Monitoring is required when dewatering underground construction sites to anticipate unexpected events and preserve nearby existing structures and/or buildings. The most accurate and widespread monitoring method to measure displacements is leveling, a point-like surveying technique that typically allows for tens of discrete in situ sub-millimeter measures per squared kilometer. Another emerging technique for mapping soil deformation is the interferometric synthetic aperture radar (InSAR) method, which is based on SAR images acquired from orbiting satellites. This remote sensing technique can provide better spatial point density than leveling, more extensive spatial coverage and lower-cost acquisitions. This paper analyses, compares and discusses leveling and advanced multi-temporal InSAR measurements when they are used to measure the soil deformation induced by the dewatering associated with underground constructions in urban areas. This comparison, which has not been considered in previous works, is of paramount importance to ascertain the most suitable technique (or combination of techniques) in these contexts. To do so, an experiment was performed in the future railway station of La Sagrera, Barcelona (Spain), in which leveling and advanced multi-temporal InSAR were used to quantify ground deformation by dewatering. The results showed that soil displacements measured by leveling and InSAR were not always consistent. In the context of soil deformation measurements produced by dewatering in urban areas, InSAR measurements appear to be more accurate for investigating soil deformation, whereas leveling was more appropriate for quantifying the real impact on the nearby buildings.