A residential pneumatic mailbox and mailing system includes a mailbox, a receiving unit, pneumatic tubing, a courier canister, a compressor, and a control unit. The mailbox is positioned along a curbside of a home. The receiving unit is positioned inside the home or on the outside of the home. The pneumatic tubing is connected between the mailbox and the receiving unit. The courier canister is sized to hold mail and is configured for moving back and forth in the pneumatic tubing between the mailbox and the receiving unit. The compressor and control unit are configured to control the movement of the courier canister within the pneumatic tubing back and forth between the mailbox and the receiving unit. Wherein, the residential pneumatic mailbox and mailing system is configured to transport the mail inside of the courier canister from the mailbox to the receiving unit, and vice versa.