Oakland Town Real Estate

**Discover the Charm of Oakland Town: Your Ideal Subdivision in Central Florida**

Nestled in the heart of Orange County, Oakland Town is a picturesque subdivision that embodies the perfect blend of small-town charm and modern convenience. Just a stone's throw away from the vibrant city of Orlando, this tranquil community offers residents an inviting atmosphere, rich history, and a strong sense of belonging.

The streets of Oakland Town are lined with beautiful homes that showcase a variety of architectural styles, from traditional Florida ranches to contemporary designs, each reflecting the unique character of the neighborhood. With lush greenery and well-maintained parks, residents can enjoy the great outdoors, whether it’s a leisurely stroll, a family picnic, or an invigorating bike ride along the scenic West Orange Trail.

Families will appreciate the top-rated schools in the area, providing quality education and a nurturing environment for children. The community’s commitment to family-friendly activities is evident in its annual events, farmers' markets, and local festivals that foster connection and camaraderie among residents.

For those who crave adventure, Oakland Town is conveniently located near Lake Apopka, one of the largest lakes in Florida, offering a plethora of recreational activities such as fishing, boating, and bird watching. Plus, with easy access to major highways, residents can quickly reach the excitement of Orlando's theme parks, shopping centers, and dining hotspots.

In Oakland Town, you’ll find not just a place to live, but a community to thrive in. Experience the warmth and charm of this delightful subdivision—your new 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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