399 Marlborough was designed by architect J. Pickering Putnam and built in 1884 by John Mack, Jr., and John McDonald, builders, as the home of Dr. William Herbert Rollins and his wife, Miriam W. (Phillips) Rollins. They had been married in April of 1882 and previously had lived at 112 Charles. Miriam Rollins is shown as the owner on the original building permit application, dated July 25, 1884, and as the owner on the 1888, 1898, 1908, 1917, and 1928 Bromley maps.
William Rollins was a dentist, and was a pioneer in the use of x-ray technology. When he and his wife lived on Charles Street, he maintained his offices at 28 Chestnut. When they moved to 399 Beacon, he moved his office to 248-250 Marlborough, sharing the office with Dr. Wilbur Bates Parker, who also lived there. Dr. Rollins continued to maintain his office there until about 1911.
Miriam Rollins died in 1925. William Rollins continued to live at 399 Marlborough until his death in October of 1929. The Heirs of Miriam Rollins were the assessed owners through 1931.
In the Fall of 1931, 399 Marlborough became the Chi Sigma Chi (Boston University) fraternity house. It was the assessed owner of 399 Marlborough from 1932 through 1940 and is shown as the owner on the 1938 Bromley map.
Chi Sigma Chi continued to maintain its fraternity house at 399 Marlborough until about 1938.
By 1939, 399 Marlborough was the Alpha Kappa Psi fraternity house.
The property was shown as vacant in the 1940 and 1941 City Directories.
The Smithsonian Institution in Washington DC was the assessed owner of 379 Marlborough in 1941 and 1942.
In April of 1941, the Holden Realty Trust applied for (and subsequently received) permission to convert the property from a fraternity house into a lodging house.
In the spring of 1942, the Holden Realty Trust acquired 399 Marlborough from the Smithsonian Institution. The transaction was reported in the Boston Globe on March 29, 1942.
By 1942, 399 Marlborough was the home of Earl R. Westcott, a salesman, and his wife, Esther J. (Thrasher) Westcott, who operated it as a lodging house. They previously had lived at 11 Durham. Earl Westcott et al were the assessed owners of 399 Marlborough from 1943 through 1949.
The property changed hands, remaining a lodging house, and by 1965 was owned by James J. Maher and Myrtle A. Maher, who operated it as the Marlboro Arms Guest House.
In February of 1966, James Maher applied for (and subsequently received) permission to remove the second floor oriel window, replacing it with four new windows and brick.
By mid-1966, 399 Marlborough had been acquired by Franklyn G. Bill and Sidney R. Handler, trustees of the C & S Realty Trust. They continued to operate it as a lodging house. In December of 2008, the Trust transferred the property to the 399 Marlborough LLC.
399 Marlborough remained a lodging house in 2015.