Paint the rest—including the brick—gray to match the gray siding.

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#2

I like the eclectic nature of the different colors. Instead of painting right off the bat, I would do a much better path to the front door and get some landscaping.

Is the fireplace painted black or is that unfinished black paper or something on it? I'd paint the whole front of the house to match the great color of the siding. You have enough interesting elements without several different colors.

Your original windows in your brick appear to have black metal framing so you should consider painting all the door and window trim and the fascia black (including storm door and large window beside it that now appears to have "orange" wood trim.

That chimney is trying to overpower everything, including the front door. Consider ways to make the chimney and entry door all one section of the house. For example, you could create a porch or front patio floor that is in front of the both the entry and the chimney -- maybe six deep in front of the chimney ... that would make it closer to seven feet deep at the front door -- and put either roof or arbor over that area. Make that entire area the same ?black? color as the chimney, except choose your favorite bright bold.

If you don't need that second black tower, remove it altogether. If you cannot remove it, paint it the same color you choose for all the rest of your siding that isn't a part of the entry,.

Not usually a fan of painting brick but your house is truly the exception. Your home will look a lot better if, other than the black entry and window and door trim, the rest of your home's siding is all the same color or, if you decide to not paint the brick, if it is all the dominant color in the brick.

With a black roof and entry, you could pick any color you actually like for the siding. You might consider a medium brown or green if you don't want gray.

Not sure what's going on with the ?garage? on the right to the right of that second tower covered in a material resembling the chimney but, unless that is a barn for animals rather than a garage for cars, you should seriously consider extending (or creating a new wall against/beside that existing wall that doesn't curve but extends straight out toward the road.

Let us know how your redo turns out.

Hmmm, since your house is a definite "rambler" with a variety of materials I'm wondering if painting it a mostly uniform color would unify it into a better composition.

I almost never paint exterior brick but in this case the 2 1/2 s do not make a whole there is nothing to connect the brick 1/2 to the new so I would paint it the light gray. I am curious what the purpose of the tall black tower was and how you will access the right hand side garage without falling off the edge.

I don't understand why you didn't build an addition that matched the original look of the house?

If your house was a car....

Here is final result after painting all gray. Like?

Much better...I'd still probably paint the black chimneys/stacks to match, but the rest looks very nice

I agree with Nelly Bluth that you should paint all the exterior walls, including the brick, the light grey to match the house area on the right. I also would suggest you paint all the trim, including the orange sections, a bright white for contrast.