| Title | Artist | Medium & Support | Creation Date |
| Hemlock Pool | Twachtman, John Henry | Oil on canvas | c. 1900 |
| Outside the Big Tent | Bellows, George | Oil on canvas | 1912 |
| Salutat | Eakins, Thomas | Oil on canvas | 1898 |
| The Way of the Cross | attributed to Ryder, Albert Pinkham | oil on canvas | n.d. |
| Benjamin West | Allston, Washington | oil on canvas | n.d. |
| Fishing | Marin, John | Watercolor, graphite on wove paper | 1909 |
| Blue Sea, Crotch Island | Marin, John | Watercolor on wove paper | 1923 |
| Golf Course, East Gloucester | Prendergast, Maurice | watercolor, pastel, and graphite on wove paper | c. 1920-1923 |
| Summer, Sea, Window, Red Curtain | Hartley, Marsden | Oil on Masonite | 1942 |
| Sea Gulls—Gaspé | Avery, Milton | Oil on canvas | 1938 |
| Red Cart | Davis, Stuart | Oil on canvas | 1932 |
| Ridgefield | Man Ray | Oil on canvas | 1913 |
| Artist and Model | Avery, Milton | oil on canvas | c. 1939 |
| Figures on Green | Asawa, Ruth | Oil on Masonite | 1947-1948 |
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