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    (845) 398-1717 susan@ImagineProperties1.com
    • 100 Dutch Hill Rd Suite 260
      Orangeburg, NY 10962
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    Home / Shelter Island / 64A Midway Road
    64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 64A Midway Road Shelter Island, NY 11964 View All Photos

    $2,199,000

    | Active

    64A Midway Road

    Shelter Island, NY 11964

    2,642
    Square Feet
    5
    Beds
    4
    Baths
    1.00
    Acres
    42
    Days on Market
    1029569
    MLS#
    House
    Structure
    Residential
    Zone
    Contact

    A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property offers remarkable versatility to fit your lifestyle. The welcoming ranch-style main home offers a comfortable living space with 3 bedrooms and two full bathrooms. A spacious kitchen with abundant cabinetry flows seamlessly into the dining area, creating an inviting setting for everyday living and entertaining. The living room, anchored by a wood-burning fireplace, provides a warm and cozy gathering place throughout the seasons. Step outside to the expansive rear deck, complete with a hot tub overlooking a large, private backyard with room for a pool, an ideal setting for entertaining, relaxing, or enjoying peaceful evenings. A welcoming front porch, an attached one-car garage, and a carport. Privately positioned toward the rear of the property, the stunning barn-style home feels like a secluded retreat. Overlooking a tranquil pond, this approx. The residence is filled with warmth, character, and natural light. The dramatic main room features soaring vaulted ceilings with exposed beams, a gas fireplace, and an impressive wall of windows that captures beautiful views while flooding the home with sunshine. French doors that open onto an expansive 500 square foot mahogany deck with built-in storage, creating the perfect place to enjoy morning coffee, outdoor dining, or simply unwind. The barn home also features two spacious bedrooms, two full bathrooms, a large loft, and a well-appointed kitchen. The oversized lower-level garage offers exceptional storage for vehicles, recreational equipment, bicycles, tools, and more, while additional facilities and energy-efficient solar panels further enhance the home’s appeal. The beautifully landscaped .95 acre property provides an uncommon sense of privacy while remaining just minutes from the Shelter Island beaches, marinas, restaurants, shops, farm stands, and nature preserve. 64A North Midway Road offers possibilities that are rarely available on Shelter Island.

    Property Details
    Interior
    First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Cathedral Ceiling(s), Ceiling Fan(s), Central Vacuum, Crown Molding
    Cooling
    Central Air
    Heating
    Ducts, Forced Air, Hot Water, Oil
    Cooling Features
    Central Air
    Bedrooms
    5
    Bathrooms
    4.0
    Full Baths
    4
    Acres
    1.0
    Square Feet
    2642.0
    Parking Features
    Private
    Parking
    1
    Parking Spaces
    3
    Parking Type
    Garage
    Parking Garage
    1
    Parking Carport
    1
    Parking Garage Spaces
    3.0
    Parking Carport Spaces
    1.0
    Property Type
    Purchase
    Basement
    1
    Basement Description
    Bilco Door(s), Full
    Year Built
    1977
    Sewer Information
    Septic Tank
    Utility Source
    Well
    Utility Features
    Electricity Connected, Phone Connected, Propane, Water Connected
    Appliances
    Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Range, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Re
    School District
    Shelter Island
    Elementary School
    Shelter Island School
    Middle School
    Shelter Island School
    High School
    Shelter Island School
    County
    Suffolk County
    Region
    Shelter Island
    Original List Price
    $2,199,000
    Days on Market (Cumulative)
    42
    Taxes Annual
    $7,216
    MLS #
    1029569
    Location
    Legal

    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

    Last Updated: Sep 2, 2026 12:35 PM. Source: ONEKEY

    Provided By
    Listed by Christine M. Beckwith (#KEY159784), 631-354-8100
    Listing Office: Douglas Elliman Real Estate (#KEYDERE72)

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