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Posted by The Real Estate Reporter on Sep 6, 2016 4:58:41 PM

Leesburg, FL: From Watermelons to Bikefest - a look at 'then & now'


Residents of Leesburg have been drawn to the city's charm and welcoming atmosphere since the 1800's. More than a place to live, Leesburg offers a sense of community.

Here's a quick look at its rich past and why residents love living in Leesburg today - 

A Place to Call Home


In the 1840's, Evander Lee, Leesburg's Namesake, settled in what would later become the heart of Leesburg, Florida. In the 20 years after he arrived, Leesburg grew to have a newspaper, churches, schools, shops, and government buildings. 

Since then, Leesburg has become one of the most popular Central Florida hometowns. So where do residents of Leesburg live today?

Popular Home Options

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Real estate choices can range in type, size, and location. From waterfront abodes, luxury estates, and 55+ communities to acreage or even condos, the selection is vast. However, one of the most popular searches in the area encompasses lakefront real estate and it's easy to see why.

Leesburg is almost completely surrounded by water and provides serene lake views at almost every turn, hence the county name - Lake. The pristine Harris Chain of Lakes is one of the main attracting factors for the area, and helps make Leesburg an ideal boater's paradise and sought-after lakefront living destination.

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Past Meets Present


In its early years, Leesburg was at the heart of Lake County's produce production. In fact, Leesburg's most famous crop was the watermelon!

In 1930, the very first annual Leesburg Watermelon Festival was held to celebrate the fruit - a tradition that continued until 1957 but still lives on through local memory.


Some of my fondest memories as a child were made at the Annual Watermelon Festival.

"I can vividly remember the beauty contest was held on a flatbed trailer in Venetian Gardens. I thought that they had to be the most beautiful girls in the world…I was only 10 years old," says Tom Grizzard, Commercial REALTOR® in Lake County and the founder of ERA Grizzard Real Estate. 

While the Watermelon Festival of the past has been replaced in popularity by today's Annual Leesburg Bikefest, the community has found numerous ways to continue honoring and remembering it's unique and historical beginnings. Residents continue to enjoy the lifestyle and celebrate life in beloved Leesburg. 

Today's Allure 


Evander Lee first came to Leesburg seeking a better climate. When he arrived, he found so much more.

From its perfect winters to its natural wildlife, breathtaking countryside living and picture-perfect waterways, everything that drew residents of the past to Leesburg is what draws modern locals still to this day. 

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Leesburg's Main Street, the heart of the city, remains a local favorite. It has been recently revitalized to maintain its historic past and offers convenience for today's locals. Enjoy local eats or shopping from numerous establishments, or partake in the one of the many events held in the main town square.

In the 1930's, Leesburg's ever-popular Venetian Gardens was started as a way to keep food on Leesburg's tables during The Great Depression. Today, it offers a beautiful and relaxing escape among Leesburg's nature and the shores of Lake Harris. It also serves as another popular location for events and meetings throughout the year as the surrounding environment is simply beautiful. 

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From Friday night football and summer Leesburg Lighting baseball games to lazy Sundays on the lake, the Leesburg lifestyle is a relaxing one with variety to match any resident's taste. Whether you prefer the 5-iron or the fishing pole, Leesburg has recreation that can be enjoyed year-round in the beautiful Florida weather.

With all it has to offer, locals and its charming hometown atmosphere embracing its historic past, Leesburg continues to enchant its residents and convince them to stay awhile.

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Topics: Leesburg