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.

We just had our little 1948 ranch painted last week and I'm extremely pleased with how the colors turned out. The neighbors are too; we're getting great feedback. Body: SW color matched to BM Wedgewood Gray (this is actually a muted blue color) Door: SW color matched to BM Rich Coral Trim: SW Snowbound (chosen because it's the same color as our vinyl windows. It's cheerful with a nod to mid-century without being too much for our very beige neighborhood.

I think your home is beautiful! I would go with a dark gray that matches the rock and I would paint the brick enclosure to match as well, a shade darker or lighter. Trim would be pretty bright white. I just love grays though. Maybe keep the red door or change to black. You have lots of options. :)

I got outvoted on sage, but we found a dark blue color at Sherwin WIlliams that I think will look really nice. We have to get some samples and try them out to test the different lighting. It's dramatic and I like it. No one else on the street has this color. What do you think? Thank you everyone for your help. It's nice to get outside perspective.