The Best Gated Communities in Windermere, FL

 

Are you dreaming of a luxurious, secure, and serene lifestyle in the heart of Central Florida? Step into the extraordinary world of gated communities in Windermere, an enchanting town that has emerged as a coveted haven for discerning individuals in pursuit of harmonious living and accessibility. Whether you're a burgeoning family in quest of your forever abode or a discerning buyer in search of an esteemed address, living in Windermere's gated enclaves presents a diverse array of choices tailored to cater to your distinct requirements and preferences.

Why We Love a Gated Community

Living in a gated community offers a unique sense of exclusivity and tranquility that is unmatched. These meticulously maintained, secluded neighborhoods provide an array of luxurious amenities, from immaculate golf courses and inviting swimming pools to cutting-edge fitness centers and thriving social clubs. With controlled entry and attentive surveillance, you can relish the assurance that you can relax and fully immerse yourself in the lifestyle and splendor of your surroundings.

7 Best Gated Communities in Windermere, FL

Windermere, Florida, is renowned for its exceptional gated communities, each offering its own unique charm and appeal. As you explore the options, you'll discover a diverse array of luxurious homes, breathtaking landscapes, and unparalleled amenities that cater to a variety of lifestyles and budgets. Discover the allure of seven premier gated communities in Windermere and uncover the unique features that make them stand out in this sought-after area.

1. Isleworth

Isleworth is perhaps Windermere’s crown jewel—an ultra-luxury, gated golf and country club community that blends exclusivity, natural beauty, and premier amenities. It sits on approximately 600 acres, wrapping around portions of the Butler Chain of Lakes and featuring a championship 18-hole Arnold Palmer–designed golf course, lush tropical landscaping, and some of the region’s most impressive custom estates. Homes here are expansive: many properties fall in the 4,000 to over 16,000 square feet range under air, with lot sizes often well over half to a full acre (or more), custom pools, waterfront or golf course frontage, and interiors built to the highest standards. The architectural styles tend toward grand, estate-scale designs with attention to detail—luxury finishes, high ceilings, sweeping outdoor living spaces, docks or private boat ramps in certain cases, and exclusivity in both design and location.

As of September 2025, the Isleworth real estate market reflects its upper echelon status. Average listing prices hover around $5.5 to $5.6 million, with the lowest active listings typically around $2.8 million and some of the most prestigious estates commanding over $14 million. The average price per square foot sits near $840-850/sq ft for many active listings. Sales tend to move more slowly here, given the high price points and custom nature of the homes; average days on market are in the range of 70-90 days or more, depending on size, finishes, and lot features.

2. Keene’s Pointe

Keene’s Pointe is one of Windermere’s most recognized luxury gated communities, blending golf course living, lakeside views, and a true neighborhood feel. The community is made up of multiple “villages,” each with its own character, whether overlooking the Jack Nicklaus-designed Golden Bear Golf Course, backing onto the Butler Chain of Lakes, or set against conservation land for added privacy. Homes in Keene’s Pointe range from around 2,000 to over 9,000 square feet, offering 3 to 8 bedrooms, open layouts, and custom finishes. Architectural styles vary widely, including Mediterranean, French Country, and classic American designs, giving buyers a range of options while maintaining a cohesive upscale aesthetic. Many homes feature private pools, outdoor kitchens, large garages, and luxury appointments that fit the needs of today’s buyers.

Amenities are another reason why Keene’s Pointe is such a desirable community. Beyond the 24-hour guard-gated entrances, residents enjoy access to The Golden Bear Club with golf, tennis, dining, and fitness options, as well as playgrounds, walking paths, boardwalks, and private docks. With its combination of natural beauty, community lifestyle, and resort-style amenities, Keene’s Pointe is considered one of Windermere’s top addresses. Its location also places it close to top-rated public and private schools, fine dining, boutique shopping, and Orlando’s world-class attractions.

As of September 2025, Keene’s Pointe remains a strong player in the luxury market. The average price of homes is around $3.1 million, though properties can be found from about $1.1 million up to $9.5 million depending on size, location, and water or golf frontage. On a square-foot basis, most listings average $550 to $565 per square foot, though prices vary with custom finishes and lot type. Recent sales also show a median closing price of around $1.5 million, reflecting the community’s wide variety of home styles and sizes. Keene’s Pointe continues to be one of the premier choices in Windermere for buyers seeking elegance, lifestyle, and long-term value.

