Newly constructed and set along the western-facing shoreline of Otter Cove, this exceptional Sag Harbor residence captures picturesque sunsets, tranquil water views, and the rare combination of waterfront living with immediate proximity to the Village. The 6-bedroom house sits in a quiet residential pocket overlooking lawns and water, yet is still located within moments of the harbor, its boats, shops, and restaurants. Set on approximately one-half acre with a private path leading directly to water access, the home encompasses 6,000 +/- square feet across three finished levels that celebrate abundant natural light and seamless indoor-outdoor living. A gracious entry introduces interiors where hand-applied plaster ceilings, textured wall finishes, Waterworks fixtures, wide-plank white oak flooring, quality hardware, and a curated palette of natural materials reflect a custom level of craftsmanship with high end details carried throughout the residence. Expansive gathering areas flow effortlessly to multiple covered terraces overlooking the cove. The great room serves as the home's centerpiece, anchored by a wood-burning fireplace and framed by walls of glass that invite the surrounding landscape indoors. The adjoining kitchen is appointed with a generous center island, breakfast area, and high-end appliances inclusive of a Bertazzoni range, creating a natural setting for both casual mornings and elegant entertaining. A private study, comfortable white oak-paneled den, mudroom, powder room, and first-floor junior primary suite with terrace access complete the main level, providing versatility for family and guests alike. Upstairs, the primary suite presents peaceful water views from a private terrace overlooking the cove, along with a gas-burning fireplace, spacious dressing areas, and a spa-inspired bath featuring a steam shower and freestanding tub. Additional ensuite bedrooms and auxiliary laundry provide comfortable accommodations while maintaining privacy throughout the second floor. The finished lower level expands the home's lifestyle appeal with an impressive collection of entertainment amenities, including a spacious recreation room with bar, game room, wine room, fitness studio, laundry, guest bedroom, and a custom bunk room. Whether gathering after a day on the water or hosting throughout the summer season, the lower level functions as a destination entirely its own. Outdoors, more than 2,000 square feet of exterior decking extends the home's living spaces, with covered terraces transitioning effortlessly to the heated pool and landscaped grounds, where a private path meanders directly to the shoreline of Otter Cove, inviting kayaking, paddleboarding, and peaceful days spent enjoying the water. Two gas-burning fire tables create inviting gathering spaces for enjoying the property's western exposure and evening sunsetspleting the property are a one-car garage and approved plans for a detached pool house featuring a half bath, outdoor shower, and built-in Lynx grilling station, creating an outstanding opportunity to further enhance the home's outdoor experienceplementing the property's active water lifestyle, nearby Mashashimuet Park features public hard and clay tennis courts set among mature trees and open parkland. For evenings on the water, Sag Harbor Yacht Club offers sunset cruises which reveal sweeping views across Peconic Bay and the historic harbor skyline. Enriched by boating, public tennis courts, acclaimed dining, boutique shopping, and the vibrant character of Sag Harbor Village, 36 Oakland Avenue offers a lifestyle that effortlessly balances waterfront recreation, refined entertaining, and the timeless appeal of one of the Hamptons' most treasured harbor communities.