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. 
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.
Prime. Dark colors, stains (once sealed), and previously unpainted surfaces (drywall, spackle, etc.) will need a primer coat, usually white. NOTE: most paint stores & home improvement centers will now tint primer (at no charge) to match fairly close to the color of the finished coat, that way two coats of primer need not be applied.[6] Although not all surfaces need a prime coat, skip this step at your peril! Dark colors will likely show through the first -- or even the first couple-- topcoats of paint. Sealants and unpainted surfaces like spackle patches will absorb or repel moisture in a topcoat at a different level than the areas surrounding them. Applying a good primer coat will help even out these differences. Primer equalizes a wall to a uniform surface. It's like erasing a canvas before drawing a new picture. Although some will argue the point, you generally don't need to spend a great deal on primer or buy special primer. A cheap, 5 gallon (18.9 L) bucket of plain, flat white paint will usually do the trick and cover a large area. Give your primer at least 24 hours to dry (follow its instructions) before applying a topcoat.
Although interior house paints can be purchased in pint-size samples or five-gallon buckets, the standard measurement is by the gallon can. A gallon can of basic water-based paint can be found on store shelves for less than $25, but the additional cost of a primer coat should be considered. One-coat paint/primer blends for most DIY projects should cost between $30 and $60 a gallon, including customized tinting. VOC levels should be lower as well. For high-end painting projects featuring designer colors or full-gloss finishes, expect to pay $60 or more per gallon.

06/14/17: Renato completed an exterior painting project for our relatively large single family home in Stamford, CT last weekend. Project did not begin well especially with the prep, repair/carpentry work, but then Renato took full control and ensured that the work done was to our satisfaction. The final result is outstanding. Minor damage to window screens, gutters and plants. Ensure that your window screens, gutters, and shutters are numbered and stored indoors or if kept outdoor covered properly against the elements. The project can be extensively delayed due to rain and you may find yourself dealing with insects and/or flooding in basement and dirty/bent/ mismatched screens/gutters/shutters. Overall we had a good team working on our project and we are satisfied with the finished product. The house looks great!
Expect to pay between $600 to $3,500 or $1.25 to $3 per square foot to coat vinyl, with prices likely increasing for the finish. It is one of the more inexpensive siding materials to have repainted, especially with recent innovations in materials. Changing the finish on your siding is not recommended unless it's completely degraded and worn away by the weather. You can save nearly half the vinyl siding installation cost of $4 per square foot by painting rather than replacing. Before adding a new coat to vinyl siding,
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