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Yes, tree roots can regenerate after they’re pruned or cut. In fact, trimming can stimulate new growth, especially in healthy trees. The tree’s roots can still grow back even after a tree is cut down, (and learning how to get rid of regrowing tree roots is a separate feat). Still, if you don’t wish to harm a tree, pruning the roots should be done with extreme care, and ideally by a professional.

Coverage varies quite a bit by policy, but most homeowners' insurance policies will cover $500 to $1,000 of the cost of removing a tree. Additionally, if your tree causes damage to your property, like your house, many policies will cover some or all of the costs to repair the damage, depending on why the tree fell.

In the case that a tree is growing directly on your property line, the cost of maintaining the tree is shared and is the property of both owners in common. In this case, all decisions regarding the maintenance of the tree must be made jointly, and both parties must agree on a course of action. You will need to agree with your neighbor about the cutting of any roots before you carry it out, and your neighbor must also consult with you before doing any trimming. Coming to an agreement with your neighbor about any shared trees ahead of necessary trimming and maintenance will make this process much simpler.

Although the terms tree trimming and tree pruning are used interchangeably, they are very different types of tree maintenance. Tree trimming involves enhancing the appearance of your tree by removing unruly branches, providing your tree with ample sunlight and nutrients and prevents unsightly overgrowth. 

Tree pruning helps keep your trees disease-free. This process removes unhealthy growths, dead branches, and other unhealthy parts of the tree. It’s more common for deciduous and ornamental trees but not so common for evergreen trees. To determine which method you need, discuss it with a tree trimming specialist.