[2] The collection offers a panoply of character studies, exploring relationships between parents and children, spouses, lovers, and friends.

[2] Many of the situations Binchy creates "focus on people dealing with tough issues, with plenty of ambiguity and no tidy endings in sight"; others are drawn with humor and wit.

[2][7][8] Among the themes explored in the stories are "love, romance, marriage, divorce, greed, regret, miscommunication, come-uppance, change, connection, understanding".

[9][a] The Sunday Express gave the work 4 out of 5 stars, calling it "vintage Maeve Binchy ... with the wisdom and warmth that was a hallmark of her fiction".

[6] NPR praised the universality of the stories, adding: "Chestnut Street has everything that makes Binchy special, in small delicious bites; her ability to capture human nature, describe individual life arcs, and breathe life into characters ... Binchy's storytelling is so astute that we regard unlikable characters with understanding, if not sympathy".

[8] The Boston Globe noted the uneven nature of the stories, some "more fully realized than others, while some remain closer to fragments, vignettes, or even character sketches".