Historic Captain's Row Modernized with Water Views Located in the heart of Sag Harbor's prestigious Main Street Historic District and directly overlooking Otter Pond, this meticulously renovated 1850s Captain's Row residence delivers the rare combination of restored historic architecture and contemporary luxury. With sweeping water views, walkability to Sag Harbor Village, and thoughtful upgrades throughout, 356 Main Street offers a lifestyle that is both sophisticated and soulful. The main level is designed for effortless daily living and refined entertaining. Multiple light-filled sitting rooms, a cozy library, spacious dining area, and TV/den lounge provide flexible gathering spaces enhanced by custom lighting, designer furnishings, and curated contemporary art. The chef's kitchen features a Bertazzoni five-burner stove, Miele dishwasher, oversized refrigerator, and breakfast nook, along with dual coffee options (French press and Nespresso) and a fully outfitted glassware bar. A full bath with shower and separate laundry room complete the first floor. Upstairs, the primary king bedroom enjoys postcard-perfect water views across Otter Pond. Two additional guest bedrooms overlook the landscaped backyard and capture stunning sunset light. A serene bath with soaking tub serves the second floor. A fully renovated lower level extends the home's livability, offering heated and air-conditioned space ideal for a media room, gym, studio, or play area-providing valuable flexibility for year-round use. Outdoors, lush landscaping frames a private rear garden with a sculptural cement dining table, lounge seating, and sun chairs-ideal for al fresco dining and relaxation. The classic front porch offers another vantage point to enjoy morning coffee or afternoon breezes with peaceful water views. A rare opportunity made even more compelling by Board of Health approval that allow expansion for a fourth bedroom and a 10' x 18' pool, adding further value and future potential. Just moments from Sag Harbor Village's shops, restaurants, marinas, and cultural attractions-and one block from the local park-this home delivers a uniquely balanced lifestyle of history, design, privacy, and convenience. 356 Main Street is more than a residence-it is a refined Sag Harbor experience where heritage, architecture, and natural beauty seamlessly converge. Owner/Broker