Jesse Walsingham came to central Pinellas in the mid 1890s, married Mary O'Quinn of the McMullen and O'Quinn pioneer families, and settled in the Largo area, where they started a family. Over the next 30 years, Jesse worked in many occupations, including delivering ice across the peninsula, operating a meat and citrus packinghouse, managing a hardware store, working as a butcher, and selling fertilizer. When truck farming was at its height, he became a leading grower who raised strawberries, potatoes, cabbage, eggplant, navy beans, and some citrus for regional markets. After purchasing land in 1913, the family moved in 1915 into their newly built home, which became the center of their agricultural, commercial, and civic activities, including Jesse's leadership in the Largo Truck Growers Association, the effort to form a separate county in western Hillsborough, and the Pinellas County Fair. In 1929 they sold the home but remained in the area, and later owners rented rooms there to boarders. Mary Walsingham and other members of the Woman's Club of Largo helped launch the first successful fair for the new county of Pinellas in 1916, and the family won many medals there for its produce. As the fair expanded, Jesse became its first general manager in 1928 and served until 1935. Built on a ridge in a sparsely settled part of the peninsula, the house once dominated the landscape, combining ornamental rusticated concrete blocks on the lower floor with a wood-framed second story; in later years, tenants used rear stairs when the property became rental housing. Their son Sumter Walsingham also became a farmer and made front-page news in 1917 as a Largo Agricultural School student and Corn Club member when he produced nearly 50 bushels of corn on one acre. Walsingham Road and Walsingham Park preserve the family name.