The objective of this study was to research grief and depression in oldest-old people living in urban congregate housing by examining the various types of grief that they experience by using a stress process model for depression among the oldest old. This study used a convenience sample of the 128 participants aged 80 and older living in congregate housing. We found that the two types of grief most significantly associated with depressive symptoms were grieving about relocating, and loss of health. Our findings demonstrate the need to explore a variety of grief which influences mental health among oldest-old.