Joseph Reynolds House // 1698

This three-story wood-frame house is one of the oldest buildings in Bristol and the oldest known three-story building in Rhode Island. The home was built by Joseph Reynolds (1679-1759), a patriarch in the Reynolds Family, who later built the Reynolds-DeWolf House I featured previously. The house is five bays wide and three deep with the roof extending lower to the rear, giving the house a classic New England saltbox appearance. Joseph built this house, and also operated a tannery and gristmill on his land. The home is nationally significant as during the ownership of the house by his son Joseph II, Marquis de Lafayette occupied the north parlor chamber. Lafayette was a general in the Continental Army and was responsible for the defense of Bristol and Warren from September 7 to 23, 1778 during failed military operations to drive the British from occupied Newport. The home was added onto and altered in 1790 to give it the current design, with Federal detailing. The home remained in the Reynolds Family until 1930.

“Hey Bonnie Hall” // 1808-1944

Formerly located on the Poppasquash Peninsula in Bristol, Rhode Island, the William DeWolfe House, also known as Hey Bonnie Hall, was constructed in 1808 for William DeWolf (1762-1829) and his wife Charlotte Finney (1764-1829). William DeWolf was a member of the infamous DeWolf Family of Rhode Island, which is believed to have transported tens of thousands of enslaved people to the United States and Caribbean before the African slave trade was banned in Rhode Island. The Ocean State played a leading role in the transatlantic slave trade. Not only did Rhode Islanders have slaves—they had more per capita than any other New England state. The beauty of Hey Bonnie Hall, and its melodic name hid the dirty money with which it was built. With his extreme wealth, William hired Providence architect Russell Warren to construct the home in a high form of the Federal style. Eventually, the home was willed to Anna DeWolf, who married Nathaniel Russell Middleton, from a slave-owning family in Charleston, South Carolina (birds of a feather…). It was Anna Middleton who gave the house its curious name of “Hey Bonnie Hall”. When she was younger, she used to sing an old Scottish song called “Hey The Bonny Breast Knots” over and over again to delight her grandfather, William, the first owner of this home. After Anna’s death, the home was willed to her two unmarried daughters. The Great Atlantic Hurricane of 1944 proved fatal for the grand estate, when the front portico was ripped off the home and flew away. The damage was deemed too expensive to repair and the home was demolished that year.

Beckett’s Castle // 1874

On a rise above the Cape Elizabeth’s rocky shore stands Beckett’s Castle, a picturesque Gothic cottage of a century ago. Designed and built by the Portland literary figure Sylvester Beckett for his summer residence, the Castle was begun in 1871 and finished in 1874. It is said that Beckett constructed the cottage from local gray fieldstone largely with his own hands, though he must have had help, or fabricated this fiction as he would have in his own books. The home was patterned after a typical English castle, but on a much smaller scale, and is tucked away from the street. Sylvester Blackmore Beckett was born in Portland, Maine in 1812, as the son of English parents. Although never attending college, he acquired a modest education and became a prominent journalist and articulate writer. He was admitted to the bar in 1859 and spent much of his time administering and settling estates becoming well-connected in town. Beckett held massive parties in the home, and invitations to the social gatherings held there were highly prized; guests were served expansive dinners cooked in primitive fashion in a large fireplace. Sylvester Beckett died in 1882, and went to his only child, Lizzie. The home fell into disrepair in the 1970s, but was restored by the most recent owner. It was sold in 2018, and the listing photos show some great interior spaces.

312 Ocean House Road // c.1870

This charming home in Cape Elizabeth, Maine looks to have been built after the American Civil War, as an interesting Italianate cottage. The home is clad with scalloped shingle siding which works well with the paired round headed windows facing the street. The deep overhanging eaves are supported by brackets. Running under the eaves on the sides are octagonal windows, a very unique detail. The home is located at the center of town, away from the summer cottages which sprouted up along the rocky coastline in town starting around this time. It was converted into condominium units sometime in the late 20th century.

