Some siding on older homes might need so much repair that it is more cost-effective to replace the siding rather than repair it all and then paint over it. Expect to pay between $1,550 and $3,050 for the removal and disposal of old siding and $4,000 to $14,000 for new siding and installation. Expect to pay more if the wood underneath is wet and rotten and needs structural repair work.
Prep work should include removing all loose paint, either with a pressure washer or by scraping; removing any trace of mildew using bleach and water or a commercial solution, and sealing or covering dark stains; caulking all seams, corners and around windows or trim; applying epoxy filler to repair serious woodwork problems; covering dark stains; sanding all rough surfaces, and priming the bare wood with a bonding primer.

While vinyl siding salespeople claim it never needs to be painted, it does lose its color strength over time, and the degree of fading can vary depending on which sides get the most exposure to sunlight. Perhaps it still hasn’t faded, but you don’t like the color much. You can’t go any darker than its current color, though, because the siding is designed to absorb only so much heat, and a darker color could cause it to buckle. Vinyl paint is available in many colors. Brush painting and roll painting vinyl siding costs $43 per 100 sq. ft., and spray painting costs $34 per 100 sq. ft.
Begin prepping your walls by removing any outlet covers or lighting fixtures (if possible). Next, inspect your walls for any defects. If you encounter cracks, dents, or holes in your walls, simply fill them in with caulk or spackling compound. There are also a number of DIY tips to fill nail holes. Once your repairs dry, smooth them down with sandpaper and wipe the walls down with a damp sponge.
Choose the best quality paint you can afford; it lasts longer. Experts estimate that the outside of a house should be painted every 5-7 years, but less-expensive paint may start peeling or fading in 4 years or less while really high-quality paint will hold up a bit longer. Better Homes & Gardens[1] describes and compares the different types of exterior paint while FastFacts.com[2] reviews specific brands.
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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