A measurement system includes an imaging unit mounted to a swing body of a work machine to image a shape around the work machine, a position detection unit which determines a position of the swing body, an imaging unit position calculation unit which calculates a position of the imaging unit when the imaging unit performs imaging while the swing body swings, and a three-dimensional position calculation unit which determines a three-dimensional position around the work machine during the imaging, on the basis of a position of the imaging unit calculated by the imaging unit position calculation unit.