Oakland Hills Homes with Private Pool type

Welcome to Oakland Hills, a picturesque subdivision nestled in the heart of Winter Garden, Florida. This charming community, located in Orange County, offers a perfect blend of suburban tranquility and vibrant local amenities, making it an ideal place for families and individuals alike.

As you explore Oakland Hills, you’ll be captivated by its beautifully designed homes, many of which feature private pools. Imagine stepping into your backyard oasis, where you can unwind under the warm Florida sun, host lively summer barbecues, or simply enjoy a refreshing dip in your own pool. These private retreats provide the perfect escape from the hustle and bustle of everyday life, allowing you to create lasting memories with family and friends.

The neighborhood is not just about stunning homes; it also boasts a strong sense of community. Residents of Oakland Hills enjoy access to well-maintained parks, scenic walking trails, and a variety of recreational activities. The local schools are highly regarded, making it a great choice for families seeking quality education for their children.

Conveniently located, Oakland Hills is just a short drive from the charming downtown Winter Garden, where you can explore boutique shops, delicious dining options, and vibrant farmers markets. Plus, with easy access to major highways, you’re only a stone's throw away from the attractions of Orlando.

Discover the allure of Oakland Hills, where the comfort of home meets the luxury of private pool living. Come and experience the lifestyle you’ve always dreamed of in this enchanting Winter Garden community!

Newest Oakland Hills Homes with Private Pool type

$1,899,999

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