Set in the heart of Sag Harbor Village, 207 Madison Street is a rare and masterfully reimagined historic compound where timeless architecture, exceptional craftsmanship, and modern luxury converge. Originally built in 1841, the residence has undergone an extraordinary four-year restoration and expansion, thoughtfully executed by Riostello Studio, Further Development, and Halcyon Design with landscaping by By the Bay Land Design. The result is a refined village residence that honors its nearly two centuries of heritage while delivering the ease, scale, and sophistication of contemporary living. Every element of the home reflects a meticulous attention to detail. The historic residence was carefully lifted to allow for a new foundation and a seamless 1,400 +/- sq. ft. addition, creating a gracious 5,000 +/- sq. ft. residence. Original architectural details - including solid timber porch columns, front door with rim lock and sidelights, hand-hewn beams, and early brick and granite from the chimneys and foundation - were preserved and artfully repurposed throughout, lending the home an unmistakable sense of character and permanence. Inside, the interiors balance historic warmth with elevated modern design. A gracious entry foyer introduces formal living and dining spaces, while wide-plank white oak floors, Belgian bluestone, custom millwork, Waterworks fixtures, and radiant-heated baths create a consistent language of understated luxury. The eat-in kitchen is a centerpiece of the home, beautifully appointed with custom white oak cabinetry, a leathered quartzite island, a La Cornue gas range, and premier appliances by Sub-Zero and Miele. Designed for both intimate daily living and effortless entertaining, the main home offers five bedrooms, six full bathrooms, and two powder rooms, including a private lower-level guest or staff suite with its own entrance. Additional amenities include a fitness center with steam shower, a home theater, Lutron home automation, and thoughtfully integrated modern systems throughout. Outdoors, the property unfolds as a private village compound on 0.38 +/- acres of newly landscaped grounds, enhanced by mature hornbeams, pleached lindens, lush perimeter plantings, and garden spaces framed by original granite. At the center is a heated 17' x 40' saltwater gunite pool with an 8' x 8' spa, surrounded by expansive Kota limestone terraces designed for lounging, dining, and entertaining. The restored glass conservatory, currently set up as a fifth bedroom, includes a full bathroom and offers a charming and flexible destination for guests, studio use, entertaining, or poolside living. A separate garage and pool cabana further extends the property's functionality, creating a true multi-structure compound ideal for hosting, extended stays, and generational living. Perfectly positioned moments from Sag Harbor's celebrated restaurants, shops, marinas, and cultural destinations, 207 Madison Street offers the rare ability to enjoy privacy, scale, and resort-like amenities in one of the Village's most coveted settings. A once-in-a-generation offering, 207 Madison Street is more than a restored historic home - it is an exquisitely finished Sag Harbor Village compound designed for modern living, enduring beauty, and legacy ownership.