Pres­ton began his ca­reer as an ar­chi­tect in the of­fice of his fa­ther, Jo­na­than Pres­ton, in 1861, ha­ving pre­viously stu­died at Cam­bridge and at the Ecole des Beaux-Arts in Paris. He was the ar­chi­tect of many pro­mi­nent buil­dings, in­clu­ding the Ro­gers Buil­ding of the Mas­sa­chu­setts In­sti­tute of Tech­no­logy, the Mas­sa­chu­setts Cha­ri­ta­ble Me­cha­nics As­so­cia­tion Buil­ding, the Cadet Ar­mory on Co­lum­bus Ave­nue, Bos­ton Uni­ver­sity School of Law on Ash­bur­ton Place, thirty or more buil­dings of the Mas­sa­chu­setts School for the Fee­ble Min­ded, and the State In­dus­trial School for Girls at Lan­cas­ter. He was elec­ted an As­so­ciate of the Ame­ri­can In­sti­tute of Ar­chi­tects in 1870 and a Fel­low in 1884.