"...the downspout is connected to a drainpipe that the previous owner tells me used to daylight in the backyard. It's covered over now and I can't see where it would have been, but it does still drain well when it rains."

Please try to explain this paragraph again. I'm not following.

If it still drains, then where is the water coming from? Have you observed how it actually comes during the rain? I'm 2nd guessing, but this has a look of clogged underground pipes that will accept the first few minutes of rainwater, but then will start backing up as soon as the pipe is full. It would be important to study this DURING the rain.

You're probably looking at a 2-pronged approach. When I work with homeowners such as yourself, I tell them that I'll handle the grading and any drainage away from the house, and I'll work with whomever they settle on for a waterproofing company. That way everyone's scope of work is what they're comfortable with.

Northern VA or elsewhere?

Thanks marcinde, that makes sense. I'm in Richmond.

Yardvaark, good question. What I mean is, when it's raining, I can hear the water flowing down into the pipe, and I haven't noticed it backing up. Yet I don't know where the daylight end is...I've looked and don't see anything obvious. I would guess it's a perforated pipe so it's also draining along the way.

During the next rain I'll check it out. We should get some within the next week.

I called some basement waterproofing contractors to set up estimates, and at least one of them said they don't do exterior waterproofing. I also called some general contractors to see if they do it. Haven't heard back from everyone yet but hoping to get some things set up soon.

"I would guess it's a perforated pipe so it's also draining along the way." And I would guess that it's also being infiltrated by roots here and there. Maybe a lot. It is important to find the point of outfall in order to check that the pipe is functioning. Usually, you can dig down a little and see what direction it goes. Dig a ways down the line and check it again. Usually, it's traceable without too much effort.

You need to check it for several minutes during a hard rain in order to know that it is still accepting water. (A slow rain probably won't tell the story.)

The rain we had yesterday wasn't hard enough to cause a problem, only an inch or two. What I will do is put a hose down the pipe and see whether it backs up, and see if I can find a soggy spot where the pipe used to daylight.

Today I met with two contractors. One proposed a trench and sump pump in the crawl space, but I'd rather not encourage all the water in the yard to flow through my foundation. The other proposed regrading along the entire front of the house and removing the slate and concrete path. I think the regrading is a better option and I hope I can afford it.

I have seen on here that the recommended action is to hire a professional to create a plan, then get contractors to bid on that specific plan. What kind of professional creates that plan, and how do I find one in the Richmond area?

Thanks for the feedback so far.

"What I will do is put a hose down the pipe" The trouble is that a hose is a "drop in the bucket" compared to a healthy rain. It would be better to observe during a big rain. Don't worry ... one will come.

Right about that on how to approach design and resolution. But find out as much as you can about the problem before you hire the professional, to better keep them on track. A landscape architect would be the place to start. If one who you call won't do it, ask for a recommendation of who might and call them. You could also call landscape contractors and ask them if they know who might DESIGN this for you.

I found two local landscape architects and emailed them. So far one has responded. The initial site visit will be $125 which seems like a fair rate for a technical professional.

Can you get me in the ballpark of how much the design and project might cost? If it's a $20k project I will not be able to proceed anytime soon, so I'd rather tell the architect now before wasting his time and my $125.

There is a bit of efflorescence on my crawl space walls, but the grading done by the previous owner has improved the drainage in general, so I may have to live with an intermediate solution and only deal with the carport flooding for the present.

There are far too many variables, including your locale (which I know nothing about.) Have a conversation with the pro before he comes out and see if you can elicit a ball park range of cost.