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Chesapeake Shores follows Abby O Brien (Ory) , a high-powered career woman, divorcee and mother to twin daughters, as she adjusts to life back in her hometown of Chesapeake Shores. Abby now balances a budding relationship with her former high school sweetheart, Trace (Metcalfe) , working for a firm that does business with her uncompromising father Mick (Williams) and raising two young daughters. Returning to her hometown means engaging in the lives of her siblings: Jess (Mailey) a free-spirit trying to succeed as a bed and breakfast owner; Bree (Ullerup) , a playwright who buys a bookstore in Chesapeake Shores after moving back home from Chicago; Kevin (Penny) , a soldier adjusting to civilian life and new romance; and Connor (Francis) , a new lawyer establishing his professional career. Having returned to Chesapeake Shores shortly after Abby, the O Brien s once-estranged mother Megan (Niven) strives to reestablish relationships with Abby and her siblings, though the O Brien clan primarily looks to its wise grandmother Nell (Ladd) for guidance.

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