Wildfires are a major environmental issue that have an impact on land degradation. Remote sensing spectral indices provide valuable information for short-term mitigation and rehabilitation after wildfires. A study area in the Centre inland of Portugal occupied with Maritime pine and Eucalypts forests and affected by wildfires in 2003, 2017 and 2020 was used. The aims of the study were twofold: (1) to compute the Normalized Difference Vegetation Index (NDVI) and with forest inventory data derivate a Maritime pine production model, differentiate evergreen coniferous forests (e.g., Maritime pine), evergreen broadleaved forests (e.g., Eucalypts), and shrubland, and monitor vegetation and its post-fire recovery; and (2) to compute the Normalized Burn Ratio (NBR) difference between pre-fire and post-fire dates for burn severity levels assessment. The plots of a previous forest inventory were used to follow the NDVI values in 2007 and from 2020 to 2022. An aerial coverage in 2007 and the Sentinel-2 imagery in 2020–2022 were used. Linear models fitted maritime pine production with the transformed NDVI by age, showing a fitting efficiency of 60%. The stratification of cover types by stand development stage and fire occurrence was possible using the NDVI time curve, which also showed the impact of fire and of low precipitation. Cover types were ranked by decreasing NDVI values as follows: mature Eucalypts plantations, young Maritime pine regeneration, mature Maritime pine, young Eucalypts plantations, Strawberry tree shrubland, Eucalypts plantations post-fire, Maritime pine post-fire, tall shrubland, and short shrubland. Vegetation post-fire recovery was lower in higher burn severity level areas. Maritime pine areas have lost their natural regeneration capability due to the wildfires’ short cycles. Spectral indices were effective tools to differentiate cover types and assist in the evaluation of forest and shrubland conditions.