Northern Ireland experienced an intense sociopolitical conflict for a period of approximately 30 years up to 1997, during which more than 3,000 people lost their lives. The majority of these deaths occurred in the cities of Belfast and Derry. Additionally, these cities were the location of much sectarian violence and intimidation. Given the potential for intergenerational transmission of conflict-related trauma, the present study examined levels of self-reported mental well-being and psychological symptomatology in adolescents living in Belfast and Derry, intermediate towns (≥10,000 residents), and more rural settings, in Northern Ireland. Unadjusted analyses revealed small-sized differences on mental well-being for place of residence and gender, and a small-sized difference on psychological symptomatology for socioeconomic status. Results adjusted for gender and socioeconomic status showed that living in more rural settings was associated with the best outcomes. Furthermore, there was an interaction between place of residence and gender such that males living in a rural setting appear to be at least risk for suffering lower mental well-being and higher psychological symptomatology.