There are also ruins at the South end of the Great House grounds which predate the House and appear to be some kind of storage facility. Because of the strategic position of Windsor at the north end of the Troy-Windsor trail, it seems likely that these were related to the British military. The trail would have been important in relationship to the Maroons who had two Wars with the British in the 18th century. The son of a previous owner of the House, Mr C.W. "Bill" Donald-Hill states that the ruins were a military hospital.

The ruins appear as a complete building in 1795, and since this was after a valuation in 1792 which values "Buildings and Utensils" at £10,000, it is likely that the present Great House was built between these dates

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