'bailiffry' originates from English, specifically formed from the noun 'bailiff' plus the suffix '-ry' (a noun-forming suffix indicating office, condition, or territory).

'bailiff' itself comes from Old French 'baillif' (12th–13th century), ultimately from Medieval Latin forms related to 'baiulivus'/'baiulus'; the formation 'bailiffry' appears in Middle English as variations such as 'bailifrie' and later stabilized to modern English 'bailiffry'.

Initially it referred to the office or territory held by a bailiff; over time the basic meaning has remained but the term has become rare and chiefly archaic in modern usage.