In the midst of a classic setting.

Located on the West Orange Trail and right next door to 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.

Oakland Park

15211 E. Oakland Avenue
Winter Garden, FL 34787

Driving Directions

From Florida’s Turnpike, take exit 272 (State Road 50) and travel east 0.8 miles to S. Tubb Street.

Turn left on Tubb St. and travel about ¼ mile to Oakland Ave.

Turn right onto Oakland Ave. Oakland Park is one mile on your left.

From SR 429 take exit 24 (Plant Street) and head west.

Travel 3.6 miles and Oakland Park is on the right.

View in Google Maps

Live in the middle of everywhere.

There are many ways to enjoy some of Florida’s most beautiful scenery. Experience the authentic feel of small-town Florida right next door in Winter Garden, and while you’re there explore the nationally ranked Winter Garden Farmer’s Market. Hike, bike, and take in the sites around the area, and visit the Oakland Nature Preserve, where you can observe abundant wildlife. Or, take a drive down the stunning Green Mountain Scenic Byway, where you’ll find the Oakland Park Information Center right on Plant Street.

A strong foundation matters.

As an Oakland Park resident you have the option of enrolling your children in one of the Winter Garden area’s several school options, all within the Orange County School District, including three private schools. Use the tool below to explore the options and discover what school is best for your family.