Isleworth Homes with Pool View

Isleworth Homes with Pool View

Welcome to Isleworth, a premier subdivision nestled in the heart of Windermere, Florida, within the scenic Orange County. Known for its luxurious lifestyle and stunning landscapes, Isleworth is a haven for those seeking both tranquility and vibrancy in their living environment.

As you explore this exquisite community, you’ll discover a collection of magnificent homes, many of which boast breathtaking views of serene pools. Imagine waking up each day to the gentle sound of water and the sun glistening off your private oasis. These homes with pool views are designed to offer a seamless blend of indoor and outdoor living, perfect for entertaining guests or enjoying peaceful moments with family.

Isleworth is not just about beautiful homes; it's a lifestyle. The subdivision features meticulously landscaped grounds, access to world-class amenities, and a strong sense of community. Residents enjoy a range of recreational activities, from golfing on the renowned Isleworth Golf & Country Club to leisurely strolls around the picturesque lakes that Windermere is famous for.

With its prime location, Isleworth provides easy access to upscale shopping, fine dining, and top-rated schools, making it an ideal choice for families and professionals alike. Whether you're looking for a serene retreat or an active lifestyle, Isleworth has it all. Experience the charm of Florida living at its finest, where every day feels like a vacation in your own backyard. Come and discover your dream home with a pool view in Isleworth 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

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