Windermere Little League operates a community softball program as part of Little League Baseball. We offer teams from teeball to junior softball (numbers permitting) for players from age 7 to 16. Our softball program is for players who meet the Little League residency requirement of either Windermere Little League or Winter Garden Little League. It is administered entirely by Windermere Little League.

As a Little League we do not hold tryouts. We accept all registrants who qualify to play in our league according to Little League residency rules. Registration is on a first-come basis and any player who registers after their age level is full will be put onto a wait list.Winderemere Little League teams are formed new every season.

In order to achieve competitive balance we hold a skills evaluation prior to assigning players to teams. All players should participate and should bring their bats, batting helmets, gloves and field shoes to the field on skills evaluation day.We have two seasons per year. Spring runs from February into May and Fall runs from September into November. You will need to register separately for each. The Spring season concludes with playoffs and tournaments with our neighboring Little Leagues.