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“Chesapeake Shores” explores the lives of the O’Brien family, after the homecoming of eldest daughter Abby O’Brien-Winters (Meghan Ory), a high-powered career woman and divorced mother of two. Over the past four seasons, Abby has leaned on her family to strike a balance between her professional and personal lives. This season, as Abby is processing the consequences of her kiss with on-and-off again ex-boyfriend Trace (Jesse Metcalfe), she contemplates a future on her own terms and proves her mettle as her father Mick’s (Treat Williams) new business partner. Still dealing with the aftermath of Mick’s legal troubles, they are thrown a new challenge when eccentric young billionaire Evan Kincaid (Robert Buckley) brings a new development project into town and gets under Abby’s skin. Mick and Megan (Barbara Niven) each evaluate the next step in their romantic relationship and whether to talk to each other about it. Megan gets a taste of her previous life in the New York art scene when she discovers an obscure painting from a reclusive, local artist. While the artist wants nothing to do with the art world, he does take an interest in his old friend… Nell (Diane Ladd). Jess and David (Carlo Marks) plan their dream wedding, but face pressure from his wealthy parents. Bree returns from England a smashing success professionally, and soon finds new options in her personal life when she reconnects with two very different men from her past (Stephen Huszar and Matthew Kevin Anderson). An opportunity for promotion opens up for Kevin (Brendan Penny) and Sarah (Jessica Sipos) at the firehouse and has them reevaluating plans to start a family. Connor (Andrew Francis) faces a dilemma at his new firm that threatens to pit him against his family and gets help from colleague Margaret (Raylene Harewood), a paralegal with whom he shares a special rapport.

Based on the novels of the same name by New York Times bestselling author Sherryl Woods.