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Shelter Island, NY Homes for Sale with Garage

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  • /48

    $2,895,000

    • 3 Beds
    • 2.5 Baths
    • 1,901 Sq Ft

    7 Gazon Rd, Shelter Island, NY 11964

    Immerse yourself in the serene charm of 7 Gazon Road, a Zen-inspired retreat tucked away on Shelter Island. This waterfront sanctuary offers the perfect balance of modern luxury and tranquil living. With three bedrooms and two-and-a-half baths, you can choose between a first or second-floor primary suite, each thoughtfully updated to exude sophistication and comfort. Nestled on 1.6 acres of lush

    Agent Photo

    Terry Thompson

    Douglas Elliman Real Estate

    (631) 800-7430

    7 Gazon Rd, Shelter Island, NY 11964
  • /36

    $6,750,000

    • 6 Beds
    • 4.5 Baths
    • 3,157 Sq Ft

    5 N Menantic Rd, Shelter Island, NY 11964

    A rare offering on Shelter Island, this waterfront estate represents a legacy of architectural pedigree and enduring luxury. Built in 1860 and renovated over the years, the home is a singular blend of history and Hamptons elegance, set on nearly 3 acres with western-facing water views, a deepwater dock, and every hallmark of refined coastal living. In an iconic Shelter Island location on West

    Myles Reilly Saunders & Associates

    5 N Menantic Rd, Shelter Island, NY 11964
  • /28

    $4,895,000

    • 6 Beds
    • 8 Baths
    • 5,622 Sq Ft

    100 S Ferry Rd, Shelter Island, NY 11964

    A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep.Boasting six bedrooms, each with their own en-suite, and two additional half-baths, this residence effortlessly blends style and

    Christine Beckwith Douglas Elliman Real Estate

    100 S Ferry Rd, Shelter Island, NY 11964
  • /16

    $5,600,000

    • 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
  • /18

    $5,000,000

    • 7 Beds
    • 7 Baths
    • 4,646 Sq Ft

    115 S Ferry Rd, Shelter Island, NY 11964

    Escape to tranquility in this shingle-style waterfront home, perfectly situated on 1.16 acres of mature plantings with 155 feet of pristine beach frontage. Enjoy breathtakingwater views from nearly every room, where nature's beauty meets relaxedliving. The main house features 4 spacious bedrooms and baths, Livingroom with build-in's, Cathedral ceiling and a wall of glass windows and doors leading

    Melina Wein M WEIN REALTY INC

    115 S Ferry Rd, Shelter Island, NY 11964
  • /19

    $4,000,000

    • 3 Beds
    • 3 Baths
    • 1,626 Sq Ft

    100 Peconic Ave, Shelter Island, NY 11964

    Infinite Views over Shelter Island Sound and extensive bulk-headed sandy beach front make for perfect, summer days and sunset filled nights spent enjoying the beauty and tranquility of this property. Charming interior with beautiful wood floors and touches of wainscoting, living room with beamed cathedral ceiling, picture window and wood burning fireplace, cooks kitchen with dining alcove, two

    Melina Wein M WEIN REALTY INC

    100 Peconic Ave, Shelter Island, NY 11964
  • /48

    $5,700,000

    • 5 Beds
    • 3.5 Baths
    • 3,325 Sq Ft

    90 Peconic Ave, Shelter Island, NY 11964

    Surprisingly larger than it looks! Value, Location and Style adorn this Rare Sunset Waterfront Green Lawns Gem on gorgeous Shelter Island. Available after 100 years of property ownership. The 190' of Silver Beach waterfront is fully bulk headed with dock on a level acre with generous side lawn. Perfect for entertaining or escaping as it's surrounded by mature landscaping. Reich Eklund custom

    Susan Cincotta Susan C Cincotta

    90 Peconic Ave, Shelter Island, NY 11964
  • /27

    $2,750,000

    • 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
  • /35

    $1,990,000

    • 3 Beds
    • 2 Baths
    • 3,170 Sq Ft

    27 Country Club Dr, Shelter Island, NY 11964

    Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant custom home was lovingly crafted by a local artist in 2011 and spans 3,170 square feet. Designed to maximize natural light, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. The home features 21' vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm

    Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

    27 Country Club Dr, Shelter Island, NY 11964
  • /26

    $1,885,000

    • 2 Beds
    • 2 Baths
    • 1,208 Sq Ft

    64 N Cartwright Rd, Shelter Island, NY 11964

    This modern architectual jewel,was desiged by the famed architect William Pedersen, who was the founding design partner of Kohn Pedersen Fox Associates (KPF). The home, studio and garage are situated on 1.3 private acres with specimen trees. Close to Coecles Harbor, nature preserves, and sandy beaches.

    Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

    64 N Cartwright Rd, Shelter Island, NY 11964
  • /35

    $7,425,000

    • 8 Beds
    • 9 Baths
    • 8,000 Sq Ft

    79 N Midway Rd, Shelter Island, NY 11964

    Every once in a while a very extraordinary property becomes available. Fox Hollow Farm, a private 7-acre horse farm located at 79 North Midway Road, is one of those. It is truly a property for all seasons. One of only a handful of true horse farms on Shelter Island, the offering includes a stately and restored 6,500 square foot main house, dating back to the 19th century; a detached 3-bay garage;

    Nick Gavin Compass

    79 N Midway Rd, Shelter Island, NY 11964
  • /12

    $2,795,000

    • 4 Beds
    • 4.5 Baths
    • 5,300 Sq Ft

    10 Sunshine Rd Unit B, Shelter Island, NY 11964

    Quintessential Hamptons estate in the heart of Shelter Island . Enjoy the best of both worlds at this traditional Hamptons style home, with approximately 5000sqft of immaculate living space across one level, and nearly an acre of land, it's the perfect setting for the best of year round and seamless indoor-outdoor living. The custom-built home welcomes you with its vaulted ceiling in the foyer,

    Adam Hofer Douglas Elliman Real Estate

    10 Sunshine Rd Unit B, Shelter Island, NY 11964
  • /39

    $2,750,000

    • 4 Beds
    • 4 Baths
    • 3,420 Sq Ft

    156 Ram Island Dr, Shelter Island, NY 11964

    Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom

    Mary Elizabeth Galle Corcoran

    156 Ram Island Dr, Shelter Island, NY 11964
  • /14

    $1,100,000

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    64 N Rd, Shelter Island, NY 11964

    Hidden away off a private drive this lovely two bedroom and one bath cottage is situated on a full acre of land. The home has an open floor plan with a chef's kitchen, large living room with vaulted ceiling and wood stove. Hardwood floors and tile bathroom. Plus, there is a 60'x 30' storage/ garage with three car/truck bays and work area. LOCATED IN "C" ZONE: GREAT OPPORTUNITY FOR

    Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

    64 N Rd, Shelter Island, NY 11964
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