Oakland Town Real Estate

Oakland Town Real Estate

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming subdivision offers a unique blend of small-town charm and modern convenience, making it an ideal place for families, retirees, and everyone in between. With its picturesque tree-lined streets and friendly atmosphere, Oakland Town is a community where neighbors become friends and memories are made.

One of the standout features of Oakland Town is its prime location. Just a stone's throw away from the vibrant city of Orlando, residents enjoy easy access to world-class dining, shopping, and entertainment options. Whether you're looking to explore the magical attractions of Disney World or savor a delicious meal at a local eatery, everything you need is within reach. Yet, when you return home to Oakland Town, you can escape the hustle and bustle and unwind in a serene environment.

The subdivision boasts a variety of beautifully designed homes, each reflecting the unique character of the community. From cozy single-family residences to spacious modern designs, there’s something to suit every taste and lifestyle. Families will appreciate the nearby parks, walking trails, and top-rated schools, while outdoor enthusiasts can enjoy the stunning natural beauty that surrounds the area.

In Oakland Town, you’ll find a perfect balance of tranquility and connectivity, making it the ideal place to call home. Discover the welcoming spirit of this community and experience the joy of living in a neighborhood that truly feels like family. Come explore Oakland Town, where your dream home awaits!

Newest Listings in Oakland Town

250 N Walker Street, Oakland
$999,000
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
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
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