Isleworth Homes with Pool View

Welcome to Isleworth, a prestigious and picturesque subdivision nestled in the heart of Windermere, Florida. This exclusive community is renowned for its luxurious homes, stunning landscapes, and a lifestyle that seamlessly blends elegance with comfort. Isleworth is characterized by its beautifully manicured lawns, winding streets, and serene waterways, creating an idyllic setting for families and individuals alike.

One of the standout features of Isleworth is its breathtaking homes, many of which offer captivating pool views. Imagine waking up each morning to the sight of shimmering waters right from your bedroom, or enjoying a tranquil evening by your private pool, surrounded by lush tropical gardens. These homes are designed with outdoor living in mind, providing the perfect backdrop for entertaining guests or simply relaxing in your own personal oasis.

In addition to the stunning residences, Isleworth boasts a wealth of amenities that cater to a luxurious lifestyle. Residents can enjoy access to a world-class golf course, a state-of-the-art fitness center, and a vibrant community clubhouse. The nearby Lake Butler and the surrounding natural beauty provide ample opportunities for outdoor activities, from boating to hiking.

Isleworth is not just a place to live; it's a community that fosters connections and a sense of belonging. With its prime location in Windermere, you'll find yourself just a short drive away from Orlando’s attractions, fine dining, and shopping. Experience the allure of Isleworth, where luxury meets lifestyle, and find your dream home with a pool view today!

Newest Isleworth Homes with Pool View

$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

$3,400,000

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

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

9731 Chestnut Ridge Drive, Windermere

Start Your Search