Yes if the old paint is not peeling you can apply primer over old paint after a little sanding.
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Most stain is applied with a brush, a roller, or spraying. The manufacturer's instructions will advise the best method to suit your chosen stain.
Your wood must be clean and dry. That means all dirt and residual paint should be removed by washing and scraping. If you want a smoother surface, you can sand the wood, which helps remove dirt and...