Proximal optical sensors (POSs) are effective devices for monitoring the development of crops and the nitrogen (N) status of plants. POSs are both useful and necessary in facilitating the reduction of N losses into the environment and in attaining higher nitrogen use efficiency (NUE). To date, no comparison of these instruments has been made on quinoa. A field experiment conducted in Tuscany, Italy, with different POSs, has assessed the development of quinoa with respect to N status. Three sets of POSs were used (SPAD-502, GreenSeeker, and Canopeo App.) to monitor quinoa development and growth under different types of fertilizers (digestate and urea) and levels of N fertilization (100, 50, and 0 kg N ha−1). The present findings showed that in-season predictions of crop biomass at harvest by SPAD-502 and GreenSeeker optical sensors were successful in terms of the coefficient of determination (R2 = 0.68 and 0.82, respectively) and statistical significance (p < 0.05), while the Canopeo App. was suitable for monitoring the plant´s canopy expansion and senescence. The relative error (RE%) showed a remarkably high performance between observed and predicted values, 5.80% and 4.12% for GreenSeeker and SPAD-502, respectively. Overall, the POSs were effective devices for monitoring quinoa development during the growing season and for predicting dry biomass at harvest. However, abiotic stresses (e.g., heat-stress conditions at flowering) were shown to reduce POSs’ accuracy when estimating seed yields at harvest, and this problem will likely be overcome by advancing the sowing date.