Est. 1750 · Dimon family settled 1704; original manor built c. 1750 · Revolutionary War Minutemen (Jonathan Dimon, Third Regiment) · John Dimon co-founded Smith & Dimon; built Rainbow (1845) and Sea Witch (1846) · Second Empire remodel 1860s by John F. Dimon · Burned 2005; rebuilt preserving architectural character
The Dimon family's connection to this parcel of North Fork land began in 1704, when they acquired a tract spanning from Sound to Bay near Herrick's Lane in what is now Riverhead. By the 1750s, the second Jonathan Dimon (1727–1787) had constructed the original farmhouse and barns on Manor Lane in Jamesport, establishing what became a multigenerational family seat.
Jonathan's son Jonathan (1756–1831) served in the Third Regiment of Minutemen during the Revolutionary War while living on Manor Lane. The family's commercial reach expanded in the early 19th century when John Dimon moved to Manhattan and apprenticed at an East River shipyard under Henry Eckford. In 1815, he partnered with Isaac Webb and Stephen Smith to found Smith & Dimon, which became one of the premier clipper ship builders in the country. Their vessels included the Rainbow (1845), considered the first of the true clipper ships, and the Sea Witch (1846), which set an all-time record of 74 days sailing from China to New York.
John F. Dimon acquired the family manor in the 1860s and extensively remodeled it into a Second Empire mansion. His daughter Margaret Olivia died in 1868 at age ten after falling from an oak tree on the property. The last of the Dimon family line, Mary Dimon, died in 1931.
The property became the Twin Oaks restaurant in 1947 and changed hands repeatedly. New owners purchased it in 2004, but a major fire destroyed the structure in 2005 before it could reopen. The building was subsequently rebuilt using new materials while preserving documented architectural details. It reopened as the Jamesport Manor Inn and later as The Dimon Estate. As of fall 2025, the property operates as 18 Bay, a fine-dining restaurant.
Sources
- https://www.thedimonestate.com/dimon-family-history
- https://www.danspapers.com/2011/10/haunted-inns-of-the-north-fork/
- https://archive.northforker.com/2022/12/coolest-stories-2022-jamesport-manor-inn-returns-as-the-dimon-estate
Child or woman visible in upstairs window of abandoned building (pre-renovation)Dining room chairs rearranged overnight by unknown meansPsychics reporting activity unprompted upon entering the buildingLightning strike immediately after a stolen object was returnedFemale apparition observed in kitchen areaBlack mist emerging from ceiling ducts and moving around staircaseDisembodied voice calling a worker's name in varying registers
The haunting accounts at the Jamesport Manor Inn span two distinct eras: before and after the 2005 fire. In the years of abandonment before the 2004 purchase, local accounts identified the building as haunted by Margaret Olivia Dimon, the ten-year-old daughter of John F. Dimon who died in 1868 after falling from an oak tree on the property. Witnesses described seeing a woman — or in some accounts, a girl — in the upstairs center window of the empty building.
After reconstruction, the activity shifted from the exterior to the interior. Owner Matthew Kar documented two specific types of events: physical rearrangement of dining room chairs that had been carefully set the night before, and unprompted reports from psychics who walked through the building without prior briefing and reported sensing presences. The psychic accounts were notable to Kar because of their consistency and their independence from the building's published history.
The most atmospheric account involves a man who came to the restaurant to return a candleholder he had taken from the property years before the fire. He described bringing back 'the ghost' by returning it. Within moments of his departure, a lightning strike knocked out power to the building. Kar acknowledged to the Dan's Papers reporter that he considers the building genuinely active: 'I think there is some merit to all this.'
The former employee accounts collected by Gothic Horror Stories describe more prolonged phenomena: a female apparition observed at the dishwashing station, a black mist emerging from ceiling air ducts and moving deliberately around the front staircase, and an entity that called a worker's name in varying voices — female, male, or mimicking people he knew — during early-morning hours.
Notable Entities
Margaret Olivia Dimon (1858–1868; died falling from oak tree; seen in upstairs window of abandoned building)