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You don’t have to be a history buff to appreciate the Southold legacy estate that is Mayfield. Constructed in 1905, this property has witnessed the North Fork through over a hundred years of change and development. With rumored ties to rumrunning, this home has stories to tell.

“This property includes a special three-story functioning lighthouse that legend (and rumor) says was used during Prohibition to guide bootleggers to an underground tunnel running from the beach to the basement of this spectacular residence, said listing agent Nicholas Planamento of Town & Country Real Estate. “Evidence of the tunnel is visible in the basement with 10’ ceilings and large windows allowing all that light in!”

In addition to the three-story lighthouse, the estate boasts a seven-bedroom main house, a bayfront beach house with a wet bar, and a multi-car garage with an office.

Upon entering the Victorian Gothic main house, you’ll be delighted to find a surprisingly current floorplan including a central entry hall featuring a sweeping staircase to the second floor, a formal living room, dining room, den and modest kitchen, plus a late 20th-century wing that features a sunroom, family room and jacuzzi room plus a half bathroom.

Upstairs, you’ll find the water view owner’s suite with an en suite full bath, two additional full bathrooms and three bedrooms. The third floor features three additional bedrooms and one full bath.

The home features several wood-burning fireplaces, a library hall, and back stairways.

“The most prominent special feature of this property is the lot: two bayfront acres of private beach and safe, FEMA-designated Zone X parkland with mature plantings all in a private village setting,” said Planamento.

The Mayfair estate has only had five owners and hasn’t changed much since its construction by one of the town’s earliest families. Each room, property feature, and beach vista speaks to you – and shares a story, unlike other homes. Stepping onto this estate is like stepping back to the Gatsby era.

“The rare opportunity to own a legacy estate residence on Southold’s Town Harbor,” Planamento added. “While there are many homes built in Southold post-WWII, few have the history and provenance of Mayfield.  This is a substantial home that rivals the great East End estates on the North Fork and the Hamptons.”

The property is listed at $5,999,000. View the complete listing here.