Three families at different times — a wartime doctor and his wife in 1951, a newlywed couple and their in-laws in 2003, and a new couple in 2024 — experience their own unique Christmas Eves in the same house at 7 Cherry Lane, all connected by their efforts to preserve the spirit of Christmas and create special holiday moments.

In 1960, a family works on a time capsule while hosting a grumpy grandfather; in 1998, a blizzard brings two strangers together on Christmas Eve; and in 2015, a wedding planner is reunited with her ex-boyfriend, who is officiating her sister's last-minute Christmas Eve wedding.

In 1966, single guy David's plans for a simple Christmas are dashed when his neighbor Stephanie arrives with news that she won a contest to have Tommy Saunders' Christmas Eve TV special broadcast live from her house – but used his address. In 1981, John and Lizzie learn that this will be their last Christmas on Cherry Lane after John receives a job offer in Michigan and Lizzie finds out she's pregnant. In 2000, best friends Matt and Rebecca find unexpected feelings developing as they try to find out who is behind a series of Christmas-themed random acts of kindness.