Discover an unparalleled offering in the heart of historic Sag Harbor Village. Situated on a rare 0.63-acre corner lot, this meticulously restored compound delivers the ultimate Hamptons lifestyle: a luxuriously appointed main residence, a charming guest cottage, and resort-like grounds with a heated gunite pool. Just moments from Sag Harbor's iconic Main Street, and directly across from the serene Haven's Beach, this property perfectly blends timeless elegance with modern luxury. The main residence spans 4,500 +/- square feet of light-filled interiors, thoughtfully designed for today's discerning homeowner. The 250 +/- sq. ft. wraparound porch, framed by lush gardens, welcomes you into a home that celebrates both the craftsmanship of Sag Harbor's maritime heritage and the sophistication of contemporary design. Inside, bright and open living spaces feature four bedrooms and four-and-a-half bathrooms as well as five grand fireplaces. Inside the 2,279 +/- sq. ft. first floor, thoughtfully curated spaces balance grandeur and comfort. At the heart of the home lies a chef's kitchen - a culinary haven complete with top-of-the-line appliances, dual dishwashers, a spacious walk-in pantry, and its own cozy fireplace. The formal dining room, also graced by a fireplace, is ideal for hosting, while the sun-drenched living room, charming den, and private office offer a variety of spaces to gather or retreat. Two elegant staircases lead to the 1,660 +/- sq. ft. second floor, which offers tranquility and refinement. The centerpiece upstairs is the primary suite, featuring a fireplace, spa-like en-suite bath, and walk-in closet. A spacious en-suite guest bedroom offers privacy, while two additional guest bedrooms share a well-appointed bathroom. A conveniently located laundry room rounds out the upper level, ensuring ultimate ease for year-round living or extended stays. Set on the rear of the property, the 980 +/- sq. ft. guest cottage provides an inviting retreat for family or guests. This charming space includes a living room with a fireplace, a full kitchen, bedroom, bathroom, and a loft. Additionally, the 220 +/- sq. ft. garage offers practicality without compromising aesthetics, maintaining the compound's seamless design. Step outside into your private sanctuary: meticulously manicured and fully irrigated grounds designed for relaxation and entertaining. The 800 +/- sq. ft. heated gunite pool, with its organic freeform design, is bordered by a bluestone patio and surrounded by specimen trees for complete privacy. Additional lawn space offers the perfect setting for al fresco dining or leisurely afternoons in the Hamptons sun. Located on one of the most coveted streets in Sag Harbor, this property offers the ultimate in both privacy and convenience. Enjoy strolls to Sag Harbor's renowned restaurants, boutique shops, marinas, and cultural landmarks. With 6,652 +/- sq. ft. of total living space and the tranquility of the nearby Cormaria Retreat as your neighbor, this quintessential captains home offers a rare balance of serene escape and vibrant village life. Properties of this size, scale, and quality are exceedingly rare in Sag Harbor Village. 98 Bay Street is not just a home - it's a legacy. Opportunities of this caliber are exceedingly rare in the Village-don't miss the chance to make this remarkable estate your own.