The Winchesters are best known for being America’s most elusive dynasty. Charlie Winchester is a rich girl. She has always been a rich girl. But her family's baggage comes with a price, and theirs is designer. When Charlie's mother died unexpectedly seven years earlier, her family was left fragmented beyond repair. She has spent the years since her mother’s death running from the family she can’t seem to mend and the legacy she wants to escape. Forced to return home to Chicago after years of trying to avoid fixing herself by helping others, Charlie attempts to carve a name for herself and her own path at Winchester Holdings: their family of generations' company. Although she has never had much success in the dating department, unlike her brother Deacon whose life is an endless parade of dates and conquests, Charlie is surprised to find herself enamored with one of her colleagues. That is until someone from her past she attempted to bury along with her mother appears back in her life and turns everything she has worked to create upside down.

From Chicago to New York City, Charlie Winchester has been a rich girl —- and she is still technically a rich girl, even though she's barely on speaking terms with her father. But now she might just be a lost girl. Still reeling after her self-imposed exile, she finds herself plagued by dreams —- or nightmares, depending on who you ask —- of a life with the one person she can't have. Not only is her brother Deacon getting married to one of the most famous supermodels in the world, but he's also expanding the family business and doing it alongside his best friend —- the love of her life and the man whose heart she broke, David. After David misses his flight for Deacon's engagement party, Charlie finds him standing in the back of her classroom looking to catch a ride on her family's jet. The engagement party is like any other Winchester extravagant, isolating and heartbreaking. Charlie strikes up a friendship in the unlikeliest of places —- with Tripp Banks of all people —- and realizes she might just be well and truly adrift.

Charlie Winchester has been a rich girl, she’s been a lost girl—and she might just have been on the path to being a found girl. Until tragedy strikes the Winchester family. Again. Now, she’s back in Chicago, living in the same house she’s been avoiding for a decade. But nothing is quite as she left it. Not the two boys who hold her heart, not her brother, and certainly not her father. Even the winding halls of her family home don’t seem as desolate as they used to. Torn between two lives, Charlie has to decide once and for all where—and what—she calls home.