ABSTRACT The current study is objected to investigate the essential oil yields, chemical compositions, and enantiomeric distribution of wild and cultivated linalool rich Origanum dubium Boiss. essential oils obtained at pre-flowering, initial flowering, and post-flowering growth stages. Wild plant materials are collected from Mediterranean region of Turkey. Samples were also cultivated in Mediterranean and Aegean coastlines of Turkey in the experimental fields of Ministry of Agriculture and Forestry of Turkey. O. dubium samples yielded between 6.7 and 9.7% (mL/100 g) of essential oils. The compositions were dominated by oxygenated monoterpenes (98.2–98.9%). Linalool was detected as the major compound in all essential oils (97.0–97.6%). The dominant enantiomer was discovered as (R)-(-)-linalool with a 99.3–99.4% enantiomeric purity. The essential oil yields, chemical compositions and enantiomeric distributions were found to be constant regardless of cultivation, geographical locations or different growth stages. The result of this manuscript indicates that by culturing linalool chemotype of O. dubium, the industrial need for (R)-(-)-linalool could be met at more affordable costs.