If I divide my time equally between my winter and summer residences, can I declare a Homestead on both?

No. A homestead can be declared only on an applicant’s “principal residence”. A person can have more than one residence but the statute only allows the protection on one’s primary dwelling. There is no legislative intent to allow the exemption to apply to a vacation home that is not principal residence. For example, a husband cannot declare a homestead exemption on one residence while his wife declares the exemption on another family residence, unless each can prove that the residence is their principal residence. If a homestead declaration is filed for a vacation home and it is not your principal residence or you do not intend to reside in it as your primary dwelling, no protections shall apply. Also, the subsequent homestead on the vacation home shall terminate a prior homestead on an actual principal residence.