Cady Way Tennis & Pickleball Courts
2525 Cady Way Trail, Winter Park, FL 32792, USA
Google rating
87 reviews
About Cady Way Tennis & Pickleball Courts
Cady Way Tennis & Pickleball Courts 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. Players give it a standout 4.7★ across 87 Google reviews — a top-rated spot in the area.
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 Tennis & Pickleball Courts 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 Tennis & Pickleball Courts is in Winter Park, Florida — pickleball facility at 2525 Cady Way Trail, Winter Park.
Coordinates: 28.59597, -81.31688
What players are saying
Recent Google reviews for Cady Way Tennis & Pickleball Courts. Reviews are pulled live and refresh automatically.
JP Lambiase· 5 months agoCady Way Park is a park with a lot going on, but I’m here strictly for pickleball—and from a pickleball player’s perspective, this place is very well organized. There are 8 pickleball courts total, and they’re divided by skill level, which makes a huge difference in play quality: First 3 courts (far left): Beginner courts Middle 3 courts: Intermediate play Last 2 courts (far right): Challenge courts The challenge courts run winner-stays-on, so it’s always 2 on / 2 off. If you plan on playing there, you’ll want to be around a 3.75 DUPR or higher to really enjoy it—and I highly recommend bringing a partner. The competition is legit, fast-paced, and not very forgiving for casual drop-ins. There’s also 1 tennis court, and all the pickleball courts have lights, which makes evening play possible and popular. Timing matters a lot here: Best weekday time: around 4:00 PM By 6:30 PM, it can get extremely busy—sometimes to the point where wait times are so long that you won’t get much actual play in. Overall, if you’re serious about pickleball and want structured, competitive games, Cady Way is a great spot. Just know your skill level, pick the right courts, and time your visit wisely.
Mike Tochinskiy· a year agoUpdate: They finished construction on the pickle ball courts! They are pretty good however they were overly packed when I was there (referred to video). Great courts overall! Old Review: There’s a lot of construction in the area, but other than that, it seems like it would be a good place when everything is finished!
David V· 2 months agoUsed it as a Trailhead to ride the Seminole Loop. Facilities and parking were more than adequate for our needs. Pickleball players seem to be having a fantastic day!
Kurtis Mohr· 2 months agoNice pickleball courts but always seems too busy and long waits to play.
Johny M· 2 years ago-6 courts, good rotation system. average wait time 10 mins between each game. -light out at 10PM
Frequently asked questions
Where is Cady Way Tennis & Pickleball Courts located?
Cady Way Tennis & Pickleball Courts 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 Tennis & Pickleball Courts?
No — most public and park facilities like Cady Way Tennis & Pickleball Courts 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 Tennis & Pickleball Courts?
Fees vary by venue. Contact Cady Way Tennis & Pickleball Courts for current pricing on drop-in play, memberships, and clinics.
Are the pickleball courts at Cady Way Tennis & Pickleball Courts indoor or outdoor?
Cady Way Tennis & Pickleball Courts is primarily an outdoor pickleball venue, which is typical for Florida parks. Check the photos for a look at the courts.
Is Cady Way Tennis & Pickleball Courts good for beginners?
Winter Park has a strong beginner-to-intermediate pickleball scene, and Cady Way Tennis & Pickleball Courts 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.