Community Playground

Community Playground in Winter Park is one of those places locals keep to themselves — a genuinely excellent free playground with a 4.8-star rating that most Orlando tourists never find because it's not near the theme parks. Located in the affluent Winter Park neighborhood about 15 minutes northeast of downtown Orlando, this playground punches well above its weight for a free municipal park.

The playground structure is large and well-maintained, with enough variety to keep kids in the 2-12 range occupied for a solid 1-2 hours. There are separate sections calibrated for different ages, and the whole area has perimeter fencing that parents of toddlers will particularly appreciate — you can let younger kids run without worrying about them bolting into the parking area.

Shade is decent by Florida playground standards. There are trees around the perimeter that cast actual shadow in the morning hours, which makes a real difference during warm months. Plan morning visits (before 10am) in summer to get the best of the shade and before the heat kicks in.

The surrounding Winter Park context makes this more than just a playground trip. Park Avenue — Winter Park's main street with boutiques, restaurants, and cafes — is about 10 minutes away by car. A common family plan is morning playground time at Community Playground followed by brunch or lunch on Park Avenue, which is one of the more pleasant walkable streets in the Orlando metro area.

For Orlando visitors who want a break from theme parks and are willing to drive 15-20 minutes north of downtown, this playground plus Park Avenue makes for a genuinely lovely morning that costs essentially nothing for the playground portion.