Jones Cottage // 1876

This charming little cottage in Oak Bluffs was built in 1876 for Charles N. Jones, a resident of Medford, MA who had a home built there in 1872. His family’s summer cottage on Martha’s Vineyard was designed by the Ripley Brothers, Alonzo and Walter, carpenters who lived in town and designed and built many of the charming little summer homes there. The home features a wrap-around porch, a covered balcony at the second floor, and pierced board balustrade and cornerboards. Oh, and the paint scheme is perfect!

Aunt Georgia’s House // c.1880

Located on the iconic Circuit Street in Oak Bluffs, this Eclectic Victorian cottage has a storied past related to Black history on the island. Even though Oak Bluffs was a relatively safe place for African Americans to be, there were still limits on their rights. In some parts of Oak Bluffs there were laws that said that certain property could only be owned by whites. The island became a vacation spot for thousands every summer in the 19th century and seeing a lack of options for Black travelers, Mrs. Georgia O’Brien and Ms. Louisa Izett began to operate an inn for people of color. The inn was one of two such residences in Oak Bluffs and has since been listed on the African American Heritage Trail of Martha’s Vineyard. The home has since been named the Tivoli Inn and retains much of the original gingerbread trim. In recent years, Martha’s Vineyard was given the nickname, “The Black Hamptons,” due to its popularity as a place for wealthy African-Americans to vacation, it remains a very diverse island in summer months.

Tall Timbers Cottage // c.1870

Tall Timbers is one of the more unique cottages in the Wesleyan Grove development, a religiously oriented summer community in Oak Bluffs on Martha’s Vineyard. The cottage was actually built in two phases. The small two story cottage was built first before 1870 and features gothic bargeboard, lancet windows, and paired doors. It was purchased around 1870 by William Newell, of Rhode Island, who had a three-story wing added to serve as a summer cottage. The addition is notable for the full-length vertical boards that rise through the entire three stories without a break like trees after harvesting, likely the inspiration for the name of the cottage. William Newell was a manufacturer of brass fixtures and ran a foundry in Central Falls in Rhode Island. Mr. Newell was active in politics and early in his career joined the cause of the anti-slavery party, which was likely solidified in his experiences in the ethnically diverse Martha’s Vineyard.

Governor Oliver Ames Summer House // 1878

This stunning Victorian home in Oak Bluffs on Martha’s Vineyard was built in 1878 as a summer home for Oliver Ames (1831-1895), a businessman, investor and Governor of Massachusetts. Oliver Ames was the son of Oakes Ames, who is credited by many historians as being the single most important influence in the building of the Union Pacific portion of the transcontinental railroad. After his father’s death in 1873, Oliver Ames became the executor of his father’s vast estate and business dealings, and spent vast sums of money on properties in the places he lived including North Easton, MA, Boston and Martha’s Vineyard. He summered at this large home fronting the ocean in Cottage City, then a part of Edgartown. He decided to run for state senate in 1879, after he was unsuccessful in securing passage for the separation of the Martha’s Vineyard community of Cottage City, where he owned a summer house, from Edgartown. Winning election, he saw through the incorporation of the town (now known as Oak Bluffs). Ames served as the Governor of Massachusetts between 1887 and 1890, and continued to summer in his beachfront home during that time. The eclectic Victorian home blends many popular styles at the time from the Shingle style with the continuous shingle siding, the Stick style with the delicate stick-work at the veranda, to Queen Anne with its asymmetric massing and square tower.

Pettee Caretaker’s Cottage // c.1840

One of the rare early stone cottages in Newton, this charming building in Upper Falls Village has an interesting history! The stone cottage was built around 1840 by Otis Pettee (1795-1853), a major mill owner in town. This cottage specifically served as a shop and later as the residence of the caretaker of the silk mill a couple blocks away. Pettee likely had this building and the adjacent barn constructed with stone to limit the chance of a fire, destroying any valuable silk inside.