Perched proudly on Captains Row, this rare four-family, five story property with a two-story owner's residence on the top floors blends timeless architectural charm with breathtaking views of Boston Harbor and the downtown skyline from every apartment. Ideally located at 191 Webster Street, this exceptional property places you in the heart of one of Boston's most vibrant and culturally rich waterfront neighborhoods. Enjoy easy access to cafés, bakeries, and an array of diverse dining destinations. Directly across from historic Brophy Park and just a short stroll to Piers Park and the Jeffries Yacht Club, the location offers an unmatched waterfront lifestyle. Commuting is a breeze with the outstanding convenience of nearby MBTA Blue Line service and the East Boston Ferry, providing quick connections to downtown Boston, the Seaport, and beyond. Inside, apartments feature soaring ceilings, oversized windows, and beautiful period details that highlight the building's historic character. The property also offers separate utilities, fenced front and rear yards and the peace of mind that comes with a roof and skylight that are just two years old. Whether you're seeking a premier long-term investment, a prime condominium conversion opportunity, or an owner-occupant property with built-in rental income, this exceptional multi-family home presents a rare opportunity to own an historic, landmark property in one of Boston's most desirable waterfront neighborhoods.