This study aims to estimate the damage caused by river flooding, using the Pesanggrahan River in Jakarta as a case study. The study estimates the actual damage that occurred during the January 2013 flooding, focusing on direct damage to the residential and business sectors in six villages along the river. The damage was calculated by employing stage damage function. The findings show that during the three-day flood from 17-19 January 2013, damage in the residential sector amounted to USD 308 per household and USD 0.5 million in total. In the business sector, damage was USD 837 per business unit and USD 0.7 million in total. By making a monetary assessment of women’s roles in relation to the three phases of flooding (i.e., before, during, and after), the individual benefit provided by each woman was estimated to be about USD 26 for families and USD 27 for society. However, only 30% of women were actually able to contribute to both flood adaptation at the family and society levels, and most of these women are elderly.