This is the best I can do on pictures, it is a dark and rainy day. The stains on the roof will be power washed off soon. I have ordered white window boxes for the two windows on the right. I would like to brighten up the doors/shutters, as the house across the street has this same color palette.

So we did some more test painting and decided on the muted gray/blue for the main sections, similar to what gracie linked. We tried 2 different trim colors and are feeling like the dark gray blends in too much with the blue. The lighter gray seems to have more contrast. What does everyone think? Also, what would you recommend to paint the lower concrete section of the house. The lighter gray trim color if we pick that? Or would you possibly paint it a darker gray like the trim we weren't digging? Gray/Blue with light gray trim: Gray/Blue with dark gray trim (on right side of garage): Closer pic of Gray/Blue with darker trim: lighter trim in the shade: Close-up of lighter gray trim: (Middle of pic): Lighter gray trim again. Lower concrete section that will need to be painted:

Chris your inspiration house has a large proportion of the natural cedar color to the blue and a lot of what we can see on that house in the photo is in shadow which makes a big difference. You're trying to choose a color for your house without a clean background - the yellow is a player in making colors look different. I took a picture of 2 colors from one of my paint decks for you - put them on a table on our porch that is similar in color to your cedar but when I compare the picture to the paint deck it's horribly off so I hesitate to post it for you. I may email it but just know that it's not representational at all. I'm looking at Benjamin Moore Everard Blue CW-575 and Wetherburn's Blue CW-580. these are from their Williamsburg collection, grayed blues with green in them. Even on the B/M website the colors are off on my computer. I'm not certain these are the *right* colors for your house but it's a slightly different direction that brings your setting into the mix and a place to start. Hale Navy is part of the Historical Color collection from B/M - that collection is a good place to be as well. The colors are dirtier which is good - what you don't want is a bright, clear color on your house. There are different ways to approach trim and house colors - they can be high contrast with crisp definition or lower contrast and more subtle transition. Neither one is better, they are just different looks but your trim will still be differentiated from the house body with less contrast. Are you planning to paint your eves and rake boards like the inspiration house?

I would match the siding to one of the brick colors you have already - lightest or darkest. Remove the stick-on faux shutters and don't put them back. Beef up your spindly, Victorian porch posts with square ones and upgrade the doors for a more stylish vibe. Match gutters and downspouts to the color of the surface they are on so they show less. See if that one running from the upstairs and onto the porch roof can be placed somewhere less visible. New landscaping will make a huge difference!