Kennebunk River Clubhouse // 1889

A canoe club formed by John B. McMaster, Prosper L. Senat and Henry E. Woods in the early 1880’s grew to a large “Lobster Club” by 1888. In 1889, the club decided to build this Shingle style boat house and the organization changed their name to the ‘Kennebunk River Club’ and hired Lowell, Massachusetts architect, Frederick W. Stickney to design a new boathouse. It opened in August 1890. The club grew quickly as Kennebunkport continued to become a premier summer destination with wealthy residents building summer “cottages” in town. In the building, canoes were built and hired out to club members by members of the Penobscot tribe who came to Kennebunkport from Old Town each summer working here. The clubhouse is one of the finest Shingle style recreational buildings in New England.

Point O’ View Cottage // 1892

The Point O’ View Cottage in Kennebunkport sits on a large lawn on the rugged Maine coast, with sweeping views of the Atlantic Ocean. Built in 1892 by Burleigh S. Thompson as a rental property (he rented it for $1,500 for the summer) the nine-bedroom “cottage” was designed in a Tudoresque version of the Queen Anne architectural style and originally named Fort Bradford. The cottage (like others built for Mr. Thompson) was designed by Henry Paston Clark, THE architect for the Cape Arundel Summer Colony in the 1890s, who also designed St. Ann’s Episcopal Church and other cottages nearby. The cottage was renovated more in keeping with the Shingle style and was entirely clad in cedar shingles, but it retains its perfect, rustic stone foundation and rounded porch. It is now known as Point O’ View Cottage. What a view it has!

Kewaydin Cottage // 1900

Every good summer cottage needs a name, and this charmer in the Cape Arundel Summer Colony of Kennebunkport, Maine, is no exception! This is “Kewaydin” a massive summer home built for Eben Caldwell Stanwood Jr. (1856-1906) a merchant and later banker of Boston, Massachusetts. Stanwood hired the Boston firm of Chapman & Frazer to design the cottage, which blends Shingle style and Queen Anne elements in a rustic composition that has such great curb appeal! The use of cedar shingles and rubblestone chimneys, paired with the vergeboards and complex roofline with dormers, makes this one of the gems of Kennebunkport!

Pine Haven Cottage // 1902

Pine Haven Cottage sits on a rise overlooking the Atlantic Ocean in the Cape Arundel summer colony in Kennebunkport, Maine. Built in 1902 for Thomas Brodhead Van Buren, Jr., a silk importer in Manhattan as a summer home, the cottage was designed by Henry Paston Clark and his partner, John W. Russell in an eclectic example of the Shingle style with gable roofs, vergeboards, stone foundation, and a prominent porch that has since been enclosed.

Chester Guild Cottage // 1902

One of the many stunning summer “cottages” built in the Cape Arundel summer colony of Kennebunkport, Maine, is this turn-of-the-century Shingle style dwelling built for Chester Guild of Boston. Chester Guild III was born into the wealthy Guild Family of Roxbury with his father being a successful leather dealer. Chester Guild spent summers with his family in Kennebunkport beginning in the 1890s, eventually had this cottage built in 1902. The Shingle style dwelling remained in the family for five generations and is very well-preserved, showcasing the hallmark elements of the ubiquitous coastal Maine architectural style.

The Billingsgate Cottage // 1892

In 1892, this large summer “cottage” was built in the Land’s End section on the coast of Rockport, Massachusetts. The large summer residence was built for the Thatcher sisters of Roxbury and was named “The Billingsgate” after their mother’s maiden name, Billings. Caroline Billings Thatcher would summer here with upwards of her four other sisters, Lillian, Margaret, Mary, and Elizabeth, to escape from the city. The large summer cottage features a rubblestone first floor with stone columns supporting the shingled floor above. A large gambrel roof and dormers punctuate the façade and showcase the simplicity and elegance of the Shingle style.

Windswept Cottage // 1909

The coastal towns of Gloucester, Manchester, and Beverly on the North Shore of Massachusetts often are known for their historic summer “cottages” but great examples can be found right here in Rockport! This is “Windswept”, the W. W. Blunt cottage, located in the Headlands section of town, just south of the harbor. Walton W. Blunt worked as the Treasurer and General Manager of the Boston Journal newspaper and resided in Boston, later purchasing multiple adjoining house lots in Rockport for a summer residence. The two-and-a-half story house was designed by a Rutherford Smith, who sought to utilize fieldstone found nearby for the foundation and chimneys and shingle siding above. Detailed descriptions of the new house were featured in a local newspaper in 1909 and mentioned tennis courts on the grounds, an apartment for servants, and a billiard room in the third floor. It is not clear when the house got its name, “Windswept”, but the name is just too fitting!

Old Granite Shore Hotel // c.1755

Reverend Ebenezer Cleveland (1725-1805) graduated from Yale College in 1749 and would move to Rockport (then a parish town of Gloucester) accepting the call as the village’s pastor for its Congregational Church. By around 1755, he lived in a house on this site next to the church before becoming a chaplain in the French and Indian War, fighting at the Battle of Bunker Hill, and helping to establish Dartmouth College. The property here was later owned by Jabez R. Gott, a deacon of the Congregational Church and the original cashier of the Rockport National Bank until his death in 1876. Sometime in the next decade, the Cleveland House was converted to a summer hotel, known as the Granite Shore Hotel. The original Georgian-era structure was heavily altered and expanded to provide new rooms and amenities for seasonal guests. An 1905 book showed rooms available at the Granite Shore for $2 a night. By 1919, the rates were $3 a day or between $15 and $18 a week! The hotel closed sometime in the 1940s and the building is now home to art galleries.

