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Seal first, repaint second, sealant is like caulking used to cover openings.
Hi Martha. It is best you reference your community's deed restrictions on driveway widths. Any modifications to the exterior of your home or property usually requires ACC/ARC (Architectural Control/Review Committee) and HOA approval prior to those changes. If you live in the jurisdiction of a municipality you may need to get permits and inspections, as well.