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late 13c., "quantity or amount of money," from Anglo-French and Old French summe (13c.), from Latin summa "total number, whole, essence, gist," noun use of fem. of summus "highest," from PIE *sup-mos-, from root *uper "over" (see super-).
The sense development from "highest" to "total number" is probably via the Roman custom of adding up a stack of figures from the bottom and writing the sum at the top, rather than at the bottom as we do now (cf. the bottom line). Meaning "total number of anything" is recorded from late 14c. Meaning "essence of a writing or speech" also is attested from late 14c. The verb is attested from c.1300; meaning "briefly state the substance of" (now usually with up) is first recorded 1620s. Sum-total is attested from late 14c., from Medieval Latin summa totalis.