It has been my experience that judges do not side with sellers or buyers - they will listen to the facts, assess credibility (when there is no jury) and render a judgment based upon the facts of the given case.
As a general rule, a seller has a duty to disclose latent defective conditions that they have actual knowledge of - and which a reasonable visual observation by the buyer would not reveal.
It appears that you may have a colorable claim. The issue will likely be whether the Seller had a duty to disclose past plumbing repairs and whether they had reason to suspect that tree roots would break your pipes after the closing.
I am not a MD attorney, laws vary from state to state, therefore you should always consult a local attorney.
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If you are asking how a judge will decide, that is a difficult thing to ask. You seem to have a claim worth pursuing if the costs to you are not too high. You might get a judgment in your favor. Try small claims court. If you can prove to the judge's satisfaction that the previous owner knew about the problem, and did not reveal it to you, then you might win some money. How much money did you spend to correct the problem, or how much will it take to correct the problem? This will likely be the measure of the damages. This is general information and not legal advice. Consult with an attorney, reveal all relevant facts and you can obtain the legal advice you need.
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If there is a known defect that cannot be detected by visual inspection, it is called a latent defect -- which a seller has an obligation to disclose under Maryland law. Failure to disclose a latent defect could constitute fraud. Consult a local attorney for more guidance.
DISCLAIMER: Brandy A. Peeples is licensed to practice law in the State of Maryland. This answer is being provided for informational purposes only and the laws of your jurisdiction may differ. This answer based on general legal principles and is not intended for the purpose of providing specific legal advice or opinions. Under no circumstances does this answer constitute the establishment of an attorney-client relationship. For legal advice relating to your specific situation, I strongly urge you to consult with an attorney in your area. NO COMMUNICATIONS WITH ME ARE TO BE CONSTRUED AS ARISING FROM AN ATTORNEY-CLIENT RELATIONSHIP AND NO ATTORNEY-CLIENT RELATIONSHIP WILL BE ESTABLISHED WITH ME UNLESS I HAVE EXPRESSLY AGREED TO UNDERTAKE YOUR REPRESENTATION, WHICH INCLUDES THE EXECUTION OF A WRITTEN AGREEMENT OF RETAINER.
The agreement signed by the parties would need to be reviewed, but generally if the Seller knew of defects and did not disclose, then the Seller could be liable. This particular issue is tough, because you said that at the time of settlement the plumbing was in working order. Before you think about a lawsuit, find out if the agreement you signed has a mediation clause that requires you to go to mediation before filing suit. If so, you should try to mediate because a lawsuit can be expensive and there are no guarantees on who will win.