Sometimes finding an ancestor's home can be extremely easy, especially if you know what city or town they lived. Of course a lot depends on the when they lived there and what kind of resources are available for you to find the address. I was lucky to find my Fanny Poole, 2nd great-grandmother's address from her 1904 obituary, it stated she died in her home, at 39 Addington Road, Brookline, Massachusetts. She was not at this address during the 1900 census or any other source.
Her death location, is a rather short distance from where I live, about 45 minutes away. To find her house, I used google maps, enlarged them and took several photos with my iPad. The old development looked complicated because of all the circular streets, and I knew I'd need simple directions. Another method, and I've used it with much success recently, is to do a google search for the address. When I typed in "39 Addington + Brookline," I was lucky to get a nice screen shot and since it was on the market, I saw the current value, plus photos of the inside. This was a bonus. With my maps, I was ready to go, except I got lost, and in spite of everything, couldn't take a decent photo of the property.
You can see Addington Road (red A to left) and how it circles around on the top of Aspinwall Hill, all the paths are just that, they are for walking only. Since we were there in the summer, every shrub and tree was full, plus lots of cars on the road, so, all three made it difficult to take a photo.
The above shot shows Claflin Path (one of seven paths) is right next to her home, and my photo is below, complete with lots of green. However, I couldn't get a decent picture of the building! I believe the best time to go is winter.
A good example how the street and property looks like in winter.
The development above has quite a history. I discovered this when I was at the Frederick Law Olmsted National Historic Site, and asked for directions from there to Addington Road, since it was rather close. I was told that Mr. Olmsted had a hand in that development. I found a good article by the Brookline Historical Society complete with photo of a path and map. "The curving, gently rising roadways that wind up and down Aspinwall Hill were originally designed by F.L. Olmsted. Subsequent designers retained the basic curvy street layout devised by Olmsted. Perhaps they appreciated Olmsted's goals of respecting the contours of the hillside and revealing the landscape from a variety of viewpoints as you passed by in your horse drawn carriage. These very same curvy streets, when traveled by foot, make for a very long and slow ascent of the hill. Addington Road is a giant S, with each half of the S traversing opposite sides of the hill. This is where the value of the path's shortcut shines."
The apartments, condos and houses in the entire area are old and beautiful. A few of the ones I liked are below.