Pickleball Courts in Winter Park, FL

Playing pickleball in Winter Park

We list 5 pickleball venues in Winter Park, FL. The 3 that publish a court count add up to 20 courts, so the real total is higher — we don't estimate the 2 we haven't confirmed. The largest single site is Life Time Winter Park Pickleball with 13 courts, followed by Cady Way Park Pickleball Courts (6).

On access, 1 is free public court, 3 are pay-to-play and 1 is a membership club. The biggest free option is Cady Way Park Pickleball Courts at 6 courts.

Every Winter Park venue we've confirmed is outdoor — there's no indoor pickleball in our Winter Park data yet. If you know of one, tell us and we'll verify it.

Where to start

• Cady Way Park Pickleball Courts — Free to play — 6 courts, no membership.
• Life Time Winter Park Pickleball — One of the biggest sites in Winter Park — 13 courts, so open play rarely stalls.
• Winter Park Tennis Center Pickleball — Hours are published and checked: Mon-Fri 7am-10pm; Sat-Sun 7am-6pm.

What we've confirmed

3 of 5 have a confirmed court count, 3 publish hours and 4 publish pricing. 4 of these listings have been confirmed first-party against the venue's own website or Google Business Profile; the rest are sourced leads we're still working through. Most recent check in Winter Park: 2026-06-11.