An observational study was set up to evaluate how the quality of the environment may influence the levels of of PCDDs, PCDFs, and DL-PCBs in sheep's milk. Seven farms under natural and anthropogenic pressures were considered, along with an inventory of the surrounding regular and natural sources of emissions. Analysis by HRGC-HRMS revealed the highest cumulative levels (2.1 pg of WHO(1998)-TE/g fat) in one organic and one conventional farm, each close to a relevant bushfire. Their pattern was characterized by a noticeable contribution (24%) from mono-ortho-PCB congeners to the cumulative WHO-TE. For the other farms, close to potential anthropogenic sources, the levels recorded in milk ranged from 0.7 to 1.3 pg of WHO-TE/g fat. The health and reproductive indicators were in all herds within the physiological range. Results suggest the environmental quality in extensive farming system should be eligible as a food safety factor, also for organic productions.