From right to left:
#1011
#1009a: Margaret J. Stout & Co. Dry Goods
#1009: Victor Goldman & Son, Tailors
#1007: Robert C. Ware, Home Method Kitchen
#1005: Heath & Co., Confectioners
#1001-3: B.A. Freeman, Provisions
#999: C. H. Hitchcock, Druggist
incl. Streets

[Courtesy of the Digital Commonwealth (CC BY-NC-ND). From the Brookline Photograph Collection published by the Public Library of Brookline]