Growing Up in a Hidden Corner of Central Florida
If you blink driving down Highway 50, you might miss Oakland. A tiny town tucked between Winter Garden and Clermont. But for me, this little blip on the map was home.
When I was a kid, Oakland was quiet. You could still smell the orange groves that stretched past our neighborhood. My friends and I would walk dirt roads shaded by oak trees and Spanish moss, head down to the docks by Lake Apopka to spot gators, or take the West Orange Trail into downtown Winter Garden, which, back then, felt like a ghost town.
Most of my neighbors were retirees who treated every kid on the block like their grandchild. Today, many of those familiar faces are gone, and a new generation of families has moved in. But the heart of Oakland hasn’t changed. It just beats a little louder now.
Watching Home Values Transform
My dad still lives in our old house in Oakland. Over the years, he hasn’t done much in the way of upgrades. A little paint here, a new appliance there. Yet the value of his home has increased by over 600 percent since he bought it, showing just how much the area has grown.
Home values across Oakland and Lake County tell a similar story. The median listing price in 2015 hovered around $250,000. By 2025, it reached roughly $645,000, reflecting strong demand as more families discovered this corner of Central Florida.
The Numbers Behind the Growth
According to U.S. Census data, Oakland’s population rose from 2,538 in 2010 to 3,516 in 2020. A 38.5 percent increase in just one decade. Current town estimates put the community near 3,800 residents. What was once mostly farmland and groves is now dotted with new neighborhoods, parks, and bike paths that connect seamlessly to Winter Garden and Clermont.
Since 2019, the town has added a new community center and police station to serve its expanding population. Oakland Avenue Charter School has become a centerpiece for local families. The West Orange Trail and nearby routes got upgrades for walking and cycling. An expanded Oakland Nature Preserve gives residents a place to hike and learn about local wildlife. And mixed-use and luxury housing developments near Highway 50 and Tubb Street bring new shops and amenities while keeping the small-town scale.
The Oakland Town Center project, currently underway, will add retail, dining, and housing options along SR 50. Proof that this once-sleepy town is evolving into a thriving gateway between Orange and Lake County.
Life Still Moves at Oakland Speed
Even with all the new development, Oakland still feels personal. At a recent Town of Oakland Block Party, I watched families mingle, kids dance, and my son pose for a picture with the Oakland PD. While waiting in line for lemonade, I met Kris Keller, who serves on the Town Commission. A perfect example of how approachable and community-minded this town remains.
And yes, you still have to watch that four-way stop and drive below the speed limit. Locals wouldn’t have it any other way.
The Bigger Picture
For longtime residents, the transformation is emotional. Oakland has grown up, but it hasn’t lost its warmth. For new buyers and families moving in, it’s a rare find. A town where you can enjoy the perks of Central Florida living without giving up that neighborhood feel.
Homeowners are seeing the benefits of patient ownership, and buyers are discovering a community with genuine roots and room to grow.
Final Thoughts
When I walk through Oakland today, I see new faces, new homes, and more energy than ever before. But I still see the same sunsets over Lake Apopka, the same oak-lined streets, and the same sense of belonging that made this place special decades ago.
My hometown has grown up. But thankfully, it still feels like home.