Here are two postcards with virtually identical perspectives looking down Bearskin Neck towards town. Both have the exact same caption, both are published by Rockport Photo Bureau and printed by The Albertype Co., Brooklyn, N.Y. Neither provides a date.
Despite the similarities between the two, there are subtle differences that suggest the top card is the older. For example, note that the rough, rocky road in the top picture is now smooth in the bottom picture. In the top picture, there is not an automobile in sight; in the bottom picture, there are several. In the top picture, the light pole in front of the house appears rough hewn and slightly crooked; the pole in the bottom picture is straight and smooth. In the top picture, there is only a small bush by the corner of the house and another, smaller bush by the front door. In the bottom picture, the side of the house appears much more overgrown. In the top picture, there is a man standing by a fence next to the house. In the bottom picture, there is no sign of the fence (or of the man).
As I’ve noted before, the Rockport Photo Bureau started publishing photos in 1907 and continuing under that name until the mid-1930s. The cars in the bottom photo look to be from around 1930, so I think it’s fair to say that postcard is from around then. That would put the top card at some point earlier — how much earlier, I don’t know.