3. Lake Butler Sound

Lake Butler Sound, located in the sought-after neighborhood of Windermere, FL, offers an unparalleled living experience in Central Florida. This exclusive gated community is renowned for its luxurious custom-built homes and resort-like atmosphere, catering to the discerning buyer with properties ranging from opulent estates to palatial mansions.

Lake Butler Sound features a variety of prestigious neighborhoods, each offering unique features and styles of homes. From the exclusive elegance of The Reserve Section to the spacious sophistication of The Estates Section and the stylish serenity of the Mediterranean Section, the community showcases a mix of architectural styles, including modern masterpieces, classical designs, and Mediterranean-style estates.

Residents of Lake Butler Sound are fortunate to have access to a wealth of amenities, including a waterfront community, guard-gated entry, a private fishing pier, and Cartmel Gardens Garden Park. The community offers an exclusive and elegant living experience, with homes boasting high-end finishes, private pools, and stunning lake views. Moreover, the community provides excellent connectivity, convenience, and the serenity of a waterfront lifestyle, making it a prime choice for those seeking a luxurious lifestyle.

Lake Butler Sound's prime location provides easy access to major points of interest in Central Florida, such as the Walt Disney World Resort, Downtown Orlando, and the Orlando International Airport. Additionally, the community is conveniently located near notable natural attractions, including Tibet-Butler Nature Preserve, Lake Down, and Isleworth Golf & Country Club, offering residents a perfect blend of luxury living and proximity to entertainment and recreational options.

Lake Butler Sound's combination of luxurious homes, idyllic waterfront lifestyle, prestigious neighborhoods, and convenient location make it another ranked best gated community in Windermere, FL, offering the epitome of elegance and sophistication for its residents.

4 Tilden’s Grove

Tildens Grove is one of Windermere’s most sought-after luxury gated communities, combining elegance, privacy, and a family-friendly atmosphere. This established neighborhood features spacious estate homes situated on large lots, many around a half-acre or more, with mature landscaping, lake and conservation views, and timeless architectural styles. Homes typically range from 3,200 to over 7,100 square feet under air and offer between 4 and 7 bedrooms. Designed with entertaining and comfort in mind, many properties include open floor plans, gourmet kitchens, expansive primary suites, three- to four-car garages, and resort-style outdoor living areas with custom pools and summer kitchens. The community also provides residents with amenities such as a clubhouse, playgrounds, tennis and basketball courts, and 24-hour gated security.

The location of Tildens Grove is another key advantage for residents. Nestled in the heart of Windermere, the neighborhood provides quick access to top-rated Orange County schools, including nearby private academies, making it especially appealing for families. Fine dining, boutique shopping, and luxury golf courses are all just minutes away, while Walt Disney World and the greater Orlando attractions remain conveniently close for both entertainment and investment appeal. The combination of tranquility, exclusivity, and proximity to Central Florida’s best amenities makes Tildens Grove a standout choice for luxury homebuyers.

As of September 2025, Tildens Grove continues to reflect strong demand and high property values in the Windermere market. Current listings average around $2.6 million, with prices generally ranging between $1.1 million and $7.5 million, depending on lot size, water frontage, and custom upgrades. On average, homes sell for $465 per square foot, though recent transactions have varied, with some estates closing closer to $330 per square foot depending on condition and finishes. With its generous home sizes, upscale amenities, and prime Windermere location, Tildens Grove remains one of the most prestigious neighborhoods for buyers seeking both luxury and long-term value.

5. Casabella

Casabella at Windermere is one of Central Florida’s most exclusive luxury gated communities, featuring just 79 custom estate homes built by Toll Brothers between 2014 and 2018. Each residence is situated on a generous half-acre to one-acre homesite, offering ample space, privacy, and beautiful architectural detail. Homes in Casabella typically range from 4,300 to over 7,000 square feet under air, with open layouts designed for both comfort and entertaining. Many properties include 4 to 8 bedrooms, soaring ceilings, gourmet kitchens, three-car garages, and outdoor living spaces with resort-style pools. Mediterranean and transitional design elements are common, creating a timeless aesthetic that appeals to discerning luxury buyers.

