The Webb-Blessing house is located on land that was originally owned by George Washington's Brother, Samuel Washington. Later, the house was deeded to Isaac and Charlotte Gray who are recorded in the land register as “free persons of color.” The property was deeded to Patty Webb ( a free African-American woman) on October 25, 1830. In 1839, Patty divided her property and deeded it to her sons, Fielding Webb and James Webb, but she lived on the property until 1850. According to the deed, there was a stone house on the property cited as “belonging to James Webb.” The left portion of Webb-Blessing house represents one of the earliest stone structures built and owned by free African Americans during the Antebellum period. The house was built between July 18, 1829 and October 25, 1830. 

Following the Civil War, a German immigrant by the name of John Blessing, was deeded the Webb's former property. Blessing fought for the Confederate Army in the Civil War serving in the Army of the Valley District. Blessing was a baker by trade and in 1859, ironically, he prepared meals for John Brown during Brown's incarceration in the Charles Town Jail. Supposedly Brown even gave Blessing his Bible as he was being led to his execution.

Blessing connected what was formerly the Webb House to his house and used the Webb House as an old stone kitchen. On April 8, 1869 Blessing fell asleep in a chair and died in the corner of the old stone kitchen.The last Blessing to occupy the property was Miss Ollie Blessing, who passed away on February 18, 1983. 

The Jefferson County Black History Preservation Society purchased the Webb-Blessing house in 2003 with intentions of restoring and historically preserving the home. The Mills Group was hired to first stabilize, then restore, and finally utilize the structure as a house museum. Both floors of the Webb House, the stone structure, are being restored to the 1860s era. One of the upper level rooms in the Blessing household will be used to store some of the exhibits developed by the JCBHPS. Another upper room will serve as a research center, which will be available to the general public. The third upper level room, known as “The Nathaniel Downing Room,” serves as a meeting room. Doug Perks and the Sons of the Confederacy have developed the exhibits and displays to be housed in the front room of the first level in the Blessing home. The second room on the first level in the Blessing house has been turned into an exhibit that honors the African American members of the military from Jefferson County who served in the Civil War to the Vietnam War. The Dolly Madison Garden Club has also restored the backyard to a nineteenth century-style garden.