One or Two Property Closings required?

[Denise Thomas]

I am the owner of 126.39 acres with two (2) homes that I am privately selling. Ten years ago when I  built the second home, I subdivided out 5.63 acres from the original 126.39 acres to put with this home. Partly to prevent the bank from collateralizing the entire property with the small loan for this cabin and partly as a strategy for "options" should I need them in the future.

The remaining 120.76 acres also holds the other home that my mother resides in and that my father built for this purpose. She holds no deed to the home, and the home is legally mine.  As I plan my future investments, and future tax situation (capital gains) I am uncertain if I must do two closings, or if I most definitely would want to do two closings to capitalize and maximize tax savings and maximize other real estate investments, such as 1031 exchange, etc. This is essentially my "retirement" and will need investments, but will also need to purchase another home. I have owned this property 25 + years and could see a substantial "capital gains" hit. The home my mother is in, according to my CPA, looses any opportunity for tax benefit to me since it is not my residence. My mother cannot benefit, since she does not own the home. The home resale value is 300,000 + ...

Do I marry for the additional "deduction" benefit? :) Since one person is buying the entire property and both homes, do I legally have to do two closings? And countless other questions that to some, are already so obvious...

Thank You!