Maisie (6b)'s idea to check for utility locations is a good one...call "Dig Safe". If you think you have any space for trees, I recommend you start your project with trees. They are the backbone of your landscaping. They say "the best time to plant a tree is yesterday. The second best is today". A small bare root tree you plant now will cost a fraction of a large Balled & Burlapped tree you buy in five years...and have a better root system. (Thus being more resistant to drought and wind). The little things can be planted whenever, and you will likely change them several times over the years. Spring is one of the best times to plant trees. See if your County Soil Conservation District has a Spring seedling sale. Generally deciduous trees go to the south (To provide summer shade but not block winter sun). Evergreens go to the north to block winter north winds, between you and the neighbor with the ugliest house, and between you and the nosiest neighbor. I'd visit a local arboretum to get a sense of what trees you like and what options you have. Also look at what grows well in the neighbor's yards...and most importantly, what doesn't. All gardening is local...you will find lots of regionally inappropriate advice online. How many feet from the road to your house? Are there above ground power lines? How far from the street is your oak? Do your neighbor's have a row of street trees you can continue? What is your USDA zone? You could put a small tree in the corner where your walkway meets your driveway. (Really small...think serviceberry or maybe Winter King Hawthorn). Foundation plantings are generally overused...but you have the kind of foundation that calls for them. I always like holly for it's winter interest and Rhododendron for it's huge flowers. Both are easy if you have acidic soil, and I think both tend to look better in irregular shapes then boxwood or yew would. Boxwood, privet and yew look formal, tend to look lousy unless maintained meticulously, and can look "dated". Really an aesthetic choice....to do you prefer the sharp-angled "formal" look or a splash of color in the right seasons? How meticulous do you think you will be about trimming? The other alternative is to pick something that can be cut to the ground and grow back for ease of maintenance. (ie Diablo Ninebark). Those sorts of plants tend to be deciduous and thus not as interesting in the winter. You don't have room for much between your walkway and your house...but you could stick some easy bulbs (eg Daffodils, liatris, nodding onion) there. Or you could turn that strip of grass into a much bed and put perennials there...although that would be more work. If you are willing to put in more work and money, I might put in a hedge (possibly holly) or a picket fence with climbing vines. (Roses or grapes) along your border between you and the pale yellow house.

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.

That front row of little pom poms needs to go too. Overall, the entry is squeezed between plantings--open it up--that is, widen the entry area for the full width of the little entry way--perhaps even widen the entire path if it's withing your budget. And the bed to the left of the walk should be at its widest at the corner of the house where a small tree would look nice.

As mentioned, by nature of the architecture, there are few places to put plants against the house at this front face. The overhang plus the lower windows does not invite foundation planting at that area. A large planter could go in front of the wall just right of the large window set. A shrub at left of the left house corner could help establish a better setting so one's view doesn't run directly off the house to what's across the street. (Maybe there are some plantings at the left side of house that can help with this, too.) Other than that, some large, circular beds around the two major trees could help give some fullness to the overall look and a sense of the patio space being more protected from the public space. The height of that groundcover could be as much as 3'+ to as little as 8", with the taller giving a more protected look. There is some opportunity for colorful seasonal blooming depending on what plants you use. My suggestions are for layout and arrangement. Plants have to be chosen from what works well in your locale. I got rid of the tall evergreen left of the door. It seems overwhelming to the porch/entrance space, IMO. To clean up the overall picture more, I'd get rid of large-tree foliage that hangs low enough to shroud the roof. This might mean hanging limbs/branches, or removing some lower branches entirely. (It is apparent at the tree at the left that some branches should have been removed way back when the tree was young ... before these turned into a major part of the trunk system and are not hard to remove without removing a lot of canopy with them.) The grass looks pretty healthy in spite of the shade. It's hard to tell if there is enough hill to warrant complaints by the grass-cutter. If it's tolerable, I'd leave as grass. Later though, since there are more trees on the way, shade could become too much and warrant conversion of those areas to groundcover. I like the house colors and think they are well suited so wouldn't change anything there.