Street View in Google Maps has now been around for over 10 years in the US. For more popular streets, the picture van has been down these roads multiple times. If you are looking for a blast from the past (at least back to 2007), Street view has the option of showing a location at different points in time.
This guide is specific to Google Maps on the desktop.
Here is how to see past pictures on Street View in Google Maps:
Open a browser (preferably Chrome) to maps.google.com and click on the yellow, faceless man at the bottom right of the screen.
The streets on the map will be highlighted in blue if they have the Street View available.
Clicking on a blue street on the map will zoom you down to the Street View. By default, you will see the latest Street View that Google has on file.
In the upper left corner of the screen, you will see a box showing the address and the month the photo was taken.
Clicking on the Street View date will open a small window showing a previous date and a slider allowing you to switch between all the dates available for that location.
Clicking on different points on the date slider will change the view in the window to that date. To show that date on the main window, click on the picture for that date. The small window will disappear and the main window will switch to the date chosen on the timeline.
As you move around the streets, the date may change, but will try to stay close to the chosen date.