Captain Abraham Osborn House // 1834

Built in 1834, this early Greek Revival house with Gothic Revival detailing, sits on Edgartown’s South Water Street, a notable street lined by large mansions built for early whaling captains on Martha’s Vineyard. The residence was built for Abraham Osborn (1798-1865), a whaling captain, soon after his marriage to Eliza Norton. Captain Abraham Osborn owned several whaling ships based out of Martha’s Vineyard and New Bedford, and one of these large vessels, the Ocmulgee, came to an untimely end early in the Civil War. When captaining the ship in September 1862, the Ocmulgee was approached by a ship flying British flags. When it got within speaking range, the British flags were replaced by Confederate colors and the rebel captain took over the ship, which contained 250 barrels of whale oil. The Confederates detained the ships officers and Captain Osborn in chains bringing them aboard their ship, the Alabama, which was known for stealthy operations to damage the economy of the Northern states. The rebels torched the Ocmulgee, forcing Captain Osborn and his crew to watch their profits burn up and sink into the ocean. The crew was detained for a few days and ultimately released near the Fayal Islands where they received help. Captain Osborn returned home and would die just three years later. The Osborn house was later inherited by his son, Abraham Jr., a retired sea captain himself, who eventually converted the large family home into a hotel called Ocean View. A famous guest at his hotel was Alexander Graham Bell, who was on island to study the extensive deafness prevalence for those on the Island. The house has since been converted back to a single-family residence and maintains its stunning Greek Revival entry portico and tripartite window in the gable with shuttered lancet openings.

Captain Tristam P. Ripley House // c.1835

One of the great old captain’s houses in Edgartown, Massachusetts, stands here on South Water Street and is emblematic of the history of the harbor community in the 19th and 20th centuries. The five-bay Greek Revival style mansion was built in about 1835 and was owned later by Tristam Pease Ripley (1821-1881) a wealthy sea captain, originally from New Bedford, who operated whaling ships while out at sea for months or a year at a time. After becoming a Master Mariner on the sea, Captain Ripley settled down back in Edgartown and worked as a coal dealer, likely bringing ships from the mainland to the island carrying coal for sale to keep these grand homes warm during the brutal New England winters. The house was purchased by a local inn during the 20th century and significantly renovated inside and out, and is owned by the Harborside Inn.

John H. Munroe House // c.1860

Built circa 1860 for Jonathan Harding Munroe, this stately Victorian house sits on Main Street in the up-scale community of Edgartown on Martha’s Vineyard. Jonathan Munroe was born in Bristol, Rhode Island and moved to Edgartown where he opened a store and worked as a high-end tailor, and became a successful businessman in town where he founded the Martha’s Vineyard Bank of Edgartown, and later financed successful whaling excursions making a large profit on his investments. With his ever-growing net worth, Mr. Munroe likely updated this house towards the end of the 19th century, with the ornate three-sided porch. Most recently, the property has operated as an inn, named after its original owner, the Jonathan Munroe House Inn.