Oakland Homes with Private Pool type

Oakland Homes with Private Pool type

Welcome to the vibrant city of Oakland, Florida, a hidden gem nestled in Orange County that beautifully combines the charm of small-town living with the excitement of nearby urban amenities. With its picturesque landscapes, friendly community, and a rich history, Oakland is a wonderful place to call home. The area boasts a variety of outdoor recreational opportunities, including scenic parks and serene lakes, perfect for those who appreciate nature and an active lifestyle.

One of the standout features of Oakland is its stunning homes with private pools. Imagine stepping into your backyard oasis, where you can unwind in your own sparkling pool under the warm Florida sun. These homes are designed for both relaxation and entertainment, providing a perfect setting for family gatherings, summer barbecues, or simply enjoying a peaceful afternoon by the water. With a range of architectural styles and sizes, you’ll find the perfect home that suits your lifestyle and aesthetic preferences.

Living in Oakland means you’re just a short drive away from the bustling city of Orlando, where you can enjoy world-class dining, shopping, and entertainment options. Whether you’re exploring the local farmers’ market, taking a stroll along the charming streets, or indulging in the vibrant arts scene, there’s always something new to discover.

If you’re looking for a home that offers both comfort and luxury, Oakland’s private pool properties provide the ideal sanctuary for you and your loved ones. Dive into a lifestyle of leisure and joy in this enchanting Florida city!

Newest Oakland Homes with Private Pool type

$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

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