Central Virginia's oaks and maples drop from mid-October into December, and a lawn left under a leaf blanket all winter comes out of it thin, matted, and prone to disease. Fall cleanup is not about tidiness. It is about what the yard looks like in April.
Leaves first. Clear them off the lawn, out of the beds, and off patios and drives. A thin scatter can be mulched into the lawn with a mower, but a full layer has to come off. If you have heavy tree cover, plan on two or three passes through the season rather than one marathon in December.
Cut back what is done. Spent perennials, ornamental grasses, and annuals come out or get cut to a few inches. Leave seed heads on coneflowers and black-eyed Susans if you like feeding the birds. Do not prune spring-blooming shrubs like azaleas now, or you will cut off next year's flowers.
Clean the gutters once most leaves are down. Clogged gutters send water over the edge to the foundation all winter, and that is how a lot of spring drainage calls start.
Finish with a final mow at normal height, re-cut the bed edges, and apply a fall fertilizer if you have not already. Then the yard is genuinely ready for winter, and the first warm week of March is a pleasure instead of a project.