Your front door currently disappears. It should be the dominant feature of your facade. Would you consider building an arbor in front of it, extending over the sidewalk, to emphasize the front entrance? Your garage door is the most noticeable element of the front. Consider painting it either the same as the trim, or the same color, but slightly darker. Doesn't thyme die back in the winter? Do you get much winter where you are? Periwinkle/vinca is my current go-go groundcover - it grows thickly and quickly and chokes out most weeds, and is evergreen. In fact, as soon as the snow melts it starts blooming.

Meet with a local landscape designer so you can address the entire plan for your home, both landscape and hardscape. It looks like your driveway could use some repair so you want to take that into account. I don't know MA plantings so I'm no help there, but I do think you could have a more inviting entry without having the asphalt run up to the steps. Maybe the parking pad could be made of different material or relocated or reshaped. This is where a great landscape designer comes in:) I like your home very much! A little softening around the entry and larger beds with a defined walkway would really enhance your entire entrance and curb appeal. https://www.houzz.com/projects/60080/lexington-historic-home

I think that some of the suggestions wouldn't be an improvement and suggest that you think about whether those changes will enhance the home's appearance and period details. The dark stripes of the shutters add interest to the facade from a distance and I don't think I would change them unless you are going to add similar wide dark trim. The glass brick are appropriate to the architecture and were common in that time period, so unless you want that to be a window that you can look out, don't change them. Similarly, the wrought iron porch supports are typical to the time period, so unless they really bother you keep them. On the other hand, I don't like the jalousie windows and consider them to be more common on beach houses and back porches, not on windows to the main house, so I would switch them out. The low wall doesn't bother me since it is so low, but if you don't like it, I don't think removing it would be an issue as long as doing so won't damage the porch or house. I think replacing the door with one more in keeping with the house's architecture would be nice, and painting it something that contrasts with the masonry while still coordinated with the house would look good, so rich deep brown or black, or a shade like the brightest brown in the masonry, or even some shade of orange. The main issue to get an appealing entry is the plantings and walkway, both of which are currently narrow and cramped feeling. So I would move the walkway to a minimum of 5' from the garage so that you have room for a row of small shrubs underplanted with groundcover and a few bright flowers near the drive and where the walk turns toward the house. The walk should be at least 5' wide so visitors don't have to approach single file, and 6' would be better. You have a lot of different masonry surfaces going on already, so I would choose concrete to match the porch surface. I like the simple squared off shape of the walk and how it relates to the building, so I wouldn't change the shape or add curves. The current plantings seem rather random with regard to the architecture, so placement when you add plants will be important. Don't put plants that want to grow tall in front of windows, and center plantings with regard to architectural details instead of the current placement of being half in front of windows and masonry details. You don't say where you are in zone 6, and soil pH, texture, and moisture are different in Cleveland vs. New England vs. Oklahoma, so at this point it is difficult to make specific plant suggestions. You will want some evergreens for the backbone of the garden to provide year round interest. If your soil is acid and has reasonable drainage, look st some of the smaller and more densely growing members of the Heath family such as smaller Pieris or mountain laurel/Kalmia, heath/Erica, Heather/Calluna, or some of the smaller Rhododendrons. The Rhododendrons and Kalmia will tolerate a good amount of shade but the heaths and heathers like full sun. Other evergreens to consider with varying tolerance for shade include: Yew/Taxis which is your current plant, but has other shapes and sizes available and has the advantage of being very shade tolerant Junipers range from groundcovers to large trees and different cultivars have varying foliage colors, but like a good amount of sun Chamaecyparis has quite a range of foliage color and texture as well as plant size, depending on species and cultivar. Doesn't like all day shade, but tolerates a range of pH.

That "both front and back yards flood during rain" is at least a major annoyance if not potentially a big problem. It needs to be addressed and solved before any planting takes place, as solving it likely would necessitate disturbing the ground surface, which would destroy plants. If the city is years behind in maintaining the ditch, it might never happen and you might want to do the basic ditch clean-out as part of your own repair to flooding problems (of course, with whatever approval is needed.) We couldn't tell based on the photographs what needs to happen in order to solve flooding problems. You'd need to get a landscape designer or someone with expertise to look at it locally. In creating greater curb appeal, the first thing that jumps out as needing correction is the dead-end front walk. Its use has apparently been abandoned some time in the past. It either needs to be made useful and attractive ... or it needs to be removed in favor of improving the driveway route to the front door. I suspect that the driveway route seems adequate and that's probably the way I'd go. But it does need improvement. Limiting the walk to only below the overhang makes it too skinny and confined such that it could never seem welcoming. Consider adding on another path outside of the overhang.You could leave a couple of cutouts for planting at the columns. As the drive is not in great shape, you might consider replacing it as part of the process, widening it a couple of feet if possible. A simple, basic landscape organization where the plants were in good condition would help the overall appearance. Given the shade and slope at the ditch, it might work out to have yard of groundcover, as opposed to turf. (The colors are not recommendations.)