I'd begin by removing hedges next to the house. Remove the mis managed topiary. They have been poorly sheared and some lean. The thin trunk trees near the foundation need to be removed. Major trees need limbed up and maybe thinned. This is the most important step, in my opinion. I am not a pro. I'd remove the shrub near the mail box. I would also transplant the grass like plants near the street. Not sure where you can use them. The bed along the foundation does not seem deep enough for shrubs. Can you tell us how deep it is? Your house has nice brick and interesting low windows. I don't think it will need an elaborate landscape. How would you feel about something less complicated? A courtyard would have to be part of your overall new landscape design.

I wonder how many won't enter because of the US flag. People are nuts over such things today, and they would probably never say that it was an issue for them, but it might be. Work with the color of the drive and the cobblestones out front. Stain the brick charcoal, paint the shingles lighter gray and then pick up white for the trim and windows. Landscaping is a big issue for me, especially around the pool. Remove the tired pool furniture, umbrella and awnings. Buy some replacements now while the end of season sales are on. Hydrangeas are a typical Nantucket bloom but it is too late for them this year. You can put some out for spring though. Hopefully, you won't be there to see them bloom.

Comparing the two main entrances (not including the middle one, as it is barely visible) the first (left) is enclosed and appears more private. The second (right) is open, visible and appears more public, since there is a paved, protected area (roofed) where people could collect. Getting guests to use the first entrance will require making it more attractive with landscaping & better walk. Even then, as the building appears more private, it might require a simple, tasteful sign that says "Guests," with an arrow pointing to where. For landscaping of that building, I'd start a new thread and take the pictures square on to the building, showing the wide view from not too far away.

House looks great as does deck rail and stair rail. Choice of plants so far ... meh ... because of lack of symmetry/uniformity visual ), hopefully, as they mature/bloom they'll look really good, too. I like redwood but I'm surprised you opted for redwood instead of stone or brick or a stucco wall with the same look as the exterior siding of your home. Surprised you have the bottom terrace extending beyond the steps and garage especially since that could block the view of traffic coming from that direction even with a clear are above the sidewalk itself. Do be careful as you exit the garage. Getting a mower onto the terraces will be a bit awkward so keep that in mind as you choose plants. I'm guessing your first decision needs to be do you want height for privacy or to just keep the plants not much higher than the redwood? Not sure large tree roots would do well in your terraces in the long term. Do you want low maintenance shrubs or flowering beds or some combination? Getting to the lower terrace and upper terrace with a hoe could be done from the sidewalk and from above without walking on the terrace as much so if you're going to put flower beds, that might be the better terraces for that. If this were Zone 7, I'd probably choose aucuba bushes or gardenia bushes or Camellia bushes -- something that keeps their leaves and looks good year round. If you have a special fondness for roses, the newer varieties (knock knock roses) that seem to keep their blooms all summer might well be worth considering. What a spectacular garden three rows blooming at the same time could be.