Nestled between the sparkling lakes and lush landscapes of Central Florida, Windermere offers a peaceful sanctuary away from the bustling excitement of Orlando and Walt Disney World. With its quaint downtown area, historic charm, and vibrant community events, downtown Windermere FL is the perfect destination for those seeking tranquility, natural beauty, and a small-town atmosphere.
Explore Windermere’s captivating charm, rich history and serene lakeside scenery.
Enjoy Main Street’s quaint charm, variety of businesses and historic landmarks.
Experience seasonal celebrations, farmers markets, golf courses & more!
A simple stroll through downtown Windermere will reveal the town’s captivating charm. Rich in history and nestled between Lake Down and Lake Butler, this picturesque locale provides a serene backdrop for the bustling Main Street, Town Hall, and surrounding lakeside scenery.
Main Street in Windermere is a haven for local businesses, dining, and shopping, offering a quaint and charming atmosphere. Walking along the historic street, a wide variety of shops, restaurants, and cafes become apparent that cater to both residents and visitors alike. Some highlights include:
Pistil Home & Garden: offering unique home and garden decor
Windermere Pizza 14: serving delicious pizza options
Bella Tuscany Italian (not far from downtown): a restaurant specializing in Italian cuisine
Main Street promises an enjoyable experience for everyone.
Steeped in history, Main Street is also home to many historic landmarks, including the Town Hall, which was constructed in 1924. With its preserved architecture and vibrant atmosphere, Main Street is a testament to Windermere’s dedication to maintaining its small-town charm while fostering a thriving community.
The Windermere Town Hall, completed in 1924, serves as a symbol of community and a gathering place for residents. Its historic architecture and enduring presence reflect the town’s appreciation for its heritage and progress. The Town Hall is not only an important landmark but also a venue for various community events and meetings, such as Food Truck Night, Light Up Windermere, and the Windermere Fine Art Show.
The preservation of the Town Hall is a testament to Windermere’s commitment to its history and the importance of maintaining a strong sense of community. The Town Hall, combining both historic and modern elements, remains a symbol of the town’s rich past and its commitment to a prosperous future.
Surrounded by the pristine waters of Lake Down and Lake Butler, downtown Windermere offers a peaceful lakeside setting that residents and visitors can enjoy. The calming ambience of the lake, coupled with the town’s commitment to preserving its natural beauty, creates an idyllic atmosphere perfect for relaxation and leisure. From fishing and boating to simply admiring the stunning views, the lakeside surroundings provide endless opportunities for outdoor enjoyment.
The town’s dedication to preserving downtown Windermere’s tranquility is demonstrated through its stormwater management programs, designed to safeguard the lakes and uphold their quality. These measures guarantee the continued enjoyment of this peaceful lakeside retreat for future generations.
Beyond the captivating downtown area, Windermere’s historic charm extends to its preserved buildings, such as the first school, and well-maintained legacy homes. These architectural treasures showcase the town’s commitment to honoring its past while also providing residents with a unique blend of old-world allure and modern luxury.
Constructed in 1890, the Historic Windermere School House, also known as the Parramore House, stands as a proud symbol of the town’s efforts to preserve its history. Recognized as a National Register Historic Site, the schoolhouse has been meticulously maintained and serves as a constant reminder of Windermere’s educational heritage.
The preservation of the Historic Windermere School House illustrates the town’s dedication to honoring its past and ensuring that future generations can appreciate the rich history that helped shape the community. As a testament to Windermere’s commitment to preserving its history, the schoolhouse remains a treasured landmark for residents and visitors alike.
Lakefront living in Windermere Florida provides a unique blend of historic charm and modern luxury. The town’s stunning legacy lakefront homes and picturesque lakeside settings offer luxury homes in Windermere FL with:
Breathtaking lakefront views
Private boat docks
Beautifully designed interiors that seamlessly merge historic charm with contemporary amenities and luxurious living.
