248

Chicago, IL Homes for Sale with Rooftop Deck

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  • /44

    $2,139,000 New Construction

    • 5 Beds
    • 6 Baths
    • 4,060 Sq Ft

    1418 W Warner Ave, Chicago, IL 60613

    Distinguished 5 bedroom, 4.2 bath new construction single-family home in the heart of Graceland West. One-of-a-kind luxury home with stunning limestone and brick exterior, fully enclosed yard, multiple outdoor entertaining spaces including roof top deck, and detached 2-car garage with second roof deck. Step inside to a welcoming living/dining area highlighted by oversized front windows and

    Jason O'Beirne Jameson Sotheby's Intl Realty

    1418 W Warner Ave, Chicago, IL 60613
  • /24

    $520,000

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft

    1440 N Maplewood Ave Unit 3S, Chicago, IL 60622

    Located on a quiet, tree-lined street in the heart of West Town, this newer construction 2-bedroom, 2-bath penthouse offers exceptional top-floor living with interior access to its own private outdoor oasis. Flooded with natural light, the home features unobstructed, floor-to-ceiling windows, expansive ceiling heights, and beautiful hardwood floors throughout, creating a bright and open living

    Amanda McMillan @properties Christie's International Real Estate

    1440 N Maplewood Ave Unit 3S, Chicago, IL 60622
  • /16

    $565,000

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    2846 N Damen Ave Unit 3, Chicago, IL 60618

    This stunningly updated 2 bed/2bath Roscoe Village PENTHOUSE unit with a PRIVATE ROOF DECK is ready for its new owners. Sophisticated and filled with natural light, this home offers an inviting open-concept living and dining space designed for both everyday living and effortless entertaining. A fireplace, recessed lighting, surround sound, and dramatic floor-to-ceiling French doors create a warm

    Jacqueline Patton Baird & Warner

    2846 N Damen Ave Unit 3, Chicago, IL 60618
  • /31

    $349,900

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    3150 N Sheridan Rd Unit 14A, Chicago, IL 60657

    Welcome home to your bright and spacious 2 bed, 2 bath home, offering stunning city, lake, and harbor views, with an expansive layout that runs East to West and fills the home with natural light from sunrise to sunset all year long. The beautifully renovated kitchen features a breakfast bar and an open concept design with space for a full dining table, creating an ideal setting for both elegant

    Kate Gaffey Fulton Grace Realty

    3150 N Sheridan Rd Unit 14A, Chicago, IL 60657
  • /33

    $379,000

    • 2 Beds
    • 1.5 Baths
    • 889 Sq Ft

    500 W Superior St Unit 608, Chicago, IL 60654

    Premier 2 bed/1.1 bath condo in River North's highly sought after Montgomery. This home has been lived in delicately. Gleaming refinished hardwood floors throughout, refreshed lighting, & window treatments. Light abounds through the floor-to-ceiling windows. Masterful kitchen update with Bosch/Kitchen-Aid/Jenn-Air appliances, white quartz counters, marble backsplash custom builtin wine rack and

    Jennifer Lapins @properties Christie's International Real Estate

    500 W Superior St Unit 608, Chicago, IL 60654
  • /2

    $5,250,000 New Construction

    • 8 Beds
    • 7.5 Baths
    • 7,118 Sq Ft

    Chicago, IL 60657

    Amazing design/build opportunity in the Southport Corridor coming soon from Environs on a 37.5' lot and a half with a breezeway attachment to an attached 3 car garage with Mudroom! This 7,100 square foot, 8 BR, 7.5 BA home will feature a highly functional, unusually open layout and offers 4 BR suites on the 2nd level including an expansive Primary Suite. The third floor features a spacious 3rd

    Kevin Wood @properties Christie's International Real Estate

    Chicago, IL 60657
  • /45

    $439,900

    • 2 Beds
    • 1 Bath

    1560 N Sandburg Terrace Unit 2403J, Chicago, IL 60610

    Stunning newly gut rehabbed two bedroom unit at James House, with large balcony on a high floor with panoramic views of the city and skyline. Be the first to live in this unit, among the many new features is the in-unit washer & dryer. The entire unit was renovated and finished to the highest standards. The beautiful open kitchen has contemporary gloss white cabinets with black accent hardware

    Eamonn Stafford @properties Christie's International Real Estate

    1560 N Sandburg Terrace Unit 2403J, Chicago, IL 60610
  • /9

    $600,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,090 Sq Ft

    1329 S Avers Ave, Chicago, IL 60612

    Introducing The Bella by Mosaic Chicago, a modern 3-bedroom, 2.5-bath single-family home offering approximately 2,090 square feet of thoughtfully designed living space on a double lot! Open-concept main level with expansive living and dining areas flowing into a designer kitchen featuring shaker-style cabinetry, quartz countertops, stainless steel appliance package, and recessed LED lighting.

