Why pay it? This is a question I encounter over and over, and there is an honest and simple solution to it. A, B, and C establish a revocable Trust, and each quitclaim their deeds to the trust. They establish and set up the trust for the '______' family in this parcel. They make themselves the trust management with percentage decision authority equal to percent equity in the trust (25/25/50). Then go to the buyer and ask how he would like to lower his closing costs and avoid a lot of redundant fees? He will say 'Yes". Then propose to sell him the management rights to the trust. As the trust maintains the same name and continues ownership of the land parcels, the land does not 'change hands' at the county seat, and thus no doc stamps, taxes, fees, etc. You and your siblings have no capital gains, for the proceeds simply go into a trust you established in advance for the '____' family in perpetuity. As manager of the trust, you each control disbursement of funds. This is a much simplified overview, and your particular situation will need close examination by legal eagles. But there is enough here for you to get the general idea. If you cannot find competent help in this area, I know a few experts who do assist others nationwide. Hope this helps.

The buyer is a millionaire...he doesn't want "management rights," he wants the land. He already owns hundreds of acres surrounding our 20 acres (our land is an "island" in the middle of all of his land). Since this was not an investment property, do we even have to pay capital gains tax in the first place? Thanks for your help, this is an angle I never would have considered but I don't think it's going to work.