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Yes, you can paint over old exterior paint, but success depends on the condition of the existing paint and proper surface preparation. If the previous coating is in good shape (not cracked, peeling, or flaky), you can paint over it with less prep work. However, for the most durable and professional-looking results, follow these key preparation steps:

• Clean the Surface: Thoroughly clean the exterior to remove all dirt, grime, and mildew. A pressure washer can be very effective for this.

• Scrape and Sand: If the old paint is peeling, cracked, or flaky, you must scrape off all loose paint. After scraping, sand the surface to create a smooth, even base for the new paint. Sanding is especially important for wood siding.

• Apply Primer: Using a quality exterior primer is highly recommended. It ensures the new paint adheres properly, improves durability, and provides a uniform finish. If you are painting a lighter color over a dark one, a tinted primer will help cover the old color more effectively.

Some brands offer paint-and-primer-in-one products for convenience. Taking the time to prepare the surface properly will not only increase your home's curb appeal but also help protect your siding and extend its life.

You can apply waterproofing over paint, but you won't get as much protection as you would if you painted the surface with a waterproof paint from the get-go. Not all waterproofing methods are compatible with painted surfaces, and they may not adhere well. This is especially true if the paint is glossy, old, or flaking. Waterproofing sealers are primarily meant to be applied to porous surfaces, like concrete, wood, or brick. 

You can sell a house with lead paint, but there are several requirements. If you are aware that lead paint exists anywhere in the home, you must disclose that to potential buyers. Required home inspections will often uncover lead paint, especially for older houses where lead paint may still be a problem. If you have taken steps to encapsulate lead, you should provide buyers with full documentation of the project so it won’t cause any problems later on.

You don’t necessarily have to remove all the old paint before repainting your deck, but it’s best to remove as much as possible to ensure a smooth and long-lasting finish. Prioritize scraping off loose, peeling, or flaking paint, and sand down rough areas to create a smooth surface for the new paint to bond with.