Chicago, Illinois listings for sale

$21,000,000 - Chicago, IL

1355 N Astor Street Chicago, IL - Once-in-a-life time opportunity to own one of Chicago's iconic estates, showcasing over 25,000 Sq. Ft. of combined living spaces and situated on nearly a third of an acre on Gold Coast's most coveted Astor street. This palatial architectural masterpiece designed by Howard Van Doren Shaw for the Goodman Family graces the market for the first time in 40 years, promising to leave you speechless. A true hallmark of Chicago's rich history, Astor Court has long captivated passersby with its magnificent neo-classical/Georgian Revival architecture spanning an impressive 80' feet across. This distinguished estate is centered around a one-of-a-kind tremendous courtyard, meticulously landscaped with lush gardens and flowing fountains, transporting you to the tranquil Italian countryside, creating a peaceful sanctuary in the vibrant urban setting. The main residence of the estate features over 10,000 sq. ft. of exquisitely renovated grand spaces blending timeless elegance with modern luxury. No expense was spared in creating this treasure, presenting a rare opportunity to own a coveted piece of Chicago's history. Every inch of the home exudes sophistication and grandeur offering unparalleled living experience featuring 13' ceilings, venetian plaster walls, incredible intricate millwork and hardwood oak flooring throughout, fireplaces with magnificent original marble mantles, and gold plated fixtures. As you enter the home, you are immediately captivated by the grand sense of space, elegant design and a sweeping curved staircase that ascends to the expansive main living areas. Every room exudes scale and sophistication offering both beauty and functionality. There are five en-suite bedrooms, each with its own style and personality. The luxurious primary suite features beautiful lake views and a grand primary spa bath adorned with exquisite Italian marble. In addition to the main residence, Astor Court showcases six gorgeous unique rental units, each with its own distinct charm and character, generating significant income. The entire estate encompasses 45 rooms, 16 bedrooms, 17 baths and 18 fireplaces offering endless opportunities to expand the main residence or transform it into a sprawling multi-generational family compound. Currently, there are two parking spaces located directly behind the property with the option to convert the coach house into a garage for additional parking. This extraordinary estate is perfectly situated just steps from Michigan Avenue, the lakefront, parks, premier shops, favorite restaurants, and world-class entertainment.

$8,950,000 - Chicago, IL

1534 N Dearborn Parkway Chicago, IL - Classic, effortlessly charming and flawlessly appointed, 1534 N. Dearborn Pkwy. is a one-of-a-kind property on the very best block in the Gold Coast. Strolling distance to Lincoln Park proper, downtown and the lakefront, this 8,300+ sq ft single-family home commands attention from the street with ornate exterior details and an oversized lot. Inside, every inch has been renovated to flaunt first-class finishes and fixtures, beginning with a stately entry and foyer that links to a light-filled living room with stunning dark walnut hardwood floors, high coffered ceilings, beautiful molding details and a marble-fronted fireplace. The formal dining room features recessed lighting, custom wallcovering panels and statement chandeliers, and connects to a gourmet chef's kitchen with custom cabinetry, Italian calacatta marble countertops, professional-grade appliances, an island with dine-up seating, a bespoke butler's pantry, and a built-in breakfast banquette. Primed for elevated entertaining, this home's kitchen-adjacent great room features more gorgeous millwork and a second fireplace - and affords access via a sliding glass wall system to a covered terrace with a Wolf grilling station. Beyond, a unique gallery hall leads to a fabulous additional family room with a built-in bar center, a glass atrium ceiling, another fireplace and additional glass sliding doors to the courtyard. Upstairs, the second level presents 3 secondary, en-suite bedrooms (one of which has a private terrace), a separate children's study with custom millwork built-in desks, and a second-floor laundry room. The third level is entirely devoted to an expansive primary suite that boasts a spacious, front-of-the-house bedroom with custom built-ins, 2 designer dressing rooms, an exercise room, a private 21' x 6' terrace, and a true spa en-suite bath with an oversized shower, separate sauna, separate steam room with cold-drip, a standalone WC, and a walk-in linen closet. There is an additional floor that acts as an access point to the rooftop, which has stunning views of Chicago and lakefront. But there's more... This home's fully finished garden level features a custom home theater with stadium seating, designed by digging lower during construction, a custom temperature-controlled wine room, a handsome WFH office/library with custom walnut millwork paneling and a fireplace, a casino room with a full bar, 2 presentation-worthy mudrooms, in the front and in the back, and access to a private 14' x 18' yard. Additional details and amenities include an attached extra wide 2-car garage, front and back staircases, an all-floors elevator, 5 total fireplaces, 4 private outdoor spaces, custom lacquered paint and automated electric window treatments, designer lighting and wallcoverings, custom carpeting and stair runners, surplus storage including a luggage room, and a state-of-the-art AV Control4 system, managing Audio in every room of the house including televisions, automatic shades, lighting, alarm system and HVAC - making everything controllable from an iPhone. Close to world-class dining/shopping on and around the Mag Mile, with immediate proximity to some of Chicago's preeminent schools (Latin and Francis W. Parker), 1534 N. Dearborn Pkwy. is unparalleled living for the homeowner who wants polished presentation and refined comforts with a modern layout.

