A personalized webpage gifting system includes a server in communication with a computing device having a processor to execute an application. Upon execution, the application generates generate a graphical user interface (GUI) to receive recipient information from each of a plurality of participants in which the recipient information user-supplied content associated with a recipient from each of a plurality of participants, and a monetary amount to be contributed towards purchase of a gift for the recipient. The application then combines the user-supplied content of each participant to form a personalized content structure, wherein the application is further executable to facilitate transmission of the gift and the personalized content structure to the recipient.