I've been thinking this was the house that used to be next to the old Christ Lutheran Church. It was on the corner of E. Main and Academy when Academy went through. The 1912 Sanborn Map (page 11) shows this house as well and the carriage house you see in DSCF0460. This house has been removed and incorporated into the Stoughton Health parking lot. This is the same house as image DSCF0460

This looks like the corner of Jackson St and Johnson Street looking North East.

I meant looking North West. I'd say he was standing Jackson Street looking up Johnson St.

Based off of the 1904 Sandborn Map I believe this is 107 S. Prairie St. The house has been changed quite a bit but you can still see the front roof shape and the wall is probably the one that is still there.

Oak Street?

I finally found this one. It is 425 Oak St. The house has been modified but all of the details line up as does the foundation and side of the house to the East.

This looks a lot like 616 W South Street. The brackets near the roof match and the windows on the top in both the front an West side of the house match up as well as does the Southern most first floor window.

I am fairly sure now that this is 840 W. South Street. The front windows line up as does the trim. You can see the larger windows through the now enclosed porch. The side windows mostly line up. The height of the foundation also lines up.

This one greatly resembles 102 N. Page St.

I think this is 412 Main Page Ct.

I meant 402 Main Page Ct.

I've been looking and the Sanborn Maps and other clues for this one. It MIGHT have been on Page Street where the rear parking lot of Main & Page Auto is. The houses in the background seem to line up without their more modern additions and the shape of the house matches the Sanborn Map. So possible about 267 S. Page St (Google's Address for this area).