Set along the serene waterfront of Dering Harbor, with about 245f of water frontage, this exceptional offering presents a rare and compelling opportunity to own a true Hamptons compound-three distinct parcels thoughtfully combined to create a private and expansive estate experience. At the heart of the property lies a beautifully appointed 4,500sf residence, gracefully sited on 1.5 acres and framed by sweeping water views that immediately captivate upon arrival. A separate .12-acre waterfront parcel features a private dock, offering direct access to the harbor, while an additional 3.2-acre parcel provides the ideal opportunity for a multi-generational compound that balances recreation, privacy, and natural beauty. A long, landscaped approach sets a stately tone, guiding you beneath a covered carport and toward the main residence, with a detached garage thoughtfully positioned nearby. Inside, a regal foyer and functional mudroom welcome you, unfolding into a gracious living room anchored by a striking double-sided fireplace. Expansive windows flood the space with natural light while framing picturesque water views, seamlessly blending indoor comfort with the surrounding coastal setting. A well-placed den offers an intimate complement for relaxation or quiet retreat. The open-concept kitchen is both inviting and functional, featuring a charming built-in dining nook nestled beneath oversized windows. A butler's pantry elegantly connects the kitchen to the formal dining room, where French doors open to a covered porch-perfect for al fresco dining with tranquil water vistas. A powder room and dedicated laundry room complete the main level. The primary suite is a sanctuary unto itself, offering generous proportions, a private sitting area or office centered around a fireplace, and an ensuite bath with a soaking tub. Additional accommodations include an ensuite guest bedroom and two guest rooms-one currently styled as a den-sharing a Jack-and-Jill bath. The third floor expands the living space further, with two guest bedrooms boasting elevated water views, a full bath, and an additional den. Outdoors, the estate is enveloped in mature, meticulously curated landscaping that enhances both privacy and beauty. A gunite pool provides a luxurious setting for summer enjoyment. This is more than a home-it is a legacy waterfront estate, offering a rare combination of scale, setting, and versatility in one of Shelter Island's most coveted enclaves.