Oakland Park is everything Florida living should be. With picturesque scenery and close proximity to Winter Garden, it is the perfect balance of modern conveniences and old Florida charm. Our preservation of the natural surroundings and the area’s history, character, and craftsmanship create a stunning sanctuary that you’ll want to call home.

Located just off the West Orange Trail and minutes from downtown Winter Garden, Oakland Park is Florida the way it should be – a blending of water, majestic trees, and a classic, small-town feel. It’s hard to imagine that a place so quaint is just minutes from Winter Garden and the excitement of Orlando. You truly can have the best of many worlds here at Oakland Park.

No matter where you are in Oakland Park, you are not far from a park, pool, or trail. Oakland Park amenities beckon families and friends to gather and enjoy the great outdoors, take in the vast shoreline or relax in the afternoon breeze. For those seeking shelter, the Oakland Park Clubhouse can be thought of as an extension of their own living room, a quiet nook for reading, or a festive setting for family and friends.

Oakland Park homes are inspired by historic styles and old-Florida charm and built by highly regarded regional builders. Design features such as outward-facing interiors and rear-facing garages provide a pedestrian-friendly feel, while large front porches encourage interaction between neighbors and create an organic feeling as if the community developed over several decades. And if you desire something different, our available homesites and options allow you the variety to satisfy your own personal tastes and practical needs.