Henry Smith House // c.1845

This stunning temple-front Greek Revival home on Main Street in Ridgefield, Connecticut is an absolute dream! The home was built in the mid-19th century for Henry Smith, who operated a shirt factory in town with his father. The house’s gable roof facing the street completes a pediment, which is supported by a projecting portico of four colossal Ionic columns. In the pediment, a gorgeous Palladian window adds so much character to the facade. I love a good temple-front classical home!

Keeler Tavern // 1713

Around the year 1713, Benjamin Hoyt built a home for himself and his family on Lot 2 of the laid out building lots along Main Street of Ridgefield CT. The building was originally a one room dwelling with a stone fireplace and no basement and was located next to the David Hoyt mansion (aka The Fountain Inn). After several years, he expanded the property by building around and above the structure, to give it the gambrel roof and size we see today. More than 50 years later, in 1769, the property was purchased by Hoyt’s son-in-law, Timothy Keeler. Timothy Keeler and his wife converted the building into an inn in 1772, just prior to the beginning of the American Revolutionary War. Keeler sided with the American revolutionaries and was active in the local militia. After the Battle of Ridgefield, British forces fired on the Keeler Tavern, because Keeler was an enemy. One of the cannons used to pummel the tavern is still lodged in a corner post of the house to this day. After later owners in the Keeler Family, the property was purchased by world-renowned architect Cass Gilbert, who turned it into his family’s summer home in 1907. In doing so, he made various improvements and additions to the building, in particular he designed a Garden House and added a sunken around the year 1910. Gilbert would also design a fountain as a gift to the town, which sits almost opposite his family’s summer residence. The property was purchased in the 1960s and has since been a historical museum.

The Fountain Inn // 1740

Located on Main Street in idyllic Ridgefield, in Fairfield County, Connecticut, The Fountain Inn provides one of the most welcoming and historical bed and breakfast experiences in New England! The Fountain Inn was built in 1740 as a “city home in the country” for David Hoyt, who showed off his wealth and stature in the young town by having such a high-style home built at the time. Decades later during the Revolutionary War, David Hoyt’s house became a part of the Battle of Ridgefield. After defeating the Colonial militia elsewhere on Main Street, British Gen. William Tryon‘s troops turned their attention to nearby Keeler Tavern, the local militia’s headquarters, which just happened to be neighbors with the mansion owned by David Hoyt, a known Loyalist. General Tryon’s troops practiced their artillery-firing skills on the building pummeling it with cannonballs, sending a message to the head of the local militia. David Hoyt formally demanded a cease-fire, as he was concerned about wayward cannonballs damaging his home. By 1790, with Ridgefield’s British influence diminishing by the day, David Hoyt finally left his Connecticut home and sailed back to England. The home was expanded and modernized over the next two hundred years until the present owners purchased the property and underwent a massive restoration of the Colonial house inside and out as their family residence. In the past year, the inn opened as the Fountain Inn so-named after a Cass Gilbert-designed fountain across the street.

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.

Moses Bulkley House // 1861

Constructed in 1861, this Victorian Gothic mansion in Southport, Connecticut, stands out amongst the many Classically inspired homes nearby. Designed by Bridgeport architects Lambert & Bunnell for Moses Bulkley (1796-1868), the house is designed on a cruciform plan, synonymous with the Gothic style. Expansive pointed gables trimmed with a gingerbread bargeboards, pointed arched windows, ogee arches trimmed with jigsaw tracery on the verandah, and a tall square tower topped with a steeply-pitched pyramidal roof are all seen in this beauty. If only it had a historically appropriate paint scheme to really make those details pop!

Charles Perry House // c.1830

Charles C. Perry (1795-1870) was a wealthy nineteenth-century shipowner and sea captain and a prominent figure within Southport’s community. After his father’s death in 1814, when Charles was just 25, he inherited a large sum of money from his father’s will and followed his footsteps as a career. Miah Perry’s will stipulated that in order to keep the family together, members were to reside at the family home for five years from his death if neither of the daughters married; “but in case they remain unmarried at the expiration of five years…my estate shall not be divided until eight years from my decease unless one of the said daughters should marry…partition may be immediately thereafter made.” Talk about pressure to get married!

It is unclear if any daughters got married before, (Julia, one daughter died in 1821 at 22 years old). That same year, Charles Perry seemingly got his part of the inheritance and acquired the land upon which this house stands. He was then twenty-six years old and unmarried. He appears to have built it later as a blending of the Federal and Greek Revival styles, perfectly complimenting each other.

