Redistribution of food surplus helps to prevent waste production and feed hungry people. But this has not been tested in the context of a wholesale market that redistributes fruit and vegetable surplus to homeless shelters. We aimed to compare the amount of fruit and vegetable waste between shelters that received or did not receive a surplus donation in Chile. We also explored possible causes that explained the waste. Five homeless shelters that received donations (HS+DON) and five that did not (HS) were included. For three days, fruit and vegetable waste was disposed into containers for direct quantification. The amount of waste was compared between groups using the Mann–Whitney U test, both in winter and spring. A questionnaire was applied to identify causes of waste. For vegetables, we found no difference in the median (25th percentile–75th percentile) waste of HS+DON vs. HS (winter: 152 (83–262) vs. 104 (63–163) g per person/day, p-value = 0.22; spring: 114 (61–229) vs. 63 (50–132) g per person/day, p-value = 0.41). HS had no fruit waste, thus, fruit waste was higher in HS+DON in both seasons (winter: 74 (16–134); spring: 13 (6–40) g per person/day). The main reasons explaining waste were excessive donation, looking badly, and smelling moldy. In conclusion, redistribution of fruit and vegetable surplus helped to reduce waste at the wholesale market and to feed homeless shelters’ beneficiaries with nutritious food. But efforts are still required to avoid excessive donation of surplus soon-to-be spoiled. We propose a tailored donation plan to reduce waste to the unavoidable one.