Behind the 20th century two-storey shop at 20 York Street lies a large three-storey house built by Stephen Judkin in 1765. The lots upon which this building was erected were granted to George Tucker and Robert Burton in 1713. The northern Tucker lot served as a garden for Seven Gables in the late 17th century, while the southern Burton lot was the site of an earlier house. Judkin acquired both properties by 1764 and owned the entire block. Between 1764 and 1765 his parish tax assessment increased from 16 shillings to £1.10.0, reflecting the construction of Judkin House.

The house originally faced west and consisted of a long, main section running north and south, with three one-room extensions to the east, all covered by gable roofs. At one time a room projected west from the main house toward Barbers Alley, perhaps an entry porch, but it was removed in the late 19th century. Judkin may also have built the long, low shed to the east of the house.

A sailmaker by trade, Stephen Judkin served as a juror, constable and assemblyman for the parish. A year after his death in 1794, his heirs sold the house to Samuel Adams for £680. Adams lived there with his wife and seven enslaved people until he died in 1824. In his will, he gave life tenure to his widow Eleanor and daughter Mary Mills Sears, before ownership passed to his three Sears grandsons.

In 1828 the Sears brothers sold the house to Daniel Seon for £800 but retained the northwest corner of the lot upon which a building had been erected, perhaps for the use of their mother. This is now York House, formerly occupied by the H A & E Smith store. In 1838 the Sears sold this corner house to their brother-inlaw William Edward Zuill, for £250. Merchant Daniel Seon owned Judkin House for seven years before he sold it to shipwright Claude Thompson McCallan for £500.

During McCallan’s tenure, the house had an open porch on the west side of the house. He built a smooth stone wall dividing his property from Zuill’s house to the west and a long, single-storey storehouse fronting on Water Street to the south. McCallan was probably responsible for the twostorey, hip-roofed northern addition fronting on Duke of York Street which housed a retail shop.

After Claude McCallan’s death, the house went to his son Claude Wright McCallan. His heirs sold it to Frederick Collins Outerbridge in 1923, who kept the southern storehouse but sold the house to photographer William Southworth Cooper. A decade later Cooper sold the house to Somerset merchant William Perinchief, when he moved his family to St George’s. The building is at present divided into apartments, owned until her death in 2012 by William Perinchief’s daughter, former mayor Lois Perinchief.