The value of structural health monitoring (SHM) can be quantified as the difference in expected total life-cycle costs between two different maintenance planning strategies, one representing the standard means to assessment, namely intermittent visual inspections, and the other based on availability of continuous SHM data. We show how to quantify the value of vibration-based SHM conditional on a damage history over the structural lifetime. We showcase the analysis through application on a numerical benchmark model of a two-span bridge system subjected to gradual deterioration and sudden damages in the middle elastic support over its life-cycle, simulating the case of scour. The effect of environmental variability is included in the analysis by means of a stochastic model for the dependence of the Youngโs modulus on temperature (E-T). The numerical investigations provide insights related to the effect of the temperature variability, as well as the visual inspectionsโ quality, on the value of SHM.