Make a retaining wall further away and back fill the area. Get proper folks involved so it’s all done well and do this right

Hire a good landscape contractor to build your retaining wall, perhaps with large rocks, then you could plant in between the rocks for landscape.

It looks like you might have a HOA since your home is attached. If you do, you need to run any changes by them. They may have the property dropping off in the back like that for drainage.

Usable for what? There are a lot of uses where the lawn doesn't have to be anywhere near flat. Particularly at the end closest to the camera in the first picture, it looks like minor regrading would result in a larger, gently sloping space.

thx everyone. i shpuld clarify that i want to expand the grass space and level it out. it slopes quite a bit downhill. there is so much wasted space near the fence as its also sloping downhill

Since your home is attached you need to find out what your options are.

I'm from Pittsburgh. That lawn is fine, since you don't have to be a mountain goat to get up and down.

What do you want more lawn for? To just have more grass to mow? Then plant the grass and mow it. I've mowed much, much worse.

People are allowed to want more lawn. We love our huge flat yard and purposefully bought this lot so we could have it. I would happily mow more lawn and have it for my kids and dog. Why are you commenting only to criticize what they want?

House is not attached and no HOA. single detached home

And more lawn space for kids to play on, trampoline etc

Sorry Jay! Pics are deceiving. Fully understand Wanting more yard space. Hire a good landscape person who knows what can be accomplished. This could be really amazing for you and the kids

I'm not criticizing. I'm trying to help them clarify their wants. In the Landscape Design forum, there is a recurring phenomenon that I refer to as flat earthers. People who seem to think that any lawn that is not table top level is useless, and that they need to spend thousands or tens of thousands on regrading, retaining walls, and other fixes to something that may or may not be broken. Levelling this is not going to be cheap, and it's not the sort of thing that you'll get the money back on resale.

To be honest, there is a lot of paving in this backyard. An awful lot of paving as a percentage of the area. If you really want more space, I'd consider taking out the steps. I'd also do some research into just how level ground trampolines need. You do need some slope for drainage away from the house.

Jay what is beyond the chain link fence?

Golf course

I would focus on figuring out how much flat space you need for grass, how much paved space for entertaining, and how to make sure you accommodate rainfall and drainage. Tier tue test with retaining walls and get better fencing. Add in a privacy screen of plantings that will also help with anchoring the space.

It really isn't all that complicated to figure out how to have a larger flat lawn space. To do that you have to build a retaining wall on the downhill side next to the chainlink fence. That retaining wall will then connect to your upper paver patio and lower walkout basement concrete slab.

Assuming the redone paver patio above stays at the same elevation and from your pictures, the most obvious elevation for your new flat lawn is the basement door level where the wheelbarrow and rake are sitting on that cement slab.

Having the larger level lawn at the lower elevation means you might want steps off the paver patio above down to the lawn and that the stepped walkway against the house becomes unnecessary.

I'll estimate this little project at 50k. At least more level ground is useful for more than a trampoline when the kids are over that.

Check if you need permits in your area for retaining walls. We did when we lived in LA, but they require permits ... and their fees ... for everything.

Is there enough room to get equipment between the houses? Small excavator and bobcat?

Some inspiration for Terrace Garden ideas:

Wow Joshi, thats amazing! How did you do that?

Thanks. I'm using an app for exploring/visualizing new landscaping ideas. www.dreamzar.app

You'll also have to check your easement along the back and what you can/should build there, and if you then have a high retaining wall, then that might need a guardrail, which kinda sucks for kid play in a grassy area. That just takes care of expanding it outward.

As far as leveling it, I agree on all points with what ChrisCNC said, and just reiterate that the lowest level is the one you should be basing the yard on, because you do not want to encroach with the look-out basement windows or the slab height based on steps up from the walk-up basement. A talented landscape designer might be able to either tie all the haphazard spaces (basement walk-up, basement window retaining wall/guardrail/steps, slab, pergola, yard, patio) better together or even offer other directions (e.g. a deck at main floor level instead of a patio).

Lowering the lawn to the basement level will result in a shorter retaining wall and less of a "ditch" at the back. The whole project will still be expensive, however, so you need to budget accordingly. Find a local landscape architect to sketch out alternatives and get an idea of the costs involved.