Since the British burnt almost all of Southport's structures in 1779, there is only one home built prior to that date, the Meeker House at 824 Harbor Road, which survives.

A case where a Greek Revival mansion owner placed a large sculpture on the grounds went all the way to the U.S. supreme court in 2007.

[5][6] In 1970, the NRHP nomination for the district argued it was "significant because it has been the center of trade and commerce in Fairfield and because its history is typical of the development of commercial life in many New England ports in the fifty years following the revolutionary war.

The architecture of the district consists primarily of buildings constructed after 1779 when the British virtually destroyed Fairfield.

It is a valuable concentration of Greek Revival and Victorian structures which were for the most part the homes of substantial men whose wealth came from their involvement in commerce, banking, and shipping.