Beyond the homes themselves, Casabella provides residents with an unmatched location in the heart of Windermere. The neighborhood offers a quiet, secure atmosphere, while remaining just minutes from everyday conveniences like upscale shopping, fine dining, and premier golf courses. Families also appreciate its proximity to top-rated Orange County schools and prestigious private academies. For those seeking leisure, Walt Disney World, Universal Orlando, and the vibrant Dr. Phillips dining scene are just a short drive away.

As of September 2025, Casabella continues to attract strong buyer demand thanks to its exclusivity and luxury appeal. Current listings average between $3.3 million and $3.5 million, with homes typically falling in a price range of $2.3 million to $5.0 million, depending on size, location within the community, and custom upgrades. This translates to an average of $480 to $510 per square foot, making Casabella one of the higher-end communities in Windermere. With large home sites, elegant design, and close proximity to Central Florida’s finest amenities, Casabella remains a premier choice for buyers seeking privacy, sophistication, and lasting value in Windermere real estate.

6. The Reserve At Belmere

The Reserve at Belmere is a prestigious guard-gated community renowned for its serene environment and luxurious lifestyle. Situated along the picturesque 40-acre Lake Whitney, this community offers a blend of waterfront estates, elegant villas, and spacious family homes, with architectural styles ranging from Mediterranean to contemporary. Built primarily between 2001 and 2007, homes vary in size from approximately 2,000 to over 7,000 square feet, featuring 3 to 7 bedrooms, often with private pools and stunning lake views. The community’s meticulously maintained landscaping, majestic oaks, and tranquil lakes, including Lake Whitney, Lake Butler, and Lake Rhea, create a peaceful retreat just 16 miles west of downtown Orlando and 11 miles north of Disney World. Recognized by Orlando Magazine in 2007 as one of the region’s finest gated communities, The Reserve at Belmere combines natural beauty with upscale living, making it a sought-after destination for families and professionals alike.

Residents of The Reserve at Belmere enjoy an array of resort-style amenities designed to enhance their quality of life. The community’s centerpiece is a lakefront clubhouse featuring a state-of-the-art fitness center with panoramic views of Lake Whitney, a fishing pier, and a gazebo perfect for enjoying Central Florida’s breathtaking sunsets. Outdoor enthusiasts can take advantage of two tennis courts, a pickleball court, a basketball court, a sand volleyball court, and a children’s playground, fostering both recreation and community engagement. With convenient access to top-rated schools, upscale shopping at Winter Garden Village and The Grove, and major highways like the 429 and Florida Turnpike, the community offers both tranquility and connectivity. Managed by Sentry Management, the HOA ensures well-maintained grounds and robust security, while monthly fees of approximately $221 provide access to these exceptional amenities, making The Reserve at Belmere an ideal choice for those seeking luxury and leisure in Windermere

7. Glenmuir

Glenmuir combines the best of both worlds, a prime location and an exceptional quality of life. Situated just minutes from the bustling heart of Windermere, this gated community offers easy access to shopping, dining, and entertainment, while still providing a peaceful and private oasis.

The neighborhood is distinctive for its Mediterranean-inspired residences featuring tiled roofs and Florida-style architecture, built by Pulte Home Builder. It provides an opulent living environment and a place for residents to create lasting memories and establish a home. Glenmuir Windermere homes range from 3-5 bedrooms, span 2,000 to 3,600 square feet, and are set upon generous lots. The community offers a perfect blend of style and comfort, with spacious floor plans, high-end finishes, gourmet kitchens, luxurious master suites, and private outdoor living spaces.

Residents enjoy a range of amenities, including a community clubhouse, a sparkling swimming pool, and well-manicured parks and trails. Glenmuir also features a basketball court, volleyball court, soccer field, playground, and an expansive pond-front neighborhood park.

With a variety of home styles and price points, strategic location just minutes from prestigious schools, vast shopping and dining options, and various parks and recreational facilities, Glenmuir caters to a diverse range of buyers, from growing families to empty-nesters seeking a maintenance-free lifestyle.

Conclusion

As you consider the exceptional gated communities of Windermere, Florida, you'll discover a world of luxurious living, unparalleled amenities, and a true sense of community. Whether you're drawn to the prestigious elegance of Isleworth, the serene beauty of Windermere Sound, or the maintenance-free convenience of Casabella, there is a gated community in Windermere that is perfectly suited to your unique lifestyle and preferences. Get in touch with Andy, your local Windermere, FL, real estate agent today!