$8,900,000 - Chicago, IL

159 E Walton Place Chicago, IL - Own the pinnacle of Chicago elegance in this 7880 sq ft duplex penthouse, formerly home to Vince Vaughn and the original headquarters of Hugh Hefner's Playboy enterprise. The Palmolive Building is a true Art Deco icon- its historic beacon once lit the skies to guide pilots to Midway Airport and today it shines as one of the most distinguished addresses in the city. This two-story residence is the ultimate blend of heritage and sophistication. the upper level features soaring 14-foot ceilings, timeless wood paneling in the original executive office, now reimagined as a show stopping primary suite with a lavish bathroom, an office, game. room and extensive storage. Downstairs you'll find a massive chef's kitchen, perfect for entertaining, along with formal living and dining rooms and a guest suite with its own bath. A custom temperature-controlled wine room ,part of a meticulous multi-million dollar renovation ,elevates this already extraordinary home. Enjoy three private terraces , a private elevator, two garage spaces , and the impeccable attention of a building staff renowned for best -in-class service. Qualified buyers only please.

$7,995,000 - Chicago, IL

14 W Superior Street Chicago, IL - Astonishing FULL FLOOR home with breathtaking 360 degree views, outdoor space, direct elevator access and bespoke finishes! Still time to customize your home to the caliber you have come to expect from JDL Development!! COMPLETION 4TH QUARTER 2025!! Welcome to One Chicago - 77 visionary homes in the sky, starting on the 44th floor, with spectacular city and lake views. Merging the exclusive neighborhoods of the Gold Coast and River North, One Chicago offers a whole new perspective on city living, just blocks from the lakefront on Superior Street between Dearborn and State. The covered motor court with dedicated valet marks the beginning of an elegant arrival sequence. An exclusive door team is there to welcome residents and guests to the hands-free elevators, which lead to residences with secure Latch Hardware entry systems. A sense of light and space in the open plan living area reveals awe-inspiring views and finishes, such as wide plank European oak wood floors, custom stepped ceiling details and full height windows. A custom-designed O'Brien Harris kitchen lies at the heart of each residence. Clean lines and luxurious finishes are the hallmark of every bathroom. Primary baths are sleek and flawless, offering floor-to-ceiling slab porcelain, custom-built vanities with lit mirrors and Kalista fixtures. Oversized showers are complemented with cantilevered benches, recessed storage niches, fog-free shave mirrors and effortlessly controlled with Kohler's DTV electronic, programmable system. Generous setbacks allow for uniquely large terraces, including the private ownership amenity deck. Residents will enjoy an exclusive membership to Life Time Athletic Resort and Spa's diamond level private club. Everyday fine dining, and a flagship Whole Foods are at the ground level. One Chicago offers a refined, beautifully appointed way of living in Chicago's most desirable neighborhood. With a wealth of amenities and an elegant approach to design, these residences offer the quiet tranquility of a private retreat with all the excitement of a city address.

