North Fork Agent and Painter Rita Rooney Practices the Art of the Close

By Grace Cassidy

Long before she became a real estate agent at Douglas Elliman, Rita Rooney discovered a lifelong love of painting—a passion she attributes to her grandmother’s inspiration.

“My maternal grandmother was an amazing artist,” she recalled. “She spent a lot of time with me and nurtured my love of art.”

As for who had a hand in inspiring her to continue her creative practice, the North Fork, Long Island-based agent credits a certain TV personality and joyful painting evangelist known for his renderings of “happy little trees.”

“Once I started a family I didn’t have much time to paint,” Rooney said. “But when my kids were little, we started to watch Bob Ross, and that rekindled the desire to start painting again.”

It also sparked a desire to share her love of painting through teaching others to do it themselves, leading her to launch a popular series of group classes. Since becoming a real estate agent in 2017, Rooney has begun to blend her painting practice with her property sales by presenting her clients with post-closing portraits of their new homes.

The idea to host group painting classes came to Rooney back in 2013, when she was working at a North Fork marina. To promote her first class, she painted a scene of downtown Greenport during the annual Maritime Festival and handed out flyers, hoping for the best. When 24 people showed up, she “burst into happy tears and started to sob.”

“Everyone attending understood,” she recalled. “I felt so grateful for the moment and the opportunity to share my love of painting with so many eager participants. It felt like a dream come true.”

Rooney offered the classes for the next seven years, with participants coming all the way from Maryland, Florida, Wisconsin and elsewhere in the country. When the pandemic prevented her from hosting groups, she found a way to incorporate her art practice into her growing real estate business.

“To keep art in my life, I felt the need to paint portraits of the houses that I help my clients buy or sell,” she said. “My reward is their expression of happiness when they see the painting for the first time.”

Describing herself as a Realist painter, Rooney says she is “captivated by the details of the classics” and draws inspiration from an array of artists, including Dutch Baroque master Johannes Vermeer, American Realists Andrew Wyeth and Thomas Kinkade and the contemporary American prodigy Akiane Kramarik. She also borrows from Bob Ross’s paint-on-paint style when teaching her classes.

In addition to her portrait and landscape painting, Rooney also paints oyster shells, driftwood and other natural materials she finds along the beaches of the North Fork. The Weathered Barn, an artisanal goods and home accessories store in Greenport, has sold her Christmas ornaments and wall hangings made of driftwood.

Reflecting on her life as an artist and real estate agent, Rooney sees a common thread of sharing her experience with others and guiding them to a gratifying result.

“During my painting classes, we would take a blank canvas, and I would take the participants step-by-step through the process until we got to the finished product—something they could be proud of,” she said. “In the same way, I can guide my clients, every step of the way, to the closing table.”

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