Oakland Hills Real Estate

Oakland Hills Real Estate

Welcome to Oakland Hills, a hidden gem nestled in the heart of Florida that perfectly blends serene suburban living with vibrant community spirit. This charming subdivision is known for its picturesque landscapes, friendly neighbors, and an array of amenities that cater to families, retirees, and everyone in between.

As you stroll through the tree-lined streets of Oakland Hills, you’ll be captivated by the beautifully designed homes that reflect a variety of architectural styles, each exuding character and warmth. The community is characterized by well-maintained properties and lush green spaces, making it an ideal setting for outdoor enthusiasts and those who appreciate a peaceful environment.

Residents of Oakland Hills enjoy easy access to a wealth of recreational activities. The nearby parks offer walking trails, playgrounds, and picnic areas, perfect for family gatherings or leisurely afternoons. For golf lovers, the local golf courses provide an excellent opportunity to perfect your swing while soaking in the stunning Florida sunshine.

Convenience is key in Oakland Hills, with shopping centers, restaurants, and schools just a short drive away. The community is also well-connected to major highways, making commutes to neighboring cities a breeze. Whether you’re looking to enjoy a quiet evening at home or explore the vibrant cultural scene of nearby towns, Oakland Hills provides the perfect balance.

With its welcoming atmosphere and prime location, Oakland Hills is not just a place to live—it's a place to thrive. Discover your new home in this enchanting subdivision and experience the best that Florida has to offer!

Newest Listings in Oakland Hills

15210 E Oakland Avenue, Winter Garden
$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
661 Encino Way, Altamonte Springs
$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
682 Durango Way, Altamonte Springs
$399,000
4 Beds ⋅ 2 Baths ⋅ Oakland Hills SubDv. ⋅ 32714 Zip Code
Virtually Staged. NEW ROOF! Seller will pay $5,000 towards buyers closing costs. Welcome to this beautifully renovated 4-bedroom, 2-bathroom home in the heart of Altamonte Springs, where modern upgrades meet everyday functionality. Located within a highly sought-after, top-rated school district, this move-in-ready home offers exceptional style and comfort from the moment you arrive. Step inside to discover a bright, open layout featuring all-new flooring, fresh interior paint, and a stunning designer kitchen that serves as the heart of the home. Boasting sleek quartz countertops, abundant cabinetry, an oversized farmhouse sink, and a spacious center island, this kitchen is perfectly designed for entertaining guests or enjoying everyday meals. Both bathrooms have been thoughtfully remodeled with luxurious floor-to-ceiling tile, spacious walk-in showers, and heated toilet seats, creating a spa-inspired retreat with a clean, contemporary feel. Continue outside to the private backyard, where you'll find a brand-new fence and low-maintenance gravel landscaping, offering the perfect space to relax, entertain, or personalize to your lifestyle. With a new roof, extensive interior renovations, new exterior paint, modern finishes throughout, and an unbeatable Altamonte Springs location close to shopping, dining, parks, major roadways, and everyday conveniences, this home is truly turnkey and ready for its next owners. Don't miss your opportunity to make it yours!

682 Durango Way, Altamonte Springs
6510 E 25th Avenue, Tampa
$595,000
4 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 33619 Zip Code
PRICE REDUCTION. MAIN HOME + PERMITTED GUEST HOUSE. Two full residences on one lot. NEW PRICE. 4 bedrooms, 3 baths, and approx. 2,271 total sq ft of 2024 construction on 0.30 acres. The main home offers 3 bedrooms, 2 baths, and 1,679 sq ft of concrete block and stucco construction with high ceilings, granite countertops, and tile flooring throughout; the garage is currently finished as a game room. Steps away, the permitted, detached 500 sq ft guest house includes its own full kitchen, bedroom, and bath flexible as guest quarters, home office, studio, or income opportunity (buyer to verify rental terms). No HOA, no CDD, no rental restrictions. Parking for up to 4 vehicles. Furnishings available under separate contract for a true turnkey option. Minutes to Historic Ybor City, Amalie Arena, Seminole Hard Rock, and Busch Gardens, with quick interstate access throughout Tampa Bay.

6510 E 25th Avenue, Tampa
6416 E 23rd Avenue, Tampa
$150,000
Oakland Hills SubDv. ⋅ 33619 Zip Code
The opportunity is to purchase a .79 acre parcel that could be subdivided into up to 4 residential lots. The site is wooded and the approximate dimensions are 115 feet by 299 feet subject to a survey.

6416 E 23rd Avenue, Tampa
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