A home automation (HA) system may include HA operation devices within a user living area and an audible virtual assistant device within the user living area. The HA system may also include an HA hub device to provide communications for the HA operation devices, and a controller. The controller may be configured to store historical operational data for each of the HA operation devices based upon a user within the user living area, and use machine learning to determine an operational pattern of at least one of the HA operation devices based upon the stored historical operational data. The controller may also be configured to monitor operation of the HA operation devices and cooperate with the audible virtual assistant device to generate an audible notification based upon a determined operation of the at least one HA operation device according to the operational pattern.