What plant is the tall shrub / tree to the right of the walk? Is it blocking a second window on the front?

Your door is already pretty far back. Having taller plants in front of the door gives the door a feeling like it's back in a cave. I think the bed in front of the walk with the light pole may increase the feeling that the door is back in a cave.

Would be interesting to simulate replacing that bed with grass and using lower plantings with color directly in front of the door.

The bed to the right of the walk needs to be incorporated into the entry plan. You want it to be inviting without blocking your front windows.

How far does your lot extend left of the garage? Would be helpful to see that as well. You will want to make a plan for the whole front at once to get a unified design. You might take several years to execute it but you want the bigger picture in mind if you do it in stages.

I agree with the comments about the entrance tending toward a cave-like appearance, and with the idea of doing something about (limbing up into a tree form if possible) that large plant right of the walk. Everything else should go in the direction of minimizing the entrance being obscured. Something cheery looking ought to entice one to continue on toward the entrance.

No complaints about the boxwoods per se, except that they coordinate with nothing. Shrubs would be better lined up with windows, as window boxes would be. Maybe they could be cut back hard and moved. Maybe you need other plants.

It would be an improvement to cover all the stone mulch with a solid low groundcover, in order to get rid of the scabby, blemished look. At the bed around lamp post, there could be something interesting (not too tall) around the post and the rest could be low groundcover. The stone "wall" looks cheap as the construction is haphazardly done and the "wall" thickness is so thin. It would be better to rebuild this at twice the thickness and half the height.

Not least, and this would also help with countering that the entrance is so far set back, is a recommendation to widen the walk. It could be by adding a sailor course of bricks at one or both sides.

Thank you for your thoughts. The large tree to the right of the walk, right up against the house is some sort of contorted pine. White pine maybe? It is right in front of a window, and could probably stand to be pruned, but I don't think my husband would go for removing it even though it does block the window. For some reason he really likes it. I like it, too, but I think the house could look so much better with it having a hard prune or removed altogether. On the right of that, there are three yews under the other window. They look terrible this year - I was just out pruning and they have lots of brown patches. Yews have never done much for me, so I probably will look at removing those, too, and I agree we need a master plan for doing this over the course of a couple of years vs trying to plan each section individually.

Yes, the front entry is cave like! We are also looking to make some improvements there and are exploring the idea of lightening the paint in that area, along with trim and garage doors so the whole thing looks less dingy. I like the idea of lowering the shrubbery and adding brighter vegetation in an effort to make it less cavey.

The mulch was something added last year, by the previous owner's mulch man. We have not been happy with the performance or looks. We were thinking to remove it and use a cedar mulch, but I do like the idea of a ground cover instead, so we will explore that, too.

I like the idea of just a few taller plants around the light post, but am not opposed to getting rid of that post and eliminating that bed altogether. There is enough lighting on the house at night when we need it, that we don't need the lamp for nighttime lighting.

This is the area to the left of the garage. The weigela need to go, and the flowering tree needs some pruning at the top to remove dead branches. Black-eyed Susans fill in at th base of the flowering tree. The yew to the left of the garage door can be removed. I probably should have mentioned this left side of the garage in my original post but didn't want to seem greedy for your time!!

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Our lot runs to the pine trees. The blacktop driveway you see is for the next house over - it's kind of close, but we have lots of privacy in the back and on the other side. The two tall pine trees in the center of the pic are coming out in June. There was a 3rd one in the forefront until a huge windstorm recently knocked it over. Those trees are in terrible shape and can't be saved. We had a lawn guy here last night who said that the patchy grass up against our driveway is actually golf course grass. It looks bad and very different front the adjoining neighbor's grass so we are going to replace that. Lawn guy said the easiest way to go is "solar radiation." ;)

The pine trees gave us quite a bit of privacy but we are losing that. We can't put up a fence, but I'd love to find something else that would give us at least a little privacy screen on that side.

This is another view of the side of the garage from last August, I think. Love the hydrangea! At the back of the hydrangea is a small, no-so-private-anymore deck tucked in there.

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Now that I see left of garage I don't know as I'd get rid of the lamp post bed, as it seems like it could balance the overall picture. Actually, it's best if you show one FULL side of a house at a time. One may need to see around a corner, but more or less one side is dealt with at a time.

The contorted pine ... I'll bet I would like the plant, too. But that really has nothing at all to do with whether it is used in a particular spot. I need a pet and I like elephants. So should I get one instead of a chihuahua? The trouble with plants in the wrong spot, especially if they're trees, is that at some point it will become PAINFULLY obvious that they're doing harm instead of good, and when this time comes, even getting rid of them can be somewhat painful ($$ or a lot of work.)