Sisters of Edgartown Books in Order

The Sisters of Edgartown series is less about blood relations and more about chosen family. Set in the town of Edgartown on Marthas Vineyard, it follows a tight group of women who met as girls, survived a shared tragedy, and now face their forties together, juggling careers, teenagers, aging parents, and the old grief that never quite went away.

The story begins with 2142 Green Hollow Rd, where Jennifer Connelly, one of the original Sisters of Edgartown, is still haunted by the boating accident that killed her twin sister, Michelle, decades earlier. Jennifers marriage has ended, her father has slipped into alcoholism, and her mother collapses from a stroke. Determined not to lose everything, she throws herself into running her familys bakery, Frosted Delights, only to discover that a developer has quietly bought the building and plans to tear it down. Rallying her friends Mila, Camilla, Olivia, and Amelia, she fights to protect both the bakery and the memories tied to it.

Each subsequent book shifts the spotlight. 289 Captains Walk and 37 Peases Point Way explore different sisters as they face fresh losses, romantic complications, and questions about whether to stay on the island or leave. Camilla battles depression and the feeling that she has wasted her potential, Mila navigates single parenthood and a business of her own, and Olivia and Amelia confront problems in their marriages and careers.

In 113 Katama Rd, Camilla gets a chance to claw her way back from the darkest season of her life, helped along by her friends and the steady beat of island summers. 4152 Witchwood Lane follows Mila as her twins graduate high school, forcing her to reimagine who she is when she is not needed every moment at home. A new romance and a shifting sense of purpose show her that midlife can be a beginning, not an ending.

The Hesson House and An Edgartown Christmas bring the whole group together around a crumbling old mansion that becomes a boutique hotel. Olivia inherits the property from a great aunt, and with the sisters help, she tries to turn it into something beautiful without losing its soul. End of summer fades into autumn, secrets and long simmering resentments come to light, and a festive Christmas on the island gives everyone a chance to keep or rewrite the stories they tell about themselves.

Across the series, Winters leans hard into the comforts and challenges of long friendships. The Sisters of Edgartown bicker, misread one another, and disappoint each other, but they also show up in hospital corridors, at zoning meetings, and behind the counter when bakery ovens break down. The island setting adds charm, yet the real draw is the sense that these women have a history rich enough to weather whatever midlife throws at them.