Mary Pomeroy House // 1868

Mrs. Mary Pomeroy, the widow of one of Southport’s industrious and wealthy shipping merchants, Benjamin Pomeroy, built this large residence for herself and her daughters, soon after her husband’s death. Mr. Pomeroy was a merchant who also served as a Senator. In 1866 with ailing health, he took a doctor on a private ship to try various remedies in the West Indies, to no avail, he died at 48 years old. Ms. Pomeroy appears to have taken the money her and her husband had saved and built a large mansion to cement her position in town as the most eligible bachelorette in town. While she never remarried, she sure showed the town what good taste looks like! The facade of the Pomeroy house is symmetrical with a projecting three-story central pavilion, all surmounted by a mansard roof with cresting. Rounded dormers with twin round-headed windows pierce the roof’s multicolored slate surface, making this Second Empire house one of the nicest in a town full of historic homes!

Simon Sherwood House // 1884

The Simon C. Sherwood house, built in 1884, is a fine late nineteenth-century eclectic Victorian home, somewhat unique to the Southport area of Fairfield, CT, which is dominated by early-mid 19th century styles. Simon Couch Sherwood was the son of Edwin Sherwood, a wealthy shipping merchant who made a fortune from trade between New York and Savannah. The Queen Anne-Eastlake style home was added onto with a larger porch, obscuring an original oriel window on the side elevation. Sadly, the home has a safe, yet inappropriate pale yellow body color with white trim, which does not showcase the intricacies of the Victorian era home.

Frederick Henshaw House // 1888

After the completion of the Waban Station, providing opportunity for residential and commercial development due to transit to and from Boston, two men sought to develop the area into attractive housing lots. In 1886, Dr. Morrill Wyman, founder of Mount Auburn Hospital in Cambridge, sold the old Wyman Farmhouse (still extant) and 150 acres of farmland to real estate speculators. The speculators, Charles Page and Frederick Henshaw, proceeded to subdivide the land into 87 house lots, creating this suburban neighborhood in Waban we know today. Frederick Henshaw sought to build his own home adjacent to the old farmhouse and hired H. Langford Warren (who then owned the farmhouse next door), esteemed architect and then Dean of the Harvard School of Architecture to complete designs. The Queen Anne mansion with its bold octagonal bay commands the corner lot and is a well-preserved significant home in the neighborhood.

Walker House // 1882

This house was built in 1882 for Frank Walker, a merchant who owned a feed and grain store in Downtown North Adams, Massachusetts. The Stick and Queen Anne style home was designed by architect Marcus F. Cummings, who also designed the Blackinton Mansion. The brick and freestone home was converted to multi-family sometime in the mid-20th-century due to the changing demographics of the town. Since then, the home has seen weathering and deferred maintenance, but retains much of its original detailing and character.

Penniman House // c.1885

Edmund Burke Penniman (1841-1929) was born in North Adams, a son of Mr. and Mrs. Edmund B. Penniman. His father an established lawyer, and mother died, leaving the young boy with a sizable estate. Just before the Civil War broke out, he developed a mill, which had to shut down when the war began. After the war, the company had no orders to fill and they sold the property. Penniman became treasurer for the North Adams Manufacturing Company, and later served as President of the Hoosac Savings Bank. He and his family resided in this Stick style home until his wife’s death in 1909. The home features a brick ground floor and clapboards (now aluminum) above. The Victorian home has a rusticated arched entryway protected by a projecting porch with stickwork. A large corner tower gives the house a large street presence.