John Hoyt Perry House // c.1875

John Hoyt Perry was born in Southport in 1848, and graduated at Yale in 1870. He received his professional education at Columbia Law School and was admitted to the bar in Bridgeport, CT in 1872. He had an active law career in Connecticut, later working as a judge. He served Southport in the House of Representatives throughout much of the end of the 19th century. In 1913 he was elected to the Connecticut Senate and served as the minority leader. He served as counsel for the United States in arbitration proceedings with Chile in 1902, and as counsel for the town of Fairfield. This home in Southport was constructed for him, likely around 1875 after he accepted his position as a head attorney at a major firm nearby. The home can be classified as a blending of Stick style and Queen Anne Victorian design with the asymmetrical form, tower, large porch with projecting porte-cochere, shingle siding, and bargeboards.

Wakeman Memorial Building // 1913

The Wakeman Memorial Building in Fairfield, CT, is one of a few buildings erected in the Southport area during the early twentieth century. The boldly proportioned central portico is supported by square Tuscan columns with an Ionic fretwork entablature and denticulated cornice, and topped by a spindled parapet and an elliptical shaped Palladian window on the second story. The red tiled gambrel roof, splaying beyond the exterior walls, is bracketed by decorative modillions. The building was constructed in 1913 through funds by Miss Frances Wakeman in memory of her grandfather, Jesup Wakeman, at a cost of fifty thousand dollars. The building was used by the Boys and Girls Club of Southport as a club house, offering sewing classes, a reading room, and offices. The building was converted to a home after the Boys and Girls Club moved to a larger facility.

William Bulkley House // 1767

The William Bulkley house was built circa 1767 and is one of the few extant pre-Revolution houses in Southport. In 1779, during the Revolutionary War, Fairfield and vicinity were burned and ravaged by Tory Loyalists. Only eleven houses throughout the region survived the burning; one of four in Southport was the Bulkley residence.