$6,995,000 - Chicago, IL

451 E Grand Avenue Chicago, IL - One Bennett Park has taken its place among Chicago's most elite residences. Designed by Robert A.M. Stern Architects and developed by Related Midwest, this world class building was designed from the top down. Gracing the crown of this iconic lakefront tower, Penthouse 66 is a full-floor residence being offered as raw space. Turn a blank canvas into a one-of-a-kind residence designed specifically for your lifestyle. Select your own architect and contractor to create an iconic residential experience unlike any other in Chicago. Related's Project Manager will work with your team to support the design, construction and finishing processes. This 7,147 SF top-floor residence with private elevator access features 13'-20' ceiling heights, unrivaled 360-degree views of the city and lake and a private outdoor terrace. With only 69 total condominium residences, owners at One Bennett Park enjoy personalized 24-hour concierge services and valet parking in our discreet porte-cochere offering the ultimate in service and privacy. Our full suite of building amenities is unrivaled in Chicago and includes a world-class fitness center, yoga room, pilates studio, salon and massage suite. The inviting 41st floor owner's lounge also offers residents a gracious gathering space with beautiful outdoor terraces, lounge area with fireplace, billiards room, private dining and cordial room. The two museum quality art installations in the lobby are a wonderful addition to this exquisitely designed building. Two parking spaces with valet service included. This highly anticipated Penthouse residence is available now. Reach out to learn more about this once in a lifetime offering.

$6,900,000 - Chicago, IL

9 W Walton Street Chicago, IL - Experience the pinnacle of luxury living at the highly coveted 9 W. Walton in Chicago's prestigious Gold Coast. Residence 2802 is an exquisite half-floor home spanning 4,500 sq. ft., complemented by an expansive 750 sq. ft. wrap-around terrace featuring a hot tub and overhead heaters for year-round enjoyment. This meticulously upgraded 3-bedroom + office/den, 3 1/2 bathroom home offers unparalleled craftsmanship, cutting-edge automation, and premium finishes throughout.The state-of-the-art kitchen is equipped with a Wolf 60" range, dual full-size ovens, a steam oven, warming drawer and a built-in Wolf coffee maker. Two full-size Gaggenau refrigerators/freezers, two Miele dishwashers, and The Galley sink with dual faucets ensure effortless entertaining. The 14' waterfall island, adorned with Azul Imperial Quartzite, is both a statement piece and a functional hub, complete with pop-up outlets and custom O'Brien Harris cabinetry. The living room is anchored by a 60 inch linear ventless fireplace framed in Iceland bookmatched porcelain. Custom millwork and shelving by O'Brien Harris seamlessly integrate a tall wine refrigerator, Sub-zero beverage refrigerator, and a silver hammered bar sink with an ice maker, all set against underlit Iceberg quartzite countertops. Escape to the opulent primary suite, which includes a large sitting room/office/den outfitted with closets, a built-in bar, Miele coffee maker, and a Sub-Zero beverage refrigerator. The massive walk-in closet provides generous storage, while the spa-like primary bathroom indulges with an oversized dual shower with a TV, steam, body sprays, and a rain shower, a custom bathtub with a pop-up TV lift and built-in champagne bucket, and a separate water closet with a Toto Washlet toilet. Luxurious Princess White Quartzite counters, a towel-warming drawer, custom cabinetry and large windows complete this serene retreat.Additional features include heated stone hallways with inlaid runners, heated bathroom floors throughout, a large laundry room with custom cabinetry and sink, and fully updated Control4 automation for lighting, shades, and sound. This exceptional residence includes two valet parking spaces and a storage unit. Residents of No. 9 Walton enjoy unparalleled five-star amenities, including a multi-level fitness center, an indoor pool, a steam room, and a sauna. For recreation and entertainment, the building features a golf simulator and an elegant hospitality room with a bar, catering kitchen and an expansive terrace. Additional luxuries include two well-appointed guest suites, a house car service, 24-hour white-glove door staff, and onsite professional management.

