Bess is a single mother of two whose family has lived in the area for seven generations. Her farmhouse is filled with antiques, vintage furniture and artwork. She also has a barn with old whaling equipment and even more family heirlooms. Anxious to downsize, she calls Matt and his team for help. They clear out the collections and find an assortment of historical artifacts that Bess never knew she had.

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.