The building is a simple Georgian Colonial mansion. Tobias Lear III purchased the land in October 1738 and built the house around 1740.
His son, Captain Tobias Lear IV, lived here starting in 1759 and worked for his cousin, John Langdon, a wealthy ship builder and patriot. Tobias Lear IV was a shipmaster and crew chief in charge of building John Paul Jones’s famous ship, the Ranger.
The most famous Tobias Lear, the fifth generation, was born in this house on September 19, 1762 and spent his childhood here.
After graduating from Harvard in 1783, Tobias Lear V became George Washington’s Private Secretary and personal friend for 16 years, until Washington’s death in 1799.
On the afternoon of November 3, 1789, the first President of the United States strolled down Hunking Street and called upon this house for a short visit with his Private Secretary's stepmother, her children, and her grandchildren. Also living in the house were Tobias Lear's sister and her husband, a merchant named Samuel Storer whose dry goods store was located on the corner of Hanover and Market Streets.
While a small crowd gathered in front of the house, George Washington sat in the front parlor, on the left side of the house, chatting with the families while bouncing youngsters on his knee and tousling their hair.
Tobias Lear’s stepmother lived here until 1829, and his sister continued to reside here until she sold the home in 1860. At the time, this area of Portsmouth had become a seedy warren filled with saloons, brothels, and rundown boarding houses. The Tobias Lear mansion became a tenament house.
Wallace Nutting acquired the mansion as part of his Wentworth-Gardner Mansion purchase in 1917 but then sold it. The Society for the Preservation of New England Antiquities, now known as Historic New England, bought the building in 1935 and began restoring it. In 1940, the Wentworth-Gardner and Tobias Lear Houses Association purchased the mansion and continues to mantain it.