25-27 Massachusetts Avenue was designed by architect Ernest N. Boyden and built in 1891 by John Hurley, builder, as a three-family building and store. It was built for real estate dealer Seth Russell Baker, one of three contiguous multi-unit buildings he had built at the southwest corner of Beacon and Massachusetts Avenue: 21-23 Massachusetts Avenue, 491 Beacon (25-27 Massachusetts Avenue), and 495-497 Beacon.
At about the same time, Ernest Boyden also designed two multi-family dwellings for Seth Baker at 479-481 Beacon, and probably a third at 483 Beacon (razed for construction of the Hotel Cambridge in about 1898).
Seth Baker is shown as the owner of 25-27 Massachusetts Avenue on the original building permit application, dated February 28, 1891. On the application, the address is shown as 466-468 West Chester Park; it changed to 25-27 Massachusetts Avenue when West Chester Park was renamed on March 1, 1894.
By 1892, 25-27 Massachusetts Avenue was owned by James E. Moore, who lived in one of the apartments and operated a provisions store there with his partner, Orrin W. Tweed. James Moore is shown as the owner on the 1895, 1898, 1908, and 1917 Bromley maps.
He married in August of 1893 to Mrs. Anna Delight (Souther) Graves, the former wife of Edwin Graves. After their marriage, they lived in Brookline.
By 1898, an additional (fifth) story had been added to 25-27 Massachusetts Avenue and to 23 Massachusetts Avenue.
James Moore continued to operate his provisions store at 25-27 Massachusetts Avenue, with Orrin Tweed until about 1901 and then alone until about 1926.
By 1928, 25-27 Massachusetts Avenue was owned by Caracostas Brothers, Inc., confectioners. They are shown as the owners on the 1928 and 1938 Bromley maps.
The principals of Caracostas Brothers were Angelos, John E., James, and Peter Caracostas, and Louis Pappas.
The Caracostas Brothers operated the Esplanade Restaurant (later the Esplanade Café) at 25 Massachusetts Avenue.
In October of 1949, Louis Pappas filed for (and subsequently received) permission to construct an addition at the rear of 25 Massachusetts Avenue, connecting with the rear wall of 495-497 Beacon. No opening was made between 25 Massachusetts Avenue and 495 Beacon. However, by 1950, the Esplanade Café was operating at both 25 Massachusetts Avenue and 495-497 Beacon, with the restaurant’s Zebra Lounge (with live entertainment) at 495-497 Beacon. In November of 1950, Louis Pappas applied for an license to serve alcoholic beverages at the Esplanade Café, indicating both addresses.
The Esplanade Café continued to be located at 25 Massachusetts Avenue and 495-497 Beacon until the mid- to late 1950s.
In 1961, Kennedy Café Inc. opened The Crossroads of Boston restaurant and bar at 495-497 Beacon and at 25 Massachusetts Avenue.
In February of 1962, it applied for permission to cut an opening between 495-497 Beacon and 25 Massachusetts Avenue to facilitate its operating in both locations (as had the Esplanade Café). The permit was subsequently abandoned and by 1963, 25 Massachusetts Avenue was the location of the Chung Sai Restaurant. The Crossroads continued to operate at 495 Beacon.
It was probably at about this time that the lots for 25-27-Massachusetts Avenue and 495-497 Beacon were adjusted, and a 6′ x 30′ strip of land at the rear of 25-27 Massachusetts was transferred to 495-497 Beacon. The transfer added 180 square feet to 495-497 Beacon (increasing the lot size from 2,232 sf to 2,412 sf., and reducing the lot size at 25-27 Massachusetts Avenue from 1,441 sf to 1,261 sf. The new lot lines were contained in a plan by William S. Crocker, Inc., surveyors, and filed with the Land Court on December 3, 1966.
By the 1970s, and probably before, 25-27 Massachusetts Avenue was owned by Max and Bertha (Levitt/Leavitt) Miller, who also owned 491 Beacon (21-23 Massachusetts Avenue).
In May of 1979, David G. Ricupero purchased 25-27 Massachusetts Avenue and 491 Beacon from the Millers’ three sons: Eugene, Sidney, and James Miller.
In March of 1981, David Ricupero filed for permission to combined 491 Beacon and 25-27 Massachusetts into one property, with the address to be 491 Beacon and the combined occupancy to be eleven apartments, a retail store, and a restaurant, which he indicated was the existing occupancy. He subsequently abandoned the permit.
491 Beacon remained a residential and commercial building in 2014.