Orlando Real Estate Blog - Central Florida Historical Information

Why Windermere, Florida Feels Like a Town Built to Be Outside

The history behind Windermere’s parks, paths, and lake access

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

Windermere, Florida, is often described as a small lake town in Central Florida. That part is true. Much of daily life here quietly revolves around parks, paths, courts, and water access, and that has been the case for a long time

Long before Windermere became a place people actively searched for when planning a move, parks and recreation were already part of the town’s thinking. Not as extras. Not as leftover land. As part of how the town worked.

Parks Showed Up Early, Not After Growth

Fernwood Park was formally designated in 1920, when Windermere was still very small. By the…

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5 Things You May Not Have Known About Windermere’s Town Hall

More Than a Landmark in Windermere

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

It sits right in the heart of downtown Windermere. You've likely driven or walked past it once or a hundred times and it still anchors the town. Windermere’s Town Hall has that effect. Familiar, steady, quietly central.

It’s the kind of building that feels like it has always been there. Which is true. But not in the way most people assume.

What’s easy to miss is how much history is layered into that single structure. Not in a dusty, behind-glass way. In a lived-in, still-in-use way. The kind of history that keeps showing up because it never really left.

Here are five things that tend to surprise even people…

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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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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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Trading Roller Coaster Tracks for Nature Trails: Central Florida 5 State Parks Guide

While Central Florida may be known as a mecca for some of the top theme parks in the world, did you know that there are 5 Florida State Parks within about an hour of Orlando? Perfect for a weekend adventure, these state parks offer a range of nature, history and exploration. From miles of trails to sparkling lakes and springs, these parks offer something for every member of the family.

Pro Tip: Grab a Florida State Parks Annual Pass to have unlimited park entrance access across the state. In 2024, the rates are $60 per person for an Individual Pass and $120 for the Family Pass (defined as day-use park entry for up to a total of 8 people entering as a group)*. For purchase details and any restrictions, please visit the Florida State Park website. 

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Windermere September 11th Memorial

Quietly resting behind the Windermere Town Hall Building, you will find the Windermere September 11th Memorial. Standing 8 feet tall, the 650 pound piece of steel was cut from an actual structural beam of the World Trade Center.

Ninety hand-painted, glazed ceramic tiles border the black granite memorial. The tiles commemorate each of the 90 countries that lost innocent citizens in the attacks of the Twin Towers. Each tile was hand painted by Eagle Scouts across the Central Florida area. 

The September 11th Memorial peacefully honors the loss of nearly 3,000 brave men and women; including the many fire rescue, police, and first responders who risked their lives while helping other victims.

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Historic 1890 Windermere School House

The historic 1890 Windermere Schoolhouse, located at 113 West Seventh Avenue,  Windermere, FL in the 34786 zip code, was placed on the National Register of Historic Places in 2003. Also known as the Armstrong Parramore House, the schoolhouse was built in 1890, renovated around the year 2000, and is the oldest historical site in Windermere.

The building served the community as a schoolhouse until 1916. The structure was also utilized as a community center, holding social and religious events, as well as a voting center and meeting place for the Town of Windermere Woman's Club.

In 1995, the schoolhouse structure and land was donated to the Town of Windermere by Manuel "Perry" & Eunice Armstong Parramore. Today, the schoolhouse remains situated on the…

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Windermere Gas Station

Yes, it IS true! Finally, construction is in progress on the brand new 7-11 Gas Station. The gas station will join Publix, Chase Bank, McDonalds (and more) at the Lakeside Village Shopping Center on County Road 535 & Reams Road. This new development will be a big relief for residents living on the south side of Windermere, including the communities of Keene's Pointe, Glenmuir, Casa Del Lago, Oxford Moor, and Waterstone.

Windermere residents are fortunate to have an abundance of everything from theme parks, to world class shopping, endless options for dining (from fast food to fine dining), and community events right in our own backyard. However, even with the new 7-11, the area is still strained for available gas stations. How many times have you found…

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What is the meaning of the Windermere, FL Town Logo?

Have you ever wondered about the meaning of the Town Logo in Windermere, FL?

The Town of Windermere "Among the Lakes", is well known for its beautifully scenic chain of lakes and prestigious lakefront real estate.  The design of Windermere's Town Logo was actually based on inspiration from the Town of Windermere, England. The logo is a crest, divided into four symbolic pictures; thus resembling a coat of arms. 

The top left quarter of the Windermere crest reflects three Windermere class yachts.

Ask Windermere residents what they most treasure about their town..."Boating" will probably be the number one reply.  Windermere is home to over 5000 acres of sand bottom, crystal clear lakes. Creating the perfect place to enjoy the boating lifestyle. 

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