A computer-implemented method for assessing Internet addresses may include (1) identifying an Internet Protocol address, (2) identifying a plurality of files downloaded from the Internet Protocol address, (3) generating an aggregation of security assessments that relates to the Internet Protocol address and that may be based at least in part on a security assessment of each of the plurality of files, (4) determining a trustworthiness of the Internet Protocol address based at least in part on the aggregation of security assessments and (5) facilitating a security action based at least in part on the trustworthiness of the Internet Protocol address. Various other methods, systems, and computer-readable media are also disclosed.