Solid waste is considered as one of the key feedstocks for the chemical industry to stimulate the world's transition toward a circular economy. Therefore, a novel production process, catalytic pressureless depolymerization (CPD), for conversion of waste to high-energy density liquid fuel has been studied. More specifically, the organic fractions recovered from demolition waste and municipal solid waste were liquefied and deoxygenated in a CPD pilot plant with 150 L h–1 (4.2 × 10–5 m3 s–1) liquid fuel capacity. The produced fuels were characterized by elemental analysis, comprehensive two-dimensional gas chromatography (GC × GC), and the ISO tests for automotive diesel established by the EN 590:2009 Standard. The studied fuels showed very low oxygen contents (<0.4 wt %) and a high share of paraffins (>40 wt %). The carbon range of the fuel obtained from demolition wood was wider than that of the fuel obtained from municipal solid waste (C5–C29 vs. C6–C22). The flash points (54, 46 °C), the sulfur contents (40, 80 ppmw), and the cetane numbers (43, 33) did not comply with the respective requirements for automotive diesel (i.e., ≥55 °C, <10 ppmw, and ≥51). Nevertheless, both fuels showed salient cold filter plugging points (−14, −15 °C) and cloud points (−15, −44 °C), which are indicative of good fuel performance at extreme winter conditions. The wide carbon number distribution, especially toward the lower range (i.e., carbon number < C12), suggests that the studied fuels can be split into a kerosene-like and a diesel-like cut. Overall, the fuels from the CPD process exhibit great potential as alternative transportation fuel; however, selecting the starting material is crucial for minimizing costly hydrotreating.