Warren House // 1913

This stunning townhouse on Beacon Street in the Back Bay neighborhood of Boston was constructed in 1913 for George Eddy Warren and his wife Frances Knowles Warren. The home, designed by Parker, Thomas & Rice, is one of the more elegant Classical Revival townhomes in the city, with its symmetrical, prominent bowfront, piano nobile with full-height windows, classical lintels, and thoughtful use of brick and stone construction. George E. Warren was a coal dealer, who was selected to head the U.S. Army’s Raw Materials Division during WWI for his expertise. During the war he was in charge of the fuel and forage division, overseeing an important aspect of 20th century warfare, petroleum manufacturing and distribution. His wife Frances was the daughter of Francis B. Knowles, a co-founder of Rollins College in Florida, the oldest institution of higher learning in the state of Florida. Frances volunteered her time in Boston as President of the YWCA, progressing women’s empowerment and social justice in the city. After successive ownership, the townhome was acquired by Emerson College and combined with its neighbor on the interior. In 2000, the home was reverted back to a residence and houses two condominium units.

Frederick W. Lewis Mansion // 1876

The Frederick W. Lewis Mansion in Newport, New Hampshire is a unique, late-Second Empire home constructed of brick. The home was built in 1876 for Frederick W. Lewis, a merchant who climbed the ranks as a young man, eventually purchasing the store he worked at as a 14-year-old. In 1862, he became cashier of the Sugar River Bank, and held the position until 1865, when the bank was re-organized as a national bank, taking the name of “The First National Bank of Newport.” He then leveraged his position to get into local politics, and took an active role in the development of the town, even incentivizing the railroad to build a stop in town. From this wealth and position, he built this large home. After his death, the home went to his son. By the 1940s, a group of over 30 residents of town purchased the home as a Veteran’s Home. By the end of the 20th century, the home was occupied by the Newport Earth Institute, a school created by esoteric historian and researcher Reverend Vincent Bridges, who died in 2014. The property appears to be vacant now and the home is in much need of some TLC.

Wheatleigh // 1893

Designed in 1893 by the Boston architectural firm of Peabody and Stearns, Wheatleigh is an early example of Renaissance Revival architecture which became popular for country estates in the early 20th century. The estate was constructed for Henry Harvey Cook, who purchased over 250-acres of forest and lawns overlooking Lake Maheenac for his summer “cottage”. Cook was a New York-based businessman who made his fortune in the railroad and banking businesses, and he wanted a summer house to escape to every year. He named his home “Wheatleigh” as an homage to his family’s ancestral home, Wheatley, Oxfordshire. The mansion is approached by a circular drive that terminates in a formal entrance court partially enclosed by a buff brick wall and evergreen trees, centered on an octagonal marble fountain decorated with a shell and leaf motif. Upon Cook’s death in 1905 Wheatleigh passed to his daughter, Georgie, the Countess de Heredia. Under her ownership the formal garden was opened for evening worshipping services and musical events. Following de Heredia’s death in 1946 the property was divided and changed hands numerous times. In 1976 the mansion and 22 acres were opened as a resort hotel, known as the estates historic name. The Wheatleigh remains one of the most esteemed luxury hotels in the country.

Wheatleigh Caretaker’s house (1893)

Merwin House // 1825

In about 1825, Francis and Clarissa Dresser built this charming brick Federal house in the rural town of Stockbridge, MA. Just 25 years later, the railroad arrived to town, connecting it to Connecticut and New York to the south, opening the town up as a leisure destination for wealthy city dwellers looking to escape the noise and congestion of the city. The period following the Civil War through World War I saw the Gilded Age reach the Berkshires. With artists, writers, financiers, and industrialists flocking to the rural hills of western Massachusetts for seasonal escapes. In 1875, William and Elizabeth Doane, wealthy New Yorkers, purchased Merwin House from the Dresser family to use as a summer retreat. As the Doane family grew to include two young daughters, Vipont and Elizabeth, they added a Shingle Style side addition to the original brick structure. The home became known as “Tranquility”, even after the home was willed to daughter Vipont. After a couple marriages, Vipont married Edward Payson Merwin, a New York stockbroker. Historic New England acquired Merwin House in 1966, shortly after the death of Marie Vipont deRiviere Doane Merwin, known as Vipont. It was her desire to leave Merwin House as a museum, as her will states, “as an example of an American culture which is fast becoming extinct.” The space is occasionally open for tours and is partially occupied by the Housatonic Valley Association.

