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Grandparent-headed families are diverse in nature and represent a rapidly growing family type. While challenges facing grandparent caregivers are well documented, less is known about the well-being of their grandchildren, with many early studies relying on small samples of convenience. This study used an existing large national database, the National Survey of America's Families (NSAF), to compare differences in well-being of both children and grandparent caregivers across the independent variables of family type, ethnicity, gender, and age. Findings suggested better mental health and less parental aggravation for caregivers in traditional two parent intact families as compared to grandparents co-parenting in a multi-generation home, skipped generation grandparents (raising their grandchild with no parent present) or single parents. Skipped generation grandparents in particular reported most caregiver aggravation. Child physical health was reported to be worse by skipped generation grandparent caregivers. Behavior problems were reported to be worse for children in grandparent headed households than those in traditional families, particularly for teenagers raised in skipped generation households by their grandmothers. Specific results, limitations and future directions for research on grandparent-headed households were discussed.