Well that’s strange. Your front door faces the neighbor’s driveway? I wonder how it got to be like that?

I’d tear out that tiny old sidewalk first thing. And build a new sidewalk coming off your driveway, swooping to your front door.

I agree that it's very strange. I think it's a symptom of the order in which the houses were built. I'm not sure about the house to the East (left) of our house, but the house on the West (right) was built in the 1800s while our house was built on an unused plot of land in the mid 1960s.

I also agree that we should probably run the sidewalk from the driveway to the front door to make it easier to tell where to go. From a driveway view, this house doesn't appear to have an entrance, which is a problem.

Thanks for the advice!

Maybe widen the path to the door, with a spur path to your driveway and outline the path and yard with a low boxwood hedge.

Add an arbor over path near the sidewalk to define the main entrance pathway.

I like the idea, Dig Dug Designs! We're considering staining the brick at some point to have something other than the ugly Chicago yellow brick, so I can get behind the recoloring you did.

I like the idea of the tapering fence on the property line to help separate our front door from the neighbors house/ driveway. That's definitely something to consider when we get around to putting in the vinyl fencing in the back yard next spring.

Post a picture facing the entrance.

I'm most curious about the street address number, on which street does it fall into the numbering sequence, the garage street or the "front" door street?

It looks like there are numbers placed diagonally near the house corner on the garage side. Might be best to put a plaque including the street name on the non-address side and a set of numbers on the official address number side.

I have seen corner-lot houses with the house number on a corner element, but facing the wrong street, causing a confusing break in the numbering sequence.

You could also do a pergola covered walkway to the side entry.

Even if you don't necessarily mind where the front door is located, I would like to ask if either/both of your neighbor's houses on each side have their front doors facing the street? If so, I would plan for the long term to eventually locate a front door to the front of the house. So any short term fixes could be not permanent or expensive in directing traffic to the side of the house.

I think that solving the main problems is going to boil down to two things: the walk; and the making the entrance visible. The walk should definitely be wider - 5' could be a goal, maybe wider near the stoop - and then it should make a better connection with the drive. I don't think this means to necessarily cut across the lawn with it. Given that the yard is small, you could widen the drive a bit with whatever the walk material is, continue on by widening the city sidewalk with the same material, and then turn the corner with the walk, heading to the entrance ... in effect bordering the yard with a "U"-shape "invitation" that extends from the drive to the entrance. (The portions adjacent drive and city walk would not be the same width as the main walk to the entrance. They would be like decorative borders.) When it comes to the portion of walk that heads toward the entrance, I think it would be beneficial to pull it away from the neighbor's drive and incorporate and "S"-curve into it. That way, room for a SMALL tree could be created between the walk and neighbor's drive. It would also have the benefit of making it look like it belongs to your property without any question.

Note how entrances are typically clearly marked by some type of enlarged, often raised, paved area, and a roofed covering that offers shelter from the elements. I think you need to create such a structure over the walk, in the front yard, near to the house. It would be the obvious first "entrance" that people reach when approaching the house. But after they've reached it there would be no question about where they would continue to in order to reach the actual house entrance. The structure could be a very nice arbor, or it could be more architectural in nature (such as with brick columns and an actual roof.) BTW, I don't think there's the first thing wrong with your yellow brick. Maybe you're bored of it and that is the driving force behind staining it. But I think it would be a mistake, or highly inefficient at the least, to attempt to change it to another color. If the brick was flat out ugly I'd be all for it. But it's not. You might end up creating, after spending a lot of money and effort, something that is not near as nice.

If you could replace the top panel of the garage door with one that has windows all the way across, that would resolve the boring quality of the existing door.

There seem to be two main approaches to planting: smother the house with hedges; and smother the house with a variety of all kinds of plants strewn in a randomish fashion. You might consider "matching" shrubs to windows (like steps would be "matched" to a door) as the main shrubs of the landscape scheme. Perennials and annuals can be fit around them in some artistic scheme, keeping it simple preferably. I would plan on keeping shrubs below the window sill height.

I would hunt for a spot for another small tree at the right side of the house. (We can't see that area.)

Super curious to know what you came up with!!

Me too!

To those of you wondering why the front door is on the side of the house, this is quite common in the Chicago area. I assume it’s because lots tend to be narrow and deep.