Having just finished up a long winter in NE, I know that many front yards took a beating in Boston because of snow! So when you landscape, remember that, especially if you are on the street. There will be plows and salt! I think a big budget move would be to take out the chain link fence and replace it with wood.

I agree. Would suggest switching the planter pots shown and put the larger one at the corner of the house planted with a colorful mix (tall, middle and trailing plants). The smaller one, and more like it, can go along a new fence as suggested.

Window planters with bright flowers and hanging vines (ivy for example) will add some height. Since you are in a cold area consider using dwarfed evergreens in the planters. They will add a unique look, remain small, and add color in the winter. Remove that strip of grass in the front. Plant some type of vine (that grows well in your area) and allow it to grow on your stair way. I can't tell how close it is to the street but you may consider making that more of a rock garden so that plants won't be damaged. Or you could add easy to move planters in the midst that you could pull in for the winter. If you are able to, line that fence with planters also. And like others mentioned consider replacing it with wood and you could add some over the rail planters. In your planters make sure to follow the "thriller, filler, spiller" guide when planting. Meaning, thriller for something eye catching (vibrant flower, something on the tall side or a dwarf evergreen); filler is something that remains low but spreads, such as mondo grass (or something similar); and spiller such as a trailing vine, one that flowers is optimal. Just make sure your plants and planters match so it doesn't look trashy. Try picking about 5 plant varieties and using them throughout the landscape. (An example would be two flower types, a white and a color; 1 vine, one that flowers would add more color; a couple different dwarf evergreens (This counts as 1 since it's in the same family), and some type of grass. Hope this helps and good luck!

You might want to put a flowering shrub infront of your brick. It would make the entry feel larger and more inviting.

You could do some planters along the fence to cover that chain link fence. In the front, you can do some small evergreens such as soft holly..some small grasses that do well in your area. I'm in DE, so a bit warmer than in your area, but this year the so called zone 7 was more like zone 5.