A truly rare offering on one of Chicago's most coveted residential streets, this is the northernmost home on Astor, distinguished by its commanding position and oversized windows overlooking the Cardinal's Mansion and Lincoln Park. The result is extraordinary privacy and natural light rarely found in the city. Designed as a mid-century modern residence by noted Chicago architect I. W. Colburn, the home was later completely reimagined with an Art Deco-inspired interior by two of the city's most respected firms, Marvin Herman & Associates and Suzanne Lovell Inc. In 2025, the exterior was extensively renovated, including all new stucco on the walls enclosing the private courtyard. Today, the home offers approximately 6,500 square feet of refined living space, exceptional private outdoor areas, and two-car garage parking. Interior finishes are of the highest caliber and include custom-stained hardware, bespoke millwork and cabinetry, hand-cast plaster moldings, a dramatic curved staircase with artisan-fabricated bronze and steel balusters, three distinctive gas fireplaces, inlaid rift-sawn white oak, limestone and marble floors, custom Donald Kaufman paint finishes, vellum wall coverings, and more. An elegant foyer with a walk-in coat closet, climate-controlled wine storage, and a guest bath featuring a hand-carved marble sink sets the tone. One level up, the main living level includes a gracious living room with wet bar and built-in Miele coffee maker, a separate dining room, a beautifully upgraded kitchen with built-in banquette, a den or office with a white alabaster fireplace, and access to a large terrace. A standout feature of the home, the north-facing terrace offers a serene setting for al fresco dining and relaxation. The top level includes a luxurious primary suite with a spa-caliber bath featuring a soaking tub carved from a single block of Noir St. Laurent marble with P. E. Guerin hardware. A second en suite bedroom and a family room/third bedroom with an additional full bath complete the level. Curved rear stairs lead to a separate street-level suite, ideal for a home office, guest quarters, or in-law arrangement. With its own entrance from a historic Wooden Alley, this private suite allows guests to enter independently. Features include knotty pine paneling, a kitchenette, generous closets, an en suite bath, and French doors opening to a tranquil koi pond. The landscaping was designed by award-winning Scott Byron & Co. Mechanical systems include four-zone heating and central air conditioning, central humidification, dual water heaters, a security system, and smart home functionality. Ideally positioned near Lincoln Park, the lakefront, and downtown, this exceptional Gold Coast residence is for the buyer who demands architectural significance, privacy, and uncompromising quality.