Shoukoushi Cedie

The protagonists of both series are similar in appearance and character, have a dog as friend, and live with their grandfather since they were orphaned. However, the grandfathers are very different in character and wealth, which results in very different fates for the boy protagonists... If you want to see similar boys on top (Shoukoshi Cedie) or bottom (Flanders no Inu) of society, these titles may be of interest for you. 

These 2 shows have quite some similarities. A nice kid lives with his/her loving parents. But the parents die one after the other. Finally, the protagonist gets to live with the rich grandfather. The old man is a harsh person, who tends to exploit his workers. Initially, the protagonist has a tough time with the old man, but little by little, the grandchild gets accepted and changes the grandfather for the better... If you like this kind of story, both series may make you feel warm and fuzzy inside. 

A blond kid gets to live in a castle in England with a noble family, but life there is not exactly rosy... If you have seen one of these series, you will recognize a lot of familiar elements in the characters, the story and the setting. However, the overall story is different, and other things are emphasized. So I think both of these little prince/princess stories can be enjoyed in their own right, even at this time and age... 

Both are anime adaptations of a well-known children's story author Frances Hodgson Burnett.