Oakland Hills Homes with Deed Restrictions Community Features

Welcome to Oakland Hills, a picturesque subdivision nestled in the heart of Winter Garden, Florida. This charming community is part of Orange County and offers a unique blend of suburban tranquility and vibrant local amenities. Oakland Hills is ideal for families, retirees, and anyone in between, providing a welcoming environment that feels like home.

One of the defining features of Oakland Hills is its commitment to maintaining a high quality of life through deed restrictions. These regulations ensure that the community remains visually appealing and well-kept, encouraging residents to take pride in their homes and surroundings. You’ll find beautifully landscaped yards, thoughtfully designed homes, and a sense of community that fosters lasting relationships among neighbors.

As you explore Oakland Hills, you’ll discover a variety of home styles that cater to diverse tastes and preferences. From modern single-family homes to charming traditional designs, there’s something for everyone in this delightful neighborhood. Many homes feature spacious layouts, updated kitchens, and serene outdoor spaces perfect for entertaining or enjoying a quiet evening under the stars.

Beyond the homes, Oakland Hills boasts a range of community features that enhance the living experience. Residents can enjoy nearby parks, walking trails, and recreational facilities, making it easy to stay active and engaged. The close-knit community often hosts events and gatherings, providing opportunities for neighbors to connect and build friendships.

With its prime location in Winter Garden, Oakland Hills offers easy access to shopping, dining, and entertainment, all while maintaining a peaceful suburban atmosphere. Come experience the charm of Oakland Hills, where your dream home awaits!

Newest Oakland Hills Homes with Deed Restrictions Community Features

$1,924,999

4 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code

Custom-built by Justice & Wood Builders, this 4-bedroom, 3-bathroom Modern Farmhouse sits on a rare 0.47-acre lot in Oakland Hills, an intimate community of just 17 homesites minutes from Historic Downtown Winter Garden. Towering, moss-draped oaks frame the property and set a peaceful tone from the moment you arrive. Inside, wide-plank wood floors and abundant natural light flow through an open-concept living space crowned by cathedral ceilings and exposed timber beams. The kitchen goes well beyond standard gourmet, with shaker cabinetry, quartz countertops, a massive blue-gray center island, a deep farmhouse sink, professional stainless steel appliances, and a natural gas range built for serious cooking. The bedrooms are generously sized and well separated. The upstairs bedroom is flexible enough to serve as a home office, gym, media room, or guest suite, and it has air-conditioned storage and a large walk-in attic. The bathrooms feature clean lines, modern fixtures, and custom tilework. The laundry room has extensive cabinetry, quartz counters, and a patterned tile backsplash. The three-car garage includes an EV adapter in the third bay. Out back, the fully fenced yard feels like your own resort, with a pool and spa surrounded by a spacious paver patio and a fire pit area for evenings outside. Downtown Winter Garden's Farmers Market, Plant Street Market, boutiques, and restaurants are minutes away by car or golf cart.

15210 E Oakland Avenue, Winter Garden

Start Your Search