David Bradley House // c.1803

According to a dated board in the attic, this house was built c.1803! The David Bradley House on Old South Road in Southport, Connecticut is a great example of a traditionally designed house that does not need all the bells and whistles to stand out! The house was owned for a number of years by David Bradley, who worked as the village’s postmaster. It was David who likely added the Gothic Revival gable with lancet window and a (since removed) front porch.

Henry Sturges House // 1834

In the mid-1830s, Henry Sturges, the eldest (and only) son of Jeremiah Sturges, built what just may be my favorite house in all of Southport, Connecticut, this transitional Federal/Greek Revival style manse on Harbor Road. It may have been owned by Jeremiah and updated later by Henry. The house features a symmetrical, five-bay facade with central entry. A gabled pediment extends the roof and includes a leaded-glass oval window and the absolutely stunning full-length front porch and second floor balcony is supported by slender Ionic columns.

William W. Wakeman Mansion // c.1833

William Webb Wakeman was born in Southport, Connecticut on June 19, 1799, the son of Jesup Wakeman, an eminent citizen of the community. As a young man, William worked with his father in his commercial and trade enterprises. He acquired his own vessel early in his career, and gradually accumulated a line of trade vessels, sailing to New York, Savannah, Georgia and Galveston, Texas. By mid-century he was involved in the East Indian and China trade under the firm name of Wakeman, Dimon & Co. He built and owned a line of steamships during the late 50s, and was commissioned by the Federal government during the Civil War to transport troops and equipment. His massive Greek Revival mansion was built around 1833 on one of the largest house lots in the village, perched high on a hill overlooking the harbor. The three-bayed facade is framed by a two-story portico. Supported by four fluted columns, the capitals and entablature are similar to the “composed” order of Minard Lafever and the “composite” order of Asher Benjamin, popularized in the 1830s and 40s in their pattern books for architects and builders. After William died in 1869, it was likely his widow, Mary Catherine (who lived to be 99 years old, outliving all of her six children) who enlarged the home with massive two-story ells.

Jennings Block // c.1787 & c.1860

Old buildings always have so many stories to tell, and many of those stories are much more than what you can see at first glimpse. This commercial block on the main corner in Southport Village, Fairfield, Connecticut was originally built as a two-story Georgian house with gambrel roof. You heard that right! This corner was the site of a c.1787 Georgian house built for Miah Perry (1766-1814). By the 1860s, the building was owned by Nehemiah Jennings, who took advantage of the prominent site and lack of commercial buildings elsewhere and lifted the old Miah Perry House up, adding a ground commercial floor, extended the building to fill the site, and changed the roof to be a more fashionable Mansard style. Today, the building looks indistinguishable from the late 18th century beginnings, but according to researchers, some of the old beams are still in there!

Ms. Sarah Wakeman House // 1871

The Southport Chronicle reported on March 1, 1871 that “W. W. Wakeman, is about to erect, on the Hill, a very handsome residence”. The house would be built on Harbor Road in Southport, and was for his sister-in-law, a widow, Sarah Ann Fowler Wakeman and her two daughters, Mary and Frances. The Bridgeport-based architectural firm of Lambert & Bunnell (made up of Henry A. Lambert and Rufus W. Bunnell) teamed up to furnish the plans for this stately Second Empire style mansion. Sarah died in 1872, and the house was occupied by her daughters until 1913.

Chidsey-Dimon House // c.1850

Located on Harbor Road in Southport, CT, this stunning Italianate residence is properly sited on a small bluff overlooking the village’s harbor. According to historic maps, the house was owned by an “I. Chidsey” who appears to be Isaac Chidsey (1793-1865). The large Italianate style home is boxy in form and stands three full stories with two original one-story side wings. Sleeping porches were added in the early 20th century; those along with the rooftop belvedere, would allow for sweeping views of ships entering and exiting the harbor here. The house was recently restored by the architectural firm of Fairfax & Sammons and it looks amazing!

Oliver Perry House // 1843

This imposing Greek Revival house is located in Southport and is one of a handful of the stunning Classically designed mansions near the waterfront. The house was built in 1843 for Oliver Perry a Yale Law School graduate who did not work in law, but became a successful merchant and businessman instead. Oliver H. Perry established his fortune as a shipowner and a merchant and was Treasurer and Director of the Southport National Bank. He was active in civic affairs and served as speaker of the house of the Connecticut General Assembly and commissioner to survey and settle the border dispute between Connecticut and New York. His Southport house is a stunning example of the Greek Revival style in the temple form with a two-story projecting pedimented portico supported by four Doric columns.

Charles Gilman House // 1871

Southport, the coastal village in Fairfield, Connecticut is an old house lover’s dream! Case-in-point, the Charles Gilman House. Charles Gilman, a Bridgeport lawyer, constructed this house on the ridge parallel to Main Street in Southport between 1871-1874. The building is a fine example of the Stick style of architecture, in which the decoration on facades and gable ends reflects the building’s internal structure. Gilman used the services of two New York architects, J. Cleaveland Cady and William H. Beers, to design the house and the later (1900) library addition, respectively. In the 20th century, the house was owned by Richard Joyce Smith, an attorney who was hired to guide the New Haven Railroad through a long and tricky bankruptcy reorganization ending it it being acquired by the Penn Central in 1975.

Samuel Bradley House // 1715

Welcome to Southport, one of the most walkable and charming seaside villages in all of Connecticut, and it’s also in Fairfield! Southport became a leading coastal port on Long Island Sound, its ships carrying produce and goods back and forth to New York City. Sea captains houses, historic banks, and stunning churches line the streets in the village and are all in a great state of preservation. This is because much of the old village area is part of a local historic district, first established in 1967, where buildings from three centuries are protected for future generations. This house was built in East Haven, Connecticut by Samuel Bradley in 1715. The saltbox house is evocative of many early Colonial homes of Connecticut built at the time with a large central chimney and symmetrical facade. The house remained in the family until the mid-1940s when it was purchased, disassembled, shipped and reconstructed on this site on Harbor Road in Southport.

Hastings House // c.1941

Many neighborhoods in New England held on to historical revival styles even when the International style and Mid-Century Modern homes began to proliferate all across the region. Some owners (even today) prefer traditionally designed houses to blend into their surroundings and historical context. This charming gingerbread Tudor Revival style house in Fairfield is one of them! The Hastings House was built in 1941 and designed by the powerhouse design couple of Cameron Clark (architect) and Agnes Clark (landscape architect) who designed and renovated properties all over Fairfield. The house is notable for its use of stucco with half-timbering, steeply pitched roofline, red tile roof, and more Colonial-inspired door treatments.