The cost to Paint Vinyl Siding starts at $. $. per square foot, but can vary significantly with site conditions and options. Get fair costs for your SPECIFIC project requirements. See typical tasks and time to paint vinyl siding, along with per unit costs and material requirements..Until now, there were limitations to painting vinyl. Using a dark color on top of a lighter would cause the substrate to buckle. Your only option was to choose the same color or lighter. No longer. Sherwin Williams VinylSafe paint colors allow you the freedom to choose from color options .Cost of New Vinyl Siding. Replacing aluminum siding with vinyl costs much more than a simple paint job. In late , MSN reported the average cost of a mid range vinyl siding replacement job at $,..Painting vinyl siding can work, Yet, as relatively inexpensive as it is, it can cost a lot more than painting, especially if you plan on doing your own painting..