Things to Do in Windermere, FL

Windermere, Fla., is a charming lakeside town that perfectly blends natural beauty with upscale living. Nestled among the picturesque Butler Chain of Lakes, Windermere offers a serene environment complemented by luxurious homes, well-manicured landscapes, and an unmistakable sense of community. It’s no surprise that Windermere attracts those seeking a peaceful lifestyle with easy access to Orlando’s bustling amenities just a short drive away.

The real estate market in Windermere is as diverse as it is impressive. From sprawling lakefront estates with private docks to elegant townhomes in gated communities, the area caters to families, professionals, and retirees alike. Its proximity to top-rated schools, high-end shopping, and world-class golf courses makes it an ideal place to call home.

In this guide, we’ll explore some of the top activities and attractions that make this town so special for residents and visitors alike.

Downtown Windermere offers a charming blend of small-town appeal and unique experiences. The relaxed atmosphere makes it the perfect spot to grab a coffee, shop for handmade goods, or chat with friendly locals. Stop by the Windermere Farmer’s Market, where you can browse fresh produce, gourmet treats, and handmade crafts. It's a fantastic way to support local businesses and connect with the community while discovering hidden gems for your home or kitchen.

Windermere’s renowned Butler Chain of Lakes offers stunning views and a selection of waterfront dining options. You can savor fresh seafood or classic American dishes while enjoying the serene beauty of the water. Many of these restaurants have outdoor patios, allowing you to soak in the warm Florida breeze as you dine. Whether you’re indulging in a casual meal with friends or celebrating a special occasion, the setting adds a touch of tranquility to every dining experience.

The historic Windermere Schoolhouse is a testament to the town's rich heritage. Built in 1890, this landmark showcases the area's commitment to preserving its past. Visitors can take a guided tour to learn about Windermere's early days and its evolution into the sought-after community it is today. The building itself is beautifully restored, featuring period architecture and informative displays. It's an excellent way to connect with Windermere's history while gaining a deeper appreciation for the area’s cultural roots.

Art enthusiasts will appreciate Windermere’s vibrant arts scene. Several galleries and studios in the area showcase works by talented local artists, offering everything from contemporary pieces to traditional landscapes. These venues often host exhibits, workshops, and community events, creating opportunities to meet the artists and learn about their craft. Purchasing local artwork supports the creative community and adds a personal touch to your living space.

One of the most enjoyable ways to experience Windermere is by taking a scenic boat tour of the Butler Chain of Lakes. These guided tours provide a close-up view of the area's natural beauty, including lush landscapes and stunning lakefront homes. Tours often include interesting commentary about the local ecosystem and the history of the lakes. It's a peaceful and informative activity ideal for families, couples, or solo explorers looking to enjoy Windermere's outdoor charm.

Wine enthusiasts will enjoy visiting one of Windermere's wine shops or tasting rooms. These establishments often feature selections from around the world and knowledgeable staff who can guide you to the perfect bottle. Many locations host wine-tasting events or offer pairing suggestions for a complete culinary experience.

Windermere’s coffee shops offer more than just a great cup of coffee; they provide a cozy atmosphere and a sense of community. Spend some time at a local café to enjoy specialty drinks, delicious pastries, and friendly conversation. Many of these spots also double as venues for local art or live music, adding an extra layer of enjoyment to your visit.

Windermere’s access to the Butler Chain of Lakes provides ample opportunities for water-based activities. Rent a paddleboard, kayak, or canoe to explore the lakes at your own pace. For those who prefer a more leisurely experience, consider packing a picnic and enjoying the views from one of the lakefront spots. The calm waters and scenic surroundings make it an ideal way to relax and enjoy the outdoors.

Windermere offers luxurious spas where you can relax and rejuvenate. Book a massage, facial, or other treatments to unwind after a busy week. These spas provide top-notch services in serene settings, making them a perfect escape for a few hours of self-care. Whether you’re a resident or a visitor, treating yourself to a spa day is a fantastic way to enjoy Windermere’s upscale offerings.

Ready to take the next step in your Windermere real estate journey? The Core4 Group is here to guide you every step of the way. With over 75 years of combined experience in residential and commercial real estate across Florida, our team brings unmatched local insight and expertise. Whether you're buying, selling, or investing, we are dedicated to earning your trust and providing a seamless experience. Let us show you how we can be caring, organized, reliable, and exceed your expectations — contact us today to get started!