Old Town single-family home with 5300sf, situated on an oversized DOUBLE LOT (54 x 125) with incredible outdoor spaces & a side huge yard with a separate studio/office! The first lot has a stunning all brick contemporary home, recently upgraded with three fabulous decks, a top-floor East-facing terrace with city skyline views + a 3 car garage with 2 electric car chargers, the second lot has a newly rehabbed 400sf building with a large skylight, perfect for a home office, gym, or playroom plus an expansive, very secluded side yard professionally landscaped featuring lush grass, mature trees, a limestone patio with fire pit, an irrigation system, or sell off separately! This gated compound is completely surrounded by a high designer metal fence for ultimate suburban living with serenity, privacy & security! 5BR/6BA main home boasts an extraordinary open floor plan with high ceilings, hardwood floors, floor-to-ceiling windows, allowing for an abundance of natural southern light to flow throughout. Chef's kitchen with top-of-the-line stainless steel appliances, double oven, breakfast bar, and custom cabinets transitions seamlessly into the dining room featuring custom built-ins. There are 4 ensuite bedrooms including the master suite features a custom walk-in closet, a spa-like bath with new heated floors & soaking tub, steam shower, and double vanity. The large top-floor terrace has a spectacular, panoramic view of the skyline. Adjacent to the terrace is a penthouse room/bedroom with windows that capture the skyline as well. Completely open & spacious lower level family room with concrete floors, built-ins, cathedral ceilings, wet-bar with concrete countertops + dishwasher, and a wall of very large windows overlooking the yard - an entertainer's dream. Mudroom & storage, a large number of closets, 2 fireplaces, central vacuum, Very extensive upgrades have been recently been made throughout the main house and home office: masonry, landscaping, the decks & terrace, sizable electric upgrades, HVAC & tankless water heater, plumbing, all bathrooms, added smart home & security with built-in speakers. A contemporary work-of-art in one of the best neighborhoods in the city. Steps to the Lakefront, North ave beach, restaurants, whole foods, New City, and transportation. Walk to Catherine Cook, Franklin, British, LaSalle, Walter Payton Schools! This property has 2 PIN #, the house has a lot size of 26 x 125, the office & yard is 28 x 125.