Oakland Town Real Estate

Welcome to Oakland Town, a charming subdivision nestled in the heart of Oakland, Florida, within Orange County. This delightful community is a hidden gem that perfectly blends suburban tranquility with vibrant local culture, making it an ideal place for families, young professionals, and retirees alike.

Oakland Town stands out for its picturesque landscapes and friendly atmosphere. The subdivision features beautifully designed homes that reflect a variety of architectural styles, catering to diverse tastes. Residents enjoy spacious lots, lush greenery, and a strong sense of community. The tree-lined streets invite leisurely strolls and friendly conversations with neighbors, creating a warm and welcoming environment.

One of the most appealing aspects of Oakland Town is its proximity to nature and outdoor activities. The area is surrounded by stunning parks and scenic trails, perfect for hiking, biking, and enjoying the great Florida weather. Lake Apopka, one of the largest lakes in Florida, is just a stone's throw away, offering opportunities for fishing, boating, and picnicking by the water.

In addition to its natural beauty, Oakland Town is conveniently located near essential amenities. Residents have easy access to shopping, dining, and entertainment options, with downtown Orlando just a short drive away. The local schools are highly regarded, making it a great choice for families looking to provide their children with a quality education.

Whether you're seeking a peaceful retreat or a vibrant community, Oakland Town offers the perfect balance of both. Come discover your new home in this enchanting subdivision, where every day feels like a breath of fresh air!

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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