Orlando Real Estate Blog - Windermere Florida

What The New Ward Trail Means For Living In Windermere, Florida

What’s the construction happening along Maguire Road & Main Street in Windermere?

Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty

If you’ve driven down Maguire Road & Main Street in recent weeks and wondered what the construction is along the road, you’re not alone.

The construction marks the beginning of the Ward Trail, a new multi-modal path that will connect parts of Windermere in a whole new way. Once finished, it’s expected to make daily movement safer and more convenient.

Located near the north end of town along Maguire Road and Main Street, extending over the canal connecting Lake Down to Wauseon Bay and beyond to Lake Butler, the project is already taking shape. From dirt movement and tree removal to the early…

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Town of Windermere vs. Windermere 34786: Understanding Orlando’s 34786 ZIP Code

What is the Difference between the Town of Windermere vs. The Windermere 34786 Zip Code?

Blog Author: Renee Funk | Co-Founder The Funk Collection, Speaker, Trainer

When considering a move to Windermere, Florida, buyers may not realize there are actually two distinct governance structures within the 34786 ZIP code. The Town of Windermere is an incorporated municipality with its own local town government. The remaining areas within 34786, while still considered Windermere by mailing address, are unincorporated Orange County and governed at the county level.

Both share the same ZIP code. Both share the Windermere name. But they operate differently. Here is what residents and future buyers should understand:

What Is the Town of Windermere?

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Windermere Then and Now: Homes, Land, and the Town That Grew With Them

How Windermere Quietly Became What It Is today

Blog Author: Jeffrey Funk | Co-Founder, The Funk Collection, Brokered by eXP Realty | ICON Agent

It’s a little like driving past the house where childhood memories were made. The street feels familiar, but things look different. Bigger. Fuller. More layered.

Looking back at Windermere’s early days brings that same feeling and raises a simple question worth asking:

What did real estate here actually look like in the beginning?

A Town Before the Town

In the late 1800s, Windermere was barely a village. Fewer than 100 people lived here, and the railroad had only just arrived. There were no subdivisions, no tidy blocks of homes, and no clear sense yet of what the town might become.

Land…

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A Conversation With Windermere Mayor Gary Bruhn That Still Rings True 7 Years Later

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.

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Celebrating Past and Present at the Windermere Flower Show

What Makes the 2025 Flower Show Special

This year's Windermere Flower Show isn't just any event; it's part of the town's Centennial Celebration. Hosted by the Windermere Garden Club, "Celebrating Windermere Past and Present" is all about honoring 100 years of history, the present, and tomorrow. And honestly, what better way to celebrate Windermere than with flowers, trees, and plants that truly show off the place we call home?

What you will experience at the Show

From the moment you step inside the Windermere Town Hall, you'll find find entries in three divisions (Horticulture, Design, and Education). You'll experience everything from exhibits featuring horticulture that celebrate local flowers, trees, and plants to creative floral displays that…

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Windermere Run Among the Lakes 5K & 10K

What Is The Windermere Among The Lakes? 

Blog Author: Jeffrey Funk | Co-Founder, The Funk Collection, Brokered by eXP Realty | ICON Agent

The Windermere Among the Lakes is a 5K & 10K Run, showcasing the beauty and charm of downtown Windermere. Runners pass under the canopy of mature Oak trees, along dirt roads, and amidst the natural beauty of the surrounding lakes, including Lake Butler, Lake Down, and Lake Bessie. This year is extra special as the town is celebrating its Centennial. 

When And Where Is The 2025 Run Among The Lakes?

The event will be held on Saturday, October 11th, in downtown Windermere, Florida. Runners will meet at the Windermere Town Hall at 520 Main Street for packet pickup between 6am - 7:30am. Early pick up is…

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Windermere Celebrates 100 Years: A Centennial To Remember

2025 marks a significant historical milestone for Windermere, Florida—its Centennial celebration! Over the course of the year, the community will honor its 100-year journey with special touches that highlight its unique charm, history, and community spirit.

Festive Updates Across Downtown

Downtown Windermere is ready to dazzle with:

• Centennial Banners: New flags now line the streets, adding a cheerful and celebratory vibe to the town’s heart.
• New Entry Signs: The town’s entryways have been updated with commemorative Centennial signs, welcoming everyone to this once-in-a-lifetime celebration.

These thoughtful touches remind residents and visitors alike of the rich history that makes Windermere so special.

The Centennial Lobby: A…

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