In trying to find the location of the photo, I found myself with almost too many options. Uncle Milton and his parents lived all over the neighborhood and never appear in the same home from one year to the next in city directories. Luckily though, the addresses were confined to three streets, all in Cabbagetown.
A lot of the old addresses are no more, or have been heavily redeveloped. For example, I can pretty much disregard the address where the modern condos and high rises now sit. Other homes are still there, but have obviously had some remodeling done. Still, I held out hope that the house in the picture still existed.
Next, I looked at the homes in detail on Google Maps. There were a few key features in the photo that I used to try and identify it: the shape of the roof, the fact that it was a duplex (hard to see, but the door on the left is open), that it was built off the ground, and that it wasn't much longer than the length of the car. I also noted that it was very close to the house on the right.
One of the addresses, 196 Savannah Street, seemed like a possibility: it was obviously a former duplex (two chimneys and space for a second door), it was built off the ground and had the same type of roof design. The problem was two fold: the house next door and the address. The other house wasn't close enough, nor of the correct design. Considering the ages of the homes, however, it was certainly possible that the other house had been renovated. The street number was also off; this house was 193 Savannah Street. But considering that it had been changed from a multi to a single home, it was possible that street numbers had changed.
This could be the house - but I need proof!
I looked at the two houses in question. The top house was clearly a duplex with basically the same design as today. The bottom house though, the one that should have been closer, had obviously undergone serious renovation. It had previously been a triplex, with the left/top most home pushed back. Today, that space is a driveway, and that's what clinched it for me. In the original photo, you can see that the porch is pushed back and that there is more siding along the right side. Compare the original photo and the Sanborn map and you can see it.
So today my sister and I went to visit the house and take some photos. It really neat to walk through the neighborhood where my ancestors lived and visually connect the past and present.
Edit: I didn't mention this, but I left the photo behind on the house's doorstep, with a note saying that it was a photo of my Great-Great Uncle in front of their house. The home owner actually blogged about finding the photo, and then found this blog post. Read about it here: Oakdale Onward.