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For sale
    • $699,998

    108 High Street, Port Jefferson, NY 11777

    4beds
    2,768sqft
    Loading
    Single Family Residence, Residential
    Built in 1830
    0.25 Acres Lot
    $-- Zestimate®
    $253/sqft
    $-- HOA

    What's special

    Gas fireplaceCentral air conditioningDetached two-car garageCenter islandLarge formal dining roomOversized walk-in pantry
    BACK ON THE MARKET!!! Circa 1855, the Captain Lewis Tooker Home sits prominently in Port Jefferson Village, offering historic charm with thoughtful modern updates. Designed by architect Geysea Sarkkany, this residence features a chef’s kitchen equipped with a 6-burner Viking stove, cabinetry, and a center island, oversized walk-in pantry. Just off the kitchen is a large formal dining room, two formal living rooms with gas fireplace, and a flexible layout offering 3–4 bedrooms, including an office or optional fourth bedroom. Third floor Scenic views of Port Jefferson Harbor. Recent improvements include heating system upgrades with a new radiator and rebalanced lines for improved efficiency, concrete repairs to the rear chimney, and the addition of a gas line for a fireplace insert. Exterior updates include a widened driveway with new blacktop/Belgian block border, white PVC fencing with gate, and additional wood picket fencing along the side and rear. The home has been newly sided, and the roof is approximately 15 years old. Additional features include central air conditioning, separate hot water heater, a detached two-car garage and back yard patio. 2 blocks from shopping and events in Port Jefferson Village, residents enjoy access to village beaches, country club amenities, live music, seasonal festivals. TAX GRIEVANCE FILED
    86 days
    |
    184
    |
    15
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    Zillow last checked:

    Listing updated:

    Listed by:

    Douglas Elliman Real Estate 631-751-6000,

    Lisa A. Jaeger 631-751-6000

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 991204MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Heating
      • Oil
      Cooling
      • Central Air, Ductless
      Appliances
      • Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
      • Laundry: Washer/Dryer Hookup, Laundry Room
      Features
      • Chefs Kitchen, Crown Molding, Eat-in Kitchen, Entrance Foyer, Formal Dining, Kitchen Island, Pantry, Primary Bathroom, Storage, Walk-In Closet(s)
      • Flooring: Hardwood
      • Basement: Crawl Space
      • Attic: None
      • Number of fireplaces: 1
      • Fireplace features: Bedroom, Family Room, Gas, Living Room
      Interior area
      • Total structure area: 2,768
      • Total interior livable area: 2,768 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Detached, Driveway, Garage
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: Three Or More
      • Patio & porch: Covered, Patio, Porch
      • Exterior features: Fire Pit
      • Fencing: Back Yard
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      Lot
      • Size: 0.25 Acres
      • Features: Back Yard, Landscaped, Near Public Transit, Near School, Near Shops, Views
      Details
      • Additional structures: Garage(s)
      • Parcel number: 0206008000300018000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence, Residential
      Materials
      • Frame, Vinyl Siding
      Condition
      • Actual
      • Year built: 1830
      • Major remodel year: 1855

      Utilities & green energy

      • Sewer: Cesspool
      • Water: Public
      • Utilities for property: Electricity Connected, Natural Gas Connected, Trash Collection Private, Water Connected

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Port Jefferson

      Financial & listing details

      • Price per square foot: $253/sqft
      • Tax assessed value: $3,280
      • Annual tax amount: $12,196
      • Date on market: 4/28/2026
      • Cumulative days on market: 40 days
      • Listing agreement: Exclusive Right To Sell
      • Electric utility on property: Yes

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/23/2026Listed for sale$699,998$253/sqft
        Source: OneKey® MLS as distributed by MLS GRID #991204 Report a problem
        6/6/2026Pending sale$699,998$253/sqft
        Source: OneKey® MLS as distributed by MLS GRID #991204 Report a problem
        5/9/2026Price change$699,9980%$253/sqft
        Source: OneKey® MLS as distributed by MLS GRID #991204 Report a problem
        4/28/2026Listed for sale$699,999+16.7%$253/sqft
        Source: OneKey® MLS as distributed by MLS GRID #991204 Report a problem
        3/21/2022Sold$600,000$217/sqft
        Source: Public Record Report a problem
        12/9/2021Sold$600,000-4%$217/sqft
        Source: OneKey® MLS as distributed by MLS GRID #L3340466 Report a problem
        10/5/2021Pending sale$625,000$226/sqft
        Source: OneKey® MLS as distributed by MLS GRID #3340466 Report a problem
        8/29/2021Listed for sale$625,000+7.9%$226/sqft
        Source: OneKey® MLS as distributed by MLS GRID #3340466 Report a problem
        12/4/2019Listing removed$579,000$209/sqft
        Source: Jolie Powell Realty Inc #3137761 Report a problem
        10/2/2019Price change$579,000-1.7%$209/sqft
        Source: Jolie Powell Realty Inc #3137761 Report a problem
        7/12/2019Price change$589,000-1.7%$213/sqft
        Source: Jolie Powell Realty Inc #3137761 Report a problem
        6/12/2019Price change$599,000-7.7%$216/sqft
        Source: Jolie Powell Realty Inc #3137761 Report a problem
        4/19/2019Price change$649,000-7.2%$234/sqft
        Source: Realty Connect USA L I Inc #3108998 Report a problem
        3/14/2019Listed for sale$699,000-6.8%$253/sqft
        Source: Realty Connect USA L I Inc #3108998 Report a problem
        2/8/2007Sold$750,000+174.7%$271/sqft
        Source: Public Record Report a problem
        9/1/1998Sold$273,000$99/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $3,280
        2024-- $3,280
        2023-- $3,280
        2022-- $3,280
        2021-- $3,280
        2020-- $3,280
        2019-- $3,280
        2018-- $3,280
        2017$7,040 $3,280
        2016-- $3,280
        2015-- $3,280
        2014-- $3,280
        2013-- $3,280
        2012-- $3,280
        2011-- $3,280
        2010-- $3,280
        2009-- $3,280
        2008-- $3,280
        2007$5,933 +33.5%$3,280
        2005$4,445 +5.4%$3,280
        2004$4,215 +5%$3,280
        2003$4,016 +4.4%$3,280
        2002$3,846 +2.2%$3,280
        2001$3,764 -3.6%$3,280
        2000$3,906 $3,280
        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.
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        Climate risks

        Neighborhood: 11777

        Getting around

        72 / 100
        Very Walkable
        28 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Port Jefferson Elementary School
        • Middle: Port Jefferson Middle School
        • High: Earl L Vandermeulen High School

        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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