A working machine target position estimating apparatus for estimating a target position supposed by an operator operating a working machine including a machine main body having a cab which allows an operator to seat therein, an attachment mounted on the machine main body, and a leading end device provided in a leading end portion of the attachment, the working machine target position estimating apparatus comprising: a posture detecting part for detecting posture information being information related to a posture of the working machine; a manipulation detecting part for detecting manipulation information being information on the basis of which the operator manipulates the working machine; a sight detecting part for detecting sight information being information related to sight of the operator; a distance information detecting part for detecting distance information on a region in front of the working machine; and a controller for estimating a target position of the leading end device supposed by the operator when the operator manipulates the working machine to move the leading end device, wherein the controller includes: a locus region setting section for setting, on the basis of the posture information detected by the posture detecting part and the manipulation information detected by the manipulation detecting part, a prospective locus region being a region which includes a prospective locus along which the leading end device is prospected to move and which is associated with the distance information; a gaze region setting section for setting, on the basis of the sight information detected by the sight detecting part, a gaze region being a region which includes a gaze point of the operator and is associated with the distance information; and a target position estimating section for estimating the target position of the leading end device on the basis of a region where the prospective locus region set by the locus region setting section and the gaze region set by the gaze region setting section overlap each other. a posture detecting part for detecting posture information being information related to a posture of the working machine; a manipulation detecting part for detecting manipulation information being information on the basis of which the operator manipulates the working machine; a sight detecting part for detecting sight information being information related to sight of the operator; a distance information detecting part for detecting distance information on a region in front of the working machine; and a controller for estimating a target position of the leading end device supposed by the operator when the operator manipulates the working machine to move the leading end device, wherein the controller includes: a locus region setting section for setting, on the basis of the posture information detected by the posture detecting part and the manipulation information detected by the manipulation detecting part, a prospective locus region being a region which includes a prospective locus along which the leading end device is prospected to move and which is associated with the distance information; a gaze region setting section for setting, on the basis of the sight information detected by the sight detecting part, a gaze region being a region which includes a gaze point of the operator and is associated with the distance information; and a target position estimating section for estimating the target position of the leading end device on the basis of a region where the prospective locus region set by the locus region setting section and the gaze region set by the gaze region setting section overlap each other. a locus region setting section for setting, on the basis of the posture information detected by the posture detecting part and the manipulation information detected by the manipulation detecting part, a prospective locus region being a region which includes a prospective locus along which the leading end device is prospected to move and which is associated with the distance information; a gaze region setting section for setting, on the basis of the sight information detected by the sight detecting part, a gaze region being a region which includes a gaze point of the operator and is associated with the distance information; and a target position estimating section for estimating the target position of the leading end device on the basis of a region where the prospective locus region set by the locus region setting section and the gaze region set by the gaze region setting section overlap each other.