His talent as an artist was recognized and encouraged early by his art instructor, Theophilus Hope D'Estrella (1851-1929), and in 1890 Redmond enrolled at the California School of Design in San Francisco studying for three years under Arthur Matthews (1860-1945) and Amedee Joullion (1862-1917). He won the W. E. Brown medal of excellence, and in 1893 was awarded endowment funds from the California School of the Deaf that enabled him to continue his art studies at the Academie Julian in Paris under Jean Paul Laurens and Benjamin Constant.
His talent continued to blossom, and in 1895 his huge painting "Matin d'hiver" was accepted at the Paris Salon. In 1898 Redmond moved to California, and in 1899, he married Carrie Ann Jean, who attended the Illinois School for the Deaf. The Redmonds decided to make California their home, and at various times, they lived in Los Angeles, San Mateo (1910), Tiburon and Parkfield (Monterey County), California.
Deeply inspired by the California landscape, Redmond painted primarily coastal landscapes between Laguna Beach and Monterey, California. By 1905 Redmond had become widely recognized as a leading California landscape painter, known for his impressionist landscapes of Northern and Southern California. Through his distinctive style Redmond showed a remarkable understanding of color and depth, always painting with sympathies to the delicate beauties of nature. With a style that was sometimes compared to Monet and Pissarro by the art critics of his day, Redmond glorified California's sunsets with soft moody glows and he adorned the state's expansive coastal views and rolling hill scenes with golden poppies (the California State flower) and blue lupine. He painted enchanting coastal nocturnes, San Pedro harbor, the majestic oaks of Monterey and scenes of Catalina Island.
Redmond held memberships in the Bohemian Club, California Art Club, Laguna Beach Art Association and San Francisco Art Association. He won a medal at the Louisiana Purchase Exposition in 1904 and later the silver medal at the Alaska-Yukon Pacific Exposition, Seattle, 1909.
His works can be found in public collections including The Oakland Museum, Oakland, California; New York City Museum, New York; Los Angeles County Museum of Art, California; Laguna Art Museum, Laguna Beach, California; Stanford University Museum of Art, California; Mills College Art Gallery, Oakland, California; California School for the Deaf, Fremont, California; National Center on Deafness at California State University Northridge; Springville Museum of Art, Utah; Bancroft Library, University of California at Berkeley.
