Plan the workforce. If you intend to not hire a professional crew, you'll need lots of help. There are many jobs to be done. First there's the furniture moving, then wall preparation, floor covering, materials gathering and prep, cleaning, and don't forget everyone will have to eat. It can easily take a team of five people a full ten days to paint a two-story (approx 2000 sq.ft.) home. Get as many people to help as you can. If some can only come one or two days, great. Maybe others can fill in. Ensure you plan with your workforce members in mind. They'll need plenty of time to arrange days away from work. Identify a few key personnel:
If you have two weeks, a ladder and some experience, this makes an excellent DIY project. On most surfaces, it is forgiving of mistakes and easy to work with. Correcting mistakes only adds more time and not much more expense. However, a professional will get it done faster and with a better finish. If you don’t have 2 to 3 weeks to spare, find a professional painter near you today.

Painting a brand new house with smooth surfaces dramatically reduces prep work. On the other hand, if you’re painting an old home with peeling walls or siding, it’s going to take a lot longer. When deciding whether to hire house painting professionals or do it yourself, take the current state of the paint into consideration. If you’re not up for the challenge of scraping and sanding for hours, you should hire help to get the best results.
Determine the coverage area for each color and estimate the number of gallons you'll need for each. For odd walls with angled ceilings, make your best guess. If you're not comfortable doing this, measure the wall at its highest height and multiply that by its width. Now subtract the lowest height from the highest height, multiply that number by the width, cut that answer in half, and finally subtract that new number from the original height by width. That should give you the wall area.
Your homeowner’s association might limit you as to how unique you can be with your exterior paint choices. Check with them first to make sure you don’t have to redo your hot-pink-plus-unicorns murals. It can help to drive around your neighborhood to see what your neighbors have chosen and come up with a color scheme that fits in. If you’re not sure, stores can give you small cans of paint so you can paint patches of color in discrete parts of the exterior to see how they look before purchase.

Repainting is key to maintaining exterior house paint. The material that your home is made of affects how often you should repaint. For instance, wood-paneled homes need to be repainted twice as often as those made of stucco. Environmental factors also play a role in how often you should repaint, since harsh climates can be hard on a home. As a general rule of thumb, homeowners should repaint their home every six to ten years.
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.
While you may choose to paint a door, ground-level window trim and other parts of your house’s exterior, it’s really a job best left to the professionals. One of the main reasons is experience. An experienced painter knows how to handle the prep work, spot problems and identify sources of future trouble, all while getting the job done more efficiently. They are also experienced with spending long hours on tall ladders. If you want high-quality work, it’s best to hire a professional painter near you. 
On average, expect to pay $0.60–$1.60 per square foot for exterior painting. The average for painting labor across the country is $30–$40 per hour before you pay for paint, painting supplies, location costs, and equipment. To get a very general estimate, though, painting contractors will take into account the square footage of your home and the number of stories and also factor in normal prep work.
If the exterior of your home is unpainted or has been scraped and sanded, you will want to lay down a coat of primer. Make sure that the primer you’re using is right for the surface you’re painting. While most surfaces can be treated with acrylic primer, some surfaces, like cedar and redwood, require oil-based primers. The oil stops the wood tannins from bleeding through the topcoat.

Supplies and Equipment – Scraping, sanding, and stripping tools and supplies; patching compound; power washer rental; primer; caulk; masking supplies; painters’ tape; ladders and scaffolding; paint pans; brushes, sprayers, and roller brushes all cost money, even if you do it yourself. Consider all of those tools and equipment sitting in your garage for the rest of your life vs. paying an experienced painter to do it all for you at a price that saves you weeks of time. Expect to pay $5–$6 per 100 sq. ft. for supplies and materials.

Wood is probably the most time-consuming when it comes to preparing it for paint. It has to be scraped and sanded until there isn’t a single chip or bit of loose paint in sight. Any wood siding or trim with wood rot will need to be replaced, and all cracks and holes need to be filled with epoxy filler. Brush painting and roll painting wood siding costs $43 per 100 sq. ft., and spray painting costs $34 per 100 sq. ft.
Staining a deck costs $540 to $1,000. Covered porches might hit $2,000. Consider negotiating the price a bit lower by combining it with a full exterior job. Painting handrails can run anywhere from $1 to $2 per linear foot, depending on whether it’s wood, metal or some other material. Although you might think this is an easy $30 to $100 job, most painters charge a minimum fee regardless of the size of the project. You’ll probably end up paying at least $150.
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