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It is likely you'll do it as two purchases, contingent upon each other. Do your best to keep the sales prices as low as possible, mainly for property tax implications. (your neighbors will hate the low sales price, but you have to take care of yourself first).
The mortgage will almost for sure need to be paid off, and you will need new mortgages. The only thing that is possible is if one or both houses have assumable mortgages. The person assuming the new mortgage would need to go through the approval process, and once approved, can assume the mortgage. The loan would remain exactly how it was previous, just under a new persons name. This could be a huge benefit as they both likely have better rates than are attainable at this point in time.
I think the best thing to do would be to discuss this with a reputable title company, as well as possibly enlist the services of a real estate attorney, or real estate agent. I think the attorney would be the best choice personally.
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