The present property had on its original estate the site of the first dwelling built in Holliston, the abode of Jasper Adams of Medfield. Next the site was occupied by Deacon James Russell, who kept the Russell Tavern near the present location of the Whiting House.
Colonel Asa Whiting built this Georgian Federal home about 1812 quite near the road in front of the present barn, which was constructed in 1817. The house contained fifteen rooms and seven fireplaces, served by two massive chimneys. Timbers are of hand hewn solid oak, each timber still numbered as it was on the day it was put in place. The casings are sheathed with white birch and the rooms are wainscoted and paneled. The fireplace mantels are hand carved and the staircases hand fashioned. Some of the old wide floor boards can still be seen in the upper rooms.
In the early 1930s, the house was moved back away from the road to its present location, set on a new foundation, and the porches at each end were added, giving it its present exterior appearance.
Asa Whiting, who was born in Holliston in 1782, lived here until his death in 1858. He was a member of the Massachusetts Militia (4th Regiment 1st Brigade 3rd Division) and rose from the rank of Sergeant in 1811 to Colonel in 1820 before retiring in 1822.
Colonel Whiting’s grandson, George Flagg, who occupied the Italian Revival style house to the south of this property, operated a model dairy farm on the present site of the Whiting House. During the late 1800s, the unique architectural style of the dairy barn was well known throughout the area. Tragically in 1893 the dairy barn was burned to the ground.
The Holliston Historical Society purchased the property consisting of the hip-roofed house and present barn in 1967 from Mr. and Mrs. Charles Cole, Mrs. Cole being a direct descendant of Colonel Asa Whiting. Members of the Society then undertook extensive redecoration, including merging two downstairs rooms into one large meeting room.