Simon Couch Sherwood (1845-1906) of Southport was the son of Edwin Sherwood, a wealthy shipping merchant involved in the trade between New York and Savannah. Simon C. Sherwood is described in the Commemorative Biographical Record of Fairfield County, Connecticut (1899):
Aside from his investments, he is living retired, in the enjoyments of a well-regulated life. On October 14, 1868, Mr. Sherwood was married to Miss Matilda Simpson, of Southport, daughter of John Simpson, and two sons—Simon W. and Richard S.—have been born to them. Mr. and Mrs. Sherwood are identified with the Congregational Church, and he is a member of the executive committee of same. In his political preferences he was once a Democrat, but for some years past has been a Republican. He is a trustee of the Southport Savings Bank. Mr. Sherwood’s honorable business methods and his upright life have gained for him prestige in the community where he has so long made his home, while his genial manner enables him to make friends easily, and when once a friendship is won it is always his. He is a member of the Sons of the American Revolution.
Sherwood’s house, built in 1884 at 67 Westway Road in Southport, features an eclectic mix of Victorian-era stylistic elements. After his death in 1906, the house continued as the residence of his widow and his son Simon Wakeman Sherwood until 1916.