chiefly Brit an official employed by a sheriff to serve writs, seize property, make arrests, etc
chiefly Brit somebody who manages an estate or farm, or who acts as the agent of a landlord
NAmer an official in a law court who is responsible for prisoners and keeping order
Brit formerly, the chief officer of a sovereign in a district
bailiffship noun
[Middle English baillif, bailie, from Old French baillif, from bail: see bail1]