Windsor Hill Homes with Pool

Windsor Hill Homes with Pool

Welcome to Windsor Hill, a picturesque subdivision nestled in the heart of Windermere, Florida, within the vibrant Orange County. This charming community offers an idyllic blend of luxury and comfort, making it the perfect place for families and individuals alike to call home.

Windsor Hill is renowned for its stunning homes, many of which come equipped with private pools, allowing residents to enjoy the Florida sunshine in style. Imagine stepping out of your beautifully designed home and into your own tranquil oasis, where you can unwind after a long day or host unforgettable gatherings with friends and family. The allure of a poolside lifestyle in this serene neighborhood is truly unmatched.

The subdivision is characterized by its lush landscapes, tree-lined streets, and a friendly atmosphere, making it a welcoming environment for all. Residents benefit from a strong sense of community, with opportunities for social gatherings and events throughout the year. The nearby parks and recreational facilities provide additional options for outdoor activities, ensuring there’s always something to do.

Windsor Hill’s prime location offers convenient access to top-rated schools, shopping centers, and dining options, making it an ideal choice for families and professionals alike. With the stunning backdrop of Windermere’s natural beauty and the luxury of homes with pools, Windsor Hill is more than just a neighborhood; it’s a lifestyle. Experience the charm and elegance of Windsor Hill, where your dream home awaits.

Newest Windsor Hill Homes with Pool

$1,499,900
5 Beds ⋅ 6 Baths ⋅ Windsor Hill SubDv.
Rare opportunity to purchase in the Windermere's Windsor Hill community on a quiet cul-de-sac. This spacious 5-bedroom home offers over 5,300 square feet of flexible living space designed for both everyday living and entertaining. Situated on nearly half an acre, the property features a functional layout with large gathering spaces, high ceilings, and plenty of natural light throughout. The kitchen includes stainless steel appliances, ample cabinet space, a center island, and connects directly to the main living areas, making it ideal for hosting or family life. The first-floor primary suite offers dual walk-in closets and a large ensuite bath, while the additional bedrooms and living spaces provide room for guests, work-from-home setups, or multigenerational living. One of the standout features of the home is the custom Indiana Jones-themed movie room, creating a unique and immersive entertainment space. The home also includes a bonus enclosed patio area that can function as a home gym or creative workspace. Outside, enjoy a large backyard, covered outdoor areas, and a private pool setting perfect for Florida living. Conveniently located near top-rated schools, shopping, dining, and major roadways, this Windermere home combines size, character, and functionality in a desirable location.

9527 Queensbury Court, Windermere
$1,450,000
4 Beds ⋅ 4 Baths ⋅ Windsor Hill SubDv.
Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throughout the home, combining sophistication with durability and low-maintenance living. Designed for both everyday comfort and entertaining, the flexible floor plan includes an oversized upstairs BONUS ROOM, with a built-in-closet and a full bathroom, ideal for a home theater, game room, executive office, fitness studio, or private guest retreat/in-law suite. Major upgrades provide exceptional value and peace of mind, including a 2021 roof, dual high-efficiency HVAC systems (2 units/ 2026), new water heater, upgraded sliding glass doors, and an epoxy-coated garage. The expansive backyard offers endless possibilities to create your dream outdoor oasis, resort-style pool, or entertaining space. Located just minutes from the renowned Butler Chain of Lakes, championship golf courses, upscale dining, shopping, and top-rated schools, this exceptional property combines luxury, privacy, and convenience in one of Central Florida’s most desirable locations. Rarely does a fully updated home with this level of quality, land, and location become available. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.

9548 Crown Prince Lane, Windermere
$12,999,999
9 Beds ⋅ 16 Baths ⋅ Windsor Hill SubDv.
Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.Two Pools one outdoor with a swim up bar and grill area and the other indoor pool with a spa and massage room ! Highlights: • Custom-built mansion in progress — secure it now to choose your colors, flooring, cabinetry, countertops, lighting, and finishes • Private helicopter pad for seamless arrival and departure • Luxury bowling alley in development — your private entertainment retreat of turn into extra car show storage garage area ! • Grand open floor plan, soaring ceilings, and estate-level architecture • Massive gourmet kitchen + walk-in pantry, ideal for chef-level entertaining • Space for home theater, gym, wine cellar, or guest quarters • Oversized garages and motor court • For our equestrian lovers, you are permitted one horse for each acre. Location Perks: • Situated in one of Windermere’s most coveted neighborhoods • Minutes to Lake Butler Chain, championship golf, and elite private schools • Close to Winter Garden Village and exclusive dining/shopping This is a rare opportunity to own a truly bespoke estate before completion — where every detail is yours to design, and your view is forever protected. Inquire now for private plans, customization walkthrough, and completion timeline. Step into your own private paradise with this one-of-a-kind resort-style property featuring every amenity for ultimate relaxation and recreation. Highlights include: • Lagoon-style pool with a swim-up bar, perfect for hosting or unwinding in luxury • Private spa sanctuary with a designated massage room and indoor heated pool, offering year-round wellness experiences • Full-size tennis court for active days and fun with friends or family • Charming barn – ideal for equestrian use, storage, or a stunning rustic event space Whether you’re dreaming of daily spa treatments, evening swims under the stars, or tennis matches followed by cocktails poolside, this property delivers the ultimate blend of luxury and leisure.

9621 Windy Ridge Road, Windermere
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