This research presents the theoretical model, simulation and experimental verification of the maximum stepover estimation for different cases on the machine surface profile using the end-filleted cutter in multi-axis machining. Where in this research, the equations that detect the maximum stepover at allowable scallop height value have been taking into consideration and derived to predict the tool path generation for different inclination angles of tool axis. A set of inclination angles of cutter tool axis that can machine the workpiece have been taken into consideration depending on the shape of the workpiece. The inclination angle of the tool axis, effective cutter radius, and the geometrical shape of the workpiece have been studied and experimentally verified for milling operation. The results show that the proposed model for estimating stepover at constant scallop height can predict the tool path generation for machining sculpture surfaces using CNC multi-axis machine.