    Michael Saladino Keller Williams ONEChicago

    1329 S Avers Ave, Chicago, IL 60612
  • /6

    $229,000

    • Studio
    • 1 Bath
    • 534 Sq Ft

    400 N Lasalle Blvd Unit 1603, Chicago, IL 60654

    Perfect Unit in Highly Sought Premiere River North Building & Location*Not Your Average Studio w Open East Views & Juliet Balcony to Expand Your Home*Separate Pass Through Kitchen w Granite, Dishwasher, & Maple Cabs Plus Huge Walk-in-Closet & Full Size W/D*24/7 Doorstaff, Sundeck w Grills, Pool/Hot Tub, Fitness & Party Room, Garage & More! All Steps to the Heart of River North Entertainment &

    Jenny Fultz Jin's Group Corporation LTD

    400 N Lasalle Blvd Unit 1603, Chicago, IL 60654
  • /37

    $800,000

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    800 W Cornelia Ave Unit 407, Chicago, IL 60657

    Welcome home to this beautiful penthouse duplex-condo in a boutique elevator building in East Lakeview. This condo spans the entire length of the north-end of the building for East and West exposures. A truly unique condo, the only floorplan of it's kind in the building. 1,800+ square feet of interior living space. Spacious and open floor plan with plenty of storage. Kitchen has granite

    Mike Rasmussen @properties Christie's International Real Estate

    800 W Cornelia Ave Unit 407, Chicago, IL 60657
  • /42

    $2,850,000

    • 5 Beds
    • 5.5 Baths

    1938 N Hudson Ave, Chicago, IL 60614

    East Lincoln Park single family home walking to Park, lake and the Lincoln Park Farmer's Market! This sensational, light-filled residence combines timeless style with modern updates, and includes a beautifully appointed coach house. East-facing bay windows bathe the main level in natural light and offer serene views of tree-lined Hudson St. The newly renovated kitchen is a fabulous design

    Emily Sachs Wong @properties Christie's International Real Estate

    1938 N Hudson Ave, Chicago, IL 60614
  • /54

    $2,573,999 New Construction

    • 6 Beds
    • 7 Baths
    • 5,200 Sq Ft

    3920 N Bell Ave, Chicago, IL 60618

    30' WIDE LOT | 5,200+ SQ FT | BELL SCHOOL DISTRICT | 6BR/5.2BA | THERMADOR | ROOFTOP DECK + PERGOLA | SNOWMELT STEPS | HEATED 2.5-CAR GARAGE (EV-READY) Rare North Center new construction-just completed January 2026 (prelisted during construction)-with the opportunity for the next owner to personalize select finishes and design details where available. Built by GT Builders-celebrated for 30+ years

    Tricia Ponicki HomeSmart Realty Group

    3920 N Bell Ave, Chicago, IL 60618
  • /35

    $3,195,000

    • 5 Beds
    • 6 Baths
    • 5,000 Sq Ft

    Unlisted Address

    Step into the timeless elegance of 2103 N Clifton, a distinguished 5 bedroom, 4.2 bath home in the heart of Lincoln Park. This 5000 SF residence combines classic architecture with a flexible floor plan perfect for today's lifestyles. The gracious living room features arched windows, impressive moldings and fireplace flowing seamlessly into the formal dining room with bespoke butler's pantry.

    Catherine Egan Jameson Sotheby's Intl Realty

    Unlisted Address
  • /23

    $439,000 New Construction

    • 2 Beds
    • 2 Baths

    3204 N Kostner Ave Unit 204, Chicago, IL 60641

    ALMOST 60 PRCNT SOLD! MOVE IN READY! Introducing 3204 Kostner! You will be blown away by the sweeping views! We are pleased to present one of Avondale/Kilbourn Park's ONLY and its NEWEST condominium development! This best-kept-secret neighborhood has long awaited high-quality new condominium homes and they're here! Come early to select your home from 30 fantastic units. Offering various open,

    Karen Biazar North Clybourn Group, Inc.

    3204 N Kostner Ave Unit 204, Chicago, IL 60641
  • /23

    $949,000 New Construction

    • 3 Beds
    • 2.5 Baths

    1910 N Kedzie Ave Unit 2F, Chicago, IL 60647

    BRAND NEW CONSTRUCTION 3-bedroom, 2.5-bathroom PENTHOUSE home in Logan Square just two blocks from Palmer Square Park. With a wide-open main floor, this space is perfect for a party of any size. Upon entry, you find the formal living/dining area, to the left is the kitchen with a long island and high-end finishes and appliances and a mud room just beyond that. On the second level, the primary

    William Goldberg Fulton Grace Realty

    1910 N Kedzie Ave Unit 2F, Chicago, IL 60647
  • /17

    $175,000

    • 7 Beds
    • 3 Baths

    9720 S Exchange Ave, Chicago, IL 60617

    Don't miss this updated 2 unit property featuring 3 bed and 4 bed units. This property has plenty of natural light and a finished attic adds flexible space ideal for a home office or recreation. Recent updates include a new water heater (2023), furnace (2022), and fresh interior and exterior improvements completed in June 2024. The fenced yard offers privacy and potential for personalization.

