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Vain says

I just checked the property records and it does confirm it indeed is a very large house, larger than I have seen. Six bedrooms confirmed. But it doesn’t mean they have not added a kitchen after the inspection. I’d need to look at the 3R.

what's a 3r?

The 3R stands for RRR, or Residential Requirement Report which you SHOULD get a copy of when purchasing a home. It basically lists out what the house has that is documented on the property records. I think the 3R has the final say as to what was permitted and what was not.

Vain says

But lets say I bought this property thinking it was all legal, and 3 years after purchase, the city comes to me and wants me to tear it down. Will the seller be held liable?

In this situation... your screwed. The owner is off the hook after the sale, and your reps have finished their (supposedly thorough) due diligence on your behalf prior.

At that point you'll have to either prove the owner actively withheld the info, and/or your reps and lawyer were incompetent and blew it, causing you damages. I'd say good luck with those lawsuits.

If your serious about the house and have these nagging doubts, Perhaps put the concerns into writing and tell the lawyer to investigate them thoroughly prior to sale. Get answers in writing. Maybe even ask the same of the City. They most likely won't give you statements in writing but perhaps you can keep the correspondence in email format that can be saved. Get it from a more senior staff person, not a junior clerk.

But lets say I bought this property thinking it was all legal, and 3 years after purchase, the city comes to me and wants me to tear it down. Will the seller be held liable?

When you ask questions like this, you need to think to yourself, what will be the outcome. Suppose you are able to prove that the seller actually misrepresented the information. What damages do you expect the court to award you? Even if they force the seller to pay for the unpermitted aspects to be fixed, that could be very inconvenient for you. The seller could possibly claim bankruptcy if the costs wind up being significant. You probably will have to spend a lot in attorneys fees which you likely won't get back. You don't ever want to purchase a problem like this - your best case scenario is that the additions become permitted but you are likely going to be inconvenienced and will have to pay an attorney. Plus, if you suspect an issue and don't deal with it, the seller could possibly have a defense against you in court since you basically consented to it by not acting.

I suppose if issues arrive years after sale, that they can some how go back into the MLS listing claiming additions were legal (per seller). Which is exactly what it says on the MLS.

I agree with Mthom. Even if the seller pays to have the unpermitted additions torn down; it doesn't hide the fact that I already paid for the items thinking it was permitted. After demolition, it'd be hard to negotiate a partial refund on the property (in terms of concluding to a dollar amount), even if the seller is willing.