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As in many parts of Italy and Europe, the Sicilian Trazzera regional property has been for a long time the main land infrastructure supporting the agro-pastoral economy. Throughout its slow evolution, this land heritage has been affected by transport transformations and illegal appropriations by neighboring landowners, which have reduced its potential public function in the current renewed prospects of sustainability and a new balance between territories concerning the issue of the inland areas. A further issue concerns the management of the relationship between private interest and prospects for public reuse in progressively urbanized territorial contexts where this infrastructure takes on considerable economic and real estate interest. The current regional legislation suggests some measures for inter-municipal planning that also include the legitimization of illegal appropriations. From this twofold prospect, according to the wide-spread information and communication technologies (ICTs), and also including the geographic information systems (GIS), this work provides the application of two assessment tools based on a GeoDatabase of the current heard roads in the two areas of quantitative–monetary and aesthetic–qualitative assessment. The first shows the extent to which the fair compensation to be charged for legitimizing land parcels is underestimated today, to the detriment of urban social fixed capital development. The second demonstrates the way that common awareness of landscape value can be nurtured for the benefit of land and ecological–environmental rebalancing.