Walk Main Street on a Friday morning today and the storefronts between 5th and 6th Avenue look almost nothing like they did two years ago. A hardware store where a design studio used to be. A pizzeria that didn't exist eight months ago, tucked into the corner where a real estate office once sat. A wine bar going in next to it. If you live in Windermere, you've probably already noticed. What you may not have connected is why this particular stretch filled in the way it did, and why almost none of it looks like the kind of development that usually shows up when a town's real estate gets hot.
The obvious story is that Windermere is growing and outside money is chasing the address. That's not what happened here. The people who built this block already lived on it, and the thing they were solving for wasn't foot traffic from visitors. It was the fact that getting anywhere else in Windermere by car is genuinely unpleasant, and a two-minute walk from your own driveway has become the most valuable amenity anyone on Main Street can offer.
A hardware store proposal that became six or seven businesses
The redevelopment sits on a 2.17-acre lot at the northeast corner of Main Street and East 6th Avenue, inside the town's Town Center Overlay District, according to the West Orange Times & Observer's coverage of the 2023 approval. When the project was first proposed in 2021, the plan called for demolishing three existing businesses on the site, Elysium, Karr Realty, and Spa Affair, according to the Observer's coverage of that initial workshop. By the time the 2023 approval went through, the plan had grown into a mix of six to seven businesses, not a single anchor tenant surrounded by empty suites.
The property is owned by the Jim Gissy family and the Jim Karr family. Karr has lived in Windermere since 1970. Gissy is the CEO of Westgate Resorts, but his connection to this project is personal rather than corporate. V-3 Capital Group, led by CEO Trey Vick, handled design and leasing. The general contractor was Hembree Construction, run by brothers Jay and John Hembree, who grew up in Windermere. None of that is incidental. It's the reason the finished product doesn't read like an outside developer's idea of what a small Florida town should look like.
The project wasn't universally welcomed while it was under construction. Gissy told The Orlando Life that some residents pushed back on bringing new businesses downtown at all. His read on it now: "once the project was finished, many of the same people who fought it told me how much they loved it."
The town made the developer pay for the sidewalk you're using
Here's the part that doesn't show up in the ribbon-cutting photos. As a condition of approval, the developer was required to make a $47,000 transportation mitigation payment, split into $20,000 toward improving the Main Street and East 6th Avenue roundabout and $27,000 to install a signalized pedestrian crossing at East 6th and Oakdale Street, according to town planner Brad Cornelius's presentation covered by the Orange Observer. The developer was also required to mitigate 151 inches of trees removed from the site.
That crosswalk and that roundabout improvement aren't cosmetic. They're the infrastructure that makes it possible to walk from a house on Oakdale or 6th Avenue to a restaurant on Main Street without crossing traffic on foot. The town used its approval leverage to extract exactly the kind of small-scale walkability investment that a resident would never think to ask for by name, but would absolutely feel the absence of.
Why the new pizzeria skips the sit-down menu
Fresco Pizzeria opened December 1, 2025, at 527 Main Street. It's the second location from the Scialoia family, who have run Fresco Cucina Italiana on Turkey Lake Road in Dr. Phillips since 2006. Achille Scialoia runs the front of house, his mother Teresa and brother Luigi handle the kitchen.
The Windermere location was designed differently from the original on purpose. Scialoia told the Orange Observer that the new spot leans toward grab-and-go, Italian sandwiches, pizza, pastries, cannoli, built for people picking up kids or squeezing in a meal between errands rather than sitting down for a full dinner. His reasoning had nothing to do with menu trends. It had to do with Windermere's traffic. "It's very difficult for them to go to places, because the town only has so many restaurants," he said. "But a lot of people are very happy, because traffic is a nightmare. So a lot of people are excited, because they can walk."
That's a business owner sizing up a town's actual daily friction and designing around it, not a franchise plugging a proven format into a new zip code.
A wine bar built by the people who'll drink there
The same block is bringing in a high-end wine bar and restaurant led by Arjun and Sara Kumar, who live in Windermere and Keene's Pointe. Their concept was described in the same Orlando Life coverage as community-focused, aimed at the people who already live within walking distance rather than at drawing outside traffic. Pair that with Fresco's grab-and-go redesign and a pattern starts to show up across the new tenant list: the people opening these businesses are also the people who'll be walking to them on a Tuesday night.
What's constant while the storefronts change
Two fixtures on the block predate all of this and aren't going anywhere. Windermere Brewing Company, at 111 W 5th Avenue, opened in July 2022 and has been the town's closest thing to a living room ever since. When Fresco Pizzeria was preparing to open, Windermere Brewing made an Italian-style beer specifically for it, a small collaboration between two locally owned businesses on the same three blocks, not a marketing partnership dreamed up by anyone outside the neighborhood.
The Friday morning Windermere Farmers Market at Town Square Park, on Main Street between 5th and 6th, is the other constant. It's been the town's weekly gathering point for years, long before anyone was pouring concrete for the new development, and it's still the easiest way to see the whole town in one place on a Friday.
Main Street itself has been the spine of this layout since 1889, when the town was first platted along the shortest dry-land crossing between Lake Butler, Lake Down, and Lake Bessie. Windermere Town Hall, built in 1924, sits on the National Register of Historic Places alongside the Cal Palmer office building and the 1890 Windermere Schoolhouse. The three roundabouts on Main Street, two installed in 2004 and a third in 2010, were built specifically to keep the street walkable rather than letting it turn into a through-road. None of that is new information to anyone who's lived here a while, but it's worth remembering that the same instinct, keep cars slow and people on foot, is what shaped the 2023 approval and the mitigation payment that came with it.
If your drive has felt off this year, here's why
Two pieces of construction from this year explain some of the detours you may have hit. Orange County closed a portion of Main Street at 720 Main St. on April 7, 2026, for the installation of shortline water service, according to the Orange Observer. In early July, the town ran curb forming and pouring work on Bessie Street, East Boulevard, and 8th and 9th Avenues, with temporary lane closures through the week of July 6. Neither closure is dramatic on its own, but together they're a reminder that the infrastructure underneath Main Street is still catching up to what's now sitting on top of it.
The short version
None of the businesses that filled in this block needed to be here for Windermere to keep functioning. A hardware store would have satisfied the original approval on its own. What actually showed up, a family pizzeria redesigned around foot traffic, a wine bar from neighbors who live a few blocks away, a custom beer brewed as a favor between two local businesses, only makes sense once you understand that the people building it were solving their own daily problem. That's a different kind of growth than most Florida towns get, and it's worth knowing if you're the one walking past it every morning.
If you're weighing what any of this means for your own property or your next move in Windermere, The Hazera Team knows this stretch of Main Street block by block. Request a private consultation to talk through what's changed and what it's worth.
