We propose an effective methodology using electromechanical impedance characteristics for estimating the remaining tensile force of tendons and simultaneously detecting damages of the anchorage blocks. Once one piezoelectric patch is attached on the anchor head and the other is bonded on the bearing plate, impedance responses are measured through these two patches under varying tensile force conditions. Then statistical indices are calculated from the impedances, and two types of relationship curves between the tensile force and the statistical index (TE Curve) and between statistical indices of two patches (SR Curve) are established. Those are considered as database for monitoring both the tendon and the anchorage system. If damage exists on the bearing plate, the statistical index of patch on the bearing plate would be out of bounds of the SR curve and damage can be detected. A change in the statistical index by damage is calibrated with the SR curve, and the tensile force can be estimated with the corrected index and the TE Curve. For validation of the developed methodology, experimental studies are performed on the scaled model of an anchorage system that is simplified only with 3 solid wedges, a 3-hole anchor head, and a bearing plate. Then, the methodology is applied to a real scale anchorage system that has 19 strands, wedges, an anchor head, a bearing plate, and a steel duct. It is observed that the proposed scheme gives quite accurate estimation of the remaining tensile forces. Therefore, this methodology has great potential for practical use to evaluate the remaining tensile forces and damage status in the post-tensioned structural members.