You could use a "pergola" over the garage doors as well. Difficult challenge, but I wish you well.

I think all of Flo's suggestions would really help. Much can be done with landscaping. The shutters need to go. They're too small on the window to the right and make no sense on a bay window.

Thanks for the great feedback! I was toying with the idea of painting it a darker navy blue and maybe adding and iron or copper accents-thoughts? My mom suggested adding a wrap-around porch but I'm not sure if there is room.

I think the right navy with white trim could be nice.

Deeper blue with white trim would look nice. I considered a porch but there are probably setback local rules and i assumed after just purchasing this home, budget might not support a $10-15k addition to this house. Since this home looks like a “Flip” to me i also assumed the siding was new. I could be wrong and certainly many improvements could be done to this home. What budget are you trying to stay within?

We certainly don't want to over-improve and I think a front porch might be over doing it. We haven't really thought of a budget- we are in a great area and home values keep climbing so putting some money into the curb appeal could greatly up the value. Probably want to keep it under $15K though.

Congrats on your first home! Cute house!

I think part of the problem is that it's unclear where the focal point is. (Is the "front" entrance on the side of the house?) I think proper landscaping (maybe a curved bed/path along the sidewalk up to the door?) and accessories around the front door can help with that. A larger light fixture by the door, and tall planters would help too.

I'd suggest coming up with a plan first, rather than doing a little here and there, so it doesn't come out looking cluttered.

Come Spring; carefully match the siding color and paint the downspouts, paint the front porch white, (if possible) add a roof structure over the front door (white), remove the "shudders", remove all the edging around the planting beds, a white picket fence would be perfect. Get a landscaping plan from a local plant nursery. Your front area is small and would be enhanced by "cottage garden" or "meadow look" which would also eliminate the need to mow a lawn. Both of these types take a few years to become established but, either would add tremendous curb appeal.

I agree the porch would be overkill. I would start with the front yard and get that developing.

A cute garden like this would be great.

Thank you all for the input! The front yard does not get much sunlight. I am also in Chicago so the weather is...well...crappy. The sidewalk that leads to the front entry stairs wraps around to just in front of the corner white picket fences so I am afraid a curved pathway from the driveway to the stairs would look a little silly-would it? I love the idea of adding a structure over the door, I'm just not sure that would yield much of a return since that side of the house isn't seen much- there is a house right next door and most of the traffic/views are of that big blank wall. What about trellises? A Sconce or 2? Do trellises ruin siding? Forgive my ignorance here;)

Do you mind posting photos from farther back, so we can get a better feel for the lot and orientation of the house? Maybe from across the street, or from the street as you're approaching the house?

This might help you get some better suggestions.

Free help available here;

https://web.extension.illinois.edu/cook/hort.html

A shady yard can be dealt with, lots of plant options. If you make the front yard the focal point the big blank wall will be ignored.

I will try and remember to take some additional photos later today- thanks everyone!

bigger windows and no fake shutters

The biggest improvement you could make is taller windows, and that's fairly easy as long as you go down. The header is already in place, so extending down doesn't involve any structural changes to the wall.

North can be a GREAT exposure for plants......and allows fewer weeds, a nice side benefit. Do some research on shade gardens - starting with hostas, of course - and go from there. Start a file with plantings and layouts that look good to you. Agree that the front is out if scale and different windows would help, but if that isn't feasible,, let some garden plantings capture the eye and minimize the facade flaws.

Thanks for all the advice! Here are a few more pictures. Like I mentioned, this is the main view of the house- people rarely approach it from the other direction.

I like the idea of adding a pergola to your home! It would give character and shade! Win win situation! Looking forward to seeing what you have decided on! Good luck!

A pass-through carport? A few images for inspiration (although none of these are pass-through, they can easily be made to!)

Is there some smart way of making the upper windows not look so crowded under the roof. Is that because the main level ceilings are high or is it that the upper windows are just very high. Can they be enlarged vertically or some trickery (not shutters) employed to make them more dominant in the front view.
It’s going to be a great house.

On further looking, an entire, large side of a house w no windows seems a bit....odd. What rooms are on that side of the house?

I like the idea for a car port but don't think it would be possible- its basically a shared driveway and I don't think our neighbors would be happy with it. The upper windows are very small and I don't know why- making them bigger would make it look nicer but I dont think it would have a great enough impact on the curb appeal. Its that big blank side that is indeed odd. On the other side of that wall is the guest bedroom- adding a window there would be great. The addition with the 2 small windows in the back is a dining room- making those windows larger would probably balance out the house. My husband is not sold on painting the exterior but I think it would look great in a deep blue!

Oh yeah, a shared driveway is almost impossible to put anything over - dang! I would resort to punching windows into that wall then... just about all you can do. You have to break up that blank space somehow! Haha

I would love to see a gray blue brick, with black or navy door and nice landscaping.

Windows on the big blank wall would help but you need to take care where they go so you don't loose wall space in the room inside. You could do high windows in a dining room, but that would look odd on that big wall, so I don't think there are any good solutions there. Perhaps a "faux dovecote" in the top area might bring some interest without impinging on your neighbor and would break up the look somewhat.

You don't have a peak but you could design Something that would span the top say 4' and add some trim for detail. It is a tough problem for sure.