Pickleball Courts in Winchester, Massachusetts (2026 Guide)
Winchester, Massachusetts has 14 pickleball courts across 5 venues.
Winchester has 5 places to play pickleball. Confirmed court counts add up to 14 courts across these venues.
Award-winning pickleball clubs near Winchester
2026 CourtSource Awards winners in the Winchester area.
Picks list 2026 award winners first, then CourtScore, a data-only score. How we rank venues.
Winchester has 14+ pickleball courts across 5 venues. Top venues include Leonard Field (4 courts) and Winchester - Leonard Field (4 courts).
For year-round play regardless of weather, the best climate-controlled options are Winchester Indoor Tennis (4 indoor), and Winchester Recreation Department (1 indoor).
The city features public and municipal courts open to all players. 2 venues offer indoor play for year-round access.
Pickleball Courts in Winchester
5 mapped
How do Winchester pickleball venues compare?
| Venue Name | Courts | Indoor/Outdoor | Access Type | Lighted |
|---|---|---|---|---|
| Leonard Field | 4 | 4 Outdoor | Public | |
| Winchester Indoor Tennis | 4 | 4 Indoor | Public | |
| Winchester - Leonard Field | 4 | 4 Outdoor | Public | |
| Winchester Recreation Department | 1 | 1 Indoor | Public | |
| Winchester Swim and Tennis Club | 1 | 1 Outdoor | Public |
Court Conditions in Winchester
Indoor Only
2
venues
Outdoor Only
3
venues
Pickleball in Winchester: common questions
Where can I play pickleball in Winchester, Massachusetts?
Winchester has 5 pickleball venues with 14 total. Top options include Leonard Field (4 courts), Winchester - Leonard Field (4 courts), Winchester Indoor Tennis (4 courts). Browse all locations on CourtSource for current hours and fees.
Are there indoor pickleball courts in Winchester?
Yes. Winchester has 5 indoor pickleball courts across 2 venues. Options include Winchester Indoor Tennis (4 indoor courts), and Winchester Recreation Department (1 indoor court).
How many pickleball courts are in Winchester, Massachusetts?
There are currently 14 verified pickleball courts in Winchester, Massachusetts. This includes 5 indoor courts and 9 outdoor courts. CourtSource tracks 5 venues in the area.