5. Kona estate
16 bedrooms • 17 full and 3 half bathrooms • 15,614-square-foot interior
The owner of this lavish Kona estate is, to our knowledge, the only one to have owned two of the houses on this list (even if it wasn’t simultaneously). John W. Hoffee II is the retired founder of Temecula, California-based Professional Hospital Supply. He started the company in 1981 and it’s today headed up by his daughter, Jenise Luttgens. He sold his mansion on the Bluffs of Mauna Kea (No. 13) in order to move a few miles down the coast to one of Kukio’s newer developments.