CIRCA 2ND CENTURY A.D.

Isaac Newton Phelps Stokes (1867-1944) was an American architect and philanthropist who pioneered social housing and co-authored the 1901 New York tenement house law. A portrait of Phelps Stokes and his wife painted by John Singer Sargent in 1897 forms part of the collection of the Metropolitan Museum of Art.
For two similar heads with curling ivy leaves surmounting grape bunches, see "Dionysus," in Lexicon Iconographicum Mythologiae Classicae, Vol. III, Zurich and Munich, no. 201 A and B. These two heads are said to be Roman copies of works attributable to the circle of Praxiteles.