335 South Church Street - Sinclair House 
Built circ. 1758

South Church Street - Sinclair House (circa 1758)

The original part of this home is believed to have been built by Andrew Mackie after he purchased the lot in 1758.  Mackie and his family occupied the house until 1778, when he sold it to Captain John Sinclair.  Sinclair occupied the house from 1778-1796.  He was a colorful character who was the captain of a blockade runner during the Revolutionary war.  As a blockade runner, he would secretly maneuver his ships through the blockade of British warships in order to bring in supplies to the colonists.  After the war, he operated as a privateer against British trade ships.

Chronological Tour

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Stop-By-Stop Tour

22 of 44


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Adapted from the original hard copy walking tour designed by the Smithfield & Isle of Wight Convention & Visitors Bureau.
For additional information about the walking tour, contact the Visitors Bureau at: 757-357-5182 or 800-365-9339.
Unless otherwise noted, the homes shown on this site are private residences and are not open to the public.

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