Cady Way Playground
2525 Cady Way Trail, Winter Park, FL 32792, USA
Google rating
7 reviews
About Cady Way Playground
Cady Way Playground is a pickleball facility in Winter Park, Florida, and one of the go-to spots for pickleball players in the area. You'll find it at 2525 Cady Way Trail, Winter Park, FL 32792, USA, easy to reach whether you're a local looking for open play or a visitor planning a session on your Florida trip. It sits at 4.0★ across 7 Google reviews — a solid, playable option.
What to expect
- A dedicated pickleball setup with striped courts, nets, and typical local rotation for open play.
- Hours aren't posted online for this location — call ahead to confirm before you drive over.
- Bring your own paddles and balls unless you've confirmed otherwise. Water fountains vary by venue, so pack water for hot Florida afternoons.
Planning your visit
Quick tips to make your session at Cady Way Playground smoother — from a player who's spent a lot of Florida mornings on the court.
- 1Play early morning or after 5pm to beat the Florida heat — court surfaces can hit 100°+ in mid-afternoon sun.
- 2Weekends fill up fastest. If you're targeting a specific time, arrive 15–20 minutes early to get in the paddle rotation.
- 3Check the Google reviews below for recent condition notes on the court surfaces and nets.
Location & map
Cady Way Playground is in Winter Park, Florida — pickleball facility at 2525 Cady Way Trail, Winter Park.
Coordinates: 28.59595, -81.31722
What players are saying
Recent Google reviews for Cady Way Playground. Reviews are pulled live and refresh automatically.
Snow Lam· 4 years agoPros: Small playground for little kids A lot of shade under the picnic tables Tennis courts Baseball field Community swimming pool Plenty of parking lots Bike and walking trail nearby Clean restrooms Cons: Although there’s a lot of shade, there’s hardly any shade hovering the actual kids’ play area. My son got bored and tired after 30 minutes. I think it will be boring for my 7YO.
Michael Van· 2 years agoRestroom has no power, no running water. Bottle water refill has no power. Charging station has no power. The infrastructure of this park is functionless!
Jeanette Foss· a year agoGreat place to bring the kids of all ages
Matt Johnson· 4 years agoSmaller, but decent park closer to the trail than Ward Playground.
Mercedes Pena· 2 years agoGreat place for child and parents
Frequently asked questions
Where is Cady Way Playground located?
Cady Way Playground is located at 2525 Cady Way Trail, Winter Park, FL 32792, USA in Winter Park, Florida. You can get one-tap driving directions from the button above.
Do I need a reservation to play pickleball at Cady Way Playground?
No — most public and park facilities like Cady Way Playground run on open play. Show up, sign in on the paddle rack, and rotate in.
How much does it cost to play pickleball at Cady Way Playground?
Fees vary by venue. Contact Cady Way Playground for current pricing on drop-in play, memberships, and clinics.
Are the pickleball courts at Cady Way Playground indoor or outdoor?
Cady Way Playground is primarily an outdoor pickleball venue, which is typical for Florida parks. Check the photos for a look at the courts.
Is Cady Way Playground good for beginners?
Winter Park has a strong beginner-to-intermediate pickleball scene, and Cady Way Playground is one of the popular local spots. Show up during open play, tell someone you're new, and you'll almost always get pulled into a friendly game.