Don Sondag and Casa Feliz have a long history together. One of the city’s most renowned artists has created spectacular paintings of one of its most renowned historic homes over the years—beginning back in the days before the James Gamble Rogers II architectural masterpiece was hauled from its original Lake Osceola lot on North Interlachen Avenue to its current location on North Park Avenue adjacent to the Winter Park Golf Course.
Can you believe that all happened 25 years ago? “I grew up here and saw Casa Feliz many times from the road and the lake,” recalls Sondag, known for his portraits of prominent Central Floridians and his landscapes of scenic areas in Winter Park.
“I remember my mom pointing out the home when we would drive by on Interlachen and asking what I thought of it,” he continues. “I told her that it was beautiful and she said it had an elevator. I thought that was really cool.”
Years later, after the endangered structure was saved from demolition and plans were made to move it, architect Jack Rogers—brother of Gamble who had led the grassroots rescue effort—asked Sondag to paint a picture of the house before it was moved for restoration and repurposing. That image, shown on this page, still hangs above the parlor fireplace at the Casa Feliz Historic Home Museum.
Once the relocation was completed, Sondag was commissioned to paint a collage-like image of key participants in the herculean effort. Then, just last year, he was asked to paint a new rendering of the home to mark its silver anniversary as a community venue. That photorealistic work appears on the cover of this issue of Winter Park Magazine.
Sondag, who is in fact the magazine’s most prolific cover artist, has a BFA from the Rhode Island School of Design and studied painting and portraiture at the National Academy of Design and the Art Students League in New York City. Early in his storied career he did portrait illustrations for Harcourt School Publishers.
In addition to his painting practice, Sondag teaches at Crealdé School of Art, where he joined the faculty in 1990. He also taught at Seminole State College, Walt Disney Engineering and Walt Disney Animation Studios.
Portrait commissions for the artist have come from the Dr. P. Phillips Foundation, Rollins College, the Tupperware Brands Corporation and the University of Central Florida, among many other high-profile clients. His work has also been featured on posters for the Winter Park Sidewalk Art Festival.
Among Sondag’s most popular exhibitions was Venetian Canals of Winter Park: The Art of Don Sondag, which was staged during the pandemic at the Albin Polasek Museum and Sculpture Gardens. Many people had to view it online when the museum was closed during the lockdown.
Sondag continues to be fascinated by the city’s iconic canals and most recently a new work, Venetian Canal: From Lake Osceola to Lake Maitland, made its debut on the Spring 2026 issue of Winter Park Magazine. The more impressionistic style of that stunning painting showed the artist’s versatility and was sold just days after it appeared in print.
A portfolio of Sondag’s images from New Smyrna Beach were published in the magazine’s summer issue, which featured an editorial package about the historic ties between the funky beach town and its more buttoned-down inland neighbor an hour’s drive away.
To see more of Sondag’s work, visit Arts on Douglas, 123 Douglas Street, New Smyrna Beach. You can call the gallery at 386-428-1133 or visit its website, artondouglas.net, for more information.