Winderwood Real Estate

Welcome to Winderwood, a charming subdivision nestled in the heart of Orlando, Florida, within the vibrant Orange County. This delightful community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

Winderwood is characterized by its picturesque tree-lined streets and well-maintained homes, each exuding a unique charm that reflects the warmth of the neighborhood. Residents enjoy spacious yards, perfect for outdoor gatherings, gardening, or simply soaking up the Florida sun. The community is known for its friendly atmosphere, where neighbors become friends and everyone feels at home.

One of the standout features of Winderwood is its strategic location. Just a short drive away, you'll find an array of shopping, dining, and entertainment options that Orlando is famous for. Whether you're looking to explore the magical realms of theme parks, indulge in fine dining, or enjoy a day of shopping at local boutiques, everything is within easy reach. For nature enthusiasts, nearby parks and recreational areas offer opportunities for hiking, biking, and enjoying the great outdoors.

Families with children will appreciate the access to highly-rated schools within the Orange County School District, ensuring a quality education for the younger residents.

In Winderwood, you’ll find not just a house, but a community where memories are made and cherished. Discover the warmth and charm of Winderwood—your perfect slice of Orlando awaits!

Newest Listings in Winderwood

$700,000

4 Beds ⋅ 3 Baths ⋅ O6438658 MLS

Under contract-accepting backup offers. Virtually Staged. Welcome to 4425 Winderwood in sought-after Dr. Phillips! This fantastic 4-bedroom, 3-bath pool home is tucked away in Winderwood, a quiet, tree-lined neighborhood of just 49 homes. The home features a desirable split-bedroom floor plan, an open family room and kitchen, a wood-burning fireplace, and separate formal living and dining rooms, with the living room easily serving as a home office or flex space. All of the bedrooms have new LVP flooring, and the bedrooms and bathrooms have been freshly painted. The popcorn ceilings have also been removed and replaced with a fresh knockdown finish, giving the home an updated look and feel. Step outside and relax on the screened porch overlooking your private pool and beautifully landscaped backyard. The pool enclosure has been re-screened, new ceiling fans have been added to the back porch, and the exterior of the home has been freshly painted with the brick sealed as well. It’s a great space for entertaining, relaxing, or simply enjoying the Florida lifestyle. Rest easy knowing many of the big-ticket items and updates have already been taken care of for you, including a new roof in 2024, A/C in 2024, and a new water heater in 2026. Winderwood offers a great Dr. Phillips location approximately 20 minutes from Downtown Orlando and Walt Disney World, 10 minutes from Universal Orlando, and just minutes from all the great dining options along Restaurant Row. Zoned for sought-after Windy Ridge K-8 and Olympia High School. Great house, great neighborhood, and a great location. Call David today to arrange your private showing!

4425 Winderwood Circle, Orlando

$649,900

3 Beds ⋅ 2 Baths ⋅ O6429389 MLS

Under contract-accepting backup offers. Welcome to Winderwood, a desirable and rarely available community in the heart of Dr. Phillips, featuring just 49 homes along a single circular, tree-lined street. Situated on an oversized .36-acre lot, this pool home offers charm, character, and the ideal Florida lifestyle. The light-filled open floor plan features elegant archways, spacious living and dining areas, a great room with vaulted ceilings, gas fireplace, and impact-resistant skylights. The kitchen offers 42-inch cabinetry, generous counter space, gas range, bar-top seating, and a breakfast nook overlooking the pool. The flexible layout includes 3 bedrooms, 2 full bathrooms, plus a versatile living room/flex space with the option to convert back to a fourth bedroom. The spacious primary suite features dual walk-in closets, a newer sliding glass door leading to the lanai, and an updated primary bathroom with granite countertops, three separate vanities, and a walk-in shower with frameless glass enclosure. The secondary bathroom has also been updated with granite countertops and a tiled walk-in shower with frameless glass door. Enjoy Florida living with a screened outdoor retreat featuring a PebbleTec-finished pool, covered lanai, summer kitchen with bar-height seating, and paver deck. Beyond the pool area, a private garden retreat awaits with winding reclaimed Old Chicago brick pathways leading to a fire pit surrounded by brick sitting walls, brick patio areas, a large storage shed, and lush mature landscaping with an abundance of flowering plants, including crepe myrtles, azaleas, callistemons, and more. The fully fenced backyard offers beautiful sunset views. Notable improvements include a 2017(Dec) roof, upgraded windows and sliding glass doors, updated flooring (2022), and a new water heater (2026). Conveniently located near Restaurant Row, shopping, major highways, and zoned for Windy Ridge K-8 and Olympia High School.

4507 Winderwood Circle, Orlando

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