Increasing wildfire frequency in the Mediterranean Basin could affect future plant-soil–water-dynamics. The capacity of soils to retain water is a key parameter affecting plant post-fire regeneration. Yet, few research has looked at how different soil properties related to water retention is affected by increasing wildfire frequency. This study aimed at understanding the relationship between wildfire frequency, soil–water-related properties and the dynamics of surface water in soils. To this, after a 2012-summer wildfire in Portugal, three sets of three replicate maritime pine stands with contrasted wildfire frequency were selected (0 vs. 1 vs. 4 fires since 1975). At each of the nine study sites, three re-sprouter shrubs and neighbouring bare soil were chosen (54 microsites). There, soil cover, soil–water retention curves and surface (0–5 cm) soil–water-related properties (texture, bulk density, organic matter content, soil moisture, soil surface water repellency) were monitored for one year. Furthermore, records of post-fire soil moisture dynamics were analysed continuously using 72 probes installed at 2.5 and 7.5 cm depth. The hillslopes affected by 1 fire showed higher plant recovery than the 4 fires hillslopes. During the dry season, the threshold for water stress was reached 17 days sooner in the 4 fires hillslopes, and also 10 days sooner on bare microsites. Periods of plant water stress were longer and bare soil patches size bigger. The increase in wildfire frequency promoted high soil organic matter contents but less available water content, stressing the importance of soil organic matter quality characterization in water-related properties.