Set on an oversized lot in the heart of Shippan Point, this beautifully updated home offers a rare combination of character, space, and modern amenities just moments from the water. Thoughtfully renovated while preserving its original charm, the home features expansive living spaces, wide plank and hardwood flooring, a stunning vaulted great room with exposed beams and stone fireplace, and a spacious eat-in kitchen designed for everyday living and entertaining alike. The private backyard is an entertainer's dream, offering exceptional outdoor living space rarely found in the neighborhood. Whether hosting large gatherings or enjoying a quiet evening at home, the setting provides the perfect backdrop for both. The generously sized primary suite serves as a true retreat, complete with fireplace, walk-in closet, and luxurious bath. Additional highlights include a dedicated wine room, fitness/yoga space, finished lower level, mudroom, and multiple flexible living areas throughout the home. Ideally located just a short walk from Stamford Yacht Club and only minutes from downtown Stamford, residents enjoy convenient access to express train service to Manhattan with approximately 45-minute travel times and multiple departures throughout the day. A rare opportunity to enjoy the best of coastal living, neighborhood charm, and commuter convenience in one of Stamford's most sought-after waterfront communities.