It depends on what you are trying to do. If you are talking about two separate transactions with 2 warranty deeds, each paying transfer taxes and no bank involved, possibly. The issue you run into with double-closings is when there is a bank involved there is generally a seasoning issue. Even if your end buyer is going to take out a mortgage, their funding bank may want to see 60 to 90 days of ownership. Also, that bank may require an arm's-lenght transaction meaning the parties can not be related in any way. While you can buy a house for x amount of dollars, if you turn and sell it for more than x amount of dollars the same day it seems to me the end buyer is either a fool or the transaction stinks of possible fraud. Although these types of transactions were popular several years ago, you will be hard pressed to find a title agency that can or will insure it.