Oakland Hills Homes with Sidewalk Exterior Features

Welcome to Oakland Hills, a picturesque subdivision nestled in the heart of Florida, where community charm meets modern living. This delightful neighborhood is renowned for its well-maintained homes and inviting atmosphere, making it the perfect place for families, retirees, and everyone in between.

One of the standout features of Oakland Hills is its commitment to creating a pedestrian-friendly environment. With beautifully designed sidewalks lining the streets, residents can enjoy leisurely strolls or invigorating jogs while soaking in the scenic surroundings. The sidewalks not only enhance the aesthetic appeal of the community but also foster a sense of connection among neighbors, encouraging friendly chats and spontaneous gatherings.

The homes in Oakland Hills boast a variety of architectural styles, each exuding character and warmth. Many properties feature lush landscaping and spacious yards, perfect for outdoor entertaining or simply unwinding after a long day. The community’s thoughtful layout ensures that each home is situated to maximize privacy while still being part of a vibrant neighborhood.

Living in Oakland Hills means embracing a lifestyle that values both comfort and community. Residents can take advantage of nearby parks, recreational facilities, and local shops, all just a stone’s throw away. Whether you’re sipping coffee on your porch or taking a leisurely evening walk, you’ll find that Oakland Hills is more than just a place to live; it’s a place to thrive.

Discover the charm of Oakland Hills today, where your dream home awaits amidst the enchanting Florida landscape!

Newest Oakland Hills Homes with Sidewalk Exterior 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

$295,000

3 Beds ⋅ 2 Baths ⋅ Oakland Hills SubDv. ⋅ 32714 Zip Code

Excellent opportunity in Altamonte Springs! This 3-bedroom, 2-bath home is ideal for investors seeking income potential as well as future homeowners planning ahead for their next move. The home features a comfortable open floor plan, an updated kitchen with modern appliances, a new roof, and plenty of natural light throughout. The primary suite provides privacy with its own en-suite bath, while the additional bedrooms create flexibility for family, guests, or a home office. Step outside and enjoy the spacious fenced backyard surrounded by greenery, creating an inviting space for outdoor living, entertaining, gardening, or future enhancement. Located in a quiet, established neighborhood, this property places residents close to schools, shopping, dining, parks, and everyday conveniences. With easy access to major highways, commuting throughout Altamonte Springs, Orlando, and the surrounding Central Florida area is simple and convenient. 661 Encino Way brings together location, functionality, outdoor space, and long-term value.

661 Encino Way, Altamonte Springs

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