Isleworth Homes with Recreation Facilities Amenities

Welcome to Isleworth, a prestigious subdivision nestled in the heart of Windermere, Florida, within the scenic Orange County. This exclusive community is renowned for its luxurious homes, world-class amenities, and breathtaking natural surroundings, making it a sought-after destination for those seeking both comfort and elegance.

Isleworth boasts a collection of stunning residences that cater to a variety of lifestyles, from sprawling estates to contemporary masterpieces. Each home is designed with meticulous attention to detail, featuring expansive living spaces, gourmet kitchens, and private outdoor retreats that invite relaxation and entertainment. The architectural styles reflect a harmonious blend of modern sophistication and timeless charm, ensuring that every property is as unique as its owner.

One of the standout features of Isleworth is its exceptional recreational facilities. Residents enjoy access to a range of amenities that promote an active and vibrant lifestyle. The community is equipped with state-of-the-art fitness centers, sparkling swimming pools, and meticulously maintained tennis courts, providing ample opportunities for exercise and leisure. For those who appreciate the outdoors, scenic walking trails and lush green spaces encourage exploration and relaxation amid the beautiful Floridian landscape.

In addition to its recreational offerings, Isleworth is conveniently located near premier shopping, dining, and entertainment options. With its close-knit community atmosphere and a commitment to excellence, Isleworth is not just a place to live—it's a lifestyle. Discover the perfect blend of luxury, leisure, and community in this idyllic Windermere enclave. Welcome home to Isleworth!

Newest Isleworth Homes with Recreation Facilities Amenities

$2,999,999

4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two-story living room with a fireplace, creating an impressive yet inviting setting for entertaining. Providing access from all rooms to the outdoor living area, the thoughtfully designed floor plan blends elegance and functionality throughout. The kitchen is designed for both everyday living and entertaining, featuring Thermador appliances, including a cooktop, double ovens, warming drawer, microwave, dishwasher, icemaker, and beverage refrigerator. The space overlooks a generous dinette area with direct access to the patio, seamlessly connecting indoor and outdoor living. A formal dining room and a spacious great room provide additional gathering spaces for family and guests. The primary suite, located on the first floor, is a private retreat complete with three closets and a spa-inspired bath showcasing a large walk-in shower, soaking tub, and dual vanities. A second ensuite bedroom is also conveniently located on the main level, along with a well-appointed laundry room featuring built-in cabinetry. Upstairs, the travertine staircase with iron railing leads the way to a large game room with wet bar and French doors opening to an expansive balcony overlooking the pool and golf course. Two additional ensuite bedrooms complete the upper level. Throughout the home, you’ll find plantation shutters, travertine flooring, and hardwood floors, adding warmth and sophistication. The property also features an oversized three-car garage with storage and a large driveway for ample parking.Outdoor living is truly exceptional, with a large swimming pool, covered patio with half bath, and summer kitchen with beverage refrigerator—perfect for entertaining while enjoying serene golf course views. The oversized fenced backyard offers privacy and space to relax or play. Conveniently located to shopping, dining and expressways, as well as top-rated public and private schools, this home has it all!

5145 Latrobe Drive, Windermere

$6,000,000

7 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.

9725 Chestnut Ridge Drive, Windermere

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