Historic 1887 Astor Graystone, originally designed by Cobb and Frost, offers captivating, unobstructed views of Lake Michigan. This 136-year-old residence has been meticulously gut-rehabbed, providing four floors of luxurious living space with five above-grade bedrooms and all-new infrastructure, including electrical, water, and gas systems, along with a full perimeter drainage system. For all intents and purposes, this is a new build within the timeless charm of a historic landmark. The sophisticated Graystone welcomes you through a charming gas-lantern-lit iron door, leading to an inviting garden-level foyer. Inside, you're greeted by imported French White Oak chevron hardwood floors, two Aroma360 systems, and an integrated overhead sound system. The foyer features a coat closet, a half bath, and an extra-wide staircase with a continuous handrail, designed to symbolize a healthy lifeline across all levels. Designed to evoke the "wow" factor, the main level landing opens to custom brass dividers that embody the elegance of true Gold Coast living. The western-facing formal living room is anchored by a historic fireplace, illuminated by a stunning 5' x 6' teardrop chandelier, and framed by near floor-to-ceiling Marvin windows. Adjacent to the living room, the formal dining space boasts a substantial chandelier and offers direct access to the rear terrace. The eat-in Chef's kitchen, accessible through an 8' pocket door, is a culinary dream. It features another historic fireplace, a 45" prep sink with dual Kohler faucets, and a Kohler pot filler. The kitchen is outfitted with imported Italian cabinetry, a mix of Blum and Hettich hardware, Italian porcelain finishes, and a glass wall that adds to the modern aesthetic. The elite WiFi-enabled Dacor appliance package includes a 48" gas range with a Thermador insert, a double oven, and a microwave drawer. Additionally, the kitchen is equipped with two dishwashers, a plumbed Miele coffee system, a standalone camera equipped refrigerator, freezer, and a full-height zoned wine refrigerator. The layout provides ample storage, three appliance garages, multiple prep areas, and an adjacent space for casual meals and guest mingling. The kitchen also offers access to a massive terrace with raised porcelain pavers, lighting, sound, a gas connection, and an iron pergola with an infrared heater. Down the rear staircase from the kitchen, you'll find a media room with 7.1 surround sound-perfect for movie nights or watching the big game. The lower level also includes a half bath, a laundry room with a dog washing station, and a mudroom, which is conveniently accessible via the service entrance for easy access when bringing in kids, dogs, or discreet guests. Ascending to the upper floors, the second level features a gallery wall that leads to an expansive primary bedroom, a guest bedroom, and a second laundry room. The primary suite offers generous closet space and a spa-like bathroom adorned with large-format Virginia Tile and Newport Brass fixtures. Highlights include a dual vanity with ample storage, a stone soaking tub, a private water closet with a urinal, a custom dual-head walk-in shower, and heated floors. Guest Bedroom 2 includes a full bath and secured access to the rear terrace. On the fourth level, you'll discover an additional gallery wall leading to an ensuite bedroom and two additional "Jack-and-Jill" bedrooms, bringing the total to five above-grade bedrooms. The rear bedroom features outdoor space with breathtaking Lake Michigan and city views. This historic residence seamlessly blends timeless elegance with modern amenities, offering an unparalleled living experience in one of Chicago's most prestigious neighborhoods.