To make it possible to improve user convenience.Provided is a control device including: a control unit configured to control a position and an attitude of a microscope unit by driving an arm unit that supports the microscope unit on the basis of a captured image of an operating site photographed by the microscope unit during an operation so that a position and attitude condition set before the operation is satisfied. The position and attitude condition is a condition that prescribes a position and an attitude of the microscope unit with respect to the operating site to obtain a desired captured image corresponding to the position and attitude condition.