Oakland Town Real Estate

Welcome to Oakland Town, a picturesque subdivision nestled in the heart of Oakland, Florida, within the vibrant Orange County. This charming community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, professionals, and retirees alike.

Oakland Town boasts a diverse selection of beautifully designed homes, each exuding unique character and charm. From contemporary single-family residences to cozy townhouses, there’s something to suit every taste and budget. The lush, tree-lined streets and well-maintained landscaping create a warm and inviting atmosphere that residents are proud to call home.

One of the standout features of Oakland Town is its commitment to community and outdoor living. The subdivision is surrounded by scenic parks and nature trails, perfect for morning jogs, leisurely strolls, or family picnics. The nearby West Orange Trail offers miles of biking and walking paths, allowing residents to immerse themselves in the natural beauty of the area.

Convenience is at your fingertips, with Oakland Town located just minutes away from major shopping centers, dining options, and entertainment venues. Families will appreciate the proximity to highly-rated schools, ensuring that children receive a quality education. Additionally, the vibrant city of Orlando is just a short drive away, providing access to world-class attractions, cultural experiences, and employment opportunities.

Whether you’re looking for a peaceful retreat or an active lifestyle, Oakland Town is the perfect place to call home. Discover the charm of this delightful subdivision and experience the warmth of community living in Oakland, Florida. Your dream home awaits!

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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