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For sale
  • Price cut: $299.5K (7/7)
    $2,399,999

    9 Watercrest Court, Head Of The Harbor, NY 11780

    8beds
    6,475sqft
    Loading
    Single Family Residence, Residential
    Built in 1986
    2 Acres Lot
    $-- Zestimate®
    $371/sqft
    $-- HOA

    What's special

    Guest bedroomThree additional en-suite bedroomsFull guest bathPowder roomPrivate resort-style backyard oasisProfessionally landscaped groundsFull regulation-sized bowling alley
    New Price. Fresh Presentation. One Extraordinary Opportunity. *A Private Resort Where Luxury Meets Everyday Living* Motivated seller has thoughtfully repositioned this exceptional estate with a compelling new price, creating a rare opportunity to own one of Head of the Harbor's most distinctive luxury residences. Hidden at the end of a quiet cul de sac in the prestigious Incorporated Village of Head of the Harbor, 9 Watercrest Court is more than a home. It is a private retreat where holidays become traditions, generations gather, and every weekend feels like a vacation. Thoughtfully designed for exceptional entertaining and everyday living, every space encourages connection while offering the privacy and comfort of a true estate. Spanning approximately 10,000 square feet across all levels, the residence seamlessly blends timeless architecture with modern luxury. A dramatic two story foyer leads to expansive living spaces filled with natural light, soaring ceilings, radiant heated floors, custom millwork, and walls of windows. At the center of it all is a spectacular chef's kitchen featuring Wolf, Sub Zero, and Miele appliances, an oversized island, walk in pantry, coffee bar, and effortless flow into the surrounding gathering spaces. The primary suite offers a peaceful retreat with a spa inspired bath and oversized walk in closets, while the private guest residence, complete with its own kitchen, living room, bedroom, full bath, and separate entrance, provides exceptional flexibility for multigenerational living, extended family, long term guests, live in support, or a private executive suite. Designed for entertaining on a level rarely found in residential real estate, the lower level features a professionally designed private bowling alley, fitness area, recreation spaces, and multiple gathering areas that make birthdays, holidays, game nights, and family celebrations unforgettable. Outside, the resort style backyard offers an in ground pool, expansive patios, beautifully landscaped grounds, and multiple outdoor living spaces designed for everything from peaceful mornings with coffee to summer barbecues and evenings with family and friends. Ideally located in one of Long Island's most sought after North Shore communities, Head of the Harbor offers estate living just minutes from Stony Brook University, renowned hospitals, yacht clubs, golf courses, beaches, fine dining, and major transportation. This is more than a luxury home. It is where your family's next chapter begins. Notable Features • Approximately 10,000 square feet across all levels • Private guest residence with separate entrance • Professionally designed private bowling alley • Resort style in ground pool with expansive outdoor entertaining areas • Chef's kitchen with Wolf, Sub Zero, and Miele appliances • Radiant heated floors • Whole house generator • Fitness area and expansive recreation spaces • Located in the prestigious Incorporated Village of Head of the Harbor
    103 days
    |
    1,459
    |
    95
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    The Agency Northshore NY 631-870-0753,

    Nicholas Campasano 631-848-6515,

    Kyle Roskot 631-521-1844,

    The Agency Northshore NY

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 976021MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 8
      • Bathrooms: 8
      • Full bathrooms: 6
      • 1/2 bathrooms: 2
      Other
      • Description: Entry Foyer, Living Room, Dining Room, Den, Kitchen W Breakfast Nook & Bar, Primary W 2 Walk-Ins & En-Suite, 3 Additional Bedrooms W En-suites, Office, Bathroom, Laundry
      • Level: First
      Other
      • Description: Bedroom, Full Bath, Office/Flex Room
      • Level: Second
      Other
      • Description: Private Guest Residence: Living Room, Kitchen, 2 Bedrooms W Walk-Ins, Bathroom
      • Level: Second
      Other
      • Description: Finished: Living Room, Bathroom, Bowling Alley, Gym, Billiard Room, Bar, Table Tennis Room, Storage
      • Level: Lower
      Heating
      • Oil, Radiant Floor
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Dryer, Gas Range, Refrigerator, Washer
      • Laundry: Washer/Dryer Hookup, In Hall, Laundry Room
      Features
      • First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Breakfast Bar, Built-in Features, Cathedral Ceiling(s), Central Vacuum, Chefs Kitchen, Crown Molding, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, High Ceilings, His and Hers Closets, In-Law Floorplan, Kitchen Island, Primary Bathroom, Master Downstairs, Quartz/Quartzite Counters, Sound System, Speakers, Storage, Walk-In Closet(s), Wet Bar
      • Flooring: Hardwood, Tile
      • Basement: Finished,Full,Walk-Out Access
      • Attic: Partial
      • Number of fireplaces: 1
      • Fireplace features: Living Room
      Interior area
      • Total structure area: 6,850
      • Total interior livable area: 6,475 sqft

