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!

Haven Avenue Cottages // c.1877

When Andrews Point in northern Rockport, Massachusetts, was opened for development by speculators Eben B. Phillips and George Babson, they envisioned the colony, “Ocean View” as a rival to other nearby summer colonies of Beverly Farms, Gloucester, and Magnolia. Roads were laid out and house lots were plotted with larger lots for big summer cottages along the coast and smaller cottage lots at the interior of the development. The rocky coast and more limited access compared to its rivals, caused Ocean View to lack in sales, but there are still some great remaining cottages to be found here. These two early cottages are great surviving examples of the modest, middle-class homes for summer residents. These two charming Victorian cottages sit side-by-side and were owned by an L. Brigham and Benjamin Lewis and both are in a great state of preservation 150 years later.

Oak Knoll Cottage // c.1877

One of the earlier cottages built in the Oceanview summer colony of Rockport, Massachusetts is this charming example of a late-Italianate style residence on Phillips Avenue. Local lore states that the cottage was owned by Lucy Canney, the wife of Edwin Canney, who operated multiple granite quarries in town. Oak Knoll was possibly used as a boarding house for visiting guests of the quarries to stay at when inspecting the quality of the granite. The Canney’s sold off much of their property in the area by the end of the 19th century, and the cottage was later owned or occupied by Dr. Helen Morton (1834-1916), a Boston-based obstetrician and one of the early generation of women physicians practicing in Boston in the nineteenth century. Dr. Morton spent most of her time in a townhouse on Marlborough Street in Boston’s Back Bay with her possible partner, another obstetrician, Mary Forrester Hobart, but likely escaped to this cottage for some rest and relaxation for the summers.

Eben Phillips Cottage // c.1877

In the mid-1800s, Rockport, Massachusetts was best-known as one of the main ports for the quarrying and shipping of fine granite up and down the east coast of the United States. While the rocky coastline made granite a prime industry, the natural scenery also made the coastal areas desirable for residential development. While many of the coastal developments here never took-off as they did in nearby Gloucester, Magnolia, and Beverly, there are some notable summer colonies that sprouted up! In 1855, Eben B. Phillips an oil dealer in Boston, purchased undeveloped wooded lots and pastures, and slowly began to lay out roads and survey for developable lots for summer cottages on a peninsula near Pigeon Cove. The development was named “Oceanview” and it was marketed as the extreme point of Cape Ann. Development was very slow to materialize, and started in earnest in the 1870s. Eben Phillips built this summer cottage before 1877 (possibly as early as 1850), where he would spend summers until his death in 1879. The cottage retains much of its original character and is a rare survivor of the rustic style cottages which were built before the phase of larger Shingle and Queen Anne residences were built in later decades.

Whelen Cottage // c.1891

For the last cottage on Grindstone Neck, I present the stunning Whelen Cottage. Charles S. Whelen (1850-1910), a banker and philanthropist who served as one of the directors of the Gouldsboro Land Improvement Company and as one of several of its stock agents in Philadelphia, purchased a house lot for him and his wife Migonette Violett. The couple did not hire Lindley Johnson, like so many other cottage-holders did, but they worked with esteemed architect Wilson Eyre to design the home. The Whelens were typical of the type of person who chose to summer on Grindstone. While comfortably well off, they were not in a financial position to commission the sort of cottages built on an ever increasing scale in Bar Harbor. The property left the Whelen’s ownership in 1897, and the house was altered and enlarged in 1900. The large porte cochere, porch, and additional rooms added at this time by William Winthrop Kent, an alumni of H. H. Richardson’s office.