Notable individuals, such as Shaquille O’Neal and Johnny Damon, have resided in Windermere’s historic homes, further adding to the town’s prestige and allure. Living on the lakefront in Windermere offers residents the best of both worlds – the charm of the past and the comforts of modern living.
Golf enthusiasts will find Windermere to be an undiscovered paradise with many golf courses nearby, including those close to Walt Disney World. The proximity of esteemed golf courses such as Bay Hill allows residents and visitors to relish world-class golfing experiences amidst beautiful surroundings.
Bay Hill, established in 1961 by Arnold Palmer, has become a popular golf destination in the Windermere area, near the beautiful Butler Chain of lakes. Designed by Dick Wilson, the private course is only accessible to club members and visitors of the lodge. With its exceptional facilities and challenging layout, Bay Hill is an essential stop for any golf enthusiast.
Regular visits from renowned golfers like Tiger Woods have bolstered Bay Hill’s status as a leading golf course in the area. Regardless of whether you’re a seasoned professional or a casual player, a round at Bay Hill offers a memorable experience, highlighting the pinnacle of Windermere golf.
Downtown Windermere, Florida boasts a vibrant scene that brings the community together through weekly farmers markets, seasonal celebrations, and lively community events. These gatherings provide a welcoming atmosphere for residents and visitors alike, showcasing the town’s unique charm and spirit, similar to what you can find in downtown Orlando.
Every Friday, the Windermere Farmers Market brings a buzz of activity to Town Square Park on Main Street. From 9:00 am to 2:00 pm, visitors can browse a wide selection of goods, including:
fresh produce
bread
jewelry
flowers
and more.
The weekly farmers market provides a laid-back environment for local residents and visitors to interact while enjoying the finest local food and shopping. Specialty food vendors provide a variety of tempting treats, while the market also serves as a gathering place for the community to come together and celebrate the town’s vibrant spirit.
Beyond the weekly farmers market, the community unites for seasonal events and celebrations that highlight the town’s vibrant spirit. From the week-long food festival in Lake Windermere to the Halloween Costume Parade, these festivities provide opportunities for neighbors to connect and create lasting memories.
These events, while emphasizing Windermere’s small-town character, also fortify a tight-knit community, cultivating a sense of belonging and pride among Windermere residents. As the town comes together to celebrate the seasons, the vibrant downtown scene reflects Windermere’s unique charm and spirit.
Roundabouts in downtown Windermere, Orange County:
Simplify navigation
Enhance traffic flow for residents commuting to Orlando or Disney World
Ensure a smoother driving experience
Enhance the town’s infrastructure
Windermere’s roundabouts positively influence traffic flow, leading to up to a 50% increase in traffic capacity and improved flow at high-volume left-turn intersections. The introduction of roundabouts has diminished congestion and resulted in fewer traffic accidents, proving them to be a beneficial enhancement to the town’s infrastructure.
Roundabouts in Windermere, enhancing traffic flow and promoting safety, have proven to be an effective remedy for the town’s traffic challenges. As residents and visitors navigate the charming streets of downtown Windermere, the presence of roundabouts ensures a more convenient and enjoyable driving experience.
Windermere, Florida, offers a delightful retreat from the bustling city life of Orlando, with its enchanting downtown area, historic charm, and serene lakeside surroundings. From the lively Main Street and its weekly farmers market to the prestigious golf courses like Bay Hill, Windermere is a quaint gem that captivates residents and visitors alike. As you explore this charming town, you’ll soon discover that Windermere provides a unique and unforgettable experience, where the past meets the present and the best of both worlds awaits.
Windermere is a peaceful town with a high safety level, plenty of job opportunities and schools, and beautiful places to visit. The local people are friendly and the weather is moderate. It's also part of Orange County, one of the best places to live in Florida, and most residents own their homes. Windermere is thus an excellent area to live in.
Yes, there are annual events and festivals held on Main Street in Downtown Windermere, including the Windermere Art Affair.
407-575-5392
Mouse Asset Management LLC
DBA Morris & Co
Licensed in the State of Florida
BK 3146762
16797 Broadwater Avenue
Winter Garden, Florida 34787
