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Riverfront Bootleggers Trail Estate in Smithtown Asks $4.7M

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Courtesy Compass

Bootleggers Trail Estate, a historic 23-acre estate along the Nissequogue River in Smithtown, is on the market.

The estate’s Manor House was built in 1828 and is nearly 6,000 square-feet. The home lies along the Bootleggers Trail and borders 60 acres of preserved land. The property has potential for agricultural, commercial and/or residential use, and its listing agent, Margaret Trautmann, says it could be sold to a CBD farmer.

“The 23 organic acres are incredible; they have never been touched,” Trautmann says. “This is a rare and unique opportunity for commercial or residential use. The dining room is 200 years old and the living room has incredible details and charm.”

This charming riverfront property offers seven bedrooms, five full bathrooms, and one half bathroom. Aside from the main house, there are horse stables and paddocks, barns, outbuildings, workshops, and more, according to the listing.

The interior blends modern amenities with a farm-chic aesthetic. Some notable features include the two-story home’s five fireplaces, three chimneys, office and study rooms, foyer, courtyard, and butler’s kitchen.

The home is located in the Smithtown School District, two miles away from the nearest Long Island Rail Road station and six miles away from the historic Village of Stony Brook.

The asking price is $4,700,000, not including the annual property tax of $33,651.

The real estate agents listed for the property are Trautmann, of Compass, who can be reached at [email protected] or 516-361-4646, and Melissa D’Angelo, of Compass, who can be reached at [email protected] or 516-324-8826.

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