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Penny lives with her mother, Emma, in the Hamptons and treasures her time with Henry Wyatt, a famous artist who has made Sag Harbor his home. When Henry dies and leaves his estate, most importantly, his home Windsong, to Penny, Henry's old friend, Bea, is furious. Years ago, she and Henry agreed that when he passed away, Windsong would be turned into a museum. Bea also wonders why Henry would give his estate to a teenage girl. Leaving Manhattan, Bea arrives at Windsong, vowing not to leave until the home is in her hands. Emma is not happy with Bea's appearance, but has her hands full. She is helping Penny manage her OCD, has a job at the American Hotel and must adapt to their newfound wealth.