The Webb House was built in the 18th century (most likely circa 1790) near Sterling Creek in Greenport. The early history of the building has been difficult to decipher, and there is a possibility it was built earlier and extensively remodeled in the late 18th century. (According to a journal written by Augustus Griffin, an early Orient diarist, in 1757 General George Washington purportedly stayed at the Inn while en route to Boston.) Perhaps one day documents will turn up that establish a definitive date. Webb House is thought to have been built as an inn or tavern and functioned as such until it was moved in the first part of the 19th century. The building preserves significant details which confirm its early use as a tavern; among these details are, for example, the three ovens in three separate rooms.
Owner Orange Webb first moved the structure sometime in the first part of the 19th century to the north side of the main road, just west of the current-day Kontokosta vineyard and on its new site it functioned as a farm house. It sold again in 1820 to the Wiggins family, and changed ownership several times (including the King and Young families) until 1955 when it was bought by OHS co-founder George Latham. Latham wanted to save it from demolition and use it to house his collection of antiques. He had the house floated by barge from Greenport to Orient (view a fascinating 22-minute video of the move
here), and ultimately bequeathed it and most of its contents to the Oysterponds Historical Society.
