The door color makes it look like an old school house. I would say something bold but traditional. Dark green would look good or an indigo . Even eggplant or a deep wine red. I'd take the ball shaped hedges out of the planter, restack the stones then fill it with flowers of your choice. Ask at the nursery for low maintenance perennials in bright colors , it's better if they bloom at different times so you always have something in bloom. Where the evergreen was to the right of the screen you could do some flowering ground cover. I would sod the rest because a little grass can't hurt. Also the large tree , it's hard to tell what it is, needs pruning.

I have to say the door would be perfect if it was stripped and stained back to its original glory. That's a gorgeous wood door and would be very elegant if restored. I lived in an apartment in Wrigleyville just like that years ago. Best to your son!

I think a black door with a couple of really nice black planters and a stone veneer on the walk way would be nice.Some grass and a nice black bench sitting out on the grass

Thanks everyone,yes we are seeding as we speak,he didn't take the big tree down yet he met with some resistance over that one and wants to see it when it fills in this spring/summer.Patricia,if he put a bench,where do you see it placed and what sized planters.Thanks again everyone.Will take all under advisement.

The bench sounds like a great idea. Black doesn't. It's the wrong color for that era.

North side Chicago? Looks like my childhood home neighborhood

My parents grew up near there. I was born there. Lived there until I was three. Neat buildings in that area.

Something like this and the bench angled under the tree the other color that might be nice is a very dark green

You could really highlight that nice brick with some well placed automated lighting. Trees and landscaping can also be highlighted with lights for maximum impact. Lighting an exterior also helps increase your home's security as the lights discourage criminal activity and lighted walkways and stairs reduce the chances of falls.

A couple things to remember about exterior lighting:

Mimic the Moonlight, it will help you to choose lights that aren't too bright or too dim. You want highlights and shadows without a glaring spotlight effect.

Use uplights, this adds drama and catches the eye as something opposite to our usual perception of light shining downwards.

Automating your lighting will give you maximum security benefit, hands free ease of use, and energy conservation as you won't have to worry about forgetting to turn them off at dawn.

Consider beauty and function simultaneously. Lighting a walk way will reduce falls but it is easy to create a runway strip look. Highlighting different features along a walkway like trees and plants will achieve a more pleasing aesthetic

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Agree with Beverly. Nothing too complicated. Not for that area.

Beverly I hadn't remembered the likelihood of walking benches. Good point. I like the hosta idea too. Simple.

Dream systems,yes,love uplighting.Thanks for the tips.Beverly,hostas will definitely be added,thanks.S Mistry Interiors,yes north side all the buildings are being modernized and just looking for those simple things to do for curb appeal right now while he starts inside.

I am a huge hosta fan and have a large hosta garden myself, but remember, if you go all hostas in Chicago, you will have a yellow dying front yard in the fall and an empty front until May.

Hostas and perhaps pachysandra ground over would work well especially as it looks as if there is a garden apartment that would benefit from light. Prune the existing deciduous tree.
Lovely three flat.....I am a former Chicagoan.

Oops, pachysandra groundcover.

Let me know if interested in purchasing my mom's 3 flat :) We haven't listed but she doesn't even live there.

S Mistry,I will pass this info on to my son.He's the realtor of the family,I'm sure he would want to know where it's at etc.Gnujko and Pat the hosts will be a part of the landscaping but not a major player :).

Hostas

You might also consider replacing the round shrubs with 4-5 clumps of an ornamental grass -- something compact like Little Bluestem. This would provide modest height (24-36") near the foundation, add some year-round interest to the garden, and complement the hosta and pachysandra already suggested.

Yes dahenders,planning to move those shrubs to the side,love ornamental grasses.Thanks