Sends a penny for the toss, maybe (5)
I believe the answer is:
posts
'sends' is the definition.
('post' can be a synonym of 'send')
'a penny for the toss maybe' is the wordplay.
'a penny' becomes 'p'.
'for' is a charade indicator (letters next to each other).
'maybe' indicates anagramming the letters.
'toss' anagrammed gives 'osts'.
'p'+'osts'='POSTS'
(Other definitions for posts that I've seen before include "Is dispatching" , "Mails the uprights?" , "a couple seen propping up the bar?" , "Stakes" , "Positions, for guards say" .)