitting, on Main Street in front of Town Hall, for years before any of the new storefronts broke ground. It sits a few doors down from the 1924 Town Hall building and the 1890 Historic Windermere School House, a National Register site that's been standing since long before anyone was arguing over rezoning applications.
The market still runs the way it always has: local produce, baked goods, honey, plants, the kind of vendor list where you start recognizing faces after a few visits. What's different now is what happens after you've filled your bag. A Friday morning at the market used to be the whole event. Now it can lead straight into an afternoon glass of wine at the Kumars' bar or a cannoli at Fresco, without moving your car.
What actually changes on a Tuesday night
The honest version of what changed in downtown Windermere isn't about property values or square footage counts. It's that the walk from a house near Main Street to a real dinner out used to end at a coffee shop, and now it ends at a wood-fired pizza oven, a wine bar run by people from Keene's Pointe, and a beer brewed specifically for the pizzeria next door by a brewery that's been part of downtown for four years.
The town still runs Food Truck Nights, Light Up Windermere, and the Windermere Fine Art Show at Town Hall throughout the year, the same events that have anchored the calendar for a while. The 5K/10K Run Among the Lakes and Windermere PetFest still draw the same crowd of neighbors. What the new block adds isn't a reason to leave the house. It's a reason to stay on Main Street a little longer once you're already there.
If you've been putting off checking out the new storefronts because you assumed it would feel like every other retail redevelopment in Central Florida, that's the part worth reconsidering. The names on the leases aren't from somewhere else. They're from here.
Windermere Isle sits close enough to this stretch of Main Street that a Friday market run and a Fresco Pizzeria dinner fit into the same evening without much planning. If you're weighing what daily life actually looks like in this corner of Windermere, or you're further along and thinking about a move, Pristine International Realty can walk you through it in English or Português. Request a Free Consultation via WhatsApp and we'll answer the questions the listing photos can't.
