34 Gloucester was built in 1880 by Frank Jones and E. S. Landes, builders, for building contractor William Seavey Rand, one of four contiguous houses (30-36 Gloucester) designed as a symmetrical composition and built for speculative sale. William Rand is shown as the owner on the original permit applications, dated May 26, 1880. The architect of the buildings is not indicated on the permit applications.
By the 1882-1883 winter season, 34 Gloucester was the home of Charles Whipple Smith, a real estate and insurance broker, and his wife, Harriet Elizabeth (Farnsworth) Smith. He is shown as the owner on the 1883 and 1888 Bromley maps. They continued to live there in 1889, but had moved to 302 Marlborough by 1890.
By the 1889-1890 winter season, 34 Gloucester was the home of Mrs. Meta Telfair (Wilson) Pitts, the widow of Charles Hall Pitts. Charles Pitts had been a bank cashier; he had died in November of 1887, less than a month after their marriage. They were living at the Parker House hotel at the time of his death. Meta Pitts is shown as the owner of 34 Gloucester on the 1890 and 1895 Bromley maps. She continued to live there until her death in January of 1897.
34 Gloucester was not listed in the 1898 Blue Book.
By 1898 34 Gloucester was owned by Walter Yates and his wife, Marie (Howe) Yates. Maria H. Yates is shown as the owner on the 1898 Bromley map. They had married in July of 1897 and probably purchased 34 Gloucester as their home. However, they first lived at 31 Gloucester and then at 29 Gloucester, in both cases with Marie (Howe) Yates’s father, John Chase Howe, and his second wife, Mabel Allison (Yates) Howe, who also was Walter Yates’s sister.
By the 1898-1899 winter season, the Yates leased 34 Gloucester to Linzee Prescott and his wife, Frances (Brown) Prescott. They previously had lived in Greenwich, Connecticut. He was treasurer of the Atlantic Cotton Mills. The Prescotts continued to live at 34 Gloucester in 1901, but had moved to 30 Gloucester by 1901-1902 winter season.
By the 1902-1903 winter, 34 Gloucester was the home of Walter and Marie Yates. She continued to be shown as the owner on the 1908 Bromley map. John Howe had died in September of 1901 and Mabel (Yates) Howe lived with the Yates at 34 Gloucester.
John Howe had been a dye stuff, paint, and isinglass dealer in the firm of Howe & French. Walter Yates had been a ship chandler prior to John Howe’s death. He subsequently became treasurer of Howe & French. In 1908, Marie Yates and Mabel Yates Howe purchased Howe & French from John C. Howe’s executors.
By the 1910-1911 winter season, 34 Gloucester was the home of Charles Anderson Proctor and his wife, Grace (Hopkins) Proctor. They previously had lived at 42 Gloucester. Grace H. Proctor is shown as the owner of 32 Gloucester on the 1912 and 1917 Bromley maps.
Charles Proctor was a leather merchant. He retired in 1918.
The Proctors continued to live at 34 Gloucester during the 1921-1922 season, but had moved thereafter and by the 1923-1924 season were living at 297 Commonwealth.
During the 1922-1923 winter season, 34 Gloucester was the home of real estate broker and investor John Babson Thomas and his wife, Marietta (Shea) Reece Thomas. John Reece, her son by her previous marriage to John Reece (inventor of the buttonhole machine), lived with them. They had all previously lived at 315 Commonwealth. They had moved from 34 Gloucester by the next season, and were living at 20 Hereford by the 1924-1925 season.
By the 1923-1924 winter season, 34 Gloucester was the home of Brigadier General Charles H. Cole and his wife, Grace Fletcher (Blanchard) Cole. They previously had lived at 90 St. Mary’s. Grace F. Cole is shown as the owner of 34 Gloucester on the 1928 and 1938 Bromley maps.
General Cole served as Chairman of the Boston Police Commission from 1905 to 1907, and as Boston’s Fire Commissioner from 1912 to 1914. From 1914 to 1916, he was Adjutant General of Massachusetts. During the World War I, he served in France with the rank of Brigadier General (his brother, Edward Ball Cole, was killed at the Battle of Belleau Wood). In 1928, he was the Democratic nominee for Governor, losing to Frank G. Allen. In 1934, he was defeated for the Democratic nomination for Governor by Boston Mayor James Curley.
Grace Cole died in February of 1949. Charles Cole continued to live at 34 Gloucester until shortly before his death in November of 1952.
By 1953, 34 Gloucester was owned by Abraham S. Boyadjian. In March of 1953, he applied for permission to convert the property from a single-family dwelling into a lodging house with an office on the first floor. His application was denied and he did not appeal the denial.
Notwithstanding the denial, the property was used for these purposes. From 1953 to about 1958, it was the location of the Spaulding Brick Company (operated by Elizabeth S. Spaulding, who lived in Sharon), and also was a multiple dwelling.
By 1964, 34 Gloucester was owned by the Mifro Realty Trust. In August of 1964, it applied for (and subsequently received) permission to convert the property from a single-family dwelling into a lodging house.
In 1965, it was the Saint Philip Neri Student Residence. It moved to 11 Gloucester in about 1966.
In 1966, Chamberlayne School and Chamberlayne Junior College acquired 29 Gloucester, 34 Gloucester, and 278–280–282 Commonwealth from the First Community Investment Company. Chamberlayne already owned 260–262–264–266–270–274–276 Commonwealth, which it had acquired earlier in the 1960s.
Chamberlayne may have used 34 Gloucester as a dormitory; however, was shown as vacant in the 1967-1972 City Directories.
In the mid-1970s, Chamberlayne went bankrupt and in June of 1975, it transferred 29 Gloucester, 34 Gloucester, and 278-280-282 Commonwealth to Bernard P. Rome of Newton, Trustee in Bankruptcy.
In October of 1976, 34 Gloucester was purchased from Bernard Rome by Arthur E. Simons. On the same day, he transferred the property to himself and Ronald Luccio as trustees of the B & L Trust.
In November of 1976, 34 Gloucester was purchased by Rafael Pons, trustee of the R. S. V. P. Realty Trust. In December of 1978, he applied for (and subsequently received) permission to legalize the occupancy as three apartments and a retail store, which he indicated was the existing condition.
In November of 1983, he applied for permission to cut doors between 34 Gloucester and 36 Gloucester (279A-279B Newbury) at the basement level and install a kitchen for use in conjunction with a restaurant to be located at the other property. The application was denied and his appeal was dismissed.
The property changed hands, remaining a mixed residential and commercial building in 2014.