The exact date of its construction is unknown. Originally the house was a three bay, side hall, two room deep plan with two interior chimneys. It contained double sash windows, wooden lintels with end blocks that remain on the second floor, a Flemish bond front wall terminating in the brink mouse-tooth cornice which is still visible on the rear of the house.
It is known that 416 Park Street was standing circa 1824. It was first occupied by Francis Bowman, pastor of the Presbyterian Church. Rev. Bowman was involved in building the First Presbyterian Meeting House at the corner of Second and Market Streets in 1828. He was also known to preach occasionally at the Court House.
He sold the house to J.W. Saunders around 1850. Mr. Saunders was involved in the temperance movement and even petitioned the legislature for tougher alcohol laws. On February 15, 1856, Mr. Saunders petitioned for “Setting forth the widespread evils resulting from intemperance, the good result of temperance legislation and asking further legislation on the subject.” Mr. Saunders most likely added the recessed southern section and the handsome Victorian trim which includes the bay window, bold overhanging eaves and bracketed cornice and double gallery on the front of the house.
Captain W.O. Fry of the Confederate Army, and descendant of Col. Joshua Fry, purchased the property from Mr. Saunders’ estate in 1881. Mr. Fry, a descendant of Col. Joshua Fry, was also a prominent attorney in the area and member of the Confederate House of Delegates.
Mr. Fry’s widow, Lucy, sold the house in 1902 to George Burnley Sinclair. Mr. Sinclair was an 1888 graduate of the University of Virginia. Mr. Sinclair was also a prominent attorney in the area. He was involved in a scandalous murder case of an ex-mayor’s wife, Fannie McCue. Mr. Sinclair represented J. Samuel McCue who was convicted of murdering his wife and was hanged. An article detailing the history can be found here. Mr. Sinclair eventually became the judge for the City Corporation Court (now the Circuit Court) by unanimous endorsement of the Charlottesville Bar, succeeding George Watts Morris.
Mr. Sinclair sold the house in 1912 to University of Virginia Professor Richard Wilson. Prof. Wilson resided in the house until his death in 1948. His daughter, Marie-Louis Judy sold the house to Lewetta Waldron.
Mrs. Waldron rented the house as law offices until she sold the property in 1965 to 416 Park Street Inc.
In the 1970s a porch was enclosed to become usable office space on the second floor. An exterior wall outlining the property was repaired in 1997. Today, the interior contains much of its original structure with robustly fluted Adamesque mantle, bold chair rails and baseboards, and a fine fisheye transom between the first-floor rooms.