In this study, a health monitoring system was developed for the two most vulnerable parts of a wind tower support structure: the connection between steel towers (L-Flange) and the concrete foundation-steel tower connection. To select assessment parameters for health monitoring, detailed FEM analysis was conducted using the ABAQUS program. Additionally, a testbed was established near the Jeju Woljeongri wind turbine farm to evaluate the applicability of measurement data by installing sensors. Through computational analysis and relevant criteria review, we defined limits for measurement parameters by vulnerable section. We categorized the structural safety evaluation into four stages: normal, caution, warning, and danger, and selected management criteria for each stage. From this, an algorithm to evaluate safety was developed, and a visualized monitoring platform based on the established critical parts monitoring system was developed.