I would make the front door more prominent. Right now it looks like a dark hole. Are the steps painted? I think they would look better a darker color. I think the shade from the trees and their roots are probably part of why the grass isn't growing well. I would seek advice about how to resolve that. Hopefully someone will jump in here with ideas about the foundation plantings

Its hard to tell if your brick is painted, or naturally a light color. If it is unpainted, powerwash.

Clicking on you link, I see that the front door is a nice blue, but it looks like the storm door is black. You could try just painting the storm door to match the blue to see if that brightens the entry.

Paint the trim a slightly darker color than the house.

Remove the hedge and plant individual shrubs in between the windows. Sorry, I can’t help with specifics there.

Powerwash the sidewalk and add a brick edging if budget allows.

As jck910 said, figure out something with the grass. Maybe you can just overseed with a full shade variety.

Sidewalk idea:

Trim color ideas:

Add a little entry porch.

The tree is spectacular.

What "look" did you have in mind? Cottage-y?

Is the house stone, brick, or wood?

The most unsavory feature of the yard, IMO, is the way the walk slopes down to the bottom of the steps, only so you can climb up them. The stoop would be nicer if it were higher -- to just under the threshold. And then regrade to eliminate 2 or 3 of the bottom steps. (I'm saying this based on the single photo. Advice may differ if it's not actually as it appears in the picture.) A retaining wall would be useful to help level out the yard at the face of the house. A wider walk would be nicer.

There are going to be significant areas of the yard where groundcover would need to be installed instead of turf. There is no point in placing shrubs below windows that are low to the ground Instead, use annuals, perennials or groundcover that does not exceed the window-bottom height.

More options

Appreciate all this feedback as our house has been a work in progress for last 15yrs. Was an ugly orange one-tone brick that we painted when purchased and repainted about 3yrs ago off-white with same color trim. There were sage green shutters on all the windows that were rotted and removed. We couldn’t afford to replace at the time. Should we add them back in updated style? We put a new roof on last year and went with brown tones. I like the idea of a darker trim color and maybe even a dark gutters.

We’ve struggled with the lawn due to heavy shade and drainage issues. Our House sits below street level on the right side. Two years ago we removed one lg oak that was also on the right-side and limbed up all the other tree. We are considering sodding the entire front yard and tearing out the front walkway to the street we don’t really use it-we live on a really busy street. We moved our mailbox to the side street years ago and added a friends entrance w/porch with a walkway from the street.

If we tear out the walkway from street straight to the front door we would replace it with a walkway from the friends entry porch around The house to the front door In front of a landscaped bed along the front foundation.

I would say that I’m looking for an overall cottage-look.

Im a very visual person so your drawings and pics are VERY helpful!

I’m not a huge gardener, but these articles have some ideas to try before going with sod

https://www.charlestoncrafted.com/ive-learned-growing-grass/

https://www.pennington.com/all-products/grass-seed/resources/how-to-grow-grass-in-the-shade

Is that a historic house? Just curious. The part with the 4 windows is very old? The other part is a new addition?

You have no interest in fixing the grade around the house then?

Why would you consider sodding a whole front yard that has heavy shade conditions?

This is great!! Thank you!