The paper examines some interconnected problems of the study of the ancient chora of Chersonesos, in particular land division of the Herakleian Peninsula and archaeological sites of the Mayachny Peninsula (Strabo’s ancient Chersonesus), where the author carried out excavations in 1985–1990. The author comes to the conclusion that the hypothesis of two stages in the formation of the chora of Chersonesus on the Herakleian Peninsula is still quite tenable. The Mayachny Peninsula, which is the western end of the Herakleian Peninsula, was divided first. It is thus the earliest chora of Chersonesus. Its division allowed the polis to secure the remaining part of the Herakleian Peninsula lying between Chersonesus and the Mayachny. The chora was planned according to a strictly regular pattern known as the system of Hippodamus of Miletus. This system formed the basis of both the city and the adjacent agricultural territory. On the isthmus of the Mayachny Peninsula a fortification was built. It defended the land plots and also functioned as an outpost of the polis.