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    (845) 398-1717 susan@ImagineProperties1.com
    • 100 Dutch Hill Rd Suite 260
      Orangeburg, NY 10962
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    Home / Southold / 150 Baywater Avenue
    150 Baywater Avenue Southold, NY 11971 150 Baywater Avenue Southold, NY 11971 150 Baywater Avenue Southold, NY 11971 View All Photos

    $850,000

    | Active

    150 Baywater Avenue

    Southold, NY 11971

    2,100
    Square Feet
    3
    Beds
    4
    Baths
    1.05
    Acres
    139
    Days on Market
    985489
    MLS#
    House
    Structure
    Residential
    Zone
    Contact

    Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and the charming village of Southold, with its shops, waterfront, and access to the Long Island Sound. The land at 150 Baywater Avenue is tied to the remarkable story of Maltby Freeman, a formerly enslaved man who earned his freedom in 1807 and, through extraordinary determination, came to own this very property along Bayview near South Harbor Road. Maltby and his wife, Dorcus Benjamin, began with a single-room structure, gradually expanding it into a family homestead in the early 1800s. Their descendants continued to acquire land, eventually owning a house and 30 acres. The Freeman family’s story is one of the earliest documented examples of Black land ownership and upward mobility on Long Island, and this property stands as a tangible connection to that chapter of American history. The property is offered strictly as-is, presenting a rare opportunity for a developer, preservationist, or visionary owner-builder. Included in the sale is a complete set of fully approved architectural and construction plans, a process that required two years of review by the Historic Preservation Commission, Town Planning Department, and Building Department. This extensive approval represents significant time, cost, and expertise that the next owner will not need to replicate. With permits and plans already secured, construction can begin immediately upon closing. For those seeking a property defined by history, character, and forward potential, 150 Baywater Avenue is ready for its next chapter.

    Property Details
    Interior
    Other
    Heating
    See Remarks, Other
    Bedrooms
    3
    Bathrooms
    4.0
    Full Baths
    4
    Acres
    1.05
    Square Feet
    2100.0
    Parking Features
    Driveway
    Parking Type
    Driveway
    Property Type
    Purchase
    Year Built
    1900
    Foundation
    Other
    Sewer Information
    Cesspool, Septic Tank
    Utility Source
    Public
    Utility Features
    See Remarks
    Appliances
    Other
    School District
    Southold
    Elementary School
    Southold Elementary School
    Middle School
    Southold Junior-Senior High School
    High School
    Southold Junior-Senior High School
    County
    Suffolk County
    Region
    Southold
    Original List Price
    $850,000
    Days on Market (Cumulative)
    139
    Taxes Annual
    $7,527
    MLS #
    985489
    Property Subtype
    Single Family Residence
    Parcel Number
    1000-078-00-03-00-022-000
    MLS #
    985489
    Date Listed
    April 15, 2026
    Address
    150 Baywater Avenue
    Location
    Legal

    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

    Last Updated: Sep 2, 2026 12:35 PM. Source: ONEKEY

    Provided By
    Listed by Marco L. Maida (#KEY207266), 917-499-2824
    Listing Office: Compass Greater NY LLC (#KEYCMPA15)

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