As urban areas expand around the world, there are growing efforts to restore and protect natural and agricultural systems for the multitude of ecosystem services they provide to urban communities. This study presents a researcher-farmer collaboration in a highly urbanized area of O'ahu focused on understanding the historical and current challenges and opportunities faced by a culturally and socially valued spring-dependent urban farm, Sumida Farm, which produces the majority of the state of Hawai'i's watercress. We conducted a long-term trend analysis (25 years) of factors identified by the farmers to be important historical drivers of crop yield, including groundwater pumping, pest outbreaks, temperature, Oceanic Niño Index, and precipitation. We combined this analysis with a year of intensive spring water sampling on the farm to evaluate nutrient and contaminant composition and flow to understand water-related stressors, as well as evaluate the potential of the farm to provide nutrient retention services. We found negative correlations between historical crop yields and increases in the Oceanic Niño Index, temperature thresholds, and pest outbreaks. Despite the surrounding urbanization, we found on-farm water quality to be very high, and microbial analyses revealed an abundance of denitrifiers (nirS gene) suggesting that the farm provides a nutrient retention service to downstream systems. Finally, we found that socio-cultural values including heritage value, aesthetic value, and educational value are increasingly important for the Sumida family and surrounding community. These socio-cultural benefits alongside highly valued local food production and nutrient retention services are essential for continued community and political support. Collectively, our study demonstrates that challenges facing urban agricultural systems shift through time, and that recognition of the beyond crop-yield benefits of these systems to urban communities is essential to their long-term survival.