The building at 227 Main Street in the village of Southport in Fairfield was built in 1833 as a bank. It was originally a branch of the Connecticut Bank of Bridgeport, chartered in 1832. The branch later became the Southport Bank, independently chartered in 1851 (it became the Southport National Bank in 1865). After an embezzlement (Oliver T. Sherwood, the bank’s Cashier, was charged with defaulting on bank notes after he fled town; he was later imprisoned) the Southport National Bank went into receivership in 1903 and was reorganized as the Southport Trust Company. The building was converted into a residence in 1923.
The oldest house in Fairfield is the John Osbourne House at 909 King’s Highway, West. The oldest section consists of the original center-chimney block, which probably began as one-room and was then expanded. A lean-to added several decades after the house was built. The traditional date of construction is 1673, but the later date of 1734 is more likely. The house is traditionally associated with John Osborne, who married in 1673. His father Richard fought in the Pequot War and received a grant of land for his services. The last battle of the war was fought in 1637 in Pequot Swamp, which is located adjacent to the house. The colonial-era section of the house is flanked at both ends by two twentieth-century wings.
The house at 608 Harbor Road in Southport was built in the early nineteenth century (perhaps c. 1834) for Capt. Jeremiah Sturges, a shipbuilder. As related in the Commemorative Biographical Record of Fairfield County, Connecticut (1899), Sturges
also carried on a drug store and a coal yard. He owned some oceangoing ships, having nine vessels in the Mediterranean trade, besides several in the coastwise trade and in the West Indies trade. He was one of the most public spirited men of his times, and a great benefactor to humanity. He was largely instrumental in securing the building of the breakwater, himself being the contractor. Jeremiah Sturges married Maria Shelton. daughter of Philo Shelton, of Bridgeport, and by her had children as follows: Henry, and Henryetta, who married Henry Perry, a brother of Francis and Charles Perry. Jeremiah Sturges was prominent in political affairs, and he was president of the bank for many years. He taught navigation to all the sea captains of the State, keeping what was substantially a school of navigation. He died in the year 1845, his wife in 1861.
Jeremiah Sturges was also in charge of the Mill River Fencibles, a militia unit of the War of 1812. His son, Henry Sturges, succeeded to his father’s business. As further related in the Commemorative Biographical Record of Fairfield County, Connecticut (1899):
Though he followed shipbuilding only for a time, yet he retained his interest in the marine business for some years, retiring altogether early in life. Some time previous to the breaking out of the Civil war he purchased a farm in Plymouth, Litchfield county, on which he lived for some ten or twelve years, and then he purchased a plantation in southwest Georgia, which he kept seven years. This he exchanged for various properties, inclnding a farm on the Raritan river, and engaged in dairying on a large scale. After six or seven years thus spent. he retired from farming and dairying and returned to Southport, where he lived the remainder of his days. Though he was a graduate of Trinity College and a licensed lawyer, yet he never practiced law. Politically, he was a Republican, and had much to do in the way of administrator of estates, holding also several minor offices.
Mr. Sturges married Henryetta Baldwin, daughter of Abram Dudley Baldwin, of Greenfield Hill. He and his wife had six children, viz.: Jeremiah; Henry, living in Montreal, Canada; Henryetta Maria, married to Dr. William L. Wells; Dr. Abram Baldwin Sturges, of Southport; Anna B., married to John A. Gorham, of Southport: and William Shelton Sturges. Henry Sturges died in 1885
Episcopal services in Fairfield were first held by visiting ministers starting in 1705. Trinity Parish was established in 1725 and its first church was built on Mill Plain in Fairfield. A new and larger church was built in 1737 in the center of Fairfield. During the Revolutionary War, the church was burned during the British raid on Fairfield in 1779. Trinity’s third church building was erected after the war on Mill Plain Road in 1790. In the early nineteenth century, the Borough of Southport in Fairfield was flourishing. The first Episcopal services in Southport were held in 1828 in the house at 95 Main Street. As attendance grew, services were held at the Old Academy. Eventually Trinity constructed its next building, affectionately called “The Old Church on the Hill,” in 1829 on Rose Hill Drive in Southport to serve the growing community. The first Southport church burned down in 1854, so it was replaced by a new church on Pequot Road in 1856. That same year, parishioners in the center of Fairfield, who felt that the Southport church was too far away, established St. Paul’s Parish. Trinity’s fifth building survived until it was destroyed in 1862 when a tornado caused the steeple to crash down through the roof. The current Trinity Episcopal Church was quickly built on the foundations of its predecessor and dedicated on December 11 of that same year.
William Bulkley, a storekeeper, built the house at 824 Harbor Road in Southport in Fairfield before 1766. Having been spared during the burning of Fairfield by the British in 1779 because Bulkley’s wife had provided hospitality to British troops, it is today the oldest house still standing on Southport Harbor. A colonial three-quarter house, it was remodeled in the Federal period with a fan window in the attic gable and a cornice with triglyph ornamentation. The changes may have been made by David Banks after he purchased the house in 1816. Wakeman B. Meeker bought the house in 1832. Together with his partner, Simon Sherwood, Meeker organized the merchant shipping firm of Meeker & Sherwood, which constructed a wharf and three warehouses across from the house. In the 1850s Meeker built a new house just north of the Bulkley House.
The saltbox house at 450 Harbor Road in Southport in Fairfield was originally built in 1715 by Samuel Bradley in East Haven. Occupied by his descendants until 1945, in 1945-1948 it was moved and reconstructed at its current address.
At 3171 Bronson Road in the Greenfield Hill section of Fairfield is a gambrel-roofed house built in 1757 by Rev. Seth Pomeroy. The son of Seth Pomeroy, a gunsmith and soldier from Northampton, Mass., who would serve in the Revolutionary War, Rev. Pomeroy, a graduate of Yale, served as the minister of the Greenfield Hill Congregational Church from 1757 until his death at the age of 37 in 1770. After Rev. Pomeroy died, the house was owned by Captain David Hubbell who used it as a store until it was purchased by Reverend William Belden, who served as pastor of the Greenfield Hill Church from 1812 to 1821. At one point the house served as an insurance office.