It’ll cost you between $500 and $1,000 to paint the exterior yourself. Not including paint, it’ll cost you no more than $200 to $300 at a home improvement store like Home Depot, Lowes or Menards. You may end up spending more if you buy high-quality products from specialized shops. Professionals can get the same supplies for about half what you’ll pay.
Like the rest of your home’s exterior, you should start from the top down when painting exterior trim. If your window sills look particularly weather-beaten, you might want to give them a second or third coat of paint. When painting doors, paint the panels first, then the rails and stiles, and finally the edges. For more details, read up on trim painting guidelines.

Each type of siding will need to be treated differently when it comes to primer and paint at different price points. Exterior paint costs between $35–$80 per gallon depending on the quality you choose. It’s not always true that the more you pay for your paint, the longer-lasting your paint job will be, but you do need to be careful when researching exterior paints to make sure it can weather the local elements well.
Whether you decide to do the preparation work yourself or have a professional do it as part of your project, proper preparation makes all the difference in creating a smooth and lasting finish. Do it correctly the first time or you’ll quickly end up spending more to fix peeling and chipping paint. Follow this process before starting on your home's exterior. Keep in mind that the process may vary based on your siding materials:

Dirt and grime are bound to develop on exterior house paint after some time. Luckily, you can easily clean your home with a pressure washer. It’s recommended that you pressure wash your home about five or six years after the initial paint job. For areas like porches and overhangs, you should clean them more often. Taking a garden hose to these areas once a year should do the trick.
Most of a projects price is the cost of labor at $25 to $75 per hour. However, most contractors bid out based on the entire project which includes all work hours. Hourly rates are only useful if your pro asks to do the job as “time and materials.” However, be wary of this pricing structure, it usually shows the contractor is uncertain how long the project will take.
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