Oakland Town Homes with Private Pool type

Welcome to Oakland Town, a charming enclave nestled in the heart of Orange County, Florida. This picturesque subdivision offers a delightful blend of suburban tranquility and modern convenience, making it the perfect place to call home. With its tree-lined streets and friendly atmosphere, Oakland Town embodies the essence of community living, where neighbors become friends and families thrive.

One of the standout features of homes in Oakland Town is the presence of private pools, providing residents with a personal oasis right in their backyards. Imagine basking in the Florida sun, sipping your favorite drink, and taking refreshing dips in your own pool whenever the mood strikes. These homes are designed for both relaxation and entertainment, making them an ideal choice for families, couples, and anyone who enjoys outdoor living.

In addition to the luxurious pools, Oakland Town is conveniently located near top-rated schools, shopping centers, and recreational parks, ensuring that all your daily needs are just a short drive away. The nearby West Orange Trail offers endless opportunities for outdoor activities, including biking, jogging, and walking, allowing residents to embrace an active lifestyle amidst the stunning natural beauty of the area.

Whether you’re seeking a serene retreat or a vibrant community filled with amenities, Oakland Town delivers on all fronts. Explore the charming homes with private pools and discover the perfect blend of comfort and leisure in this inviting Orange County subdivision. Your dream home awaits 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

Oakland Town Homes with Private Pool type

Newest Oakland Town Homes with Private Pool type