Over the last century, relative sea level has risen by more than 1 ft in Annapolis, Maryland. The rise in sea level has resulted in frequent flooding in the City of Annapolis. According to National Oceanic and Atmospheric Administration (NOAA), Annapolis has experienced a 925% increase in flooding days over the past 50 years. This flooding is directly affecting roadway transportation in Annapolis in terms of traffic disruptions, which may result in disconnected mobility among communities, road accidents and travel time delays, just to name a few. This study proposes a general modeling framework to identify roadway segments that are most likely to be flooded and by what depth, due to relative sea level rise and employs the model in the coastal area of Annapolis. To do this, roadway and bridge elevations extracted from LiDAR DEM and DSM respectively, were compared with the annual exceedance probability tide levels provided by NOAA. Roadway segment elevations below the selected tide levels (1%, 10%, and 99%) are considered to be inundated by 100-year, 10-year and 1-year sea level respectively. Results suggest that, out of 36 roadways (excluding local roads) examined, one minor arterial roadway segment may be flooded by a depth ranging from 0.075 inches to 7.22 inches, at a 99% tide level of 2.17 ft (0.66 m). Three minor arterial and one major collector roadway segments may be flooded by a depth ranging from 0.1 inches to 27.3 inches (2.27 ft), at a 10% tide level of 3.84 ft (1.17 m). Three minor arterial, four major collector, and two minor collector roadway segments may be flooded by a depth ranging from 0.002 inches to 52 inches (4.4 ft) at a 1% tide level of 5.97 ft (1.82 m). For the city’s transportation network to become more resilient against sea-level rise, these roadway segments should be prioritized for future capital investment in response to seal level rise.