Extreme weather events are increasingly recognized as major stress factors for forest ecosystems, causing both immediate and long-term effects. This study focuses on the impacts experienced by the forests of Valdisotto, Valfurva, and Sondalo (28% of the total area is covered by forests) in Upper Valtellina (Italy) due to the Vaia storm that occurred in October 2018. To define the immediate impacts of Vaia, we assess the economic value of forest ecosystem services (ESs), particularly those provided by timber production and carbon sequestration, pre- and post-Vaia and during the emergency period. We used the market price method to assess the economic values of timber production and carbon sequestration, as these are considered to be marketable goods. Based on data processed from Sentinel-2 satellite images (with a spatial resolution of 10 m), our results show that, despite the reduction in forest area (−2.02%) and timber stock (−2.38%), the economic value of the timber production increased after Vaia due to higher timber prices (i.e., from a total of €124.97 million to €130.72 million). However, considering the whole emergency period (2019–2020), the total losses are equal to €5.10 million for Valdisotto, €0.32 million for Valfurva, and €0.43 million for Sondalo. Instead, an economic loss of 2.88% is experienced for carbon sequestration, with Valdisotto being the more affected municipality (−4.48% of the pre-Vaia economic value). In terms of long-term impacts, we discuss the enhanced impacts due to the spread of the bark beetle Ips typopgraphus.