Oakland Hills Homes with Deed Restrictions Community Features

Welcome to Oakland Hills, a charming subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This community offers a delightful blend of suburban tranquility and modern convenience, making it an ideal place for families, retirees, and everyone in between.

As you drive through the picturesque streets of Oakland Hills, you’ll immediately notice the well-maintained homes that reflect a strong sense of pride in ownership. Each residence is designed with thoughtful attention to detail, showcasing a variety of architectural styles that cater to diverse tastes. With deed restrictions in place, residents enjoy the benefits of a cohesive neighborhood aesthetic, ensuring that the community remains beautiful and inviting for all.

Life in Oakland Hills is enhanced by its array of community features. Enjoy leisurely strolls along tree-lined sidewalks, or gather with friends at the local park, which offers playgrounds and picnic areas perfect for family outings. The community fosters a friendly atmosphere where neighbors become friends, and social events are often organized to strengthen these bonds.

Convenience is key in Oakland Hills, with easy access to major highways, shopping centers, and top-rated schools. Whether you’re looking for a cozy café, a vibrant farmers market, or a night out in downtown Winter Garden, everything you need is just a short drive away.

Discover the charm and warmth of Oakland Hills, where community spirit meets the beauty of Florida living. Come and experience the lifestyle that awaits you in this enchanting subdivision!

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

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