| Portrait, No. 3 | | 1934 | | | |
| Portrait, No. 3 | | 1935 | | | Third Prize |
| Portrait, No. 3 (Mr. Hugh Seaver) | | 1929 | | | First Prize |
| Portrait, No. 4 | | 1934 | | | |
| Portrait, No. 4 | | 1930 | | | |
| Portrait, No. 4 | | 1934 | | | Honorable Mention |
| Portrait, No. 5 | | 1930 | | | |
| Portrait, No. 5 | | 1930 | | | |
| Portrait, No. 5 | | 1929 | | | Third Prize |
| Portrait, Vinc | | 1933 | | | Honorable Mention |
| Portrait: Mother | | 1923 | | | |
| Portrait--Chinese | | 1922 | | | Second Prize |
| Portrait-Conrad Quimby | | 1926 | | | |
| Portrait-Theodore Sizer | | 1926 | | | |
| Portygee Neighborhood | | 1925 | | | Honorable Mention |
| Positano, Italy | | 1929 | | | |
| Positano, Italy | | 1933 | | | |
| Potential Steel | | 1932 | | | |
| Potted Plant | | 1934 | | | |
| Pouring Firt | | 1936 | | | |
| Prayer for Rain | | 1935 | | | |
| Preponderance | | 1929 | | | Honorable Mention |
| Pretty Hippopotamus | | 1939 | | | |
| Price Hill | | 1935 | | | |
| Priceless | | 1937 | | | Honorable Mention |
| Pride of the Prairies | | 1938 | | | |
| Primitive Man | | 1922 | | | |
| Primrose | | 1929 | | | First Prize |
| Primrose | | 1934 | | | |
| Primrose and Batik | | 1934 | | | |
| Primula | | 1930 | | | |
| Print No. 2 | | 1935 | | | |
| Print No. 8 | | 1935 | | | |
| Prisoner | | 1928 | | | |
| Procession in Czechoslovakia | | 1937 | | | |
| Productive Industry | | 1937 | | | |
| Proposal | | 1936 | | | |
| Provencal Fantasy - | | 1922 | | | |
| Provincetown | | 1937 | | | |
| Provincetown | | 1935 | | | |
| Provincetown | | 1936 | | | |
| Provincetown Artist | | 1929 | | | |
| Provincetown Houses, Provincetown, Massachusetts | | 1919 | | | |
| Provincetown Scene | | 1932 | | | |
| Psalm 43 | | 1933 | | | |
| Psalm 90 | | 1932 | | | |
| Pueblo | | 1936 | | | |
| Pueblo Ramada | | 1939 | | | |
| Pueblo Village | | 1936 | | | Honorable Mention |
| Puente Viejo at Ondarroa | | 1930 | | | |
