The Warner Guptill Home located at 558 S. Osprey Avenue was built circa 1916 and as such is an "early" Sarasota structure. The structure is notable for its fine Craftsman Style construction, and its association with the early Sarasota pioneer family of Captain Frank Guptill. The integrity of the site contributes to our understanding of early Sarasota subdivisions.

The Anna Cosden Berry House, located at 1910 Datura Street in DeSota Park Subdivision, is a Spanish Eclectic Style bungalow with easily identifiable characteristics and details of that style of architecture. The Spanish Eclectic Style was the most popular style built during Sarasota's boom years whereas, the bungalow was the American democratic ideal of the emerging middle class, providing quality low-cost housing with an excellence of craftsmanship.