The present work focuses on the techno-economic assessment and multi-objective genetic algorithm optimization of small-scale (40 kW_th input), solar Organic Rankine Cycle (ORC) systems driven by medium-to-high temperature (up to 210 °C) parabolic dish (PDC) and trough (PTC) collectors. The ORCs are designed to maximize their nominal thermal efficiency for several natural hydrocarbon working fluids. The optimization variables are the solar field area and storage tank capacity, with the goal of minimizing the levelized cost of produced electricity (LCoE) and maximizing the annual solar conversion efficiency. The lowest LCOE (0.34 €/kWh) was obtained in Athens for a high solar field area and low storage tank capacity. Meanwhile, the maximum annual solar conversion efficiencies (10.5–11%) were obtained in northern cities (e.g., Brussels) at lower solar field locations. While PTCs and PDCs result in similar efficiencies, the use of PTCs is more cost-effective. Among the working fluids, Cyclopentane and Cyclohexane exhibited the best performance, owing to their high critical temperatures. Notably, the systems could be more profitable at higher system sizes, as indicated by the 6% LCoE decrease of the solar ORC in Athens when the nominal heat input was increased to 80 kW_th.