Hi zig, great house. I would plant something tall in the corner of the front bed beside the stair. Because it is retaining wall made bed, I'm guessing you can't plant a real tree or the roots would probably destroy the wall. I'd suggest a shrub with arching branches. I think bridal wreath spirea would be lovely. In the spring its long branches are covered in white blooms and after that it is just nice green backdrop. Make sure you buy a variety that will grow tall (at least 7' for that corner I'd think). Another nice shrub for that spot might be a tall variety of hydrangea. I just bought one that is suppose to grow to 6' and has lime coloured leaves. Next to the taller shrub in the corner you could do two other smaller shrubs - maybe a purple leaf sand cherry or european cranberry (red leaves) and a goldmound spirea. In the front of the bed, depending on your level of gardening and how much work you want to do, you could either plant colourful annuals every year or do some low maintenance perenials that will come back every year. A row of yellow stella d'oro daylilies across the front of the bed would look lovely and be almost maintenance free. A few hosta stuck in among the daylilies would add interest. If it was me, I'd probably do 3 or 4 large clumps of plants in the front of the bed - one clump of the stella d'oro's another of hostas, etc. Then you could do a couple of trailing vines in between. Another option for the back of the bed would be to still do the tall spirea in the corner, but then do a row of controlled hedge all the same height along the rest the wall. Two or three alpine current could be trimmed to have a very clean profile. Or two or three hydrangeas for a more flowing free form hedge. Just some ideas. No matter what you do, it's already gorgeous. Enjoy. A series of books I've found really helpful are by Lois Hole. You could look for the one on trees and shrubs and another on perennials.

OP - You didn't indicate your budget but I can imagine it might feel overwhelming to find a house that's almost perfect for you except for curb appeal, and to hear that you should change all the windows and the posts and all that along with the paint or siding. In my opinion, all of that is completely unnecessary unless your aim is to restore the house to its original period style. If your priority is finding a house that meets all of your needs in the right area for the right price and this hits all of those items with the exception of the siding color or brick, then change those elements to your liking. If the siding can be painted (not vinyl) then choose a color and paint the brick a nice complementary contrasting color. What might help is to look around at all the other homes in the neighborhood. Does this one stand out like a sore thumb for not staying strict to the original period, or have they all been modified so this one doesn't look out of place other than your color preferences?

You can also print out house photos and do some doodling on them with sharpie markers to work out ideas. You will want to make a to scale plan view where you actually lay out measured beds with circles that represent the growth of shrubs at 10 years and the ultimate expected canopy of trees at maturity before you start purchasing or get out the shovel. The placement of your sugar maple isn't ideal since it blocks sight lines to your front entry to some extent. I am not at all suggesting removal, but you do want to limb it up to at least the roof line of the house so that only the trunk is in front of the door and not branches as well. Do your best to avoid the root zone of this tree if you reroute the path, both for the longterm well-being of the tree and the path (be sure to make it at least 4' wide) as they are shallow rooted. Don't plan on doing extensive plantings under the maple since the maple will win over most new plantings with its extensive shallow root system. Mulch and a tough groundcover such as the perennial Geranium 'Biokivo' may be the answer there to fill the space. Comments about using color to reduce the impact of the garage doors is spot on and I totally agree with the need for better landscaping. I don't know where your septic is if you have one, but you want to avoid planting woody plants such as shrubs and trees on top of or close to the septic. Having a tree to the side off the front corner on either side of the house can give it a frame that grounds it and also ties it into the woods in the back visually.

The windows on the peak, the stone inside the front porch, the window inside the porch says that was a later add on to me. I agree working with the stone is your best bet since it's inside too. #1DD just purchased a home that yours reminds me of. Lots to do to these post war homes. Have fun!!! If you expand your front steps/decking to the right with maybe even a pergola, perhaps the brick won't be so loud and proud as the back drop to a nice front patio.