Penelope Moore
Penelope A. Moore
Shelter Island Real Estate
Licensed Associate Real Estate Broker

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$5,675,000 Active

41 Manhanset Road
Shelter Island, NY 11964

6 beds, | Residential
5,015 sq ft - MLS# 10132172
Property Photo


SHELTER ISLAND ESTATE SECTION CLASSIC WITH BARN Oriole Farm is one of the largest, most prestigious historic estates in the coveted Shelter Island community of Dering Harbor Village. Set on 7.68+/- acres of manicured lawns and nestled behind more than a quarter mile of century-old copper beech hedge, the property boasts numerous statuesque specimen trees. The Barnes Coy designed home blends quality craftsmanship, vintage references, and state of the art systems. The property was once the site of a private arboretum, gardens, and orchard owned by the family of Alice Fiske, the celebrated horticulturist of Shelter Island's first plantation, Sylvester Manor. Today, the sprawling residence showcasing double-height ceilings and five fireplaces offers a flowing layout and scenic estate views. An allee of ancient weeping beech trees nearly 40 feet high is majestic. Originally constructed by Lord & Burnham, the greenhouse at Oriole Farm has been meticulously restored. Currently serving as a pool cabana, occasional dinners are hosted here under the stars. Nearby, the 55' gunite pool with hot tub and lounge area offers space for leisure and outdoor entertaining. A Zen garden with flowering shrubs, yoga patch, and outdoor shower completes the resort-like ambience. The estate is also home to one of the last remaining turn of the century barns on Shelter Island. Renovated with a new roof and foundation, it maintains its original detail. Adjacent to the barn is nearly half an acre for a tennis court or other recreational facilities.Entirely in a class of its own for space and style, the estate maintains much of Shelter Island's rural character and country charm. Located less than 100 miles from New York City, it embraces the very best of Hamptons living year 'round. Oriole Farm offers absolute privacy with luxury living at its finest and a special provenance. More importantly, it's a place for you to call home and offers the opportunity to create a magnificent compound. Dering Harbor Village fees for water, sewage & highway are $12,100.61/yr.


  • Basement: Ful/Finished
  • Dock: Shared
  • Fireplace: 5
  • Garage: Detached
  • Heating/Cooling: Central, Geo Thermal heat
  • Levels: 2
  • List Date: 07/26/2013
  • Lot Size: 7.68
  • Pool: In Ground, Heated, Gunite
  • School District: Shelter Island
  • Type: Single Family
  • Year Built: 2008
  • View: Mainland
Penelope A. Moore
Shelter Island Real Estate

PO Box 1034
Shelter Island Heights, NY
Mobile: 917-208-5519
Office: 631-749-5801
Fax: 631-204-6947 
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A Standard of Excellence Your First Choice in Shelter Island Real Estate


We had been looking for over 2 years, in part because there was not a lot on the market and in part because we had very specific requirements. Penelope was the first broker I ever met who actually listened to what those requirements were and acted on them. After several intensive days searching she understood what we needed. For the following few months we heard from her on a regular basis but there was nothing worth making a special journey out from the city for. Then finally she found a house that you could tell was important to see asap and this was the house we bought. Having found it and agreed on the price, I was keen to close asap to make sure I didn’t have to spend another 2 years looking and Penelope worked round the clock to get things done. We’ve now lived here for two years and regularly keep in touch with Penny socially. She is definitely more than your regular real estate broker... 
A.C. New York, NY
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