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.

Captain John Maltbie House // 1766

On July 7-8, 1779, the Red Coats marched through Fairfield torching houses to punish the locals for seeking independence. They killed locals, destroying anything they could find on their way out, setting fires to homes and civic buildings around the Green. This home was built by Isaac Tucker, later sold to Jonathan Maltbie, sea captain involved with East Indies trade. He later would fight against the British during the Revolution, and after the war, was hired as captain on one of the first cutter ships built, the Argus. During the British invasion of Fairfield, they attempted to set fire to this home three times, but it seemed to never go up in flames when they returned. The tradition holds that an elderly servant, hiding upstairs, put out the flames and saved the house from destruction, after the British Troops torched it. Burn marks apparently remain inside to this day. Since the home was built, the front door facing the street was relocated to the side, and a large multi-pane bay window was installed in its place.

Captain Fisher House // 1892

Standing out amongst the Federal and Greek Revival homes in Edgartown, this Victorian home was constructed in 1892 by Captain Charles W. Fisher (1835-1905) for his new wife. The Fisher family includes many members who were active in the local whaling industry. Fisher is said to have caught the largest sperm whale on record in 1884 and apparently loved being on the open ocean. The next year he married Parnell Pease and she sailed with him to the Pacific on a whaling voyage, lasting five years! At the time of their marriage, Fisher was in his 50s and his new wife in her 20s. Upon their return, Fisher built his wife this “modern style house on the pretentious side with Victorian ornamentation.” Unfortunately, his wife preferred her former house, which was a block a way and obscured any views of the water. Tradition states that apparently, Mrs. Fisher had seen enough of the water during her voyage, as her diary on the five year trip detailed her many unfortunate bouts with sea-sickness, a stay on an island, and dangerous storms.

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.