Drive down Main Street on a Friday afternoon this fall and the corner at East 6th Avenue will not look like the corner you remember from 2023. Where aging structures once stood on 2.17 acres inside the Town Center District Overlay, there is now a low block of buildings holding a hardware store, an Italian pizzeria, a wine bar in progress, a boutique brokerage, an interior design studio, and a jeweler. The parking sits behind on Oakdale, screened by a wall and a 20-foot landscape buffer that keeps the Oakdale-side neighbors out of headlight range.
For residents who have watched this project since the pre-application days of 2019, the interesting question is not whether the corner opened. It did. The interesting question is what it changed about how the town gathers. The short answer: the center of gravity has moved about 200 feet, and Friday is now a longer day.
What actually opened on the corner
The developer is V-3 Capital Group under CEO Trey Vick, working for owners Jim Gissy and Jim Karr through Downtown Windermere Properties. The general contractor was Hembree Construction, run by Windermere-raised brothers Jay and John Hembree. The building sits on the northeast corner of Main and East 6th and holds six to seven suites. Leasing is complete.
Here is who is inside:
- Toole's Ace Hardware of Windermere, 517 Main Street, opened Saturday, May 24, 2025 with a formal ribbon-cutting on June 9. It is the 14th store for Walter and Patricia Toole, who have lived in Windermere for 31 years. Hours run 7 a.m. to 8 p.m. Monday through Saturday and 8 a.m. to 7 p.m. Sunday, which matters because it means the store is open before the Farmers Market starts and after Food Truck Night ends. Manager Clayson Richmond is a decade-long company veteran.
- Fresco Pizzeria, the Scialoia family's second location, opened December 1, 2025 on the Main and 6th corner.
- Revel Realty, formerly Suzi Karr Realty, has rebranded under broker-owner Chris Sapp.
- Elysium Interiors, an interior design firm returning from the previous buildings on the site.
- Victoria Jewelers, another tenant from the original downtown footprint.
- Solvio and Allstate Insurance, filling out the everyday-services mix.
- A wine bar and restaurant from Arjun and Sara Kumar, Keene's Pointe residents, still preparing to open.
Note the pattern. Only two tenants on that list are new to the town's business roster. The rest either lived in Windermere already or lived on this block already. Gissy and Karr said publicly that they never wanted a corporate brand on the corner, and the leasing sheet reads accordingly.
The Fresco question everyone was actually asking
For nineteen years the Scialoia family ran Fresco Cucina Italiana out of Bayhill Plaza on Turkey Lake Road. The Windermere location, run by Achille Scialoia with his mother Teresa and brother Luigi, is a different concept. Original plans called for a smaller fast-service spot, and the project grew when a larger unit opened up in the leasing plan.
What that expansion produced: wood-fired pizza on a 48-hour proofed dough, fresh pasta made in the kitchen, Italian sandwiches, cornetti and bomboloni in the morning paired with cappuccinos and lattes, and a wine list intended for evening tastings. Cheese comes from a South Florida producer. Gluten-free options are on the menu. Windermere Brewing Co., which opened downtown in July 2022, is producing an Italian-style beer specifically for the restaurant. The grab-and-go counter is real, and it is aimed at the school-pickup window between 3 and 4 p.m. The wine bar is aimed at the hour after 6.
For a resident who has driven ten minutes east to Sand Lake Road every time they wanted a real Italian dinner, the math on a Wednesday night just changed.
Why April 24 mattered more than it looked
On the fourth Friday of April, before Food Truck Night could start, Grandma's BBQ went up in flames roughly twenty feet high in front of Town Hall. A portion of Smoothie Express caught next, along with a small generator. Ocoee Fire Department controlled the blaze, Police Chief Dave Ogden called it accidental, no one was hurt. Miller Environmental Group handled cleanup and the Florida Department of Environmental Protection was notified about potential drainage runoff. The event was canceled.
What happened after is the part that matters. The town scheduled a summer special for Friday, July 24 and brought back every truck from the canceled April lineup, including Grandma's BBQ and Smoothie Express. Lucky to Be played. The Windermere Library set up its craft station. Sponsors Power Home Remodeling, Mary Kay through Nora Penaloza, and Central Florida Racquet Sports covered the tab. The April event had been paired with the Windermere Legacy Fund's first community initiative, a food drive for Second Harvest Food Bank of Central Florida with monetary donations matched dollar for dollar up to $2,500. That campaign carried forward.