$6,750,000 - Chicago, IL

363 E Wacker Drive Chicago, IL - 6106 is a premier residence at the 5 Star St. Regis Chicago with jaw dropping views and quite possibly the best amenities in town. In the architectural landmark by Jeanne Gang, this 4708 SF 4 bed/5.1 bath home has an 80' wide great room with unobstructed N / E / S panoramic views of Lake Michigan, Chicago River, Grant Park, and the city skyline. Ideal for entertaining, this open-concept space integrates a formal living area, a dining space with a built-in wet bar, and a family room along with a 32' long terrace. The gourmet kitchen is outfitted with Gaggenau and Thermador appliances, sleek Snaidero cabinetry, cantilevered countertops, a seamless natural stone backsplash and an oversized island with seating for four. Thoughtfully curated fixtures and finishes throughout including wide-plank hardwood floors, designer lighting, and custom wall coverings and window treatments. The luxe primary suite comes with two generous walk-in closets and two spa-inspired en-suite baths featuring full-height stone, Robern cabinetry, Kallista fixtures, heated floors, and glass-encased showers (one with a built-in makeup station and freestanding tub). The three secondary bedrooms are separated from the primary and each have their own en-suite bathroom. Additional features include a stylish powder room, a large laundry room, and plenty of storage. Residents of The St. Regis Chicago enjoy unmatched amenities: the private 47th-floor owner's level features an outdoor pool, hot tub, fire pit, fitness and training studios, a private dining room for 20, a demonstration kitchen, a wine tasting room with private storage, a kids play center, and a secure dog run. Other amenities include a luxurious indoor pool, a full-service spa, a sky terrace, and 24-hour concierge and butler service, ensuring every need is met. Better still, culinary excellence is just an elevator ride away with renowned on-site dining options Tre Dita and Miru. Steps from the Chicago Riverwalk, Millennium Park and the Magnificent Mile, 363 E. Wacker Dr unit 6106 offers unsurpassed luxury, location, and lifestyle in the heart of Lakeshore East. One valet space and one premium self-park space are included.

$5,995,000 - Chicago, IL

1407 N Hoyne Avenue Chicago, IL - A sophisticated presence, landmark status, architectural integrity, and an unprecedented outdoor footprint for Wicker Park, 1407 N. Hoyne Ave. is a one-of-a-kind opportunity for the homeowner who wants an expansive city estate with pedigree and a modern program. Originally built for beer baron John H. Rapp in 1886, this 8250 SqFt-square-foot, 5+ bed/5.5 bath single-family home underwent a 2-plus-year renovation and restoration by Rugo Raff Architects. The current owner acquired and reunited the original 2000 square foot coach house with this lovingly restored home which is now included in this offering. Preserving elements of its Victorian charm while optimizing sightlines and integrating first-class finishes was paramount. This special home's unheard of 98' x 150' lot - a combined oversized 4-5 city lots! - affords multiple green spaces, including a deep front yard with mature landscaping, a side yard with raised garden beds and a European-style pergola, and a meticulously manicured backyard. Inside, an elegant entry plus an oval-shaped entry hall link to a lovely living room with an abundance of natural light, a traditional turret, and a wood-burning fireplace, and a formal dining room just beyond with hand-scraped walnut floors. The custom chef's kitchen stuns with O'Brien Harris cabinetry, white quartzite countertops, professional-grade Wolf/Sub-Zero appliances, an herb garden, a full butler's pantry, a breakfast dining space with banquette seating, and a built-in desk. The main level also features an intimate family room with built-in walnut cabinetry and a chic beverage center, and two beautiful limestone terraces accessed via French doors: a 12' x 23' west terrace for open-air entertaining and a 12' x 17' side terrace that's perfectly appointed for large-scale alfresco dining with an outdoor kitchen and a built-in grill. A striking example of this home's flawless interior architecture is the centrally located, curving suspended staircase. The second level is devoted to two secondary bedrooms (one with custom bunk beds), the first of two laundry rooms, and an impressively spacious primary suite with a sitting area, a custom dressing room, a walk-in closet, and a marble-clad ensuite bath with two vanities, a soaking tub, and a deluxe shower. The third floor presents two designer offices--a handsome den with knotty alder wood floors and a gas fireplace, a cozy den with a wet bar, an exercise room, and yet another polished guest bedroom. But there's more... This truly magnificent home also comes complete with a fully finished garden level with a massive playroom that opens onto a basement terrace, a wine room, a kitchenette, another large guest bedroom with den perfect for related living, a second laundry room, a walk-in storage room, and a custom mudroom that connects to a two-car garage. Plus, the property features a standalone coach house - a wonderful blank slate that can be transformed into a guest cottage, a recreation or art space, offices, or added parking if needed. Additional callout details and amenities include restored original doors and hardware, custom woodwork and trim throughout, designer lighting and wallcoverings throughout, four total fireplaces, 97 Marvin windows, geothermal heating and cooling plus radiant heat in the lower level playroom, a Lutron lighting system, self-irrigating planters on both terraces, and an excess of custom interior storage. Walking distance to Wicker Park proper and the world-class shopping and dining that extends from the neighborhood's famed Six Corners, 1407 N. Hoyne Ave. is a one-of-a-kind home with uncompromising design and comforts.

