306 Marlborough was designed by architect Frederic H. Moore and built in 1878 by Daniel W. Beckler, builder, and Michael Nolan, mason, on lot 3 of land formerly owned by Harvey Jewell, one of five contiguous houses (302-304-306-308-310 Marlborough) built for speculative sale. Daniel Beckler is shown as the owner on the original building permit application, dated January 2, 1878. Harvey Jewell is shown as the owner (and Daniel Beckler as the former owner) on the building inspection dated December 23, 1878. Daniel Beckler also had built six contiguous houses across the street (309-311-313-315-317-319 Marlborough) between 1874 and 1877.
By the 1879-1880 winter season, 306 Marlborough was the home of George Addison Sawyer, a haberdasher, and his wife, Hannah E. (Russell) Sawyer. They previously had lived in the Longwood district of Brookline. C. U. Cotting, et al, trustees, are shown as the owners of 306 Marlborough on the 1883 Bromley map, and Hannah E. Sawyer is shown as the owner on the 1888, 1898, and 1908 Bromley maps.
The Sawyers’ three children — Mary (Mamie) J. Sawyer, Frederick Russell Sawyer, and George Addison Sawyer, Jr. — lived with them. Hannah Sawyer’s niece, Grace L. Dow, an artist, also lived with them. She was the daughter of Hannah Sawyer’s sister, Martha M. Russell, and her husband, Nahum M. Dow.
Fred Sawyer, who worked in his father’s haberdashery story, married in November of 1878 to Cora F, Austin. After their marriage, they lived in Melrose. Mamie Sawyer died in May of 1886 and Grace Dow died in August of 1890.
In February of 1892, their son, George A. Sawyer, Jr., married to Isabel Finch. After their marriage, they lived with George and Hannah Sawyer at 308 Marlborough. He died in September of 1897 and his widow continued to live with his parents.
Hannah Sawyer died in December of 1907. George Sawyer and his daughter-in-law, Isabel, continued to live at 306 Marlborough until his death in December of 1910, after which she moved to Passaic, New Jersey.
306 Marlborough was not listed in the 1912 and 1913 Blue Books.
By the 1913-1914 winter season, 306 Marlborough was the home of George and Hannah Sawyer’s son, Fred Sawyer, who had inherited his father’s haberdashery store and continued to operate it. He previously had lived in West Roxbury. He is shown as the owner of 306 Marlborough on the 1917 Bromley map.
Fred Sawyer’s first wife, Cora, died in June of 1905. He remarried in August of 1907 to Edna Willard (Brooks) Prescott. They separated by 1913. In about 1916 he married again, to Hazel McClary. They lived at 306 Marlborough and also maintained a home in Swampscott.
In 1924 and 1925, Earl Gill, a salesman with Frederick Sawyer’s haberdashery, lived at 306 Marlborough with the Sawyers.
The Sawyers continued to live there during the 1925-1926 winter season, but moved thereafter to 304 Commonwealth.
In the summer of 1926, 306 Marlborough was purchased from Frederick Sawyer by department store heir Harold Leufroi Chalifoux and his wife, Elizabeth Alice (Burrage) Chalifoux. The transaction was reported n the Boston Globe on August 18, 1926. They previously had lived at 230 Commonwealth. They also maintained a home in Beverly. Elizabeth Chalifoux’s mother, Alice H. Burrage, is shown as the owner of 306 Marlborough on the 1928 and 1938 Bromley maps.
On August of 1926, Elizabeth Chalifoux filed for (and subsequently received) permission to remodel the house, adding a new bay at the second story in the rear. The addition was designed by architect William Chapman.
In about 1935, they were joined at 306 Marlborough by Ernest Harvey Pentecost, a widower, and his children. They previously had lived in Brookline. They also maintained a home in Topsfield. Ernest Pentecost was a former sea captain, having served as captain of the Cunard Line’s Saxonia from 1897 until his retirement soon after his marriage in November of 1908 to Marion Wentworth Peirce (who died in 1921). During World War I he served as a flotilla commander in the British Navy.
The Chalifoux and the Pentecosts continued to live at 306 Marlborough until about 1941. Harold and Elizabeth Chalifoux moved to Beverly and Santa Barbara, California; Ernest Pentecost moved to an apartment at 1 Gloucester.
In October of 1941, 306 Marlborough was purchased from Alice Burrage by real estate dealer Henry Joseph O’Meara. The transaction was reported in the Boston Globe on October 19, 1941.
The house was shown as vacant in the 1942 City Directory.
By late 1941, 306 Marlborough was owned by Mathew J. Mansworth. In December of 1941, he filed for (and subsequently received) permission to convert the property from a single-family dwelling into three apartments.
By 1955, 306 Marlborough was owned by H. Leon Sharmat. By that time, the property had been remodeled to be five, rather than three, apartments. In September of 1955, he applied for permission to convert the property from five apartments into five apartments and a dance studio. His application was denied and he did not appeal the denial.
The property changed hands and in December of 1981 was purchased by Julius R. Cavadi, trustee of the 206 Marlborough Street Renewal Trust. In March of 1984, he filed for (and subsequently received) permission to legalize the occupancy of 306 Marlborough as five apartments, noting that a “prior owner and mortgagee purchased property as five family on October 10, 1962, and had continuously used it for that purpose.”
In June of 1984, Edward F. Godfrey and his wife, Judith C. Godfrey, purchased 306 Marlborough from Julius Cavadi In August of 1984, they filed for (and subsequently received) permission to convert the property back into a single-family dwelling.
In February of 2001, Andrew G. Winton and his wife, Suzanne, purchased 306 Marlborough.
In November of 2003, the Wintons entered into a “Preservation Restriction Agreement” with the National Architectural Trust for the purpose of ensuring the preservation of 306 Marlborough’s exterior.
The property changed hands. It was assessed as a two-family dwelling in 2014.