The paper presents a case study in which the structural condition assessment of the East Bay bridge in Gibsonton, Florida is evaluated with the help of remote health monitoring techniques. The bridge is a four-span, continuous, deck-type reinforced concrete structure supported on prestressed pile bents, and is instrumented with smart Fiber Optic Sensors. The sensors used for remote health monitoring are the newly emerged Fabry-Perot (FP), and are both surface-mounted and embedded in the deck. The sensing system can be accessed remotely through fast Digital Subscriber Lines (DSL), which permits the evaluation of the bridge behavior under live traffic loads. The bridge was open to traffic since March 2005, and the collected structural data have been continuously analyzed since. The data revealed an increase in strain readings, which suggests a progression in damage. Recent visual observations also indicated the presence of longitudinal cracks along the bridge length. After the formation of these cracks, the sensors readings were analyzed and used to extrapolate the values of the maximum stresses at the crack location. The data obtained were also compared to initial design values of the bridge under factored gravity and live loads. The study showed that the proposed structural health monitoring technique proved to provide an efficient mean for condition assessment of bridge structures providing it is implemented and analyzed with care.