$4,995,000 - Chicago, IL

2120 N Lincoln Park West Chicago, IL - If Chicago had an Upper East Side, this would be it... Professionally designed and park-adjacent, 2120 N. Lincoln Park West, unit 5-6, is an incredible 5 bed/4.5 bath, 6,000+ square-foot duplex in East Lincoln Park with flawless fixtures and finishes, five spectacular private outdoor spaces, and sublime lake, park and skyline views. Located in a highly sought-after, intimate doorman building where units rarely turn over, this extraordinary apartment was renovated by an award winning design team to combine and transform this residence into a luxury condo that lives like a single-family home. (There are only 11 total units in this boutique building). Featuring private elevator access on both levels, the main level footprint effortlessly supports everyday living and large-scale entertaining across a lake-facing living room with hand-scraped hardwood floors and a marble fireplace, a formal dining room with a coffered ceiling and built-in buffet, a standalone lounge with temperature-controlled wine storage, a handsome WFH office with built-ins cabinets and bookshelves (potential 5th bedroom), an editorial-worthy chef's kitchen, a family room with a second fireplace, and the first of five beautiful bedrooms. The stunning de Guilio kitchen features custom Shaker cabinetry, wraparound natural stone countertops, professional-grade appliances including an eight-burner Wolf range with dual ovens, an island with dine-up seating, and an incredible walk-in pantry with extra storage and counter space for food staging. Plus, in addition to two covered park/lake-facing terraces, the main level also comes complete with an impossibly rare, truly extraordinary walk-out 1750+ SF private terrace complete with an outdoor kitchen with a gas grill and fridge. Accessed via a central staircase, heightened attention to detail continues upstairs. The second level presents two additional secondary bedrooms, both of which are ensuite, a gallery that serves as a bedroom foyer, a second family room with an adjacent wet bar and beverage center, a media room with a third fireplace, two more mirror-image terraces, and an unbelievable primary suite with a large bedroom with sitting area, a custom dressing room, and a luxe ensuite bath with a marble-topped dual vanity, a deep soaking tub, and a glass-encased steam shower. Additional callout details include designer light fixtures and wallcoverings throughout, custom window treatments, an upstairs laundry room, excellent storage, and four parking spaces in the building's attached heated garage. Steps to Lincoln Park's gorgeous green spaces, including the Nature Walk and Lincoln Park Zoo, and an easy walk to North Avenue Beach and the Mag Mile, 2120 N. Lincoln Park West, unit 5-6, is next-level luxury with the very best of Chicago right outside your front door.

$4,850,000 - Chicago, IL

2015 N Dayton Street Chicago, IL - A truly special offering - a 7,000 SF single-family home on a 33' wide lot just off coveted Dayton and Armitage with 4 bedrooms on the 2nd floor and an attached 3 car heated garage. The timeless brick and limestone facade is accented by professional landscaping with mature trees along the parkway for a dramatic first impression. You enter a gracious foyer that leads to the formal living room with a stone fireplace and generous dining room. A statement kitchen with white shaker cabinetry, marble counters, top of the line appliances, breakfast table, walk in pantry, and a wet bar connecting back to the formal dining. The open concept family room really shows off the width of the home and features stunning built-ins, coffered ceiling, a stone fireplace, and large windows overlooking the backyard. Two amazing plush outdoor spaces - a blue stone patio with a wood burning fireplace and 500 SF raised deck over the garage with pergola, a pizza oven, and motorized tv that pops out of a planter box. The wide lot allows for a large primary suite with oversized windows, a 28' long closet, and elegant marble bath with dual vanities, heated floors, a tub, and a glass steam shower. Three additional secondary bedrooms, two full bathrooms, and laundry complete this floor. The penthouse level has a recreation room with wet bar, a paneled office (additional ensuite bedroom), two nice roof decks, and another powder room. The lower-level features high ceilings, a large media room with a movie screen, a wine cellar, a guest bedroom that's perfect for extended family stays or an au pair, a gym (or bedroom 7), a large laundry room, plus a mudroom that links to the attached heated three-car garage. Additional details include heated front steps, a 4-stop elevator, designer wall coverings and light fixtures, detailed millwork, custom paint and window treatments, home automation system (Nice), and an abundance of closets and storage. Just steps to Oz Park and the shopping and dining of Armitage Avenue and Halsted Street, 2015 N. Dayton St. is a spectacular property for the modern family.

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