Austin Perry House // c.1830

One of the nicest examples of residential Greek Revival architecture I have ever seen is the Austin Perry House (c.1830) in the Southport area of Fairfield, CT. Austin Perry (1798-1864) was a member of a prominent merchant family, holding businesses in Fredericksburg, Virginia, before returning to Southport to manage a general store. He retired in his forties and resided at this home until his death. His home is a balanced, symmetrical design with massive Corinthian columns surmounted by a carved anthemion motif ornamenting the gable pediment.

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.

Paschal Sheffield House // c.1826

This Greek Revival home built c.1826, is perfectly articulated in the classical temple form. It was built for Paschal Sheffield, a well-respected member of the Southport community throughout the nineteenth century. His father was a privateer during the Revolutionary War, and moved to Southport to settle and enter in the mercantile trade business. Paschal appears to have been involved in business and local politics until his death. After his death, the home was marketed as a tear down for a new summer resort, but it was retained by future owners.

Ms. Hetty Gookin House // 1874

Warren Demman Gookin (1810-1874) was born in Haverhill, New Hampshire. He was educated at Haverhill Academy and Dartmouth College, graduating from the latter institution in 1830. In 1835 he went to Cuba where he remained for ten years as a sugar planter. Later, he was engaged in a mercantile business in Oregon, finally settling in Brooklyn, NY and working as a shipping merchant in New York City until his death in 1874. After his death, his widow Hetty moved back to her hometown of Southport, CT and built this large home. Later this was the home of Mrs Gookin’s stepdaughter, Mrs Edwin Waterman.

Samuel Allen Nichols House // 1848

Samuel Allen Nichols (1790-1864) was born in Fairfield, Connecticut to a large family. He began his adult career as a farmer, but shifted towards the merchant trade after seeing how the village of Southport began to see massive wealth accumulating. He ran a store in the town and later became involved in local politics serving as the clerk from 1847-1863. A year after he accepted this position, he had this home built on Harbor Road. The 1848 home was Gothic Revival in style with gabled dormers, lancet windows, and decorative bargeboard. Nichols died in 1864 and the home was likely willed to one of his five living children. The home was renovated around 1871 with a Second Empire style Mansard roof and square belvedere to overlook the Southport Harbor. Since then, much of the detailing has been removed, but the home remains as a gorgeous home, changed over time to keep up with the changing architectural tastes of the 19th century.

Perry House-Trinity Church Rectory // 1832

I have a thing for temple-front Greek Revival homes, and this is no exception. This marvelous home was built in 1832 for Francis Dimon Perry (1809-1884), who inherited some of his father’s wealth and became President of Southport National Bank in town. He was a devoted member of Trinity Church throughout his life. Upon Mrs. Perry‘s death in 1893, couple left their residence to the Trinity Church to be used as the parish rectory.

Simon Sherwood House // 1884

The Simon C. Sherwood house, built in 1884, is a fine late nineteenth-century eclectic Victorian home, somewhat unique to the Southport area of Fairfield, CT, which is dominated by early-mid 19th century styles. Simon Couch Sherwood was the son of Edwin Sherwood, a wealthy shipping merchant who made a fortune from trade between New York and Savannah. The Queen Anne-Eastlake style home was added onto with a larger porch, obscuring an original oriel window on the side elevation. Sadly, the home has a safe, yet inappropriate pale yellow body color with white trim, which does not showcase the intricacies of the Victorian era home.

Edwin Sherwood House // 1837

Located next to his son’s house, the Edwin Sherwood House in Southport, Connecticut is an excellent example of Greek Revival residential architecture in New England. The home was built in 1837 for Edwin Sherwood, a sea captain who traded between New York and Savannah with his two ships “America” and “Georgia”. From this wealth, he became President of the Southport Savings Bank and Director of the Danbury-Norwalk Railroad. The home was renovated in 2017 with a modern interior by Ken Gemes, an interior designer.

Augustus Jennings House // c.1830

Walking around Southport Village in the town of Fairfield, Connecticut, transports you to an early-mid 19th century town with large Federal and Greek Revival homes overlooking Southport Harbor and the Long Island Sound. This home on Westway Road was built around 1830 for Augustus Jennings (1814-1886), the son of Captain Abraham Gould Jennings. Augustus became a carriage maker in Southport before founding Jennings Brothers, a paper manufacturing company; which in 1867, began to produce Japanese paper products. The Jennings House was originally located near the Pequot Library, but was relocated in 1899, which was likely when the central shingled gable at the roof with Palladian window was added.