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For sale
  • $3,625,000

    43 Gardiners Bay Dr, Shelter Island Heights, NY 11965

    5beds
    6,106sqft
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    Single Family Residence
    Built in 1985
    0.92 Acres Lot
    $3,511,300 Zestimate®
    $594/sqft
    $-- HOA

    What's special

    Fully finished lower levelThree generous guest roomsHome gymLight-filled foyerExquisite millworkMarble-clad primary suiteWalk-in pantry
    Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ≈ 6,100-square-foot coastal estate that redefines luxury through the lens of effortless living. Set on a sprawling 0.92-acre parcel with captivating winter water views of Gardiners Bay, this masterfully designed home offers a seamless daily rhythm, beginning in the light-filled foyer where exquisite millwork meets glass doors that open to the expansive grounds. Designed for both high-end entertaining and absolute ease, the flowing main level connects a stately firelit living room to a magnificent chef's kitchen—complete with a professional cooktop, a walk-in pantry, and dual dishwashers for effortless cleanup—before transitioning outside to a resort-style pool featuring an electric safety cover and direct cabana-bath access. A sanctuary of personal wellness, the second floor boasts a marble-clad primary suite with a private water-view office overlooking the bay, alongside three generous guest rooms and two laundry rooms configured for ultimate convenience. Below, the fully finished lower level serves as a private wellness and entertainment pavilion, featuring a home gym, media room, and a temperature-controlled wine cellar, balanced by an abundant bulk-provisioning storage room and an attached garage for your water toys. Situated just steps from the pristine sands of Menhaden Lane Beach and moments from the island's premier marinas, boutiques, and acclaimed dining, this estate offers a turnkey, worry-free island lifestyle where every modern luxury is already perfectly in place.
    64 days
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    442
    |
    20
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    Zillow last checked:

    Listed by:

    Daniel Gale Sotheby's International Realty 631-749-1155,

    Mackenzie Needham - Real Estate Sales Person 631-742-5165

    Source: Out East,MLS#: 396382

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 6
      • Full bathrooms: 5
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Family Room, Laundry, Office
      Cooling
      • Central Air
      Features
      • Basement: Yes
      • Has fireplace: Yes
      Interior area
      • Total structure area: 6,106
      • Total interior livable area: 6,106 sqft
      Video & virtual tour

      Property

      Parking
      • Parking features: GarageDetached
      • Has garage: Yes
      Features
      • Stories: 2
      • Has private pool: Yes
      Lot
      • Size: 0.92 Acres
      Details
      • Parcel number: 0700001000200035000

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Condition
      • New construction: No
      • Year built: 1985

      Community & HOA

      Location
      • Region: Shelter Island Heights

      Financial & listing details

      • Price per square foot: $594/sqft
      • Tax assessed value: $3,283,000
      • Date on market: 6/16/2026
      • Lease term: Contact For Details

        Estimated market value

        $3,511,300

        $3.34M - $3.69M

        $6,709/mo

        Price history

        DateEventPrice
        6/16/2026Listed for sale$3,625,000-2%$594/sqft
        Source: Out East #396382 Report a problem
        4/30/2026Listing removed$3,700,000$606/sqft
        Source: Douglas Elliman #415601 Report a problem
        8/19/2025Listed for sale$3,700,000$606/sqft
        Source: Out East #387881 Report a problem
        8/7/2025Listing removed$3,700,000$606/sqft
        Source: Out East #387881 Report a problem
        7/16/2025Price change$3,700,000-5.1%$606/sqft
        Source: Out East #387881 Report a problem
        4/11/2025Listed for sale$3,900,000+378.5%$639/sqft
        Source: Out East #387881 Report a problem
        9/5/2023Listing removed--
        Source: Zillow Rentals Report a problem
        4/22/2023Listed for rent$30,000$5/sqft
        Source: Zillow Rentals Report a problem
        1/1/2022Listing removed--
        Source: Out East Report a problem
        8/31/2021Listed for rent$30,000$5/sqft
        Source: Out East #355358 Report a problem
        8/1/2021Listing removed--
        Source: Out East Report a problem
        6/21/2021Price change$30,000-25%$5/sqft
        Source: Out East #355358 Report a problem
        6/15/2021Price change$40,000+166.7%$7/sqft
        Source: Out East #355358 Report a problem
        1/4/2021Listed for rent$15,000+57.9%$2/sqft
        Source: Out East #355358 Report a problem
        7/11/2018Listing removed$9,500$2/sqft
        Source: DERING HARBOR REAL ESTATE LLC #10488184 Report a problem
        5/2/2018Listed for rent$9,500$2/sqft
        Source: DERING HARBOR REAL ESTATE LLC #10488184 Report a problem
        4/28/2014Sold$815,000$133/sqft
        Source: OneKey® MLS as distributed by MLS GRID #L2589221 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $3,283,000 +63.7%
        2024-- $2,005,000 +8.5%
        2023-- $1,848,000
        2022-- $1,848,000
        2021-- $1,848,000 +1%
        2020-- $1,830,000 +0.2%
        2019-- $1,826,000 +0.1%
        2018-- $1,825,000 +2.4%
        2017$10,824 $1,782,000 +6.5%
        2016-- $1,674,000 +22.5%
        2015-- $1,366,000 +61.5%
        2014-- $846,000 -7.5%
        2013-- $915,000 -5.6%
        2012-- $969,000 -1%
        2011-- $979,000 -2.4%
        2007$5,123 -13.8%$1,003,000 +13.4%
        2005$5,941 +23.2%$884,500 +32.2%
        2004$4,823 +9.3%$669,300 +12.2%
        2003$4,411 +28.6%$596,300 +98.8%
        2002$3,429 $300,000
        2001-- $300,000
        2000$3,163 $300,000
        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: 11965

        Getting around

        2 / 100
        Car-Dependent
        18 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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