How soon is too soon to make low offers?

[Tony Marcelle]

How soon is too soon to make low ball offers on Zillow for sale by owner homes? I contacted a seller from his Zillow ad. The house looks to be in good condition in a decent area judging by all of the photos he took. The house has been on Zillow for like 9 days as of today. He wants $349,900 for it. Zillow Zestimate is $223,253. I wanted to make an offer well below the Zestimate. He did say he has a mortgage on it for a lot less than his asking price, but he would not tell me how much he owe. He said his mortgage balance does not effect how much the house is worth. That is not why I asked him if he has mortgage balance. I need to know that because my offer price will include how much he owes. His attitude was almost like what does the mortgage balance has to do with it type of response. I was considering offering like 50% of the Zestimate just to see what happens.