Oakland Hills Homes with Deed Restrictions Community Extras

Welcome to Oakland Hills, a picturesque subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This charming community offers an idyllic blend of suburban tranquility and modern convenience, making it the perfect place to call home.

Oakland Hills is designed for those who appreciate the finer things in life. With well-maintained homes featuring unique architectural styles, this neighborhood boasts a welcoming atmosphere that fosters a strong sense of community. The deed-restricted nature of the subdivision ensures that the aesthetic integrity of the area is preserved, allowing residents to enjoy beautifully landscaped yards and meticulously kept common areas.

Residents of Oakland Hills benefit from an array of community extras that enhance the living experience. Enjoy leisurely strolls along the scenic walking paths, or gather with friends and family in the community park, complete with picnic areas and playgrounds. The neighborhood’s commitment to maintaining a peaceful environment is evident, with regulations in place that promote harmonious living among neighbors.

Conveniently located near major highways, Oakland Hills offers easy access to Winter Garden’s charming downtown area, where you'll find delightful shops, restaurants, and entertainment options. Additionally, the local schools are highly rated, making it an ideal choice for families seeking quality education for their children.

If you’re searching for a community that combines comfort, style, and a strong sense of belonging, look no further than Oakland Hills. Discover your dream home in this enchanting neighborhood today!

Newest Oakland Hills Homes with Deed Restrictions Community Extras

$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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