Add awnings and or shutters to doll up this house. Paint the railing black.

Definitely add a portico over the front door. I like your idea of shutters and one facade material.

You have a problem with the gutter. It has a deep swale, so I imagine it overflows in heavy rains. Get a new one or have it fixed. It looks like the sidewalk also contributes to the water problem. Add a bump along the walk as a barrier, so water flows away from the parking area.

Roughly how old is the house?

135 years old

You cannot go wrong with black shutters and white siding. If you want to add a pop of color you can paint the door something bright. While awnings can be pretty I have found them to be fairly expensive to install and that they need to be replaced more often than shutters. I think a permanent awning similar to the first one Beverly posted could look good on your style house. If the drain you mention is in the driveway on the pad adjacent to the garage door you will likely have to be careful to check that nothing accumulates there or you could very easily have flooding in your garage. We had a house with a driveway that sloped that way with a grate at the and my husband had to periodically clean it to prevent water from reaching the garage in really heavy rains which we eventually outfitted with sump pumps. I think you will be able to find an attractive solution when you remove the balcony. We could never get ours fully waterproofed so if you are not using it I agree you should remove it. Have fun bringing the house back to life.

Thanks for your input, Maureen. To clarify, there is no garage under the balcony, its just the stone foundation. I’ve put a pic below to show what it looks like under the balcony. The drain is a small round one, maybe 8 niches in diameter and is very easily blocked up. I try to keep it clean but it gets blocked up easily and there’s always some level of worry that i will be away on vacation, or it will get clogged without me noticing. In the past when it was clogged, water pooled down there under the balcony and I had a puddle in my basement and then mold. I don’t want to worry about that happening again. I think I’ll put some brick or stone veneer to cover the foundation which will be exposed after removal of the balcony. Plus add some bushes or plants on the sides of where the car gets parked, hopefully that will avoid the bare look I’m worried about.

Few more pics to show dilapidated state of stairs and balcony.

Hard to give advice other than you need to do what’s called exploratory demolition- remove the balcony, brick veneer around the door, and the vinyl siding then reassess. Hopefully you will be able to figure out what the original front window looked like, (probably two windows aligned with the windows above). If you’re lucky the original siding can be restored (vinyl is great at preserving old siding)

Thanks, so you think restoring original window location would be a good idea?

100%

You are on the right tack. Do some demo and see what's there. Check out the gutter. It is adding to your water problems no doubt.

At some point in time, cheap "updated/modern" window were installed. Possibly around the same time as the aluminum siding. Just intalling architecturally appropriate sized windows with muntins will restore the colonial character to the facade. This house below reminds me a lot of yours.

I grew up a couple towns over from Marblehead, MA. The section of Marblehead known as Old Town reminds me of what your house could be. Here's a site with some pictures of houses in that area: https://historicipswich.org/2016/02/03/colonial_marblehead/

Thanks everyone. I’ll seriously consider changing the windows. Instead of having them bunched, maybe two separate ones. maybe Make them taller also.

Sounds as though you have a well thought out plan. I had a driveway that sloped toward the house as well. It cost a bit over $1000 to have a drain run across the end that went out to a bubbler in the yard. It eliminated the issue I had of water getting in the garage.

If you’re replacing windows, you may want to do black frames, which looks nice on white siding. Don’t forget that you can get paid for your recycled aluminum siding.

When standing in directly in front of the house (and not across the street), you can't see the roof and only see the gutter (see the pic for what I mean) I think it looks unsightly which is why I'd like to create a little bit of roof overhang and maybe add a cornice or brackets under the overhang to add a little visual interest instead of just having the house look like a boring square. Any thoughts?

Definitely, remove the balcony, since you don't use it, it's contributing indirectly to your drainage problem, and it has no decorative value.

Yes, stone veneer on the foundation could look really nice. I would recommend a rustic granite in dark gray tones, if available. Or whatever is used locally.

Perhaps you could eke out a square foot or two for planting a vine of some sort, while still allowing parking.

Thanks, qam999, the plan is to somehow incorporate some landscaping. I don't think it can be in front of where the car parks, because that would cause the car too protrude too far into the sidewalk; it would need to be along the sides of where the car parks.

I think you should not add any cornices. When you replace the siding, you should replace the gutter. It is not pitched correctly. At that time you could get a round black one with a white leader. With a new portico and new windows, the house will look fabulous not like a boring box. Good luck.

Here is a white house with black gutters.

Exterior Makeover in Atlanta · More Info

I think adding shutters (properly sized) to the upper windows and a pretty metal awning over the front door will go a long way toward getting rid of the flat look you think the house has.