Hi Jessica. Beautiful home! I'm not much help with paint colors, but I would suggest that if you post this in the Home Decorating forum (particularly with all those great pics). You'll get some amazing advice.

Just a warning on white. It does not hold up on the brick well and I have found it looks bad after a while. Grey, that looks nice and holds up well. there is a home decorating forum on here under "that home site" and they do a lot of photo-shopping of ideas including house exteriors. I posted my house on there and they did it in about 15 versions which included the landscaping. You might want to try them and if they help post a link on here so we can go see. I have included the link to my house. the thread is old so you will notice that a lot of photos are missing. Scroll down and you see many ideas they contributed although the best ones are missing.. Here is a link that might be useful: they helped me with my house

We suggest doing a white-washed brick and white or light gray siding. Keep the black shutters. While this is a different style of home, it's the same idea:

Check out Sarah Richardson's video on whites!!