Land tenure rights reflect the deeper structures of society, particularly gender distinctions in relation to land. Considering the structural differences between patrilineal and matrilineal customary tenure systems in East Timor are understudied, this paper explores men and women’s experiences in accessing land under such arrangements. The comparative analysis of two patrilineal with one matrilineal land tenure systems in Ainaro and Manufahi districts suggests a significant degree of flexibility within both systems with respect to the norms of gendered inheritance. Therefore, the binary constructs of ‘patrilineal’ and ‘matrilineal’ societies are limiting. Both men and women in these communities may acquire land rights under different circumstances, mainly through negotiations with their parents or hamlet chief. Daughters in the patrilineal communities could inherit family land upon their parents’ death and sons in the matrilineal community could gain land by cultivating and maintaining unclaimed customary land. Empirical evidence show that inheritance principally determines usufruct rights to land, but marriage exchange practices complicates a deeper understanding of traditional East Timorese land rights.