Climate change and human activities in particular are important causes of the possible variations in Mediterranean basin forest health conditions. Over the last decades, deciduous oak-forest mortality has been a recurrent problem in central and southern Italy. Despite the perception of increasingly visible damage in oak forests in drought sites, the role of various environmental factors in their decline is not completely clear. Among the modern methods of monitoring terrestrial ecosystems, remote sensing is of prime importance thanks to its ability to provide synoptic information on large areas with a high frequency of acquisition. This paper reports the preliminary results regarding a replicable and low cost monitoring tool planned to quantify forest health conditions based on the application of the Normalized Difference Vegetation Index (NDVI), using the diachronic images provided by the Sentinel-2 satellite. The study area is represented by a peri-urban forest of natural Mediterranean deciduous oaks, characterized by a high variability in the composition of the species and in the silvicultural structures. In order to monitor the health conditions of a specific forest canopy cover with remote sensing data, it is necessary to classify the forest canopy cover in advance to separate it from other species and from the Mediterranean scrub. This is due to the spatial distribution of vegetation and the high rate of biodiversity in the Mediterranean natural environment. To achieve this, Light Detection and Ranging (LiDAR) data, forest management data and field sampling data were analyzed. The main results of this research show a widespread decline in oak health conditions over the observed period (2015–2017). Specifically, for the studied area, thanks to the specific localization of the oak canopy cover, we detected a high potential concerning the Sentinel-2 data application in monitoring forest health conditions by NDVI application.