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    (845) 398-1717 susan@ImagineProperties1.com
    • 100 Dutch Hill Rd Suite 260
      Orangeburg, NY 10962
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    Home / Callicoon / 48 Upper Main Street
    48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 48 Upper Main Street Callicoon, NY 12723 View All Photos

    $759,000

    | Active

    48 Upper Main Street

    Callicoon, NY 12723

    1,536
    Square Feet
    3
    Beds
    1.5
    Baths
    1.14
    Acres
    217
    Days on Market
    KEY925634
    MLS#
    House
    Structure
    Residential
    Zone
    Contact

    Perched above the heart of Callicoon, this 1908 landmark stands as one of Sullivan County’s most captivating historic structures—a former schoolhouse whose legacy spans education, craftsmanship, and art. Over the decades, its grand proportions have sheltered classrooms, a dress factory, and a piano workshop—each chapter leaving its mark in the woodwork, wainscoting, and soaring ceilings that remain today. Now reimagined by artists, the building bridges eras with a rare blend of authenticity and modern livability. A bright three-bedroom, two-bath residence offers comfort and warmth with custom cabinetry, solid wood floors, and rich natural light. Beyond, the structure unfolds into vast and inspiring spaces: a 60-by-34-foot gymnasium with a 20-foot ceiling and stage; a luminous upper-floor dance studio spanning nearly sixty feet; art studios inspired by gigantic windows bringing in nature and sunlight, open workrooms, and a full stacked stone-foundation basement with walk-in access. At roughly 13,000 square feet on over an acre, the property invites both vision and versatility. Zoned for mixed use, it can evolve into a gallery and performance venue, a live-work compound, a wellness retreat, or a community hub. Every beam and window suggests possibility—every echo in the old gym reminds you that this building was made for voices, for movement, for gathering. Surrounded by ornamental trees and perennial gardens, and just a short stroll from Callicoon’s beloved cafes, the farmers’ market, and the Delaware River, 48 Upper Main offers both privacy and presence. It is that rare piece of architecture that feels both anchored in history and untethered in potential. Updated infrastructure includes a new metal roof and a new boiler (with a copper manifold that will inspire envy). A place where authenticity reigns, light abounds, and inspiration seems to gather naturally within the walls. 48 Upper Main Street isn’t just a building—it’s a living story waiting for its next author. Offering includes two tax parcels .89 acres and .25

    Property Details
    Interior
    First Floor Bedroom, First Floor Full Bath, Breakfast Bar, Built-in Features, Cathedral Ceiling(s), Entrance Foyer, High Ceiling
    Cooling
    Ductless, Electric, Multi Units
    Heating
    Electric, Forced Air, Heat Pump, Hot Water, Oil, Propane
    Cooling Features
    Ductless, Electric, Multi Units
    Bedrooms
    3
    Bathrooms
    1.5
    Full Baths
    1
    Half Baths
    1
    Lot Features
    Near Shops, Part Wooded, See Remarks, Sloped, Stone/Brick Wall, Views, Wooded
    Lot Description
    Near Shops, Part Wooded, See Remarks, Sloped, Stone/Brick Wall, Views, Wooded
    Acres
    1.14
    Square Feet
    1536.0
    Parking Features
    Driveway, Off Street, Parking Lot, Shared Driveway
    Parking Type
    Driveway
    Property Type
    Purchase
    Basement
    1
    Basement Description
    Bilco Door(s), Full, Storage Space, Unfinished
    Basement Finished
    1
    Year Built
    1908
    Foundation
    Stone
    Sewer Information
    Public Sewer
    Utility Source
    Public
    Utility Features
    Cable Connected, Electricity Connected, Sewer Connected, Water Connected
    Appliances
    Dishwasher, Electric Oven, Refrigerator
    School District
    Sullivan West
    Elementary School
    Sullivan West Elementary
    Middle School
    SULLIVAN WEST HIGH SCHOOL AT LAKE HUNTINGTON
    High School
    Sullivan West High School At Lake Huntington
    County
    Sullivan County
    Region
    Delaware
    Original List Price
    $830,000
    Days on Market (Cumulative)
    217
    Taxes Annual
    $14,852
    MLS #
    925634
    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.

    Provided By
    Listed by Dara Barr (#KEY61816)
    Listing Office: Keller Williams Upstate NYProp (#KEYKWUPNY02)

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