Program

NYS Historic

Subject

House

Location

632 Old Montauk Hwy, Montauk, NY 11954, USA

Lat/Long

41.03120537543, -71.952090962466

Grant Recipient

Montauk Historical Society

In 1661, settlers in East Hampton, New York, acquired land titles from the Montaukett people on the Montauk Peninsula to graze livestock. Management of the land was overseen by town trustees on behalf of 127 proprietors, whose grazing rights were proportional to their ownership shares. Initial land acquisitions spanned from Fort Pond westward, eventually expanding to include the area between Fort Pond and Great Pond.

The East Hampton Town Trustees commissioned the construction of a 16×16-foot residence near Fort Pond in 1746 to house a shepherd for the town’s collective flocks. Construction began in April of that year, and Nathaniel Talmage was hired as the first resident shepherd at a rate of 12 shillings per month. Trustee records indicate that a shepherd was hired annually to manage the livestock in this area for the next five decades.

By 1797, the trustees determined that the original structure required replacement. During a series of meetings in June, they contracted Jeremiah Miller and his crew to build a new residence at a rate of 7 shillings per day. Jonathan Dayton was tasked with procuring materials, including three gallons of rum authorized for the house-raising in August. While the house was initially planned as a one-story 27×27-foot structure, the trustees amended the design in September to include a second story. Isaac Edwards delivered shingles to the site in October, and the original 1746 house was sold. The shepherd Christopher Hedges moved into the completed new residence the following year.

Originally known as the Fort Pond House, the building was later renamed Second House because it was the middle of three shepherd residences built along Montauk. Of the three, Second House was the first to be rebuilt in the 1790s, followed by First House in 1798 and Third House in 1806.

As collective sheep grazing declined, the property transitioned to private ownership. During the 1870s, George Osborne operated the house as an inn, hosting visitors in the then-remote region of Montauk. Following several decades as a private residence, the Town of East Hampton repurchased the property in 1968. It was subsequently converted into a museum operated by the Montauk Historical Society. Although the structure has undergone numerous renovations, including a significant restoration in 2018, the original foundation and structural beams remain as of 2026.