32 Gloucester was built in 1880 by Frank Jones and E. S. Landes, builders, for building contractor William Seavey Rand, one of four contiguous houses (30-32-34-36 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 March of 1882, 32 Gloucester was the home of Dr. Frederick William Payne and his wife, Gertrude (Dunlap) Payne. They previously had lived at 677 Tremont. He is shown as the owner of 32 Gloucester on the 1883 and 1888 Bromley maps.
Frederick Payne was a physician with offices at the Hotel Pelham, at the southwest corner of Boylston and Tremont.
The Paynes continued to live at 32 Gloucester during the 1889-1890 winter season. By the 1890-1891 season, they were living at the Hotel Austerfield at 7-9 Massachusetts Avenue.
By the 1889-1890 winter season, 32 Gloucester was the home of Laura G. Sears and her sister, Madeleine Sears. Laura Sears in shown as the owner on the 1890, 1895, and 1898 Bromley maps.
32 Gloucester was not listed in the 1908 Blue Book.
In early 1908, 30 Gloucester was purchased from Laura (Sears) Hall by real estate broker and trustee Paul Mascarene Hamlen and his wife, Agnes Dorothy (Devens) Hamlen. The transaction was reported in the Boston Globe on March 1, 1908. They previously had lived at 845 Boylston. He is shown as the owner on the 1908, 1917, 1928, and 1938 Bromley maps. They also maintained a summer home in Wayland.
The Hamlens’ two unmarried sons, Devens Hamlen and Nathaniel Hamlen, lived with them. Devens Hamlen, a merchandise broker, married in May of 1934 to Barbara Young and moved to 42 Gloucester; Nathaniel Hamlen, a real estate agent, continued to live with his parents.
Agnes Hamlen died in January of 1936. Paul Hamlen remarried in May of 1936 to Dorothy (Draper) Gannett, the widow of Thomas Brattle Gannett, Jr., and daughter of former Governor Eben Sumner Draper. They subsequently maintained their home in Milton and Wayland.
Nathaniel Hamlen continued to live at 32 Gloucester, joined by his brother, Devens, after his divorce in March of 1936.
By 1938, they had leased the house to William B. Summers and C. Hunkins Webster, who operated their Boston School of Interior Decoration in the house. They remained there in 1939.
Paul M. Hamlen died in July of 1939.
In February of 1940, the estate of Paul Hamlen filed for (and subsequently received) permission to convert the property from a single-family dwelling into a lodging house.
32 Gloucester was shown as vacant in the 1940 City Directory.
By 1940, 32 Gloucester was the home of James Everett Preston, a shipwright, and his wife, Irene Elizabeth Preston, who operated it as a lodging house. They previously had lived at 526 Massachusetts Avenue. They continued to live at 32 Gloucester, and operate a lodging house, until the early 1960s.
The property changed hands and in February of 1972 was purchased by Jose Leopoldo Romero, Jr., trustee of the P & L Realty Trust. On the same day, he also purchased 30 Gloucester.
Jose Romero remodeled 30 Gloucester into a restaurant, Casa Romero, on the basement level, with a single-family dwelling on the upper floors, which became his home. 32 Gloucester remained a lodging house.
In July of 1974, the P. &. L. Realty Trust applied for (and subsequently received) permission to combine 30 and 32 Gloucester into one property, construct a one-story rear addition 22.3 feet by 22 feet in size, and change the occupancy to be one restaurant and five apartments (with “the present street numbering to be retained”). Jose Romero subsequently extended his restaurant into the basement of 32 Gloucester.
In April of 1980, G. Kinnear Pash and his wife, Deborah T. Pash, purchased 32 Gloucester from Jose Romero.
In February of 1981, Ken and Deborah Pash applied for (and subsequently received) permission to convert 32 Gloucester from a lodging house into four apartments and to allow the basement to continued to be used restaurant dining and storage as an ancillary use to the restaurant (Casa Romero) at 30 Gloucester.
In January of 1998, Gary J. Kleeman and Mary T. Kleeman, trustees of the Kleeman 32 Gloucester Street Realty Trust, purchased 32 Gloucester from Ken and Deborah Pash. In November of 1998, the Kleemans applied for (and subsequently received) permission for the storage area of the basement to be used for additional dining space by Casa Romero at 30 Gloucester.
32 Gloucester remained a mixed residential and commercial building in 2014.