Is there a "best" time of year is the best to level a lawn?
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Certainly, spring is an ideal time. By filling in the low spots, seed over and let it grow just as your yard is coming out of winter dormancy.
Spring or fall. See if any of these help.
https://www.gardeningknowhow.com/lawn-care/lgen/fill-uneven-lawn-low-spots-how-to-level-a-lawn.htm
https://www.lovethegarden.com/advice/lawn-care/maintenance/how-level-lawn
https://lawnsavers.com/blog/lumpy-lawn-causes-and-fixes/
Yes. Do it in the middle of summer or fall when the yard is hard. Then you can spread the soil easier and fill the holes and it will stay where you put it. Do it now-before the soil hardens and you will have created ruts and holes to go with the ones you already have.
I have 5 acres and the property got all kinds of uneven areas or pot holes. I’ve always filled my in anytime it’s nice and dry and forecast to stay nice for a few weeks hopefulily! Tip, if you’re wanting grass in those areas? I throw some grass seed on the ground before I toss all the dirt on so the birds can’t get to the grass seed and your grass germinate better under the dirt too!
We rented a sod cutter to remove the grass which we rolled up and placed on the patio so we could haul in the leveling soil. After leveling we watered it down good, then let the top dry out befor laying the sod back down. Then we watered the sod too. We did it in early spring before it got too hot.
Good luck!