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Windermere Information and Highlights

Windermere is a smaller town in Orange County, Florida. It is part of the Orlando-Kissimmee Metropolitan Statistical Area, and sits close to Walt Disney World as well as numerous others resorts, attractions and landmarks. Windermere was officially established as a residential development in 1889 and chartered in 1925. Despite its size, Windermere holds many notable people in its borders as well as all the attractions that surround it, including: Paula Creamer, Johnny Damon, Joey Fatone, Dee Gordon, Skip Kendall, Bubba Watson, Mark Tremonti, and Vince Carter. Windermere is a town with absolutely gorgeous scenery and nature surrounding it on all sides. Lush, green foliage and trees grow in abundance, making the town of Windermere one of the most gorgeous, and more low-key, areas that you can visit near the enormous attractions of Disney World and the like. On the quieter side, Windermere offers a higher standard of living as well as more peace for those who want to be near Orlando, Kissimmee and all of the major areas that surround it. Visitors and potential residents alike can enjoy this town in abundance.

Weather

Windermere experiences the typical Florida experience with high heats and high humidity stretching throughout the year. Very rarely does the temperature drop beneath fifty degrees Fahrenheit. The most humid months tend to be June through August, and the precipitation is noticeable. Windermere can also experience heavy rainfall and occasional thunderstorms, which rarely leads to flooding from the nearby bodies of water.

Recreation / Things To Do

Windermere is a phenomenal place to get out and experience some of the most famous activities in all of Florida – namely, those of Disney World, its surrounding resorts, and numerous other clubs, lounges, theme parks and outdoor activities. Windermere is one of the quieter places to enjoy your vacation, and the natural beauty of Florida, in style.

Shopping

Windermere is surrounded by shopping opportunities, no matter what kind of shopper you are. Despite its quieter nature, Windermere has plenty in the way of gift shops, fashion boutiques, and a slew of other retail outlets for you to indulge in some proper retail therapy or go treasure hunting. No matter what you are looking for, you are sure to enjoy the hunt in Windermere.

Restaurants

With Disney World and its various resorts towering nearby, the choices, variety and upscale to down-home nature of the various eateries is not in short supply, and you won’t be either. From fantastic steak, sumptuous sushi, down-home BBQ and everything in between it, and then some, Windermere is indeed an area where you get all the best sides of Florida, both inside and outside of all the star attractions.

Nightlife

Windermere is a great place to get out at night, and one of the best areas to get out in style. This little town is surrounded by glitz and glamour on all sides, and any night owl can get out and spend the night with a cold one in hand or dancing away. No matter your preference, you’ll have one memorable evening out in Windermere.

Schools

Windermere isn’t just a great place to retire or vacation, it’s also a great place to raise a family. With a fantastic school system in place for any age, Windermere can keep your kids in a nice educational program while you head off to fish, enjoy the local theme parks, or just enjoy the area for all its worth.

Demographics

  • Population: 3,113

  • Population Density: 1,319

  • Median Age: 44.3

  • Male / Female Ratio: 0.9:1

Local / Notable Employers

For those who are looking to make the move to Windermere, the local job market is not in short supply. There are a feature of many big names and hubs, as well as smaller boutiques, shops and restaurants that can make use of all kinds of varying talent residents might have to offer. There are plenty of big names, including the mouse himself, looking for talent.

Landmarks

If you want to step out of the water for a bit and enjoy some local history or culture, Windermere is in the perfect place to do so. Not only do you have the rich history of Windermere itself, but also the neighboring Walt Disney World and many other attractions and historical marvels to enjoy.

Conclusion

Windermere is not just a charming town, but an opportunity for both visitors and potential residents alike. This small area contains plenty of homes, as well as a convenient location to everything someone could want to spend their vacation doing, and then some. Windermere is the best of both worlds when it comes to living the Floridian life.

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Latest Real Estate for Sale in Windermere

$7,200,000
5 Beds 6 Baths Isleworth SubDv. 34786 Zip Code
Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.

5373 Isleworth Country Club Drive, Windermere

$3,300,000
4 Beds 6 Baths Windermere Town SubDv. 34786 Zip Code
Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living.

515 W 2nd Avenue, Windermere

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