I think a medium toned olive would be nice. Too dark, and your roof and house will just blend in together. I would do an warm white trim, not stark white. A rusty red for the front door would really stand out against the olive. Or, consider a warm fall gold color. Be sure you paint the garage door the same color as the house, otherwise the white or off-white massive door will be the focal point. Gate the same as the house color, with the raised panels in the trim color. I would get rid of the overgrown bush to the left of the garage and put a nice planter there instead. I would also think about creating a curved bed that comes from the right side of the house and meanders down to the point where the little sidewalk turns to the front door - right at the point of the angle. That lawn space isn't really useful, but a pretty bed of low plantings and bushes that come up along the front of the house will take the eye to that area of the home, and bring it forward to balance the garage being so far to the front. It is a charming house, and your new colors will really make it feel even more welcoming.

I wish the house was darker grey and the trim white. The present trim does not look attractive to me in the least. If this is front side, neither does the prickly pear look like much of an invitation to enter. The bottom of the tree canopy is in effect a ceiling. It needs limbed up to clear 10' of vertical space above grade. The stone work in the yard does not look quality and gives a junky appearance to the overall property. I'd get rid of it.

Yes, all shutters off. Whatever siding color you pick, paint both doors the same color. (A different style door would work better than the Victorian one) I vote for same siding color for all of it, a color that works well with your gray roof since a lot of it shows, although Emmeren's photo is an interesting way to handle the two finishes of the siding.. Since you're just moving in, landscaping is the last thing you're probably thinking about. But this house could look amazing with much deeper beds with taller plants in back, perennials, bushes, hardscaping, and more. When you come up for air, and if you have some budget left, a small garden center can help you come up with the plan. Good luck. It's a pretty house. Cream and gray. Add bright blue doors (replace Victorian door) (This post is a good example for people who want to paint their brick--next owners may not like painted brick, or they wish it were unpainted. I'm usually pro-brick because it adds texture to a façade and can work well with very modern colors--navy, black, charcoal. I usually suggest a brick walkway to enhance the brick and link it to beautiful landscaping. Why brick is considered worse than widely accepted vinyl siding, I don't know.)

what is the color you show in the first pick is tha your brick already painted (I sure hope not ) IMO the fastest way to devalue a house is to paint the brick . Iwould lose the shutters paint the siding the dark color get a MCM garage door and entry door and then do some nice MCM landscaping .So something like this for thebgarage and entry doors and this type of landscaping just leave the brick and BTW if you have grids in the widows change that ,