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Court Finder · Winter Park, FL

Pickleball courts in Winter Park, FL

Find pickleball courts and facilities in Winter Park, Florida. 3 locations listed, 2 free, 1 indoor. Updated June 2026.

3Facilities
All Locations/ United States/ Florida/ Winter Park

Searching for pickleball courts in Winter Park, FL? This page lists 3 pickleball locations in Winter Park, Florida — including indoor and outdoor courts, free public parks, and private clubs. Find pickleball near you in Winter Park, compare court counts, pricing, and open-play options, and get directions, hours, and contact details for each facility below.

Top-rated pickleball courts in Winter Park (2026)

Ranked by Google rating among venues with at least 5 reviews.

  1. Cady Way Tennis & Pickleball Courts ⭐ 4.8/5 (81 reviews) · Free
  2. Phelps Park ⭐ 4.7/5 (614 reviews) · Free
  3. Orlando Magic Recreation Center ⭐ 4.5/5 (209 reviews) · Indoor

Across the state: Free pickleball courts in Florida (459)  ·  Indoor pickleball courts in Florida (237)

Cady Way Tennis & Pickleball Courts

📍 2525 Cady Way Trail, Winter Park, FL 32792, USA
Public Outdoor Free ⭐ 4.8/5 (81)
View Details →
Orlando Magic Recreation Center

Orlando Magic Recreation Center

📍 4863 N Goldenrod Rd, Winter Park, FL 32792, USA
Public Indoor Free & Paid ⭐ 4.5/5 (209)
Phone: (407) 254-9025
View Details →
Phelps Park

Phelps Park

📍 1206 N Phelps Ave, Winter Park, FL 32789, USA
Public Outdoor Free ⭐ 4.7/5 (614)
Phone: (407) 599-3334
View Details →
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Pickleball courts near Winter Park

Nearby cities with pickleball courts, closest first.

Christmas, FL (5 · 2 mi)  ·  Maitland, FL (2 · 3.5 mi)  ·  Casselberry, FL (18 · 3.9 mi)  ·  Altamonte Springs, FL (2 · 6 mi)  ·  Winter Springs, FL (2 · 6.7 mi)  ·  Longwood, FL (1 · 7.4 mi)  ·  Oviedo, FL (1 · 8.4 mi)  ·  Orlando, FL (43 · 8.6 mi)  ·  Belle Isle, FL (1 · 10.1 mi)  ·  Wekiwa Springs, FL (1 · 10.1 mi)  ·  Lake Mary, FL (2 · 10.7 mi)  ·  Sanford, FL (1 · 11 mi)

Playing Pickleball in Winter Park, FL

Winter Park, Florida has 3 pickleball facilities in our directory. That includes 3 public locations, 1 with indoor courts, and 2 that are free to play. Popular spots include Cady Way Tennis & Pickleball Courts, Phelps Park, and Orlando Magic Recreation Center. Each listing below includes the details you need before you head out — court count, indoor or outdoor, public or private, free or paid, booking requirements, amenities, and a Google Maps link.

New to pickleball in Winter Park? Most facilities welcome all skill levels, and many offer beginner lessons, loaner paddles, and open-play sessions where you can jump into games. Winter Park's warm climate makes outdoor pickleball a year-round activity, while a growing number of indoor, air-conditioned clubs keep games comfortable through the hottest months. Don't see your favorite court? Browse pickleball courts across Florida or add a facility for free to help local players find it.

Frequently Asked Questions About Pickleball in Winter Park

How many places can I play pickleball in Winter Park, FL?
Our directory lists 3 pickleball facilities in Winter Park. See the full list above with details on each one.
Where can I play pickleball for free in Winter Park?
Free pickleball in Winter Park includes Cady Way Tennis & Pickleball Courts and Phelps Park. These are usually outdoor, first-come, first-served courts — check the listing for hours and exact location.
Are there indoor pickleball courts in Winter Park?
Yes — indoor pickleball in Winter Park includes Orlando Magic Recreation Center, offering climate-controlled play year-round.
Can beginners play pickleball in Winter Park?
Absolutely. Most facilities in Winter Park welcome players of all levels, and many offer beginner lessons, open-play sessions, and loaner equipment so you can try the sport before buying a paddle.
What is a popular pickleball facility in Winter Park?
Cady Way Tennis & Pickleball Courts is one of the notable options in Winter Park. Browse the full list above to compare every facility and find the best fit for your game.
When is the best time to play pickleball in Winter Park?
You can play outdoor pickleball year-round in Winter Park. Early-morning and evening sessions are most popular in summer to avoid the midday heat, and many players move to climate-controlled indoor courts during the hottest weeks.
What cities near Winter Park have pickleball courts?
Christmas (2 miles), Maitland (3.5 miles), Casselberry (3.9 miles), and Altamonte Springs (6 miles) are the closest cities to Winter Park with pickleball courts in our directory.

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