Oakland Town Real Estate

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming subdivision offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, professionals, and retirees alike. With its picturesque tree-lined streets and welcoming community atmosphere, Oakland Town is more than just a neighborhood; it’s a lifestyle.

As you explore Oakland Town, you'll find a variety of beautifully designed homes that cater to diverse tastes and preferences. From contemporary single-family residences to cozy townhomes, there’s something here for everyone. The community is known for its well-maintained properties and lush landscaping, creating a serene environment that residents are proud to call home.

One of the standout features of Oakland Town is its proximity to nature. The subdivision is surrounded by stunning parks and scenic trails, perfect for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking leisurely strolls, the natural beauty of the area will captivate you. Additionally, the nearby Lake Apopka offers fantastic opportunities for fishing and boating, making it a favorite spot for water lovers.

Families will appreciate the excellent local schools and the strong sense of community that Oakland Town fosters. With a variety of local shops, restaurants, and recreational facilities just a short drive away, residents enjoy the convenience of urban living while still relishing the peacefulness of suburban life.

Discover the charm of Oakland Town, where community spirit meets the beauty of Florida living. Your dream home awaits in this delightful subdivision!

Newest Listings in Oakland Town

$1,125,000

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv.

SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

250 N Walker Street, Oakland

$629,999

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv.

Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current market conditions, this property presents an excellent opportunity for buyers seeking newer construction without delays or renovation needs. A compelling option for buyers looking for value, condition, and immediate occupancy.

38 S Pollard Street, Oakland

Start Your Search