Timeless elegance meets village living in this distinguished 1830s Victorian on coveted Captain's Row in Sag Harbor. Once owned by merchant and whaling ship owner D.H. Douglas, this Eastlake-style residence is a true Main Street standout, defined by its ornate brackets, classic wraparound porch, and enduring curb appeal. Inside, sun-drenched double parlors with floor-to-ceiling sash windows create a gracious setting for entertaining, while the layout flows effortlessly into a relaxed den with fireplace and open-plan kitchen - perfect for everyday living. A first-floor bedroom and adjacent full bath offer flexible space for guests or a home office. Upstairs, four well-proportioned bedrooms include a spacious primary suite with fireplace and walk-in closet. A third-floor loft with full bath, tucked beneath the eaves, provides versatile bonus space for a studio, office, or media retreat. Outdoors, a gated English-style garden unfolds with brick walkways, patios, and a gunite pool, all set against a town-owned reserve for exceptional privacy-an uncommon find on Main Street. The .35± acre property also offers generous off-street parking and a one-car garage. Moments from the harbor, shops, galleries, and restaurants, this rare offering blends historic significance, architectural charm, and modern comfort in one of Sag Harbor Village's most sought-after locations.