Background and Objectives: Whether grandparenting is associated with improved health and well-being among older adults is a salient question in present-day aging societies. This systematic review compiles studies that consider the health and well-being outcomes of grandparenting, concerning (i) custodial grandparent families, where grandparents are raising children without parental presence; (ii) three-generation households, where grandparents are living with adult children and grandchildren; and (iii) non-coresiding grandparents, who are involved in the lives of their grandchildren. Research Design and Methods: This systematic review was based on literature searches conducted in September 2019 via Web of Science, PubMed, PsycINFO, and Ebsco. We screened 3,868 abstracts across four databases, and by following the PRISMA guidelines, we identified ninety-two relevant articles (117 studies) that were published between 1978 and 2019. Results: In 68% of cases custodial grandparenting was associated with decreased health and wellbeing of grandparents. The few studies considering the health and well-being of grandparents living in three-generation households provided mixed findings (39% positive; 39% negative). Finally, in 69% of cases involvement of non-coresiding grandparents was associated with improved grandparental outcomes; however, there was only limited support for the prediction that involved grandparenting being causally associated with grandparental health and well-being. Discussion and Implications: The findings are discussed separately among these three groups of grandparents, including reference to possible causal relations between involved grandparenting and grandparental health and well-being. The article concludes by considering the scope for future studies.