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.

Woodward Abrahams House // c.1768

This Georgian-era Colonial home in Marblehead, Massachusetts was built around 1768 by Woodward Abrahams, who was appointed deputy postmaster in Marblehead ten years prior by Benjamin Franklin. Abrahams was one of the seven listed “Tories” mentioned in a town meeting of 1777, which were more loyal to the British crown than the colonies. After the war, he attempted to restore his political favor, which he did over decades, later being renamed a postmaster in 1797. The old Abrahams house was later owned by Thomas Tucker, who ran a dry goods business. In 1881, he converted the first floor to commercial space, giving the house its appearance we see today.

Reverend Whitwell House // c.1756

Another of the stunning gambrel-roofed Georgian homes in Marblehead is this beauty located on High Street in the village. This house was built around 1756 but is best known for its resident from 1766-1779, as the home of the Reverend William Whitwell (1737-1781), who was the fourth minister of the Old North Church, located just a stone’s throw away. Although this Georgian dwelling looks like a single-family house from the outside, it is actually divided into two houses with separate owners, likely since its construction. Later dormers crowd the roof, but its still a pretty amazing Pre-Revolution home in one of the most charming towns in New England!

Nathaniel Backus House // c.1702

Welcome to Franklin, Connecticut, which frankly (pun intended) I had never heard of before driving through it not long ago! The town is located in New London County and was originally a part of Norwich, Connecticut and was called West Farms village. The town incorporated in 1786, creating its own town at that time, and the citizens decided to name their new town after Benjamin Franklin. I wonder if there are more place names in the United States after Benjamin Franklin or George Washington…

This is one of the oldest houses in the sleepy town of Franklin, and it was built around 1702 by Nathaniel Backus, about the same time he was married to his wife, Elizabeth. The Georgian Cape house features a large gambrel roof and a small gabled dormer. The house is representative of many of the earliest homes which once existed in this landscape in the early 18th century. The home appears to have been vacant for some time, and in 2022, was auctioned off. Its future is unclear at this time sadly.

Merritt House // c.1725

In 1725, Samuel Merritt, a fisherman, inherited some of his father’s land in Marblehead and built this house. After Samuel Merritt died in 1743, his second wife Mary, her daughters Mary and Elizabeth and her son-in-law James Dennis, lived in the house. They added the one-story lean-to, giving the house a saltbox roof in 1762. This house, and many others in Marblehead are the reason why human-scaled historic neighborhoods built before the automobile, are some of the best places to explore. Historic preservation equals tourism, which results in tax revenue and property values, stabilizing neighborhoods and cities from the ebbs and flows of the economy. Gotta love it!

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.

Daniel Walker House // 1784

One of the older extant homes in Kennebunkport is the Daniel Walker House on Maine Street. After the American Revolution, shipbuilding and other maritime industries grew along the Maine coast, especially in Kennebunkport (then still named Arundel). Sea captain Daniel Walker built the home on ample land on the outskirts of the village at the time. By the early 19th century, he sold off much of his land closer to the river to family and friends. The Georgian home is minimal, yet commanding with its massive facade, rusticated lintels and corners, an elaborate entry and a large central fireplace.