Although its use is declining, oil heating is still used in areas not covered by the methane grid. Oil heating is becoming more and more expensive, requires frequent tank refill operations, and has high emissions of greenhouse gas (GHG) and air pollutants such as SOx. In addition, spills from oil underground storage tanks (USTs) represent a serious environmental threat to soil and groundwater quality. In this paper, we present a comprehensive analysis on technical alternatives to oil heating with reference to the Aosta Valley (NW Italy), where this fuel is still often used and numerous UST spills have been reported in the last 20 years. We assess operational issues, GHG and pollutant emissions, and unit costs of the heat produced for several techniques: LPG boilers, wood boilers (logs, chips, pellets) and heat pumps (air-source, geothermal closed-loop and open-loop systems). We examine the investment to implement such solutions in two typical cases, a detached house and a block of flats, deriving payback times of about 3–8 years. Wood log boilers turn out to be the most economically convenient solutions; however, heat pumps provide several benefits from the operational and environmental points of view. In addition, including solar thermal panels for domestic hot water or a photovoltaic plant would have payback times of about 6–9 years. The results highlight the economic feasibility and the multiple benefits of a rapid phase-out of oil heating in Italy.