Flood damage assessment plays a vital role in providing information to policy developers. Nowadays, due to urbanization, the impact of flooding on communities is extensive, including tangible damage to property, the environment, and infrastructure as well as intangible damage due to stress, health hazards, and hardship. This paper provides an overview of a detailed flood assessment study conducted in the Kotturpuram Housing board area, located on the flood plain of the Adayar River in Chennai, India. A relatively simple approach to data collection was adopted, being a Questionnaire Survey (QS) as well as semi-structured interviews and observation techniques, due to data and research limitations. Losses due to damage to belongings and extra spending to buy essential commodities during flooding are also dealt with in this study. The flood mitigation costs for flooding that occurred in the year 2015 are also evaluated. A stage-damage curve was arrived at based on the information collected. Optimal and sustainable mitigation measures can be achieved only when the socio-economic aspects are adequately considered. Thus, this analysis was designed to estimate the effects of flooding on a community’s social and economic welfare, and thereby help to educate the community, including residents and officials, about the impact and magnitude of flooding. The outputs of the study will be the key inputs for designing flood mitigation and relief measures.