Canadian cities are growing and their density is increasing. These facts combined with increasing global temperatures and a rise in extreme weather events have caused the annual insured losses in Canada due to severe weather events such as floods, ice storms, hurricanes and tornadoes to increase 3.5 times since 2009. This has led to an increased interest in protecting existing homes vulnerable to flooding with retrofits aimed at improving flood resiliency in residential areas. Stakeholders aiming to encourage flood resiliency retrofits have indicated that it is more challenging to justify resiliency retrofits when compared to energy efficiency retrofits because the same tools do not exist to highlight the cost savings or return on investment. For this reason, there is an interest in better understanding the cost-effectiveness of flood resiliency retrofits. In an effort to demonstrate the successes and failures of flood resiliency retrofits in Canada, several case studies are highlighted where the residences have been retrofitted after significant flooding events, the location experienced similar flood conditions, and the retrofits have been evaluated for performance. Support to perform the retrofits is considered as well as obstacles which have made proceeding with retrofits more challenging. These examples help to provide insights into successes and failures in an industry which is required to grow significantly in the near future if Canada is to avoid the economic consequences of continually increasing uninsured losses with a warming climate and increased urban density.