The William Sherman Jennings House is significant at the state level for its association with Governor William Sherman Jennings and his wife May Mann Jennings, two individuals influential with the development of Florida at the turn of the century in the areas of Politics & Government and Conservation. The residence is also significant at the local level as an example of a Queen Anne style residence transformed to the Colonial Revival style in the 1930s in Hernando County. The house has retained much of its architectural integrity and historic landscaping as well. Evidence of the Queen Anne Style on the house includes: a bay area and turret located on the west side of the house; variations in texture, as evidenced by the wooden shingle covering on the gable end, east elevation of the residence; decorative Queen Anne chimney caps; and a Queen Anne inspired mantelpiece in the northeast parlor. Historic Colonial Revival alterations found on the front porch include spindles and railing, the front entrance with fanlight, and the back entrance door. - NRHP, 16 September 1998