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There’s no single paint that’s the most waterproof. Instead, there are several types of waterproof and water-resistant paints that suit different purposes. Epoxy paint, for instance, is commonly used to provide a waterproof coating to floors and decks. Masonry paint is an excellent choice for exterior walls. Meanwhile, there are waterproof acrylic paints that can be used for interior and exterior walls. It’s more about choosing the best type for what you’re painting instead of the most waterproof paint overall.

You should stain both sides of your fence to get the full benefits. Fences often fall along property lines, so you may want to save a buck by leaving your neighbor’s side in the dust. If you do that, all you get is a slightly better view. Moisture and UV rays can still sneak in through the side that’s unpainted or worn down and damage your fence. Rot and rust will spread, even if you can’t see it from your side of the lawn.

Moisture and rot are the largest threat to wooden fences. Stain can help your wood fence last 15 to 20 years, but only if you choose a stain with waterproofing qualities or add a sealant. Oil-based stains create a thicker moisture barrier than water-based stains, though both are mold and mildew resistant. You’ll generally need to re-stain your fence every one to eight years to get full protection.

You can apply stain over peeling stain, but it’s not a good idea. Your old stain will get in the way of your new stain bonding to the wood, so you’re likely going to see the same issue again shortly after application. Your best option is to sand off the old stain and clean the surface thoroughly before applying new stain.