I'm not obsessed with matching, per se, but strive instead for compatibility, thinking it generally offers some more interesting possibilities. So I wouldn't necessarily hunt for the same brick as the house. A stronger color might add more zip to the overall picture. But I don't want to give the impression that matching is "evil." Sometimes it works great. Get samples--a few of each color that appeals--and see what they look like in real life. I can state with certainty that a crape myrtle that close to the house ... directly in front of a window--at least partially blocking it--is not how you would best display one of the important architectural features of your house. In my book it's verboten. But it's one of the most popular things people shouldn't do. Can't imagine why someone would have their heart so set on a mistake...? And the "dwarfer" it is, the worse. Avoid foliage in front of the window as if you're trying to hide it. Are you wanting this thinking it will increase its appeal from the inside view? It won't ... anymore than having a 4-year-old show you a picture of something that's 3" from your eyes. You'd get a better view of a small tree if it were some distance from the window. The fussy aspect of the English formal garden that you're trying to re-create does not appeal to me personally, If you did it very well, I guess it would be nice, though, wouldn't it? Doing well mean all the right plants. Short Monkey grass ... what plant is that? Liriope or Ophiopogon? I've never seen Liriope that stays as short over the long haul as what you're implying. While Boxwood can be clipped to keep small, I've always found it to be a troublesome (disease prone) plant and because I'm oriented toward low maintenance, it seems too big to clip that small. But go after your vision (except for the crape in that spot!) and research what plants might work best for you.

First, let me say that I wish everyone who offered a picture of their property would start out with a picture such as you have used. It shows the wide view. It's reasonably sharp and decently lit so details can be seen. While other pictures might be needed as the thread goes on, this is the headline picture that best explains to the person who's never been there what the property is about. So good job on that! With landscaping, things generally look good when first they make functional sense. A quick way to make things look odd is to impose things in the landscape that seem to serve no genuine purpose ... like retaining walls where there is no reason to retain additional earth. If you really want a nice landscape, I think it is setting out on the wrong foot to say you like this or that without first thinking of what the house and property is saying it needs and wants. The front door sits low to the ground. Is there any reason to raise the elevation anywhere in front of the house? To me, it looks like there is not, and that has me believing that anything like a raised garden bed with rock walls in front of the house will seem like a bad idea. It looks like you have a swale at the right side with the grade falling off and an existing retaining wall at a level that makes sense. Retaining the earth against the house allow you to level out the base which is holding up the building and give the house a setting that looks more stable than a slope would provide. But the planting space this retained area creates seems pinched and far from able to provide a luxuriant looking setting. If you want to display and feature something (like the face of your house) then don't use plantings to pinch and smother it. Use vegetation AROUND AND OUTSIDE OF IT to help make sure that the house remains the center of attention. Let those plantings guide (as like a [wide] funnel) one's view to the house. You could rebuild the retained area in a larger configuration, or leave it alone and add plantings outside of it in a larger configuration. You should say where you're located if you want people to also give you actual plant suggestions.

It sounds like you have a love for plants and landscaping in general! I would consider hiring a professional to collaborate your ideas and come up with a design for your property. If you have the time and know-how to construct the whole thing I would do it. Maybe hire a contractor for the stone work and heavy lifting, and do the plantings and bed work yourself! This is quite a large project that needs a lot of consideration including grading, lay-out, style, budget and you!

There are many shades of black and charcoal, I would try some darker grays to find the perfect color for your shutters. The portico color / door color in the photoshop looks khaki, is that close to your mortar color? If so, you might try soft brown shutters with it. Tall narrow trees/ shrubs for vertical lines between the windows is a sort of dated Italianate look that might not be appropriate for your house or location. Homewood is a great area, I love the Tudor style downtown shopping, that is where I had my first lunch at Zoe's. Great schools, too, which makes your home an even better investment. I like the portico your son mocked up! You might also google pictures of a portico style that projects outward (right angle) from the house instead of upward.......like these A pic of same house from farther back: