Old Barrington introduces a prominent estate dating back to 1929, where maintaining the renowned architecture has been at the forefront of 5 previous generations from the bookkeeper of a well-known mob boss to the previous owners who maintained the home in its original state. The finest appointments continue to be preserved and, in many ways, improved! Proudly stated on just short of 5 acres with a sprawling circle drive. Upon arrival guests are greeted with stately columns reaching 3-stories tall while complimented by a bluestone porch. The charming entry opens to an expansive staircase while leading the way to an exquisite living room. The living room is finished with a brick fireplace accented by windows on each side and French door access to the porch. The living room brilliantly overshadows a beautiful music room tucked in the corner with inspiring views of the Yard. Just outside the music room are beautiful French doors leading to a state-of-the-art vaulted kitchen. The kitchen showcases exposed beams, 42" custom inset cabinets with soft close, glass facade and dove tail features, soap stone counters, Wolf range, Wolf double oven, coffee bar, beverage fridge, expansive breakfast bar with built-in extensions creating additional workspace, and pendant lighting. The breakfast bar overlooks French door access to a bluestone patio with views of a stunning English garden! The kitchen also offers a spectacular walk-in pantry. On the opposite side of the kitchen are rounded French doors that follow the roof line while entering an elegant dining setting. The dining room is filled with natural light shining in from 2 sets of French doors one of which leads to a charming screen porch. The dining room maximizes space with corner built-ins and a separate hallway leading to a back staircase and phenomenal den. The den is peaceful in design with soaring built-ins, space for seating and access to the yard. The main floor also offers hardwood floors throughout, a powder room, mud room with built-ins and soap stone counters. The second floor is equally as impressive with 2 suites each generous in size. 1 of 2 suites is the primary suite with an abundance of natural light, a walk-in closet with custom organizers, attached reading room with panoramic views of the paddocks and a remarkable new master bathroom! The master bathroom is finished with custom vanities, free standing tub and a spacious frameless glass shower. The 3rd floor offers the remaining 2 guest suites each with hardwood floors. Full partially finished lower level with a speak easy design, bar, powder room, and an amazing laundry room with penny tile and a dog wash bay. The outdoor entertaining is endless with an English garden manicured to perfection, gazebo, an outdoor fireplace, 2 paddocks, a 9-car garage and/or a 6-car garage with 4 stall barn and a 2nd floor for storage. Separate 2-car garage wide enough to accommodate 3 daily drivers. Near shops, restaurants, Metra station and night life!