Maryland - you should be in zone 7. I also like the brown; it's fitting for the style of house. As for landscaping, you can lighten up the heaviness of the old pines with the addition of a lacy dogwood or one of the many beautiful varieties of Japanese Maples out at the sunny edge of the stone retaining wall. The lamppost bed would look nice with something simple like Perovskia or Walker's Low Nepeta - both have silver grey foliage with lavender blue spikes of flowers. I'd resist the temptation to color up with the usual assortment of rhododendrons and azaleas - beautiful, but just everywhere in the Mid-Atlantic. Sometimes less is more.

I wouldn't paint the brick on this house. It will create long term maintenance and I think that currently the brick is really attractive and adds character. if there isn't good lighting on the porch, consider adding some, and you might want to paint the front door a color that will look nice with the current colors but will stand out more. Getting rid of the random stepping stones will help as will adding a path and planting a garden. Make the bed generously sized, a minimum of 6' deep with crisply maintained edge, either a masonry mowing strip set at ground level or a V shaped cut edge. I would have at least a few evergreen shrubs for year round interest and some flowers near the porch. I like the placement of the pot by the junction between the garage and the front door, but would suggest replacing it with a larger one. For the path, choose one of the types of masonry already present (red porch, gray concrete drive, yellow brick walls) and use that; don't introduce a fourth kind of masonry in such a small space. For the porch planter, use something quite shade tolerant such as fernsor many of the plants sold for indoor use since it is set well back on the porch.

It has been a few months, but we finally made a little progress. We ripped out the front bushes on both sides (haven't gotten to the giant holly trees behind the wall on the left yet) and tore down the ugly wall on the right side of pictures so at least they aren't covering the windows that are closer to the street anymore. It is hard to tell from a picture but we also leveled out the yard a little on the right side so there isn't quite as much of a hump in the middle of that side of the yard. The small wall just above the sidewalk is going to be removed in the next few days and replaced with the bricks you can sort of see we have started building up along the sidewalk up to the door. We are also looking to replace the windows on the right side of the house for now, with a combination of casement and picture windows that match. Because of the roofline there, I would like to remove the look of the horizontal bar across the middle of the. I think that might help visually open that space??? Thoughts? We get full 100 degree plus sun for several months of the year so I have some low growing drought resistant shrubs in mind for that area once we get to that point. I would love to paint the brick (I know some people hate painted brick lol) or mortar wash it in some way and put in a medium brown trim and windows, but I don't think it is in budget at this time. What do you guys think of the progress so far? Any more thoughts/recommendations would be much appreciated. :)

Box need good drainage (= root rot susceptibility), can also be prone to serious box blight damage depending on specific variety and site conditions. Most kinds of smoke bush are quite large growing - as in becoming tree sized. Some like to cut these down to near the ground each year but every time I have seen one treated in this fashion the replacement tops were sparse and leggy looking. Dwarf Alberta spruce often has bug problems even in my mild summer area. In addition it is very formal looking. As far as can be made out in these much too far away and dark pictures you have been been planting too big growing kinds of shrubs too close to the house - consider deeper beds and smaller plant choices.