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For sale
  • $2,199,000

    64 N Midway Rd, Shelter Island, NY 11964

    5beds
    2,646sqft
    Loading
    Other
    Built in 1977
    0.95 Acres Lot
    $2,097,400 Zestimate®
    $831/sqft
    $-- HOA

    What's special

    Gas fireplaceLarge loftTwo spacious bedroomsAttached one-car garagePicturesque pond next doorStunning barn-style homeExpansive rear deck
    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 homes 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.
    27 days
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    316
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    6
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    Zillow last checked:

    Listed by:

    Douglas Elliman 631-354-8100,

    Christine Beckwith

    Source: Douglas Elliman,MLS#: 424469MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 4
      Features
      • Has basement: No
      Interior area
      • Total structure area: 2,646
      • Total interior livable area: 2,646 sqft

      Property

      Lot
      • Size: 0.95 Acres
      Details
      • Parcel number: 0700014000400007003

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Other
      • Property subtype: Other
      Condition
      • Year built: 1977

      Community & HOA

      Community
      • Subdivision: Shelter Island
      Location
      • Region: Shelter Island

      Financial & listing details

      • Price per square foot: $831/sqft
      • Tax assessed value: $697,600
      • Date on market: 7/21/2026
      • Lease term: Contact For Details

        Estimated market value

        $2,097,400

        $1.99M - $2.20M

        $6,068/mo

        Price history

        DateEventPrice
        7/21/2026Listed for sale$2,199,000+149.9%$831/sqft
        Source: Douglas Elliman #424469 Report a problem
        2/1/2022Sold$880,000-3.8%$333/sqft
        Source: Public Record Report a problem
        9/1/2021Contingent$915,000$346/sqft
        Source: NY State MLS #11005229 Report a problem
        7/3/2021Listed for sale$915,000+81.2%$346/sqft
        Source: NY State MLS #11005229 Report a problem
        11/4/2009Sold$505,000+2%$191/sqft
        Source: Public Record Report a problem
        12/19/2005Sold$495,000+115.2%$187/sqft
        Source: Public Record Report a problem
        3/25/2002Sold$230,000$87/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $697,600 +153.7%
        2024-- $275,000 -13.9%
        2023-- $319,400 -41.5%
        2022-- $546,000
        2021-- $546,000 +1.5%
        2020-- $538,000 +0.2%
        2019-- $537,000 +0.4%
        2018-- $535,000 +2.5%
        2017$3,173 $522,000 +3.4%
        2016-- $505,000 +3.9%
        2015-- $486,000 +1.3%
        2014-- $480,000 +2.1%
        2013-- $470,000 -0.4%
        2012-- $472,000 -4.6%
        2011-- $495,000 +0.9%
        2010-- $490,400 -1.7%
        2009-- $499,000 -1.7%
        2008-- $507,700 +8.5%
        2007$2,389 +53.5%$467,800 +101.8%
        2005$1,557 +14.7%$231,800 +23.1%
        2004$1,357 -2.1%$188,300 +0.5%
        2003$1,386 +697.5%$187,300 +23.2%
        2002$174 $152,000
        2001-- $152,000
        2000$1,603 $152,000
        Find assessor info on the county website

        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.
        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

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