Oakland Town Real Estate

Welcome to Oakland Town, a charming subdivision nestled in the heart of Orange County, Florida. This picturesque community is a hidden gem that offers a perfect blend of suburban tranquility and vibrant local culture. With its scenic landscapes and friendly atmosphere, Oakland Town is an ideal place for families, young professionals, and retirees alike.

One of the standout features of Oakland Town is its close-knit community feel. Residents enjoy a variety of amenities, including beautifully landscaped parks, walking trails, and recreational facilities that encourage an active lifestyle. The serene environment is complemented by the stunning views of nearby lakes and lush greenery, making it a perfect escape from the hustle and bustle of city life.

Oakland Town is conveniently located just minutes away from the thriving downtown area of Oakland, where you can find a delightful mix of shops, restaurants, and local events that foster a strong sense of community. The area is also known for its excellent schools, making it a popular choice for families looking to settle down in a supportive and nurturing environment.

Moreover, Oakland Town offers easy access to major highways and is just a short drive from the attractions of Orlando, including theme parks, shopping centers, and entertainment venues. Whether you’re looking for a weekend adventure or a peaceful retreat, Oakland Town provides the best of both worlds.

Discover the charm and warmth of Oakland Town, where community spirit meets the beauty of nature. Your dream home awaits in this inviting subdivision!

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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