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See all available Shelter Island, NY Homes With a Pool

11 Jaspa Road, Shelter Island image
11 Jaspa Road, Shelter Island $1,350,000

Welcome to your private Shelter Island retreat, where comfort, character, privacy, and exceptional outdoor living come together. This inviting 2-bedroom, 2-bath home offe...

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  • 2 Beds
  • 2 Baths
  • 1049777 MLS
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4 Bayview Avenue, Shelter Island Heights image
4 Bayview Avenue, Shelter Island Heights $1,999,999

Welcome to 4 Bayview Avenue, a remarkable residence nestled in the historic heart of Shelter Island Heights. This expansive property, designed with the art of entertainin...

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  • 6 Beds
  • 6 Baths
  • 1045616 MLS
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169 N Ferry Road, Shelter Island image
169 N Ferry Road, Shelter Island $4,250,000

There are new homes, and then there is this - a turnkey Bartilucci Construction design-build masterpiece, styled by Heiberg Cummings tucked just outside the heart of Shel...

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  • 4 Beds
  • 6 Baths
  • 1036842 MLS
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6 Great Circle Drive, Shelter Island image
6 Great Circle Drive, Shelter Island $4,995,000

Brand new in one of Shelter Island's premier enclaves along Gardiners Bay, this custom 5,535 +/- SF, south-facing residence developed by Juno Homes presents a refined ble...

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  • 5 Beds
  • 7 Baths
  • 1027086 MLS
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43 Gardiners Bay Drive, Shelter Island image
43 Gardiners Bay Drive, Shelter Island $3,625,000

Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ˜ 6,100-square-foot coastal estate that redefines luxury through the...

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  • 5 Beds
  • 5 Baths
  • 1012419 MLS
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4 Irene Lane, Shelter Island image
4 Irene Lane, Shelter Island $1,850,000

Discover a serene sanctuary amidst the natural beauty of Shelter Island. This stunning residence offers breathtaking water views of Miss Annie's Creek, providing an unpar...

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  • 4 Beds
  • 3 Baths
  • 1003398 MLS
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5 Marc Street, Shelter Island image
5 Marc Street, Shelter Island $1,999,999 ▼

Welcome to your dream getaway where modern luxury meets laid-back coastal charm. This Newly renovated 4 Bedroom 3.5 Bathroom home offers perfect blend of style & tranqui...

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  • 4 Beds
  • 4 Baths
  • 991700 MLS
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11 Sunnyside Avenue, Shelter Island image
11 Sunnyside Avenue, Shelter Island $5,500,000

An architecturally significant modern retreat set on two private acres within coveted Shelter Island Heights owners association. Floor-to-ceiling glass dissolves the boun...

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  • 4 Beds
  • 6 Baths
  • 990118 MLS
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14 Freds Lane, Shelter Island image
14 Freds Lane, Shelter Island $2,239,000 ▼

Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence...

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  • 6 Beds
  • 4 Baths
  • 978923 MLS
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12 Terry Dr., Shelter Island image
12 Terry Dr., Shelter Island $2,800,000 ▼

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront ass...

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  • 5 Beds
  • 5 Baths
  • 977439 MLS
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8 Hilo Drive, Shelter Island image
8 Hilo Drive, Shelter Island $3,850,000

This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting...

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  • 4 Beds
  • 6 Baths
  • 962070 MLS
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141A N Ferry Road, Shelter Island image
141A N Ferry Road, Shelter Island $3,999,000 ▼

Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the perfect blend of luxury, comfort and privacy. Hidden at the end of a long drivew...

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  • 4 Beds
  • 7 Baths
  • 930022 MLS
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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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Educators Realty, Inc.
332 Jackson Ave
Syosset, NY 11791
(516) 517-2400

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