      Property

      Parking
      • Total spaces: 3.5
      • Parking features: Driveway
      • Garage spaces: 3.5
      • Has uncovered spaces: Yes
      Features
      • Levels: Three Or More
      • Has private pool: Yes
      • Pool features: In Ground
      • Fencing: Back Yard
      Lot
      • Size: 2 Acres
      • Features: Cul-De-Sac, Private
      Details
      • Parcel number: 0801006000200004000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary
      • Property subtype: Single Family Residence, Residential
      Materials
      • Advanced Framing Technique
      Condition
      • Updated/Remodeled
      • Year built: 1986

      Utilities & green energy

      • Sewer: Cesspool
      • Water: Public
      • Utilities for property: Propane

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Saint James

      Financial & listing details

      • Price per square foot: $371/sqft
      • Tax assessed value: $1,711,875
      • Annual tax amount: $32,217
      • Date on market: 4/15/2026
      • Cumulative days on market: 104 days
      • Listing agreement: Exclusive Right To Sell

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/7/2026Price change$2,399,999-11.1%$371/sqft
        Source: OneKey® MLS as distributed by MLS GRID #976021 Report a problem
        6/11/2026Price change$2,699,500-6.9%$417/sqft
        Source: OneKey® MLS as distributed by MLS GRID #976021 Report a problem
        4/15/2026Listed for sale$2,900,000+148.9%$448/sqft
        Source: OneKey® MLS as distributed by MLS GRID #976021 Report a problem
        12/31/2018Sold$1,165,000-2%$180/sqft
        Source: OneKey® MLS as distributed by MLS GRID #L3048515 Report a problem
        9/10/2018Pending sale$1,188,888$184/sqft
        Source: Signature Premier Properties #3048515 Report a problem
        7/17/2018Price change$1,188,888-0.8%$184/sqft
        Source: Signature Premier Properties #3048515 Report a problem
        4/5/2018Listed for sale$1,199,000$185/sqft
        Source: RE/MAX Beyond #3017717 Report a problem
        1/1/2018Listing removed$1,199,000$185/sqft
        Source: RE/MAX Beyond #2915004 Report a problem
        6/28/2017Price change$1,199,000-7.7%$185/sqft
        Source: RE/MAX Beyond #2915004 Report a problem
        2/20/2017Listed for sale$1,299,000$201/sqft
        Source: RE/MAX Beyond #2915004 Report a problem
        12/16/2016Listing removed$1,299,000$201/sqft
        Source: RE/MAX Beyond #2742731 Report a problem
        3/2/2016Listed for sale$1,299,000$201/sqft
        Source: RE/MAX Beyond #2742731 Report a problem
        12/30/2015Listing removed$1,299,000$201/sqft
        Source: RE/MAX Beyond #2742731 Report a problem
        3/7/2015Listed for sale$1,299,000-7.1%$201/sqft
        Source: RE/MAX Beyond #2742731 Report a problem
        1/1/2015Listing removed$1,399,000$216/sqft
        Source: Douglas Elliman Report a problem
        5/13/2014Listed for sale$1,399,000+55.6%$216/sqft
        Source: Douglas Elliman #2669385 Report a problem
        10/29/2013Listing removed$899,000$139/sqft
        Source: Douglas Elliman #2558982 Report a problem
        9/12/2013Price change$899,000-8.2%$139/sqft
        Source: Douglas Elliman #2558982 Report a problem
        7/18/2013Price change$979,000-2%$151/sqft
        Source: Douglas Elliman Real Estate #2558982 Report a problem
        5/25/2013Listed for sale$999,000$154/sqft
        Source: Douglas Elliman #2558982 Report a problem
        6/21/2012Listing removed$999,000$154/sqft
        Source: RE/MAX Beyond #2457571 Report a problem
        5/24/2012Price change$999,000-9.1%$154/sqft
        Source: RE/MAX Beyond #2457571 Report a problem
        4/17/2012Price change$1,099,000-2.3%$170/sqft
        Source: RE/MAX Beyond #2457571 Report a problem
        1/7/2012Listed for sale$1,125,000-13.4%$174/sqft
        Source: RE/MAX Beyond #2457571 Report a problem
        10/2/2011Listing removed$1,299,000$201/sqft
        Source: Daniel Gale Associates Inc #2306427 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $13,695
        2024-- $13,695
        2023-- $13,695
        2022-- $13,695
        2021-- $13,695
        2020-- $13,695
        2019-- $13,695
        2018-- $13,695
        2017$27,723 $13,695
        2016-- $13,695
        2015-- $13,695
        2014-- $13,695 -2.7%
        2013-- $14,080
        2012-- $14,080 -8.2%
        2011-- $15,340
        2010-- $15,340 -7%
        2009-- $16,500
        2008-- $16,500
        2007$23,549 +23%$16,500
        2005$19,145 +1.9%$16,500 -5.7%
        2004$18,785 +7.8%$17,500
        2003$17,422 +61.5%$17,500 -5.4%
        2002$10,788 $18,505
        2001-- $18,505
        2000$10,225 $18,505
        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: 11780

        Getting around

        25 / 100
        Car-Dependent
        12 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: St James Elementary School
        • Middle: Nesaquake Middle School
        • High: Smithtown High School-East

        Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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