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A traditional Shelter Island estate, Oriole Farm sits on a sprawling property that was once the site of a private arboretum, gardens and an orchard.

The 16 acres of manicured lawns are nestled behind more than a quarter mile of century-old copper beech hedge, the former arboretum was designed and owned by one of the owners of Sylvester Manor, the first plantation of Shelter Island.

“This property encompasses about 20% of the Village of Dering Harbor and has established plantings that could not begin to be replicated without investing a fortune,” said realtor Penelope Moore of Saunders & Associates.

Built in 2008, the 5,015 square foot home was designed by Hamptons architects Barnes Coy and inspired by the Arts and Crafts style made famous by English architect Edwin Lutyens. The living areas of the six-bedroom, 6.5-bathroom home look out onto vast areas of green grass and a shaded path winding beneath a canopy of weeping beech trees.

A restored Lord & Burnham greenhouse also sits on the unbounded estate, part of which has been converted to a pool cabana. The rest is still used to winter over the flowers which, during the summer, are in self-watering window boxes, according to Moore.

Even one of the few surviving turn-of-the-century Shelter Island barns, which has been restored and still has original floors and beams, has a home on this astounding plot.

A total of 20 rooms, including a formal dining room, a full basement and five fireplaces under double height ceilings can be found inside, with a design that blends craftsmanship, vintage references and state-of-the-art systems.

Only a few lots away from the house is a 300-foot deep water dock on Shelter Island Sound, including a restored cabana with a covered entertainment deck, a swimming ladder and boat lift.

“This home would appeal to anyone who has an appreciation for history, landscaping, privacy without feeling secluded and boating,” Moore said.

The home is listed at $9,250,000.

View listing here

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