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

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$4,325,000 Active

58 Westmoreland Drive
Shelter Island, NY 11964

5 beds, | Residential
6,625 sq ft - MLS# 10527695
Property Photo


SPACIOUS BAYFRONT WITH DEEP WATER DOCK AND POOL Located on historic Westmoreland Farms peninsula on West Neck Bay, this glorious traditional boasts four levels of living space and is ready for its next owner. Sited on one acre, the cobblestone circular driveway leads to a sunny courtyard with gardens and pool with mahogany entertainment decks and shaded lounge area, which are flanked by two guest suites, one with kitchenette. The main entry opens to a welcoming foyer with water views to the bay. A library with fireplace is to the south side of the home, a recently updated kitchen is to the east, with formal living and dining rooms which both have panoramic water views in the center of the home. The second floor has two generously proportioned en suite bedrooms, one of which is a master suite with a separate library and walk in closet. The top floor is an artist studio with full bath and a bird's eye view of the water. The lower level, which is partly at grade, features an en suite guest bedroom, billiards room with wet bar, lounge and study. The doors lead to the grounds which have a tennis court and green lawns leading to a sandy beach and a deep water dock. A rare offering with plenty of living space for everyone in a prime waterfront location!


  • Basement: Full finished walk out
  • Deck: Yes
  • Dock: Deep water
  • Fireplace: 4
  • Floor/Covering: Wood
  • Garage: 1.5
  • Heating/Cooling: GHA
  • Levels: 4
  • List Date: 08/03/2018
  • Lot Size: 1.00
  • Pool: Gunite
  • Roof: Shingle
  • School District: Shelter Island
  • Type: Single Family
  • Year Built: 1987
  • View: Bay
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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