Windsor Hill Real Estate

Welcome to Windsor Hill, a picturesque subdivision nestled in the heart of Windermere, Florida, within the vibrant Orange County. Known for its enchanting landscapes and friendly community atmosphere, Windsor Hill offers a unique blend of suburban tranquility and modern convenience, making it a perfect place to call home.

As you drive through the tree-lined streets of Windsor Hill, you’ll discover beautifully designed homes that exude charm and elegance. The architecture reflects a harmonious blend of contemporary and traditional styles, ensuring that each residence complements the stunning natural surroundings. With spacious lots and meticulously landscaped yards, this subdivision is ideal for families looking for room to grow, as well as professionals seeking a peaceful retreat after a busy day.

Windsor Hill is more than just a collection of homes; it’s a community where neighbors become friends. Residents enjoy access to a variety of amenities, including a sparkling community pool, playgrounds, and walking trails that wind through lush green spaces. The subdivision’s strategic location means you’re just minutes away from top-rated schools, shopping centers, and recreational facilities, making it easy to enjoy all that Windermere has to offer.

For those who appreciate outdoor activities, nearby Lake Butler provides opportunities for boating, fishing, and picnicking, while the charming downtown Windermere boasts quaint shops and delightful dining options. With its blend of natural beauty, community spirit, and prime location, Windsor Hill is not just a place to live; it’s a lifestyle waiting to be embraced. Come experience the warmth and charm of Windsor Hill, where your dream home awaits!

Newest Listings in Windsor Hill

$1,375,000

5 Beds ⋅ 6 Baths ⋅ Windsor Hill SubDv. ⋅ 34786 Zip Code

PRICE IMPROVEMENT!!!! UPDATED PHOTOS! 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. ⋅ 34786 Zip Code

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

Start Your Search