On November 27, 2007, a local health officer in central Massachusetts contacted the Massachusetts Department of Public Health (MDPH) to report listeriosis in a man aged 87 years. Pulsed-field gel electrophoresis (PFGE) performed on the patient's Listeria monocytogenes isolate produced a pattern indistinguishable from that of isolates from three other cases identified in residents of central Massachusetts in June, October, and early November 2007. MDPH, in collaboration with local public health officials, conducted an investigation, which implicated pasteurized, flavored and nonflavored, fluid milk produced by a local dairy (dairy A) as the source of the outbreak. This report summarizes the results of that investigation. In all, five cases were identified, and three deaths occurred. This outbreak illustrates the potential for contamination of fluid milk products after pasteurization and the difficulty in detecting outbreaks of L. monocytogenes infections.