Reply To: Using GREP in paragraph style to format only the first occurrence of a phrase

This example is not the same as your original request.
3 GREP to make it work, but the text needs to follow the same pattern.

Character format Bold Black for leading text
^((\w||[[:punct:]])+)(\$\d\S+)

Character format Red Prices, if these are not all ‘per’ then a list would be needed to make this work
\$\d\S+ (per\d+)?

Character format Normal (to correct the last price)
\S+ ea$