Increasing communities’ adaptive capacity is crucial to enhancing the sustainability of livelihoods and landscapes in smallholder systems. This study evaluates the contributions of an asset-based community-driven local development project, which has an objective to enhance farmer livelihoods through context-specific agricultural and agroforestry training, in line with farmers’ identities, interests, and preferences. The project was implemented in two areas of the wider Nyando river basin: the Lower and Middle Nyando sites. The project effects on farmer livelihoods were evaluated by analyzing overall income enhancement through the adoption of climate-smart agricultural practices via the computation of total values of harvest. Socioeconomic data from 183 households, half of which were involved in the project, were considered. The findings showed that locality played an important role in the adoption and success of good agricultural practices. Additional significant positive factors included project participation, size of land operated, horticulture farming, livestock ownership, ownership of a title deed, hours worked, and crop species richness. The number of years farmed had a significant negative correlation with the value of harvest. Considering the stark differences in livelihood effects in both sites, researchers conclude that external support for climate-smart agriculture uptake needs to be considerate of, and respond to, biophysical and socioeconomic context.