You’re driving through Lake County, about 40 minutes northwest of the chaos of Orlando, when the landscape starts to shift. The flat, strip-mall-heavy sprawl of Central Florida begins to roll. It ripples. Suddenly, you’re looking at hills—actual hills—and a shimmering expanse of water known as Little Lake Harris. Then you see the sign. Howey-in-the-Hills. It sounds like something out of a children’s book or maybe a 1920s real estate pamphlet. Honestly, it’s both.
Most people just chuckle at the hyphenated name and keep driving toward Mount Dora or Tavares. They’re missing out. Howey-in-the-Hills Florida isn't just a quirky geographical footnote; it’s a living relic of the Florida Land Boom, a place that feels oddly preserved in amber while the rest of the state paves over its history.
The Visionary Who Put the "Howey" in the Hills
The town didn't happen by accident. It was the brainchild of William John Howey. In the early 1910s, Howey was a developer with a massive ego and an even bigger vision. He didn't just want to build a town; he wanted to build the "Citrus Capital of the World." He bought up about 60,000 acres of land, which is a staggering amount when you think about the logistics of the time.
He was a master marketer. He’d bring potential investors down on "Howey Specials"—trains from the North—and wine and dine them. He convinced them that these rolling hills were the perfect frost-protected environment for citrus. And for a while, he was right. The town was incorporated in 1925, and by then, it was already a playground for the wealthy.
But here’s the thing. Howey wasn't just selling dirt. He was selling a lifestyle that felt European but breathed Florida air. You can still feel that today when you walk past the Howey Mansion. This 20-room Mediterranean Revival estate is the architectural heart of the town. For years, it sat in heartbreaking disrepair, overgrown with weeds and subject to the humid decay that claims everything in Florida if you let it. Thankfully, it was restored around 2017 and now hosts tours and weddings. If you go, look at the basement—it was a literal speakeasy during Prohibition. Howey knew how to party.
It’s Not Just About the Citrus Anymore
If you visit Howey-in-the-Hills Florida today, you aren't going to see 60,000 acres of orange groves. Most of that is gone, victims of the back-to-back freezes in the 1980s that crippled the industry and the inevitable march of residential development. What’s left is a quiet, somewhat upscale residential enclave that anchors itself around the Mission Resort + Club (formerly Mission Inn).
This resort is basically the town's second identity.
It’s famous for its golf courses, particularly El Campeón. Built in 1917, it’s one of the oldest courses in the South. What makes it weird—and I mean "good weird"—is the elevation. You don't expect 85-foot drops in Florida. Golfers usually spend their time here swearing at the hills while simultaneously snapping photos of the scenery. It’s got this Old World charm with its Spanish-colonial architecture and thick moss-draped oaks. It feels like a country club from a movie set in the 1950s, but with better amenities.
Living in a Time Capsule
What is it actually like to live here? Quiet. Very quiet.
The population hovers around 1,600 people. There are no major shopping malls. There isn't a bustling "downtown" in the traditional sense of a Main Street lined with boutiques. Instead, life revolves around the lake and the local parks. Sara Maude Mason Nature Preserve is a great spot if you want to see what the land looked like before the pavers arrived. It's a short boardwalk, but it puts you right in the middle of the wetlands.
- Pro Tip: If you're coming for a day trip, bring your own snacks. Options are limited unless you’re eating at the resort or hitting up one of the few local spots like The Boondocks (which is technically just outside the town limits but a local staple).
- The Vibe: It’s "Old Florida" meets "Retirement Luxury." You'll see high-end SUVs parked next to 30-year-old fishing boats.
One of the biggest misconceptions is that it’s just a retirement community. While the demographic leans older, the proximity to the Florida Turnpike has started attracting younger families who work in Orlando but want to live somewhere that doesn't feel like a concrete jungle. They want the hills. They want the lake. They want to be able to see the stars at night.
The Lake Harris Factor
You can't talk about Howey-in-the-Hills Florida without talking about the water. Little Lake Harris is part of the Harris Chain of Lakes. For the uninitiated, this is a massive system of waterways that connects all the way to the Atlantic Ocean via the St. Johns River.
Boating is the primary religion here.
The town has a public boat ramp at Griffin Park. On a Saturday morning, it’s a parade of bass boats and pontoon cruisers. The fishing is legit—largemouth bass are the prize here. But even if you don't fish, taking a boat out through the Dead River or over to Lake Harris is the best way to see the "Hills" part of the name. From the water, the elevation changes are even more apparent. You see houses perched on bluffs, which is a rare sight in a state that is mostly five feet above sea level.
Why It Matters Now
Florida is changing. Fast. Every year, thousands of acres of forest and former groves are converted into cookie-cutter subdivisions. Howey-in-the-Hills is feeling that pressure too. New developments like Venezia are bringing in more people, and there’s a constant tension between the desire to keep the town small and the economic reality of growth.
People come here because it doesn't feel like the rest of the state. It feels established. It has "soul," for lack of a better word. Whether it's the history of the Howey family or the fact that you have to drive up a hill to get to the post office, it stands out.
Actionable Next Steps for Your Visit
If you’re planning to check out Howey-in-the-Hills, don't just drive through. Do it right.
Book a tour of the Howey Mansion in advance. You can't just wander in. They do guided tours that last about an hour, and they are packed with stories about William Howey’s eccentricities and the architectural details of the house. It's worth the $25-$30 price tag just to see the stained glass and the hidden safes.
Play a round at El Campeón. Even if you aren't a "pro," the course is a historical landmark. If golf isn't your thing, go to the Mission Resort for their Sunday Brunch. It’s a bit of a local legend and probably the most food you’ll see in one place in the entire county.
Explore the backroads. Drive down Lakeshore Boulevard. It winds along the water and gives you the best views of the lake and the older homes. This is where the charm of the town really hides.
Check the local event calendar. The town hosts small festivals at Griffin Park, especially around the holidays. It’s the best way to meet the actual residents and get a feel for the community spirit that keeps this place from becoming just another suburb.
Howey-in-the-Hills remains a weird, beautiful, hilly anomaly in the heart of Florida. It’s a reminder that Florida’s history isn't just about Mickey Mouse—it’s about citrus, big dreams, and a few stubborn people who decided to build a town on a hill.