The lack of organisation in urban spaces plays a decisive role in the level of integration, communication and social bonds of the residents, impacting the citizens’ feelings of trust and security. Different personal variables and contextual characteristics have been associated with the fear of crime (FOC). The main objective of this study is to analyse how individual and social/environmental variables, and incivilities, predict crime against people and property, crime that has either happened or is feared to happen. Five hundred and fifty-four residents (M = 43.82; SD = 18.38) in the Historic Centre of Porto (HCP), Portugal, answered 61 items of the Diagnosis of Local Security (DLS) Questionnaire. The results of this study show that in the most frequent crime category, 72% of occurrences represent crime against property. In the feared crime category, there is a preponderance of crime against people (61%). Age of the respondents predicted the most frequent and feared crime, while sex predicted the most feared crime only. Social/environmental variables, as well as incivilities, also predict the frequent and feared crime in two typologies, i.e., crime against people and crime against property. Practical implications to reduce FOC and areas for further investigation are discussed.