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Christmas is fast approaching and years of long workdays employed at New York's top corporate law firm are about to pay off now that Lucy Toomey (Ali) will be made partner after the New Year. However, when her special-needs older sister Alice unexpectedly passes away, Lucy returns to Nilson's Bay, Wisconsin to attend the funeral and handle her estate. While Lucy dreads returning to her childhood home, she also feels real sorrow that she was too busy to take her sister's last call. Once back in Nilson's Bay, Lucy meets Peter (Whitfield), her high-school sweetheart and Alice's former attorney, who informs her of the terms of Alice's eccentric will: in order for Lucy to inherit the family home, she must live there for 30 days through the holidays.