Oakland Town Homes with Private Pool type

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming subdivision is an idyllic blend of serene suburban living and vibrant community spirit, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle just a stone's throw from the bustling city of Orlando.

Oakland Town is characterized by its picturesque streets, friendly neighbors, and lush green spaces that invite outdoor activities and leisurely strolls. The community boasts a variety of architectural styles, each home reflecting a unique charm that contributes to the neighborhood's character.

One of the standout features of Oakland Town is the availability of homes with private pools. Imagine stepping out into your own backyard oasis, where you can soak up the Florida sun, host summer barbecues, or simply unwind after a long day. These homes are designed with outdoor living in mind, providing the perfect space for relaxation and entertainment. Whether you’re looking for a cozy retreat or a spacious family home, you’ll find properties that cater to diverse lifestyles and preferences.

In addition to its beautiful homes, Oakland Town is conveniently located near excellent schools, shopping, and recreational facilities. Residents enjoy easy access to the scenic West Orange Trail, perfect for biking and walking enthusiasts. With its friendly atmosphere, stunning homes, and prime location, Oakland Town is not just a place to live, but a place to thrive. Come discover your dream home with a private pool in this enchanting community!

$1,049,000

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

Oakland Town Homes with Private Pool type

Newest Oakland Town Homes with Private Pool type