The VTC student, Morlene Wong, who created the architectural drawings of the Ridge Road house in 1978 stated on the plans (see image below) that "the original house was built around 1790. Later the gabel [gable or dormer] was built to accomodate [sic] an extra bedroom." I am guessing that Morlene was given this information by either Charles or Harry Cooley in 1978.
But in a very early photo of the old house from Wes Herwig's book "Early Photograh's of Randolph, Vermont" the gable dormer can already be seen in the photo (scroll down). Does that mean that the 3rd bedroom was already there in that photo? Or possibly, the gable dormer was always there for the windows and light it provided and only later the 3rd bedroom was walled off from the stairwell?
Here is a little study of how the two houses match up...the old photo vs a current one taken 1120/23.
After studying the two photos, I think you're right about the front dormer being part of the original house. I, too, wonder where Marlene got her info. I think Marlene is Wong. (Sorry, couldn't resist.)