Set on an oversized 0.62-acre parcel, formed from the merger of two original lots, 338 Main Street occupies a distinguished position along Sag Harbor Village's coveted Captain's Row, directly across from Otter Pond with serene water views and private access via John Street. Upon entry, gracious Greek Revival and Italianate archways create a sense of arrival, guiding a central axis through the home toward an impressive fireplace. The interiors retain notable period architectural elements, including marble fireplaces and well-proportioned rooms that reflect the craftsmanship and scale of Sag Harbor's maritime era. Dating to circa 1830-1840, this historic residence presents a rare opportunity to restore and thoughtfully reimagine a significant village property. Just shy of 3,000 square feet, the current home offers generous living spaces including four bedrooms, an oversized kitchen, an inviting sunroom, and a detached garage, providing both immediate comfort and exceptional long-term potential. Rich in history and architectural character, the home offers exceptional potential for restoration and expansion. The expansive grounds provide ample space to create a substantial Captain's Row estate, with opportunities for a pool, garage or carriage house, pool house, lower-level expansion, and enhanced landscaping for privacy and outdoor living. A rare offering combining historic provenance, scale, and future possibility, 338 Main Street represents a unique opportunity within the heart of Sag Harbor Village.