You do have alot of shade. Well you can research what would grow best in shade but these come to mind right away: hostas, camellias, hydrangeas, azaleas. I think the long narrow bed is too narrow, not deep enough. The porch is so pretty and the white trim really looks good with the shady setting. What I am going to suggest that you consider is widening that bed and maybe even including some of the trees into the bed. Make it curvy and grab a tree into the bed if it is close enough. I also like what is called island beds. And I have some where you make a big bed around a tree (don't go too deep with soil becoz of the tree roots) or connect two trees into one larger island. The National Wildlife Federation says that wildlife (like birds) like and feel safe in these islands. What about a brick path down the yard, I couldn't see where there was an entry onto the patio but a path would really connect the porch, long bed, and yard. I think you have a lovely setting there, if you're like me your only real problem is money!

Lilyfinch, you remind me of my dad with the veggies. Those are the only 3 he will eat. When my folks had moved my dad really wanted to experiment with a veggie garden. My mom told him if he grew it, he had to eat it. When I visited that summer and saw him eating a salad I almost choked!! He had held up his end of the bargain, but only had a veggie garden for that one year!! LOL!! Your front yard is great. I agree with widening the paths. How wide are the paths now? Could you widen them enough to incorporate the lamp post into the path? You could also have them undulate a little, but still symmetrical if you want it to be a little less formal. I would even consider at the end of the path at the house flaring the path on each side out to incorporate the area in front of your house and porch. How long is the walkway? It looks long enough that you can repeat groups of perennials. There are some great single-blooming peonies that would be pretty (and no staking), especially if planted with some May-Night Salvia and Iberis. That makes a nice little spring combo. Sedums like Autumn Joy or Matrona would give some interest down the path well into fall and even winter if you don't cut them back. Also some grasses might be nice too, like Hakonechloa. I have also fallen in love with Solidago 'Golden Fleece' planted with low purple asters. Mix in a Fairy Rose and it's magical! Have you thought about shrubs at all? If you are able to widen the path and you don't think an arbor will work for you at the end, what about a dwarf alberta spruce at the entry on each side? Also there are some small spirea like Little Princess that work in a narrow border. Hypericum Hidcote may be a nice yellow that has quite a long bloom period. Mine seemed to never want to stop and hasn't gotten to be taller than about 2'. Crimson Pygmy Barberry is a great smaller shrub with a nice color. What a great area you have to play around with. Have fun!!!

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

Step one in my book would be to remove the landscape fabric, unless of course it is just there to kill off the grass. It will be an ongoing annoyance, a soil sourer and weed habitat. Step two would be to remove the shutters since they could not cover the windows, even if they were real. Flower boxes can look great but if you mean a box attached to the wall you’d need to consider how it would be fixed, considering the weight, how it would be prevented from staining the house wall when watering and how much time you can devote to maintenance. They need frequent watering, dead heading and feeding and displays usually need changing seasonally. Flowers in the ground below the windows would be a much less labour intensive option. Repeat plants to avoid a blobby appearance. The hosta looks happy so I’d add four or five more of the same variey. Then fill in with multiples of other plants. People will need to know your location to suggest climate appropriate species.