The area near the pool is flat with no obvious high point. It seems a bit higher behind the shed but not much. It accumulates near where I dug (before I dug, that is). It should be relatively easy to grade properly behind the shed.

Not much on our property has been properly maintained. The swales are filled with dead leaves, roots, moss and weeds. It seems like they were wider a long time ago.

My left and right neighbor don't seem to have this problem because their yard is sloped, not stepped like mine.

Oh and I can't wait to get rid of that moss. You have no idea how many mosquitos live in there. I'll have to wear a beekeeper's suit when I rip this off :D :P

It appears that you are collecting water in a "swale" (of sorts) but that the swale is not tilted in a direction so that it can drain. It's more like a tiny, skinny moat.

I does work better as a moat than a drain. Unfortunately it only serves as a mosquito breeding ground.

As a general guide to creating a proper swale, you'll need to consider where its high point (that I asked you about earlier) is. Let's call it the HP. (If it's behind the shed, you'll still need to consider that grade should slope downhill, away from the building, in all directions. To make this happen, you may need to lower the HP. If not, fine.) From the Hp, following the drainage path, you'll need to make sure that the drainage path has width (for carrying capacit) and is continuously descending at least 3" for every 10' of run. This will happen running in both directions ... to the right of the HP and to the left of it. If, hypothetically, you made the path 2' wide, you could visualize this as if it was a 2' wide grass walkway inset and wrapping abound your yard. As this path continuous it will pass your house (on the right and on the left) and eventually meet yard that also slopes in the general drainage direction, or possibly a drainage swale/ditch near the street, or the street itself, where water will be carried farther away from your property without the continuation of a special drainage path (swale.) Concurrent with the drainage path, grade surrounding and running alongside it, will slope toward the path so that water from other parts of your yard run toward the drainage path.

Naturally, you would not want an engineered-looking, flat grass path rigidly surrounding your yard and standing out as oddly different from the surrounding yard. While respecting the grade of the path itself, you would reshape (grade) the soil surrounding and alongside it so that all blends gracefully. In addition, you would route the path such that its location acknowledges features of the yard; it might curve to miss a tree for example, so as not to disturb its roots, creating additional work and expense.

In addition to cleaning out/reshaping the channel to divert storm water runoff to the roadside canal, you should try to absorb as much water as possible on site, with a rain garden. Lots of state of the art designs for you to study, plus Frederick Law Olmsted's ingenious design for Staten island from c 1870! The bright side is to consider that having water - especially on a mountaintop - is a great gift once you harness it.

I assume you are on well and septic. Get all the documentation on both filed with the county health dept or whatever body regulates it, get topo maps, and talk to anyone with knowledge of water in your area -- like your well and septic companies, town planning and building departments, etc. All of this knowledge will help you understand the source and flow of the water.

If you have a septic then do what kitasei says first. Then you need to create a french drain and an area to discharge excess water (for heavy rain periods). The french drain will remove most of the puddling and excess water needs to go somewhere that has good soil for drainage.

Otherwise french drain will resolve your problem.

Good Luck.

Thanks all for the advices. I started digging yesterday. Easier than I though but lots of rocks mostly fist sized and smaller. Once I figured out what worked best it went pretty fast. Shovel, pickaxe and a wheelbarrow was all I needed. I still need to dig deeper though.

It's a feet and a half deep at this point.

This amount of water accumulated within a few hours after I was done. No rainfall that day or the day before.

This is where I stopped for the day. It got too hot and humid.

This little amount of water pooled up in five minutes.

The next day, I officially had a moath around a part of my pool

Soooo a lot of water here, no rain either during the night. I trenched about 1/3rd of what I need. I have an old pool pump to drain the moath before I start digging. I'll start on the other end though before getting there. I didn't expect that much water to be honest.

Nice to see you are following string line so it is not ugly.

You should have local drainage expert examine, diagnose and prescribe.