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Shelter Island Heights, NY Homes for Sale with Pool

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  • /20

    $2,675,000

    • 4 Beds
    • 3 Baths

    55 Peconic Ave, Shelter Island, NY 11964

    Welcome to 55 Peconic Avenue, a bold, newly built statement home completed in 2022 and set on an expansive 1.4-acre parcel in one of Shelter Island's most coveted locations. Designed for true year-round living, this residence captures southwest-facing water views, dramatic light, and a seamless indoor-outdoor lifestyle that today's buyers demand. The main level delivers a clean, open-concept

    Jack Richardson SERHANT.

    55 Peconic Ave, Shelter Island, NY 11964
  • /15

    $3,850,000

    • 4 Beds
    • 5.5 Baths
    • 3,985 Sq Ft

    8 Hilo Dr, Shelter Island, NY 11964

    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, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail,

    Enzo Morabito Douglas Elliman Real Estate

    8 Hilo Dr, Shelter Island, NY 11964
  • /46

    $6,945,000

    • 8 Beds
    • 7.5 Baths

    55 & 70 Peconic Ave, Shelter Island, NY 11964

    Presenting a rare and compelling joint offering at 55 & 70 Peconic Avenue-a modern compound opportunity in one of Shelter Island's most coveted waterfront enclaves. Together, these two distinct yet complementary properties deliver scale, privacy, and irreplaceable southwest-facing water views across the Peconic toward Southampton-creating a legacy estate unlike anything else on the market. 55

    Jack Richardson SERHANT.

    55 & 70 Peconic Ave, Shelter Island, NY 11964
  • /39

    $6,950,000

    • 6 Beds
    • 5.5 Baths
    • 7,500 Sq Ft

    55 Shore Rd, Shelter Island Heights, NY 11965

    Nestled along the shores of Shelter Island Sound, this extraordinary waterfront retreat is a modern masterpiece offering incomparable comfort, privacy, and amenities. Set on approximately 1.31 acres with an impressive 332' of private sandy beach and panoramic water views, the 7,500 SF contemporary residence spans two stories plus a fully finished lower level. With 6 bedrooms, 5 full and 1 half

    Ian Dios Compass

    55 Shore Rd, Shelter Island Heights, NY 11965
  • /27

    $2,495,000

    • 6 Beds
    • 4 Baths
    • 2,418 Sq Ft

    14 Freds Ln, Shelter Island, NY 11964

    Tucked away on a shy acre, this private retreat features a heated Gunite pool, fire-pit seating area, all framed by mature trees. The main house has an open floor plan with cathedral ceilings and exposed wood beams in the living room, a cook's kitchen with stainless steel appliances, island seating for 3-4, and a dining area that flows easily for entertaining. A deck off the kitchen sets the

    Melina Wein M WEIN REALTY INC

    14 Freds Ln, Shelter Island, NY 11964
  • /16

    $4,900,000

    • 3 Beds
    • 3 Baths
    • 2,061 Sq Ft

    68 Peconic Ave, Shelter Island, NY 11964

    Shelter Island Sound water front beach house offers stunning sunsets, sandy beach, fully bulkheaded, L'Shaped dock with lift and splash boards;a waterside 50' heated Gunite pool; and expansive unobstructed views out to Robins Island. A serene retreat with a blend of comfort and coastal charm nestled on .75 acres. Designed for relaxation as well as easy entertaining, with a straightforward layout

    Melina Wein M WEIN REALTY INC

    68 Peconic Ave, Shelter Island, NY 11964
  • /47

    $4,250,000

    • 4 Beds
    • 7 Baths
    • 5,500 Sq Ft

    141A N Ferry Rd, Sag Harbor, NY 11963

    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 driveway, the main house boasts 3 bedrooms and 3.5 bathrooms. The 1st floor main suite features include double doors that open to a private deck, a WIC and an expansive master bathroom equipped with a spa style rain shower. To add to

    Annmarie Seddio Atlas Sales Realty

    141A N Ferry Rd, Sag Harbor, NY 11963
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