Having your gutters cleaned on a routine is a great way of preventing future problems with your home down the road. It is generally advised to have your gutters cleaned at least twice a year and more if you are in an area with trees surrounded by your property. If you live in an area surrounded by trees you should have them cleaned three to four times a year. Many people wonder when is the best time to have a gutter cleaning company clean their gutters and the best times to have a gutter cleaning service are before winter and in the spring or summer. If you miss cleaning them before it gets cold, all of the water, leaves, and debris in your gutters will freeze and become trapped in there.