388 Marlborough was designed by Cummings and Sears, architects, and built in 1885 by James Smith, mason and John J. McNutt, carpenter, for wholesale grocer Alexander Pomroy Sears and his wife Elizabeth Prescott (Jones) Sears. Alexander Sears is shown as the owner on the original building permit application, dated April 7, 1885, and on the final building inspection report, dated December 15, 1885. Elizabeth P. Sears is shown as the owner on the 1888 Bromley map.
Alexander and Elizabeth Sears lived at 388 Marlborough during the 1885-1886 and 1886-1887 winter seasons. They previously had lived at 34 Dartmouth. By 1888 had moved to 68 Huntington. By 1889, they had made their home in Brookline.
By the 1887-1888 winter season, 388 Marlborough was the home of John Van Houghton Lewis and his wife, Amy L. (Field) Lewis. He was a cotton oil manufacturer from Cincinnati. Amy Lewis is shown as the owner on the 1890 Bromley map. They continued to live there in 1891, but moved thereafter to Milton.
During the 1891-1892 winter season, 388 Marlborough was the home of Mr. and Mrs. L. Higginson, probably Louis Higginson, a merchant, and his wife, Annie Louise (Eastman) Lockwood Higginson. They had lived at 386 Marlborough during the previous season. They moved from 388 Marlborough by the 1892-1893 season.
The house was not listed in the 1893 and 1894 Blue Books.
By the 1894-1895 winter season, 388 Marlborough was the home of Dr. William Elbridge Boardman and his wife, Mary Bangs (Bryant) Boardman. They previously had lived in the Longwood district of Brookline and before that at 233 Marlborough. Mary Boardman is shown as the owner of 388 Marlborough on the 1895, 1898, 1908, 1917, 1928, and 1938 Bromley maps, and was the assessed owner through 1941.
William Boardman was a physician and maintained his office at 388 Marlborough. The Boardmans’ unmarried son, Dr. William Parsons Boardman, lived with them. He was a dermatologist and later a professor at Tufts Medical School.
William Boardman died in January of 1921. Mary Boardman continued to live at 388 Marlborough with William Parsons Boardman.
Mary Boardman died in April of 1939. William P. Boardman continued to live and maintain his medical offices at 388 Marlborough until about 1951. He was the assessed owner from 1942 through 1951.
By 1952, 388 Marlborough was owned by Jennie L. Goodman, who was the assessed owner that year. In January of 1952, she applied for (and subsequently received) permission to convert the property from a single-family dwelling into nine apartments.
The property changed hands, including going through foreclosure, and in June of 1980 was purchased by the 388 Marlborough St. Corp.
In January of 1981, it converted the property into nine condominium units, the 388 Marlborough Street Condominium.