Leila and Don are lifelong New Yorkers selling their unique home in Queens and moving to the Hudson Valley. Before they can put their house on the market, they'll need Matt's assistance finding misplaced heirlooms that range from a piece of tile from Ellis Island to a radio from the 1939 World's Fair. Looking for these lost items puts Matt and his team in a New York state of mind.

Rebecca and Brian have converted a historic 10,000 square foot elementary school near Charlottesville, Virginia, into a multi-generational home filled with artwork and oddities. Matt and the team help them downsize to make room for an aging parent. Along the way, the team is inspired by the couple's self-sufficient, forward-thinking approach to family living.

Zebulon's family proudly lived in their Boston home for over 30 years. Now, with family members spread out in different cities, they're faced with the challenge of finding a new home where their mom can age successfully. Matt and his team help with the emotional clean out, coming across a special find that helps Zebulon reconnect with his recently deceased father in a powerful way.