Pea,
The project you mentioned would probably require a building permit, but, as Midge suggests, just to even see if it's feasible, contact the Deed Compliance Office. Once they give you some verbal assurance that it could be approved, then proceed with finding a contractor. Many of the local contractors are very tuned in to the Villages Architectural Review process and will file the paperwork for you. But, do make sure the Arch Review is done and approved before you proceed.
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Maryland (DC Suburbs) - first 51 years 
The Villages - next 51 years
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