"*" indicates required fields
Windermere may be small in size, but it’s sprawling in personality. Downtown Windermere is a postcard-worthy slice of Old Florida, complete with unpaved roads, towering oaks draped in Spanish moss, and a charming Town Hall that’s basically the heartbeat of the community. If you’re looking for a slower pace, it’s here—neighbors who wave at you from their front porch, kids playing hoops in the driveway, and families strolling the lakeside paths at dusk.
But there’s more to Windermere than its “downtown.” Venture out to Keene’s Pointe, a gated golf community wrapped around the famed Golden Bear Club designed by Jack Nicklaus. You’ll find luxury homes of all shapes and sizes, from Tuscan-inspired estates to modern marvels with floor-to-ceiling windows overlooking the water. This is where you move if you want that prestige factor without sacrificing the chill vibe of lakefront living.
Lake Butler Sound is another top contender if you crave upscale seclusion. The homes here often boast private docks, perfect for those sunrise kayak sessions or weekends cruising around the Butler Chain of Lakes. Meanwhile, Windermere Downs channels more of an established, family-friendly environment—spacious yards, tree-canopy streets, and local gatherings that remind you what real community feels like.
Who’s moving here? Families chasing top-rated schools and safe neighborhoods, retirees who want to soak up the Florida sun without the chaos of a major metropolis, and professionals who love that they can be at their downtown Orlando office in under 30 minutes (on a good traffic day). Windermere’s got a higher-than-average price tag, but that price buys you a certain lifestyle: pristine lakes, top-tier amenities, and an everyday pace that keeps stress at bay.
Amenities are definitely a perk. Besides the golf courses, you’ve got tennis courts, parks, and boat ramps scattered throughout. For those who need to zip in and out, main roads like Apopka-Vineland Road and CR 535 connect you to highways that lead to Orlando’s theme parks, shopping hubs, and the airport. Public transportation isn’t Windermere’s strong suit—most people rely on cars—but that’s part of the trade-off for peaceful, tree-lined living.
All in all, Windermere is that rare balance of small-town atmosphere and luxury living. You can rub elbows with CEOs and professional athletes or chat with your neighbor about the next community barbecue—it’s all part of the tapestry that makes this place so special.
The schools in Windermere consistently rank among the best in Orange County, which is a huge pull for families. Windermere Elementary has a reputation for high test scores and an active PTA that’s practically a community in itself—think movie nights, carnivals, and fundraisers that bring everybody out of the woodwork. Moving up the chain, Bridgewater Middle School stands out for strong academic programs and an environment that encourages students to explore everything from robotics to the arts.
Then you’ve got Windermere High School, home of the Wolverines. They’ve quickly carved out a name for themselves in sports, especially their basketball and soccer teams. There’s a level of school spirit here that you can literally feel on game days—students decked out in school colors, parents cheering from the stands, and a marching band that’ll blow your socks off. Academically, the school offers a range of Advanced Placement (AP) courses, and the graduation rate is typically above the county average.
If private education is more your style, Windermere Preparatory School is just around the corner. They’re known for a rigorous curriculum (including the IB Program) and state-of-the-art facilities that give kids every possible resource to succeed. Their athletics also get a lot of buzz—baseball, tennis, and golf teams have some serious talent.
Overall, Windermere’s education scene isn’t just about hitting high test scores. It’s also about fostering a tight-knit community where teachers, parents, and local businesses stay involved. There’s a sense that these schools go beyond the basics. They strive to give every kid a real shot at becoming well-rounded—academically, socially, and athletically. And trust me, for a lot of families eyeing Windermere real estate, top-tier schools are a big chunk of why they seal the deal.
"*" indicates required fields
Windermere might not have a massive commercial district, but it’s got enough retail and dining options to keep you busy—plus, you’re never far from Orlando’s world-class shopping if you want to go big. For a chill local shopping experience, check out The Grove at Windermere, where you’ll find grocery stores, boutiques, and a few casual dining spots for when you just need a quick bite.
