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For sale
  • Price cut: $155K (6/15)
    $3,695,000

    105 Waterview Dr, Southold, NY 11971

    6beds
    4,663sqft
    Loading
    Single Family Residence
    Built in 2006
    6.5 Acres Lot
    $3,544,200 Zestimate®
    $792/sqft
    $-- HOA

    What's special

    Waterfront propertyModern hardwareAll-new interior paintWarm yet refined ambienceWood-burning fireplaceUpdated lightingOutdoor shower
    Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 6-bedroom, 4-bath colonial offers sweeping water views from nearly every room. Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential. The enormous attic, featuring 8.5+ ft ceilings, offers the possibility of a third-floor buildout. The walk-out basement, with 9+ ft ceilings, two egresses, and plumbing in place, adds even more room for customization.Resort-style amenities continue across the grounds: a 16' x 32' heated saltwater gunite pool with electric cover is set into a 2,100 SF deck, a high-end 6-person hot tub and an outdoor shower. A wide path leads to a fire pit area and the private dock, which previously accommodated a 23' Grady-White and provides direct access to the bay.Inside, a chef's kitchen, wood-burning fireplace, and generous ceiling heights enhance the home's warm yet refined ambience. Radiant heat warms the eat-in kitchen, all bathrooms, and additional spaces throughout. Recent upgrades include the new pool and hot tub, a newly constructed circular driveway, freshly painted Hardie board siding, all-new interior paint, updated lighting, and modern hardware.A truly exceptional offering of space, serenity, and waterfront luxury—ideal as a full-time residence or a memorable seasonal escape.
    190 days
    |
    878
    |
    58
    |

    Zillow last checked:

    Listed by:

    Compass 631-537-7700,

    Roric Tobin - Real Estate Sales Person 917-626-1381

    Source: Out East,MLS#: 392886

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 4
      • Full bathrooms: 4
      Rooms
      • Room types: Family Room, Laundry
      Cooling
      • Central Air
      Features
      • Basement: Yes
      • Has fireplace: Yes
      Interior area
      • Total structure area: 4,663
      • Total interior livable area: 4,663 sqft
      Video & virtual tour

      Property

      Parking
      • Parking features: GarageDetached
      • Has garage: Yes
      Features
      • Stories: 3
      • Has private pool: Yes
      • Pool features: Heated
      • Has spa: Yes
      • Spa features: Heated
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      • Waterfront features: Waterfront
      • Frontage type: Waterfront
      Lot
      • Size: 6.5 Acres
      Details
      • Parcel number: 1000078000700009000

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Condition
      • New construction: No
      • Year built: 2006

      Community & HOA

      Community
      • Features: Room for a Tennis Court
      Location
      • Region: Southold

      Financial & listing details

      • Price per square foot: $792/sqft
      • Tax assessed value: $2,109,091
      • Date on market: 1/15/2026
      • Lease term: Contact For Details

        Estimated market value

        $3,544,200

        $3.37M - $3.72M

        $7,341/mo

        Price history

        DateEventPrice
        6/15/2026Price change$3,695,000-4%$792/sqft
        Source: OneKey® MLS as distributed by MLS GRID #928708 Report a problem
        10/30/2025Listed for sale$3,850,000+79.1%$826/sqft
        Source: OneKey® MLS as distributed by MLS GRID #928708 Report a problem
        12/31/2020Sold$2,150,000+13.2%$461/sqft
        Source: OneKey® MLS as distributed by MLS GRID #L3220414 Report a problem
        11/21/2020Pending sale$1,899,500$407/sqft
        Source: Daniel Gale Sothebys Int'l #3220414 Report a problem
        9/28/2020Price change$1,899,500-5%$407/sqft
        Source: Daniel Gale Sothebys Int'l #3220414 Report a problem
        8/18/2020Price change$1,999,000-13.1%$429/sqft
        Source: Daniel Gale Sothebys Int'l #3220414 Report a problem
        6/8/2020Listed for sale$2,299,900+15%$493/sqft
        Source: Daniel Gale Sothebys Int'l #3220414 Report a problem
        11/1/2019Listing removed$1,999,999$429/sqft
        Source: Daniel Gale Sotheby's International Realty #345159 Report a problem
        6/26/2019Price change$1,999,999-9%$429/sqft
        Source: Daniel Gale Sotheby's International Realty #345159 Report a problem
        5/25/2019Price change$2,199,0000%$472/sqft
        Source: Daniel Gale Sothebys Int'l #3132130 Report a problem
        5/29/2018Price change$2,199,999-8.3%$472/sqft
        Source: Daniel Gale Sothebys Int'l #3014333 Report a problem
        3/23/2018Listed for sale$2,399,999-4%$515/sqft
        Source: Daniel Gale Sothebys Int'l #3014333 Report a problem
        10/1/2017Listing removed$2,499,999$536/sqft
        Source: Daniel Gale Sotheby's International Realty #p1277374 Report a problem
        5/5/2017Price change$2,499,999-16.5%$536/sqft
        Source: Daniel Gale Sotheby's International Realty #p1277374 Report a problem
        3/6/2017Listed for sale$2,995,000+866.1%$642/sqft
        Source: Daniel Gale Sotheby's International Realty #p1277374 Report a problem
        4/1/2004Sold$310,000+63.2%$66/sqft
        Source: Public Record Report a problem
        1/2/1998Sold$190,000$41/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $11,600
        2024-- $11,600
        2023-- $11,600
        2022-- $11,600
        2021-- $11,600 +19.6%
        2020-- $9,700
        2019-- $9,700
        2018-- $9,700 -7.6%
        2017$12,434 $10,500
        2016-- $10,500
        2015-- $10,500 -16%
        2014-- $12,500
        2013-- $12,500
        2012-- $12,500
        2011-- $12,500
        2010-- $12,500
        2009-- $12,500
        2008-- $12,500
        2007$11,997 +613.4%$12,500 +525%
        2005$1,682 +4.5%$2,000
        2004$1,608 +3.6%$2,000
        2003$1,552 +4.7%$2,000
        2002$1,483 $2,000
        2001-- $2,000
        2000$1,279 $2,000
        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.
        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: 11971

        Getting around

        5 / 100
        Car-Dependent
        26 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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