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West Loop. The growing neighborhood of West Loop is home to Google and award-winning restaurants. This three-bedroom condo in the Hayden building features private elevator entry, wide-plank wood floors, a stone fireplace, smart-home technology, a private terrace, a custom kitchen with walk-in pantry and wine chiller, a principal suite with walk-in closet and marble spa bathroom, and a laundry room.
The apartment comes with two parking spots. $2,595,000. Hadley Rue, Dream Town Realty, (773) 852-4478.
Near North Side. The Ronsley is a pet-friendly building a block from the river and a waterfront park. An elevator opens directly into this three-bedroom loft with high, beamed wood ceilings and floor-to-ceiling windows, exposed brick, chef's kitchen, private deck, and a main suite with corner windows, walk-in closet, and spa bathroom with soaking tub.
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Building amenities include a 24-hour door staff, fitness room, party room, and landscaped courtyard with grills. $1,749,900. Danielle Dowell and Jamie Book, BHHS Chicago, (312) 391-5655.
West Town. Minutes from the West Loop and Fulton Market, this 10,000-square-foot, five-bedroom home also offers easy access to downtown. The 2011 modernist house has 27-foot ceilings; two fireplaces; a mezzanine; an Italian kitchen; a master suite with soaking tub, dual walk-in closets, and terrace; a lower level with fitness center, indoor driving range, and theater; and a three-car garage.
The landscaped triple lot includes a lap pool, hot tub, putting green, and dining area. $4,500,000. Ryan Preuett, Jameson Sotheby's International Realty, (312) 371-5951.
Fulton Market. This four-bedroom penthouse is on the top floor of the converted 1908 Jewel Tea company warehouse. Remodeled in 2019, the unit features hardwood floors, exposed-brick walls, 13-foot ceilings, a floating steel staircase, custom millwork, a gourmet kitchen with walk-in pantry, family and living rooms, and a glass-walled room on the roof leading out to a deck with a firepit table, built-in seating, and panoramic skyline views.
Outdoor and indoor parking are included. $2,950,000. Jim Gramata, @properties/Luxury Portfolio International, (773) 270-2474.
Near North Side. Built in 1903 for a society doctor, this house hosted Theodore Roosevelt and Adm. Robert Peary long before Hugh Hefner bought it in 1959 and made it his first Playboy Mansion.
Once the "Bunny Hutch" where the Playmates lived, this penthouse condo has been completely updated, with two wood-burning fireplaces, gallery lighting, new kitchen, four en suite bedrooms, and a south-facing terrace. Building amenities include landscaped gardens, gated entry, private storage, and garage. $2,895,000. Jennifer Ames, Engel & Völkers, (773) 908-3632.
Wicker Park. The Clock Tower Lofts, converted in 1996 from a 1906 factory, is in a Chicago Landmark District known for galleries, concerts, and art festivals.
This south-facing open-plan condo has 12-foot timber ceilings, built-ins, new kitchen, living room with gas fireplace and Juliet balcony, and one en-suite bedroom with a custom barn door. Owners have access to a fitness room, rooftop deck, heated garage, and storage. $365,000. Mike Gaffney, Compass, (773) 879-8009.
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