Joseph P. Allen Cottage // 1877

One of the most picturesque and charming summer cottages (now year-round residences) in the Salem Willows neighborhood in Salem, Massachusetts is this Victorian on Bay View Avenue. The cottage was built around 1877 for Joseph Pray Allen (1822-1897) who was a police officer who likely climbed the ranks in the force to afford a second home in the city. The 1 1/2-story cottage has decorative bargeboards at the eaves and stick bracket at the gable. Perfection!

Patrick Dempsey Cottage // c.1875

This charming mini-mansard summer cottage is located in the coastal neighborhood of Salem Willows, in Salem, Massachusetts. The neighborhood developed in the 1870s-1900s as a summer colony for middle-income families who wanted a second home away from the hustle-and-bustle of urban living in favor of ocean breezes. The cottage likely dates to the mid-1870s as one of the earliest summer homes in the neighborhood, and historic maps show it was owned by a P. Dempsey. It appears this is Patrick Dempsey (1821-1902), an Irish immigrant who settled in Lowell, Massachusetts, making it big as a liquor dealer and saloon-keeper. The Second Empire style cottage has a partially enclosed porch, but retains much of its original character and is located right on the water with sweeping views of the Atlantic Ocean.

William Bates Summer Cottage // 1885

While Salem is best-known for its First Period and Federal style buildings, the Salem Willows neighborhood features some of the finest Victorian summer cottages in the Boston area. This cottage was built in 1885 by William Marston Bates (1820-1912), a Salem-based dentist, as his summer retreat when not in the office. The Stick style cottage has a steep gable roof with jerkinhead clip at the facade and a wrap-around porch with decorative jigsawn bracketed details. The house is a well-preserved example of the style, examples of which are becoming less-and-less frequent in recent years.

Galvin Cottage // c.1882

Hull Hill is a relatively unknown enclave of summer cottages that sit on a rise overlooking Boston Harbor in the coastal community of Hull. The development of Hull Hill began in the 1870’s but became most active in the 1880’s and 1890’s. The land here was previously maintained as pasture and gardens by Hull villagers, but the land here was eventually sold and developed when the Hingham Water Company came to Hull in 1882. That same year, the railroad arrived which provided easier access to the town. This cottage on Andrew Avenue is one of the earliest summer residences built here, and dates to the late 1870s or early 1880s. The cottage was owned by Owen Augustus Galvin, a Boston lawyer, and his wife, Jane Sullivan Galvin. The unique cottage features a hexagonal section with a roof extending down to meet the wrap-around porch. The cottage exemplifies late 19th century cottage/resort architecture.

Conant-Cushing House // c.1890

Atop the Great Hill on Point Allerton in Hull, Massachusetts, this large summer “cottage” stands out for its unique architecture and siting overlooking the bluffs and Atlantic Ocean. The Shingle style house was built around 1890 by Edward D. Conant, a real estate agent and developer of Newton as his family summer home. The architect is not clear, but the house exhibits a unique four-story crenellated tower, giving the appearance of a castle from a distance. The house was later owned by Cardinal Richard Cushing (1895-1970) as his own summer residence. Cardinal Cushing served as Archbishop of Boston from 1944 to 1970 and was made a cardinal in 1958. Cushing’s main role was as fundraiser and builder of new churches, schools, and institutions, and he helped then-presidential candidate John F. Kennedy deflect fears of papal interference in American government if a Catholic became president. Kennedy grew up spending summers at his grandfather’s home in Hull (featured previously). The Conant-Cushing House remains significant even with 20th century renovations.

Winfield S. Richards Cottage // c.1890

Summer cottages of the late 19th century are always a treat to come across! While most cottages I feature on here are more high-style and were built for the wealthy, Hull, Massachusetts, has some of the best middle-class summer cottages in New England! Steamships and rail service from Boston and other cities opened up Hull and Nantasket Beach to summer residents and day visitors alike, creating a massive increase in building in the latter decades of the 19th and early 20th centuries. This cottage was owned by Winfield S. Richards and his wife Myra of Newton, Massachusetts. The cottage blends Queen Anne and Craftsman styles with complex Queen Anne massing, turned posts, and recessed second story porch, and sloping roof extension to create the Craftsman-esque front porch. The cottage is one of the better-preserved in town and an excellent blending of architectural styles.

Saunders Cottage // c.1900

Charles Saunders, a carpenter, and his wife Annie Saunders, seemingly built and lived in this Shingle style cottage in the Ocean View summer colony of Rockport. The couple shows up in census records as living here in 1910 while in their 50s. The house likely dates to the 1890s and is a great example of the Shingle style for a middle-class residence. The house features a corner tower and a wrap-around porch with continuous shingle siding and columns. The property was deeded to a Lawrence Regester in 1924 when Annie sold the property after Charles’ death. The shingled cottage has remained in a great state of preservation for its existence!