Hannah Harris House // c.1772

This cute little Georgian home in Brookline was built around 1772 for Hannah Winchester Harris, a widow at the time. Hannah’s husband, Timothy died in 1772 and it appears the widow had this small gambrel-roofed home constructed sometime soon after. Ms. Harris died in 1805 and the home was occupied by a new family, who added the saltbox addition. The home is today owned by the Town of Brookline, who maintain the building through the Brookline Historical Society. the home sits on the boundary of the old Weld Estate.

Clapp House and Barn // 1877

This Italianate home with attached barn was built in 1877 for William and Almira Clapp. William worked as a schoolteacher and shopkeeper in Boston before meeting Almira, marrying her, and moving to her home town of Hollis, New Hampshire, a big change of pace from Boston. The couple eventually built this home, behind an older home and lived here until their deaths. A subsequent owner demolished the older colonial in front to establish this farmhouse’s presence on the main road. The home was eventually purchased by Charles Stratton, and the Stratton family lived here for decades. The home and barn are well preserved examples of Victorian era agricultural and residential architecture in southern NH.

Conant House // c.1800

This stunning Federal home in Hollis, NH was built around 1800 for Josiah Conant, likely as a wedding gift to his new wife, Lucy. Conant was a cabinetmaker by trade and his shop was located across the street, and according to local sources, he used his woodworking skills on the inside and out of his home, with intricate details including mantels, wainscoting and exterior cornice. Half of the second floor was originally a dance hall and was later used for a reading or writing school school run by Lucy. The brick-end Federal home features a Palladianesque entry with sidelights and an arched transom with historic windows!

Charles Perry House // c.1830

Charles C. Perry (1795-1870) was a wealthy nineteenth-century shipowner and sea captain and a prominent figure within Southport’s community. After his father’s death in 1814, when Charles was just 25, he inherited a large sum of money from his father’s will and followed his footsteps as a career. Miah Perry’s will stipulated that in order to keep the family together, members were to reside at the family home for five years from his death if neither of the daughters married; “but in case they remain unmarried at the expiration of five years…my estate shall not be divided until eight years from my decease unless one of the said daughters should marry…partition may be immediately thereafter made.” Talk about pressure to get married!

It is unclear if any daughters got married before, (Julia, one daughter died in 1821 at 22 years old). That same year, Charles Perry seemingly got his part of the inheritance and acquired the land upon which this house stands. He was then twenty-six years old and unmarried. He appears to have built it later as a blending of the Federal and Greek Revival styles, perfectly complimenting each other.

William Bulkley House // 1767

The William Bulkley house was built circa 1767 and is one of the few extant pre-Revolution houses in Southport. In 1779, during the Revolutionary War, Fairfield and vicinity were burned and ravaged by Tory Loyalists. Only eleven houses throughout the region survived the burning; one of four in Southport was the Bulkley residence.

Ms. Hetty Gookin House // 1874

Warren Demman Gookin (1810-1874) was born in Haverhill, New Hampshire. He was educated at Haverhill Academy and Dartmouth College, graduating from the latter institution in 1830. In 1835 he went to Cuba where he remained for ten years as a sugar planter. Later, he was engaged in a mercantile business in Oregon, finally settling in Brooklyn, NY and working as a shipping merchant in New York City until his death in 1874. After his death, his widow Hetty moved back to her hometown of Southport, CT and built this large home. Later this was the home of Mrs Gookin’s stepdaughter, Mrs Edwin Waterman.

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!