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    (845) 398-1717 susan@ImagineProperties1.com
    • 100 Dutch Hill Rd Suite 260
      Orangeburg, NY 10962
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    Home / Shelter Island / 2 Prospect Avenue
    2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 2 Prospect Avenue Shelter Island, NY 11964 View All Photos

    $2,700,000

    | Active

    2 Prospect Avenue

    Shelter Island, NY 11964

    5,900
    Square Feet
    6
    Beds
    3
    Baths
    2.43
    Acres
    96
    Days on Market
    1005789
    MLS#
    House
    Structure
    Residential
    Zone
    Contact

    A rare opportunity to own a legacy compound on Shelter Island, this offering brings together three income-producing historic cottages and a separate buildable lot, all just moments from the water. Positioned at 2 Prospect Avenue and 38 Rock Point Road, the properties are offered as one cohesive investment, blending immediate revenue with exceptional future potential. Each of the three cottages features two bedrooms and one bath, with strong summer rental histories and an undeniable sense of place rooted in the island’s coastal charm. Rich in character and provenance, each residence tells its own story. The Hill Cottage, dating to the 1890s, is a one-of-a-kind former boathouse thoughtfully relocated from a grand Nostrand Avenue estate, with original architectural details preserved throughout. The Red Cottage, originally built in the 1920s as a fisherman’s retreat, has been expanded to include enclosed patios at both the front and rear. The Main House, constructed in the 1940s, has been carefully renovated to enhance modern comfort while maintaining the craftsmanship and warmth of its era. Completing the offering, the adjacent lot at Rock Point Road presents a rare blank canvas, ready for a primary residence and pool, surrounded by three established rental cottages. Whether envisioned as a private multi-generational retreat, a boutique rental compound, or a long-term development investment, this is a truly exceptional opportunity to own a piece of Shelter Island’s history with both immediate income and enduring upside in one of Long Island’s most sought-after enclaves.

    Property Details
    Interior
    Beamed Ceilings, Original Details
    Cooling
    Wall/Window Unit(s)
    Heating
    Baseboard
    Cooling Features
    Wall/Window Unit(s)
    Bedrooms
    6
    Bathrooms
    3.0
    Full Baths
    3
    Acres
    2.425
    Square Feet
    5900.0
    Parking Features
    Driveway
    Parking Type
    Driveway
    Property Type
    Purchase
    Year Built
    1920
    Sewer Information
    Septic Tank
    Utility Source
    Private
    Utility Features
    Electricity Available
    Appliances
    Stainless Steel Appliance(s), Washer
    School District
    Contact Agent
    Elementary School
    Contact Agent
    Middle School
    Call Listing Agent
    High School
    Contact Agent
    County
    Suffolk County
    Region
    Shelter Island
    Original List Price
    $2,700,000
    Days on Market (Cumulative)
    96
    Taxes Annual
    $7,523
    MLS #
    1005789
    Property Subtype
    Single Family Residence
    Waterfront
    1
    Parcel Number
    0700-005-00-05-00-017-001
    MLS #
    1005789
    Waterfront Type
    Lake Front
    Waterfront Features
    Lake Front
    Date Listed
    May 28, 2026
    Address
    2 Prospect 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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