Centrally located on picturesque Main Street, 299 Main Street offers a unique opportunity to own a two C of O family home plus studio which can also be reimagined as a single family home in the heart of Sag Harbor Village. Situated on two tenths of an acre, steps from Otter Pond and across from Sag Harbor Cove, this fully cleared property features a 2,000+/- sq ft legal two-family home with three bedrooms and two baths in the main house, expansive lawns and a 500 sf +/- cottage with full bath. In the main house, a welcoming foyer opens to a traditional double parlor living/dining room with stunning bay windows, original moldings and detailed windows all reflecting the authenticity of this special home. Also on the main floor, there are two comfortable bedrooms, a full bath and a large, bright kitchen with French doors opening to a covered patio. Upstairs, legally a separate apartment, there is a bedroom, full bath and a bright, airy and open living and dining area as well as a full kitchen. French doors open to a rooftop deck with a treetop view of Otter Pond. Period details abound throughout the home from its classic exterior architecture to the bay windows, the beautiful entrance and stairway to moldings, windows and fir floors. The special property, with deep lawn, also features a generous cottage with wood burning stove, full bath and separate bar area. Close to dining, shopping, art, theater and music, as well as the beautiful harbor with all its waterfront activities, this is a sensational opportunity. World famous ocean and bay beaches, local farmstands, the wonderful Mashashimuet Park, equestrian facilities and cultural centers are all nearby. In its present form or reimagined, this is an exceptional new offering in Sag Harbor Village.