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For sale
  • $2,875,000

    4 Winthrop Rd, Shelter Island, NY 11964

    6beds
    2,920sqft
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    Single Family Residence
    Built in 1950
    0.37 Acres Lot
    $2,776,500 Zestimate®
    $985/sqft
    $-- HOA

    What's special

    Refined yet inviting atmospherePrivate poolSophisticated and timeless designHigh-end and thoughtful designLush groundsBeautifully appointed throughout
    Set on one of Shelter Island's most coveted streets, Winthrop Road, this exceptional six-bedroom, three-bathroom residence offers the perfect blend of sophisticated and timeless design, effortless indoor-outdoor living, and an enviable location.Beautifully appointed throughout, the home showcases high-end and thoughtful design at every turn that creates a refined yet inviting atmosphere. Spacious interiors flow naturally from room to room, offering an ideal setting for both relaxed living and elegant entertaining. The well-designed layout includes two spacious primary suites, one on each floor, plus 4 guest rooms, offering flexibility, privacy, and comfort for owners and guests alike.Outside, beautifully manicured gardens curated by Buttercup Design Group surround a private pool, creating a serene retreat for long summer days, poolside gatherings, and al fresco entertaining.Ideally located within walking distance of downtown, this home offers a perfect balance of privacy and convenience, with shops, dining, and local amenities just moments away. A truly special Shelter Island offering, this six-bedroom turnkey retreat combines exceptional style, lush grounds and a pool-- your perfect island escape.
    2 days
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    484
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    29
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    Zillow last checked:

    Listed by:

    Douglas Elliman Real Estate,

    Michael Brennan - Real Estate Sales Person 917-664-3017

    Source: Out East,MLS#: 397388

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 3
      • Full bathrooms: 3
      Rooms
      • Room types: Family Room
      Cooling
      • Central Air
      Features
      • Basement: Yes
      • Has fireplace: Yes
      Interior area
      • Total structure area: 2,920
      • Total interior livable area: 2,920 sqft

      Property

      Parking
      • Parking features: GarageDetached
      • Has garage: Yes
      Features
      • Stories: 2
      • Has private pool: Yes
      • Pool features: Heated
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      Lot
      • Size: 0.37 Acres
      Details
      • Parcel number: 0700007000400050000

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Condition
      • New construction: No
      • Year built: 1950

      Community & HOA

      Location
      • Region: Shelter Island

      Financial & listing details

      • Price per square foot: $985/sqft
      • Tax assessed value: $2,047,000
      • Date on market: 8/21/2026
      • Lease term: Contact For Details

        Estimated market value

        $2,776,500

        $2.64M - $2.92M

        $7,904/mo

        Price history

        DateEventPrice
        8/21/2026Listed for sale$2,875,000+139.6%$985/sqft
        Source: Out East #397388 Report a problem
        4/20/2018Sold$1,200,000+20.6%$411/sqft
        Source: Public Record Report a problem
        12/13/2005Sold$995,000+95.1%$341/sqft
        Source: Public Record Report a problem
        5/2/2001Sold$510,000+42.7%$175/sqft
        Source: Public Record Report a problem
        7/8/1999Sold$357,500$122/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $2,047,000 +72.6%
        2024-- $1,185,800
        2023-- $1,185,800
        2022-- $1,185,800 +17.4%
        2021-- $1,010,000 +1.1%
        2020-- $999,000 +4.8%
        2019-- $953,000 +0.4%
        2018-- $949,000 +7.1%
        2017$5,628 $886,000 +3.4%
        2016-- $857,000 +4%
        2015-- $824,000 +0.5%
        2014-- $820,000 +3.1%
        2013-- $795,000
        2012-- $795,000 -4.8%
        2011-- $835,000 +0.6%
        2010-- $830,000 -9.3%
        2009-- $915,000 -1.1%
        2008-- $925,100 +5.8%
        2007$4,467 +21.1%$874,700 +49.9%
        2005$3,688 +3%$583,600 +10.7%
        2004$3,581 -4.1%$527,400 +4.5%
        2003$3,735 -6.7%$504,800 +44.2%
        2002$4,001 $350,000
        2001-- $350,000
        2000$3,691 $350,000
        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

        36 / 100
        Car-Dependent
        39 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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