As for restaurants, Yellow Dog Eats in nearby Gotha is a local favorite—imagine creative sandwiches loaded with pulled pork, brie, pineapple, and other combos you never thought possible (or so addictive). If you’re craving something upscale, Slate in Dr. Phillips is a short drive away and perfect for date night. You’ll find everything from farm-to-table fare to craft cocktails that taste like the weekend in a glass.
Fitness buffs can choose from a variety of clubs and studios. Orangetheory Fitness has a location right on the outskirts of Windermere, and there are smaller gyms offering everything from CrossFit to yoga. As for sports teams, you’ll find adult leagues for softball, soccer, and even basketball, thanks to the strong rec programs in nearby communities.
When it comes to day trips or things to see, it’s no secret you’re minutes from Walt Disney World, Universal Orlando, and SeaWorld. But if you want to stay local, the Butler Chain of Lakes is prime territory for boating, paddleboarding, or just unwinding on the dock at sunrise. That’s the real magic of Windermere: the chance to be as laid-back or as adventurous as you want, all within a few square miles of home.
If there’s one thing you’ll hear about Windermere, it’s that it has a tight-knit community feel—even with all the multi-million-dollar properties floating around. Throughout the year, the town hosts a handful of events that bring everyone together, from the Windermere Farmer’s Market (held weekly at Town Square) to seasonal festivals that celebrate everything from Halloween to the holiday season. Think bounce houses, food trucks, local vendors, and kids running around like they own the place.
Population-wise, Windermere proper has around 3,500 residents, but the greater 34786 ZIP code encompasses thousands more in the surrounding suburbs. That small official population helps keep the area feeling intimate—neighbors know each other, the mayor’s a familiar face, and it’s not unusual to have a friendly chat with a local police officer during your morning jog. But don’t let that quaintness fool you into thinking there’s no excitement. The area often sees star athletes, musicians, and high-profile CEOs calling it home, especially in those prestigious lakefront communities.
A couple of can’t-miss local traditions: the Windermere PetFest, where people bring their dogs (and occasionally more exotic pets) for a day of contests, booths, and general wagging-tail chaos. And then there’s the Windermere Fine Art Show, which transforms Downtown Windermere into an open-air gallery showcasing local and regional artists. It’s laid-back but still feels like a big deal—a celebration of creativity that fits perfectly with the town’s scenic backdrop.
What I love most about Windermere is how it strikes a balance between being a private, upscale retreat and a community that still holds onto small-town warmth. You can swing by a local coffee stand on a Saturday, chat with neighbors about the next boat parade on Lake Butler, or coordinate a pick-up basketball game at a local park. Meanwhile, Todd Schroth and our team at eXp Realty keep busy helping folks find that sweet spot of a home—whether it’s a cozy cottage under ancient oaks or a modern mansion with a killer boat dock.
Windermere is the kind of place that leaves an impression. And with over 2,000 homes sold in two decades, we’ve seen plenty of buyers light up at the first glimpse of those lakes and those tree-canopied streets. If you’re looking for that perfect blend of luxury, community, and Florida sunshine, Windermere might just have your name on it. Let’s get you home.
"*" indicates required fields
Todd Schroth has spent the last 20 years vested in the Orlando Real Estate market by helping others buy, sell, and invest while standing alongside the investing himself. Todd's passionate in serving the community, sharing knowledge he has during his real estate career, and providing the best experiences for everyone he has the opportunity to work with. His overall goal is to better serve and elevate real estate standards. He has found having a strong team made up of different strengths is the best way to provide top notch experiences.
Founder of Todd Schroth Home Selling Team brokered by eXp Realty, his team has sold over 2,000+ homes in the last 20 years and are committed to making every experience exceptional.
As a result of his extensive expertise and dedication to Real Estate, Todd has felt compelled to help other agents and brokers grow their business to the fullest potential. With that passion, he created Agents Who Win, a collaborative platform for agents all over the US to share their successes and learn and grow from one another. In just one year, this Private Group has grown to almost 1,000 members. Todd strives to believe “no one can have true success without strong support systems”. We’re looking forward to this group growing and hosting in-person events to continue our contribution to agents’ success.
"*" indicates required fields
