I also like you land.arch's idea to reduce lawn to just a sweep at the top of the slope closest to the house, and ground covers/shrubs on the slope. To reduce the size of the house from the driveway, it would seem a good idea to add either a grove of smaller trees at both sides of the walk, something in the size range of Crape Myrtles or Dogwoods; or maybe one bigger canopy tree at this corner to anchor the house. If visitors tend to park in your driveway anyway, I don't know that another walk out to the street in additions is really necessary, but it is hard to evaluate that without seeing the site and a better idea of your actual needs.

The wood colored railing stands out too distinctly for my tastes, and might look more in tune with the rest of the house if it were also painted. This is a large yard to have to landscape, I am so much more used to city lots with 50 foot wide street frontage. The amount of different plants we here in California tend to pack into much smaller spaces doesn't really apply in your larger open spaces, or would be an incredibly maintenance intensive excercise, as well as being more expensive.

The entryway, as viewed from the street, would look more welcoming if it were wider overall and more so if expanded to wider at the bottom. The current steps and siderail widths are too small for the house width. You could get away with narrower steps up the side slope, in view of the expense of wide steps there, if they led toward this more welcoming entry area. Although, you might be able to widen or otherwise "welcome-ize" the first step or 2 up from the driveway to make it look more inviting.

I probably would not try to make more steps up the slope through the middle of the front yard

I think you have a great house with good bones already in place. I do think that you need a tree in front--on the driveway side, a little down the slope--it would tend to mask the fourth gable and large expanse of roof, soften the overall look, and protect the upper house from morning sun in the summer, which is good for utility bills. Choose a deciduous tree that has an attractive form when the leaves are off, & since it looks like you've got large trees all around, one that is not so big. Just my 2 cents!

Great advice, all! You've brought some new ideas to the table. I definitely would like some trees in the front, and you've given me some great thoughts on placement, that I hadn't considered before. I've had japanese stewartias on my mind for some time- I'll have to see if those might fit the bill.

Also loving the idea of "welcomizing" the walkway. We'll have to start playing with some ideas to make that happen!

Thanks again, all.

Well maybe I'm not too good at this, but I can just picture a very large conifer on the right side of the house (when facing it), but not real close to the house. However, I do prefer deciduous trees due to liking alot of sun in winter, and not sure if a large conifer "goes" with Massachusetts. So maybe a lovely maple or oak. Not sure if there is already a large tree there, but it seems to balance the very big house, which is beautiful by the way.
I also can sort of picture a sort of half circle "patio" or informal sitting area on the left side of the house, when the steps come up from the driveway. It's a place to sit down, set packages down, or have folks drinking lemonade, some in the sun, and some on the porch, but still able to interact with one another. Boulders and stones could be used, even some large boulders to sit on, or a stone bench. You could use small grasses, herbs, groundcover roses, some things with fragrance? Hope you like some of these ideas.