Tucked behind a serene courtyard entrance off Sag Harbor's historic Church Street, this grandly scaled two-bedroom, two-bathroom Watchcase residence offers a rare opportunity to own a private sanctuary in the very heart of the village - a home once shaped by the refined eye and cultural vision of legendary New York art collector and longtime Museum of Modern Art trustee, Barbara Jakobson. Spanning over a blended 2,500 +/- square feet of exceptional indoor and outdoor living space, the residence makes an immediate statement. Enter through a cozy garden entrance to a formal entry foyer which leads to a breathtaking great room with soaring 11-foot ceilings, exposed brick walls, massive southern pine beams, and a dramatic open island kitchen designed for effortless entertaining and elevated everyday living. The scale, volume, and architectural character are simply unmatched. At the center of the home, a sun-drenched south-facing solarium creates a stunning architectural moment - functioning as both gallery and gathering space - and opens directly to the units second outdoor space, a private garden. The seamless indoor-outdoor flow captures the essence of Hamptons luxury living. Both bedrooms are thoughtfully positioned for privacy and feature dual exposures overlooking the private garden, each with its own ensuite bath. The expansive primary suite serves as a true retreat, complete with three closets and a signature five-fixture Watchcase bath highlighted by a spa-caliber wet room designed for indulgence. The secondary suite offers exceptional separation, two exposures, and a well-appointed ensuite bath, providing comfort and privacy for guests. Just one block from Sag Harbor's charming Main Street and two blocks from the Hamptons' only deep-water marina, Watchcase is one of the most coveted addresses in the village. This is a rare chance to own one of only 63 exclusive Loft, Townhouse, and Bungalow residences set within beautifully landscaped grounds. Residents enjoy a full-service lifestyle with concierge, resident building manager, porters, and superintendent staff. Amenities include a heated saltwater pool, dog park, and The Watchcase Pavilion offering a fitness center, yoga studio, spa room, sauna, locker rooms, an elegant events lounge with fireplace, and catering kitchen. The Grand Lobby Living Room - home to the Vault Bar and a dramatic two-sided fireplace - sets the tone for refined gathering. With designated underground parking spaces #73 and #44 and private storage space #32 (33 square feet), every convenience is in place. Opportunities of this caliber - combining architectural scale, private gardens, premier amenities, and a provenance tied to one of New York's most celebrated cultural figures - rarely come to market in Sag Harbor Village. This is not just a residence. It is a statement, a retreat, and an investment in lifestyle at one of the Hamptons' most prestigious addresses.