Keep the stone and replace the vertical siding with horizontal Hardi-board, painted a lighter color. I'd also get rid of the planter boxes.

I like the stone. The two windows on the left seem undersized and the shutters really aren't doing anything to help that. Does the interior layout allow for the option of enlarging the windows? I'd also think about using a different treatment for the gable area, even if it's just a change in the orientation of the siding.

I'm not a gardening expert, but maybe different plantings will also update the look.

Cawaps, we just had the windows replaced. I wish I had posted before we did because I see what you mean about the size. Do you think different colored shutters could visually expand the appearance of the windows? If we do a lighter color on the siding and maybe a shade or two darker on the shutters? Just a thought.

It's a nice house and I think the siding suggestions will look great - I'd keep the stone. One thing I'd do (sorry if others mentioned this) is darken the handrails. They seem to be the prominent feature on the house - maybe match to the shutters.

I'd probably put the most effort into improving the landscaping. One thing I would do is widen the walkway, either replacing (if budget allows) or trying to make it look wider and more welcoming. I'd probably do some plantings along the walkway (far enough back so they don't grow over it and make it even more narrow). I thought this was a creative way to make it appear wider and would look for stones that coordinate with those on the house:

Since I'm a gardener, I'd probably choose plants (either in addition to or instead of the rocks)

Or even this idea to fill in the area between the walk and the house with landscaping -it will keep the walkway from looking kind of lost in the lawn:

Can you take a less misty photo? I can't tell what is under the siding. (I like the stone too!)

Shutters aren't common in my area, so I'm going to let someone else field the question on shutter color/style. But different landscaping could also minimize the effect of window size, say with a taller shrub or small tree on the left to draw the eye.

I am not a designer but Iooking at the house the stairs bother me. Too tall and not in proportion with the house. Could you alter so that upon exiting house one would step out onto porch then instead of stairs going straight down have one or two steps left then the stairs begin again to go down. This will move the stairs to the right when facing the house and they won't appear to be such a formidable climb. A good designer could help you choose a nice width too, not as narrow as you have now. Of course your walkway will no longer line up with stairs so that will become another project, although most of it could still be used . Adding width with another material is a good suggestion as well

I agree with prior recommendations to change the siding to horizontal at least on the lower part and lose the window boxes as they are not adding to the house. If the staircase is changed an opportunity opens for a good sized box to be incorporated at the top landing in front of the entrance door

I agree with Kathleen....the steps, railing and walkway are what I would work on if $ permits. I would find a way to widen the steps...maybe rounded with curvy railings. And widen the walkway with plantings if you can't afford to redo. More landscaping in general with some color as well as paint the front door a brighter complimentary color.

Today is a sunnier day so I am posting a new picture of the house. I really like your ideas and improving landscaping and replacing the steps and rails are both doable options.

Interestingly, the step height is 6 1/2" and I'm wondering if that is in compliance with current building codes. I would love to decrease the number of steps if at all possible. Since the brick is so old, should I just do the best I can to match It for the steps?

It's a pretty house.

Unless the siding is in bad shape, I wouldn't replace it.

I'd paint the step railing a darker color. If the siding really needs painting, I'd pick a lighter color from the brick.

i like the flower boxes but would it be weird to extend them further, i.e. widen them?

My husband just built those window boxes a couple of months ago and he would not be happy with a redo. I stand a better chance of getting him to remove them completely with the plan of using them on the back side of the house.

Your house is cute. As suggested above, I would invest in new hardscape. More graceful stairs, large landing at the bottom and wider sidewalk. If you could get the proportions right, a pergola over your door would match your window boxes.

We had a tall, steep house that always seemed plopped down in our yard. Over the years we spent thousands on landscaping trying to make the house and yard look cohesive. What we really should have done is widened the skinny sidewalk. In the long run it would have saved us a ton of $.

You might be able to salvage some of your bricks for other parts of the yard but I doubt you will be able to rebuild your steps with them.

Here are some nice before/after pics with updated porches and hardscape

These pics are beautiful! Do I need to get an architect to do a design plan to change the entryway?

If you are going to make structural changes to the roof line and the porch, using an architect would be the safe route. There are great general contractors that can draft and also have good design sense but you'll really have to do your homework to find the right one.