A time-capsule conversation that highlights Windermere’s small-town charm, local history, and enduring sense of community
Blog Author: Jeffrey Funk | Co-Founder, The Funk Collection, Brokered by eXP Realty | ICON Agent
In the fall of 2018, Jeff sat down with former Mayor Gary Bruhn for a conversation about the community they both proudly call home. It felt like a casual chat at the time. Today, on the heels of Windermere’s Centennial, it reads like a snapshot of a town that has evolved without losing the character that makes it unmistakably Windermere.
Seven years after that interview, Windermere continues to honor its roots while moving intentionally into its next chapter. The names and buildings have shifted, but the spirit is the same.
Windermere’s Story Begins Along the Lakes
Windermere’s history is woven through the lakes, the trees, and the people who settled here long before the town was incorporated in 1925. Much of that early identity still shows up in everyday life.
The late 1800s brought timber operations to Lake Down. Winters invited early residents who grew oranges and shipped them north. In the early 1900s, Cal Palmer purchased what became the center of town, plotted streets named with practical charm, and built a foundation that still guides the layout today.
Mayor Bruhn captured it well when he said, *“You’re by the lakes, surrounded by woods. It’s amazing that you still feel so far away while being so close.”
How Downtown Windermere Has Evolved Without Losing Its Identity
Downtown Windermere has always been small, but never quiet. The heart of the town has a way of growing just enough to serve residents while keeping the scale and charm that define it.
One story from the 2018 conversation still makes residents smile. Jeff asked about the town clock, a familiar landmark that had stopped working. Mayor Bruhn explained that repairs would cost more than a new clock, and the Downtown Business Committee stepped up to replace it with a version that reflects the town’s crest and personality. Original clock pictured below (on left) and new clock (on right).
Small improvements like that carried into larger ones. Food Truck Friday is a perfect example. In the early days, the event came with loud generators and fumes that didn’t match the town’s atmosphere. The Downtown Business Committee invested in permanent electrical lines so vendors could plug in instead. The result is the Windermere version of a community night: relaxed, warm, and easy to enjoy.
As Jeff shared in the original interview, *“People call and say they don’t want to be near the tourists, and we tell them this is rural and quiet. You’d never know we were so close to everything.”
That truth still stands today.
A Village That Improves Thoughtfully
Much of the 2018 conversation centered on improvements that would keep Windermere feeling like Windermere while preparing for the future. That balance shows up every year.
Here are a few modern updates that nod back to themes in the original interview:
What’s New Since 2018:
- New Construction Storefronts at East 6th Avenue and Main Street
- Windermere Brewing became a Gathering Spot for Residents
- New Windermere Town of Windermere Building & Police Station
Even as the area around Windermere has grown, the town itself has stayed intentional. Mayor Bruhn said it best: “One of the things I’m most proud of is that we’ve been able to keep our small-town atmosphere.” You can see that approach in the new construction along Main Street, where updated architecture still respects the scale and character of the village center.
Seven years later, that goal still guides decisions big and small.
5 Things You May Not Know About Windermere
This “time-capsule” interview highlighted a few surprises that even locals are surprised by.
- The town of Windermere is much smaller than most assume.
- Town limits include just over 3,000 residents within 2.2 square miles, despite the much larger population of the 34786 ZIP code.
- Windermere once had only six residents.
- Mayor Bruhn shared that after back-to-back freezes in the late 1800s wiped out the orange industry, Windermere became a ghost town with a recorded population of just six people before it bounced back.
- Founders once bought the whole town for $10,000.
- Mayor Bruhn shared how early developer Cal Palmer bought what became downtown Windermere, then laid out the numbered streets and named others after the lakes and trees. That planning still shapes how the town feels today.
- Historic buildings continue to anchor Main Street.
- The Cal Palmer Memorial Building and Town Hall remain active parts of community life, hosting events such as the Windermere Flower Show.
- Food Truck Friday was re-engineered for comfort.
- Permanent power lines were added so trucks could plug in quietly and ditch the loud generators.
Looking Back, Looking Forward
Watching this conversation years later reveals something simple. Windermere hasn’t tried to become something bigger. It has tried to become something better. A town that embraces improvements without letting go of its identity. A community that continues to feel like home for the families who choose it.
For Jeff and his family, that feeling has held true throughout many years of living, working, and raising kids here.
(Pictured to right: Jeffrey & Renee Funk with Former Mayor Gary Bruhn at the Grand Opening of the eXp Realty Downtown Windermere eXp Realty Office, 2017.)
If this glimpse into Windermere’s past and present sparks curiosity about what life among the lakes might look like for the next chapter, exploring homes in Windermere and the greater 34786 area can offer a closer view of the neighborhoods that shape this community.
Posted by Jeffrey G. Funk P.A. on
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