Oakland Town Homes with Private Pool type

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming suburban community is not only known for its picturesque landscapes and friendly atmosphere but also for its stunning homes that offer a perfect blend of comfort and luxury. If you’re seeking a serene environment with a touch of elegance, Oakland Town is the ideal place to call home.

One of the standout features of this subdivision is the availability of homes with private pools. Imagine stepping into your own backyard oasis, where you can unwind under the warm Florida sun or host delightful gatherings with friends and family. These exquisite properties are designed for both relaxation and entertainment, providing ample space for outdoor living while ensuring your privacy.

Oakland Town is conveniently located just a short drive from the vibrant city of Orlando, giving residents easy access to world-class dining, shopping, and entertainment options. The community is also surrounded by lush parks and scenic waterways, perfect for outdoor enthusiasts and nature lovers alike. With its charming small-town feel, Oakland Town fosters a strong sense of community, making it an inviting place for families, retirees, and everyone in between.

Whether you’re looking for a tranquil retreat or a lively neighborhood, Oakland Town has something for everyone. Explore the homes with private pools and discover your dream oasis today! Experience the perfect blend of relaxation and community in this beautiful Florida subdivision. Welcome home!

$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

Oakland Town Homes with Private Pool type

Newest Oakland Town Homes with Private Pool type