Captain John Dexter House // 1860

This beautiful house was built by retired whaling Captain John G. Dexter in 1860. The Dexter family’s ties to Rochester, Massachusetts, began when William Dexter became the first descendant of the Dexter
family to settle in town around 1679. William, one of the 32 original grantees of the town (from land by Sachem Metacomet), died in Rochester in 1694 and his four sons and grandsons remained in Rochester through the 19th century. After being away for months or years at a time, Captain John Dexter returned to his hometown to build this home on family land that was previously undeveloped. The Dexter family remained in the house well into the early 20th century, carrying on the family’s deep rooted history in the area. The home is a blending of Gothic and Italianate styles, which work really well in the rural area.

Ward Parker Delano House // 1797

During the 1790s and early 1800s, the rise of the coastal schooner trade and whaling ushered in a long period of prosperity for coastal towns in New England, which continued unabated until the Civil War. The War of 1812 provided many Marion sailors and sea captains with the chance to experience life at sea with privateers papers issued by the United States government, these captains went to sea in their schooners to hunt down British ships, plundering them like pirates. One of these captains was Ward Parker Delano, who built this house in 1797 overlooking Sippican Harbor. Under subsequent owners in the Delano family, the home was modified on numerous occasions in styles popular at the time until the early 20th century when it was Colonialized, which added the portico, gable, and dentils.

Captain Grey House // 1845

Captain Russell Grey (Gray) was one of a handful of sea-captains who lived in Wharf Village, the downtown of present-day Marion, Massachusetts. The men would own ships that were docked in the harbor or in nearby New Bedford, and would leave for months-long excursions chasing whales, fish, or other treasures. Behind, they left their young wives and growing families, who braved the harsh New England winters and the unpredictable coastal weather events. This small cottage was built around 1845, for a young Russell Grey and his wife, Sarah Luce, who’s own family was full of mariners as well. The couple’s Greek Revival style cottage remains as one of the most charming in the village.

Josiah Talbot House // 1835

Anyone that has followed this account for a while knows at least one thing, I LOVE Greek temple-front homes. Designed by famed architect, and Bristol-native, Russell Warren, this 2-story, 3-bay, gable-roof Greek Revival house is one of the finest in the state. Its facade has a pair of fluted Corinthian columns, set in antis (where the side walls extend to the front of the porch). A simple side-hall entrance is framed by heavy Doric pilasters, supporting a broad, plain entablature, making this such a head-turning Greek Revival home. The walls are sheathed with horizontal flush boarding at the facade to give a smoother look and clapboards on the side and rear. The home was built for Josiah Talbot, a sea captain. The house is excellently preserved to this day, almost 200 years later.

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.

Melville Walker House // 1860

Built for Melville Walker, a sea captain on land gifted to him by his father, this home perfectly exhibits the changing dynamic of Kennebunkport. Melville Walker would often be out at sea for months at a time, and he apparently brought along his wife, three daughters and son on many trips to ports all over the world. The Italianate home was eventually sold out of the family, and by 1901, it was purchased by George Little, an executive with the New York, New Haven and Hartford Railroad. That year, he had the summer home renovated with Colonial Revival detailing, including the hipped roof, dormer, and other detailing. The belvedere, 2/2 windows, and Victorian era porch were retained, showing the original form and detailing of the Italianate version. In the 1950s, the home was converted to an inn, with small cottages constructed surrounding the property to house additional families. Today, Maine Stay Inn & Cottages welcomes families from all over the world to experience the beauty of Kennebunkport.