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Global Positioning System (GPS) localization has been attracting attention recently in various areas, including intelligent transportation systems (ITSs), navigation systems, road tolling, smart parking, and collision avoidance. Although, various approaches for improving localization accuracy have been reported in the literature, there is still a need for more efficient and more effective measures that can ascribe some level of accuracy to the localization process. These measures will enable localization systems to manage the localization process and resources to achieve the highest accuracy possible and to mitigate the impact of inadequate accuracy on the target application. The localization accuracy of any GPS system depends heavily on both the technique it uses to compute locations and the measurement conditions in its surroundings. However, while localization techniques have recently started to demonstrate significant improvement in localization performance, they continue to be severely impacted by the measurement conditions in their environment. Indeed, the impact of the measurement conditions on the localization accuracy in itself is an ill-conditioned problem due to the incongruent nature of the measurement process. This paper proposes a scheme to address localization accuracy estimation. This scheme involves two steps, namely, measurement condition disambiguation and enhanced location accuracy classification. Real-life comparative experiments are presented to demonstrate the efficacy of the proposed scheme in classifying GPS localization accuracy under various measurement conditions.