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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

1221 Oakdale Street, Windermere
$1,250,000
Windermere Town SubDv. ⋅ 34786 Zip Code
Build Your Dream Lakefront Home in the Town of Windermere! Opportunity is knocking in one of Central Florida’s most desirable areas! This exceptional one-acre lakefront homesite on Oakdale Street in the town offers a rare opportunity to bring your vision to life and build the custom home you have always dreamed of. With an impressive 105 feet of direct frontage on beautiful Lake Bessie, this property provides the space, privacy, and waterfront setting to create something truly special. One of the biggest advantages of this property is NO HOA. Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a stunning custom estate, a spacious family home, or a private lakeside retreat, this property gives you the opportunity to create a home that is uniquely yours. The expansive one-acre lot provides plenty of room to design the lifestyle you want. Imagine a beautiful custom residence with expansive living spaces, a resort-style pool, outdoor entertaining areas, lush landscaping, a private garden, oversized garage, and breathtaking views of Lake Bessie. With 105 feet of lake frontage, you can take full advantage of the waterfront setting and enjoy the beauty and tranquility of lakefront living right in the heart of Windermere. Instead of settling for someone else’s floor plan, start with a blank canvas and create a home designed around the way you live. Bring your architect, builder, and ideas and transform this exceptional homesite into your own private sanctuary. Location is everything, and this property offers the best of the Old Windermere lifestyle. Ideally located within a short distance of the Windermere Farmers Market, local shops, restaurants, and more, while beautiful Lake Butler is just blocks away. Town residents also have access to a boat ramp on Lake Butler and Lake Bessie, along with tennis courts, providing even more opportunities to enjoy the outdoors and the unique lifestyle that makes Windermere so desirable. Windermere is known for its beautiful lakes, charming community atmosphere, desirable residential neighborhoods, and convenient proximity to everything that makes Central Florida such a sought-after place to live. Opportunities to own a large lakefront homesite with no HOA and 105 feet of Lake Bessie frontage are truly special. This is your opportunity to stop dreaming about the perfect home and start building it. Make your vision come to life. Make this exceptional Windermere lakefront property the place you call home. Don't miss this rare opportunity!

1221 Oakdale Street, Windermere
5092 Isleworth Country Club Drive, Windermere
$8,500,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

5092 Isleworth Country Club Drive, Windermere
9310 Isleworth Gardens Drive, Windermere
$3,595,000
3 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story garden villa offers elevated garden views. The residence pairs timeless Mediterranean architecture with sophisticated finishes and a seamless indoor-outdoor design. Beautiful finishes throughout the interior include travertine flooring, wood-beamed ceilings and solid wood doors, creating a warm and gracious aesthetic. The expansive kitchen is designed for both everyday living and entertaining, with double islands, Quartzite countertops, a marble mosaic backsplash, Wolf appliances, a gas range, wet bar and butler’s pantry. A stone fireplace provides a focal point in the living room, while the spacious family room opens through panoramic sliding doors to a covered lanai, extending the living spaces naturally outdoors.The primary suite offers a private retreat with a morning bar, sitting area, spa-inspired bath and generous walk-in closet. A wood-floored study with custom built-ins provides an elegant setting for work, while additional bedrooms offer comfort and privacy for family and guests. Additional interior highlights include the laundry room, powder bath, and a three-car garage.Beyond the interiors, the home embraces its lush garden setting with tranquil pond views and an expansive outdoor living area. The covered lanai features a summer kitchen and pool bath overlooking a heated saltwater pool and spa, creating a private setting for relaxed afternoons and beautiful entertaining. The Gardens of Isleworth offer convenient living in a beautiful setting within Central Florida’s most iconic golf course community.

9310 Isleworth Gardens Drive, Windermere
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