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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.

Sometimes you can get away with simply sanding and painting over small areas of peeling paint. However, the problem will likely return quickly, and the ridge between old and new paint will be visible. If you just need a quick fix and won't worry about appearance, chip away the peeling paint as much as possible, prime and paint the area, and skip the spackle step.

Removing paint from brick can have both aesthetic and practical value. Some people prefer the timeless look of bare brick, making it worthwhile to remove old paint layers. Brick also lasts longer when unpainted, as paint traps moisture, causing the brick to deteriorate more quickly. If your brick walls are already in bad shape, stripping the paint off might do more harm than good.

Think hard before deciding to German schmear your home’s exterior brickwork. If you do not like the look, you are pretty much stuck with it, as it is impossible to remove this finish the way you can remove paint. You risk damaging the underlying brick if you have to chisel and acid-wash it away. It will also take a very long time, and remnants of the mortar wash will always remain.