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

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$2,147,483,647 Rental

6 Bootleggers Alley
Shelter Island, NY 11964

6 beds, | Residential
7,012 sq ft - MLS# 44289
Property Photo


SHELTER ISLAND SUNSET WATERFRONT ESTATE ON 3+ ACRES Located in "Green Lawns", the Shelter Island estate section established during the late 1800s, this expansive shingle-style traditional is sited on rarely found 3.1 sound front acres, with over 340+/- feet of sandy beach and dock. With vivid sunsets and advantages of prevailing southwest breezes, the property exudes "summer." The main house, which is 5,100+/- sq. ft., offers 4 bedrooms, which include a spacious master suite with water views, great room, family room, formal dining, 2nd floor library and billiards room. Adjacent is a 1,900+/- sq. ft. guest house which also has incredible water views, living room and fireplace, full kitchen, two bedrooms, two baths. Set alongside the waterfront is a 20' x 50' heated gunite pool surrounded by gardens. With a gentle elevation with sumptuous water views all around, this property is quintessentially Shelter Island.


  • Basement: Full, Finished
  • Dock: Yes
  • Fireplace: 4
  • Heating/Cooling: Central
  • Levels: 2
  • List Date: 05/16/2017
  • Lot Size: 3.10
  • Pool: In ground, Gunite, Heated
  • School District: Shelter Island
  • Type: Single Family
  • Year Built: 2006
  • View: Soundfront
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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