Zhejiang rosy vinegar (ZRV), a popular condiment in southeastern China, has a flavor profile and bioactivity that are not yet fully understood. This study aimed to determine the flavor characteristics and functional properties of ZRV from different regions. Sensory evaluation and electronic nose analysis revealed regional flavor variations. GC-MS identified 80 volatile compounds, while GC-IMS detected 22 volatile compounds. OPLS-DA models identified 17 GC-MS and 8 GC-IMS biomarkers, predominantly including 9 esters, 4 alcohols, and 4 aldehydes. Based on the analysis of odor activity values, five characteristic flavors in ZRV were identified, including acetic acid, benzaldehyde, 3-methylbutyl acetate, phenethyl acetate, and 2,4,5-trimethyl-1,3-dioxolane. Non-volatile compounds such as polyphenols, flavonoids, tartaric acid, and amino acids (isoleucine, valine, and proline) significantly enhanced antioxidant activity. The research establishes a theoretical framework for improving ZRV quality control and brand identity by mapping regional flavor signatures and bioactive components.