Situated in the heart of Sag Harbor Village, 27 Howard Street seamlessly blends historic charm with modern convenience, just moments from Main Street, the harbor, and beloved local spots. This residence opens to a sun-filled living room that flows into a formal dining area, both framed by updated casement windows and soft architectural details. A custom kitchen with a generous island and ample storage connects seamlessly to a cozy family room with a fireplace, all overlooking the landscaped backyard. Upstairs, the private primary suite offers a peaceful retreat with its own fireplace, soaking tub, and dual vanity bathroom. On the lower level, three additional bedrooms provide comfortable accommodations, including one with an en-suite bath and two that share a full bathroom. Deep egress windows allow natural light to fill the space, giving it an open, airy feel. Outside, a gunite pool and spa anchor the thoughtfully landscaped yard, which offers four distinct seating areas for relaxing or gathering. The pool house includes a dry sauna, shower, full bath, wet bar, and lounge. A fire pit, pizza oven, grill, refrigerator, exterior speakers, and landscape lighting complete the outdoor amenities, offering a versatile setting for everyday enjoyment or entertaining. Additional features include a generator, water filtration, a central vacuum system, and parking for three. This home presents a rare opportunity to own a turnkey residence in one of Sag Harbor Village's most sought-after and walkable locations.