First Time on the Market! Steeped in local history, this charming 1,600 sq. ft. home—once an Inn—dates back to 1850 and has been lovingly cared for by the same family for nearly a century. Originally part of a six-acre estate, it now sits on a rare and expansive .84-acre flat lot, offering endless possibilities for outdoor enjoyment and entertaining. Perfect for car enthusiasts, contractors, or those in need of extra storage, the property features an oversized detached two-car garage plus a spacious shed—formerly a chicken coop—that can easily be restored or repurposed. Inside, the flexible floor plan offers convenience and character, including a main-level bedroom and full bath, the bedroom can easily be converted to a Dining Room to suit your needs. The enclosed porch is a charming retreat filled with natural light, can be perfectly used as a cozy sitting room, with ample space for storage, it effortlessly blends functionality with warmth and character. Upstairs, you'll find four additional bedrooms, one with a walk-in cedar closet and another that can serve as a library, office, or sitting area. A second full bath boasts modern updates, including a whirlpool tub and separate shower. The secondary staircase provides unique charm and easy access to the kitchen. Preserving its historic appeal, this home showcases original interior doors, hardware, custom moldings, and built-ins, as well as hardwood flooring throughout most of the home, including original wide-plank floors upstairs. Additional features include gas heating & cooking, plus updates like a newer roof, vinyl siding, and Andersen windows. Conveniently located with quick access to I-495, shopping, the local train station, and MacArthur Airport, this is a rare opportunity to own a piece of Long Island history. Possible Commercial property (buyers to make inquires with Town of Islip for zoning).