Skip main navigation
For sale
  • $2,199,000

    64 N Midway Rd #A, Shelter Island, NY 11964

    5beds
    2,646sqft
    Loading
    Multi Family
    Built in 1977
    -- sqft lot
    $-- Zestimate®
    $831/sqft
    $-- HOA

    What's special

    Gas fireplaceLarge loftTwo spacious bedroomsAttached one-car garagePicturesque pond next doorExpansive rear deckSurrounded by mature trees
    A rare 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 1,316 square feet of comfortable living space with 3 comfortable 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, 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. A 1,330-square-foot 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.
    2 days
    |
    121
    |
    5
    |

    Zillow last checked:

    Listed by:

    Douglas Elliman Real Estate 631-354-8100,

    Christine Beckwith - Real Estate Sales Person 631-365-6091

    Source: Out East,MLS#: 396749

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 4
      Cooling
      • Central Air
      Features
      • Basement: Yes
      • Has fireplace: Yes
      Interior area
      • Total structure area: 2,646
      • Total interior livable area: 2,646 sqft

      Property

      Parking
      • Parking features: None
      Features
      • Stories: 1
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      Lot
      • Size: 0.95 Acres

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: Multi Family
      Condition
      • New construction: No
      • Year built: 1977

      Community & HOA

      Location
      • Region: Shelter Island

      Financial & listing details

      • Price per square foot: $831/sqft
      • Date on market: 7/21/2026
      • Lease term: Contact For Details

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/21/2026Listed for sale$2,199,000$831/sqft
        Source: Out East #396749 Report a problem

        Public tax history

        Tax history is unavailable.

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 11964

        Getting around

        28 / 100
        Car-Dependent
        32 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes