Provided is a control device including control circuitry configured to control a position and an attitude of a microscope by driving an arm that supports the microscope on the basis of a captured image of a surgical operating site photographed by the microscope during a surgical operation so that a position and attitude condition is satisfied. The position and attitude condition is a condition that prescribes a position and an attitude of the microscope with respect to the surgical operating site to obtain a desired captured image corresponding to the position and attitude condition.