Oakland Town Real Estate

Welcome to Oakland Town, a charming subdivision nestled in the heart of Oakland, Florida, within the picturesque Orange County. This serene community offers a perfect blend of small-town charm and modern living, making it an ideal place for families, retirees, and everyone in between.

Oakland Town is characterized by its tree-lined streets, beautifully manicured lawns, and a warm sense of community. Residents enjoy a peaceful lifestyle while being just a stone's throw away from the vibrant attractions of nearby Orlando. The subdivision features a variety of well-designed homes, each exuding character and comfort, catering to diverse tastes and preferences.

One of the standout features of Oakland Town is its proximity to nature. The area is surrounded by lush parks and scenic trails, perfect for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, the natural beauty of the region will captivate you. Additionally, the nearby Lake Apopka offers stunning waterfront views and recreational opportunities for fishing, kayaking, and picnicking.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a top-notch education. The community also fosters a friendly atmosphere, with local events and gatherings that bring neighbors together, creating lasting friendships.

With its perfect blend of tranquility and accessibility, Oakland Town is more than just a place to live; it’s a lifestyle. Discover the charm and warmth of this delightful subdivision, where your dream home awaits in the beautiful backdrop of Florida’s Orange County!

Newest Listings in Oakland Town

$1,125,000

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

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. ⋅ 34760 Zip Code

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

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