A town of roughly 3,400 residents inside two square miles does not simply reschedule a canceled event. It signals, in the way small places signal, that Food Truck Night is not a program. It is the calendar.
Your fall Friday, timed
The reopened corner did something quiet to the shape of a downtown Friday. Here is what the sequence looks like now, on a fourth-Friday of the month between September and December:
| Hour | Where the town is |
|---|---|
| 9:00 a.m. – 1:30 p.m. | Farmers Market on Main between 5th and 6th, in front of Town Hall |
| 12:00 – 3:00 p.m. | Lunch counter at Fresco Pizzeria, coffee at Paloma, breakfast tail at Dixie Cream Cafe |
| 3:00 – 5:00 p.m. | School pickup, Fresco grab-and-go, Toole's Ace for whatever the sprinkler did overnight |
| 5:30 – 9:30 p.m. | Food Truck Night at Town Square Park, 15 to 20 trucks, live music or DJ |
| After 9:30 p.m. | Allen's Creamery, wine at Fresco, back porches |
Before the corner opened, the day had two acts, morning market and evening trucks, with a soft middle. The middle now has an anchor. That is the structural change.
What is on the town calendar between now and Halloween
The events that shape a Windermere fall are already scheduled by the town, not invented by a marketing team. Between now and the end of October, plan around:
- Fourth-Friday Food Truck Nights at Town Square Park, 5:30 to 9:30 p.m. September through December, with fifteen to twenty trucks per event. Vendors are screened by the town's Food Truck / Farmers Market Selection Committee, and new trucks are typically slotted in zero to one times per quarter, which is why the same names keep coming back. Recent regulars include Arepa Pela Orlando, Charm City Eats, Dio Santo Street Pizzeria, Paula's Jamaican Cuisine, and Oishiimotto.
- Windermere PetFest at Town Hall, featuring police K-9 demonstrations, food trucks, doggie games, a kids' bubble zone, and a bounce house.
- Halloween Costume Parade and Hayride, run by Parks and Recreation. The October Food Truck Night is a Halloween-themed edition, so costumes get worn twice.
- 5K/10K Run Among the Lakes, the town's flagship road event, threading past the same water that makes Windermere Windermere.
The December Food Truck Night carries a free outdoor movie. The March 2026 edition, worth mentioning because it explains the town's operating culture, doubled as a farewell for outgoing Mayor Jim O'Brien with Dixie Cream Cafe, Windermere Brewing Co., and Paloma Cafe setting up tables inside the 1922 Colonial Revival Town Hall, which is listed on the National Register of Historic Places.
The quiet part
There is a version of this story that reads as a routine ribbon-cutting roundup. That version misses the point.
Windermere spent close to seven years getting the Main and East 6th corner approved, designed, and built. The V-3 team was required to make a $47,000 transportation mitigation payment, $20,000 toward the Main and East 6th roundabout improvement and $27,000 toward a signalized pedestrian crossing on East 6th at Oakdale. The applicant had to mitigate 151 inches of trees that could not be replaced on site. A six-foot screen wall runs along Oakdale and steps down to three feet approaching the driveway for sight lines. None of that reads on a Friday evening, and that is the intent. The corner was built to disappear into the town it joined.
What this means for a resident of Isleworth, Keene's Pointe, the Lakes of Windermere, or Summerport is smaller and more concrete than a redevelopment narrative. It means the ten-minute drive east to Sand Lake for a plate of pasta is now optional. It means the Friday market can spill into a lunch at Fresco and a hardware run without leaving one block. It means the town's civic calendar, still centered on Town Square Park and the Town Hall lawn, now has a commercial spine three doors down that keeps the lights on between events.
For anyone thinking about how a place actually functions when nothing dramatic is happening, that is the interesting change. The town did not get bigger. The Friday got longer.
If you would like a discreet introduction to what is trading on and off market inside Windermere's private enclaves this season, Elite Sport Network welcomes you to book a private consultation.
