Kellen and his wife Janelle maintain a charitable organization, the Kellen Winslow Jr. Foundation that gives back to the Boys & Girls Club as well as many other children’s charities.

Outside of the foundation, Kellen is constantly seeking ways to expand his philanthropic endeavors. Specifically, he is interested in addressing the problem of childhood obesity. To accomplish this goal, he is currently in the developmental stages of creating prevention programs and camps that will encourage at-risk kids to adopt healthy habits for an active lifestyle. In Cleveland, Kellen began to address this problem through charitable efforts. He has supported events such as the Special Olympics Holiday Party, Taste of the NFL, and the Browns Youth Football Camps, which stresses the importance of nutrition and physical activity.