    Michael Saladino Keller Williams ONEChicago

    9720 S Exchange Ave, Chicago, IL 60617
  • /23

    $600,000

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft

    600 N Lake Shore Dr Unit 3109, Chicago, IL 60611

    Come tour this high-floor two-bed, two-bath corner unit located in the heart of Streeterville. Upon entering, you'll be greeted by hardwood floors and a functional split floor plan. Enjoy the convenience of a private balcony where you can get fresh air and take in the city views. Benefit from a seamless flow for entertaining, living, dining, and relaxing. The kitchen boasts granite counters,

    An-An Ku Urban Living Properties, LLC

    600 N Lake Shore Dr Unit 3109, Chicago, IL 60611
  • /23

    $499,995

    • 2 Beds
    • 2 Baths

    421 W Huron St Unit 805, Chicago, IL 60654

    Sun-drenched southeast corner condo in the heart of River North with sweeping city views from every room. This highly desirable split 2-bedroom layout offers incredible natural light, 9-foot ceilings, and a south-facing balcony that spans the full width of the living room-perfect for taking in the skyline. The open-concept living space features an inviting entry foyer, wide-plank hardwood floors,

    Grigory Pekarsky Vesta Preferred LLC

    421 W Huron St Unit 805, Chicago, IL 60654
  • /27

    $230,000

    • 1 Bed
    • 1 Bath
    • 680 Sq Ft

    5415 N Sheridan Rd Unit 3008, Chicago, IL 60640

    For the buyer who wants it all! Pristine newer renovation, completely opened with expanded kitchen. Living room features panoramic views spanning the lake to city. Kitchen has miles of quartz countertops, 42" cabinets, and large breakfast bar for dining. Tons of hall closet space. Updated bathroom with granite counters and linen cabinet. Wake up to the lake view in the king-sized bedroom which

    Ann Carson @properties Christie's International Real Estate

    5415 N Sheridan Rd Unit 3008, Chicago, IL 60640
  • /41

    $1,950,000

    • 5 Beds
    • 4.5 Baths
    • 4,048 Sq Ft

    2042 N Honore St, Chicago, IL 60614

    Newer construction SFH in Bucktown for under $2M. Spectacular home nestled in the heart of Bucktown and built by an experienced builder. This classic and elegant home was thoughtfully designed and has a number of added upgrades since completion. 4,000+ sqft with 3 incredible outdoor spaces. Luxurious and high-end finishes include hardwood floors throughout, 10' ceilings, 9'6" doors, quartz

    Tim Sheahan Compass

    2042 N Honore St, Chicago, IL 60614
  • /21

    $2,700,000

    • 3 Beds
    • 3 Baths
    • 2,573 Sq Ft

    14 W Superior St Unit 4403, Chicago, IL 60654

    First resale of the unit 4403 tier - never before on the market! This remarkable 3-bedroom, 3-bathroom residence offers stunning East, North, and West views from the 44th floor of Chicago's premier luxury high-rise, One Chicago. With an ideal floor plan rarely available in the building, Unit 4403 delivers elegance, comfort, and elevated design in every detail. Situated at the intersection of the

    Chezi Rafaeli Coldwell Banker Realty

    14 W Superior St Unit 4403, Chicago, IL 60654
  • /28

    $895,000

    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    950 N Michigan Ave Unit 4303, Chicago, IL 60611

    An exceptional opportunity to own a spacious residence in one of Chicago's most prestigious locations. Priced with renovation in mind, this home offers outstanding potential for a buyer looking to design and customize their own space. Located on the 43rd floor and spanning nearly 2,400 sqft, the residence offers an excellent floor plan with breathtaking lake and city views. facing east , north

    Chezi Rafaeli Coldwell Banker Realty

    950 N Michigan Ave Unit 4303, Chicago, IL 60611
  • /51

    $999,500

    • 3 Beds
    • 2.5 Baths
    • 2,850 Sq Ft

    161 E Chicago Ave Unit 33DE, Chicago, IL 60611

    GAZE OUT AT THE LAKE & THE SKYLINE & WALK TO THE MAG MILE & EVERYTHING THE GOLD COAST HAS TO OFFER FROM THIS NEARLY 3000SQFT & COMPLETELY RENOVATED 66'+ WIDE 3BD/2.1BA SW CORNER HOME (PRESENTLY USED AS A 2BD W/3RD BEDROOM USED AS A DEN/OFFICE) IN PREFERRED TIER WITH PERFECT SPLIT FLOOR PLAN W/SWEEPING LAKE/SKYLINE VIEWS FROM EVERY ROOM IN PREMIER ULTRA-HIGH AMENITY BUILDING W/24/7 DOOR

    Mario Greco Compass

    161 E Chicago Ave Unit 33DE, Chicago, IL 60611
  • /44

    $1,749,000

    • 4 Beds
    • 4 Baths
    • 3,350 Sq Ft

    310 S Michigan Ave Unit 1100, Chicago, IL 60604

    With forever unobstructed park, lake and city views from 11 floors above Michigan Avenue, this expansive northeast corner residence offers panoramic views of many of Chicago's most celebrated landmarks, including Millennium Park, Grant Park, Maggie Daley Park, BuckinghamFountain, Navy Pier, Lake Michigan, the Art Institute, Shedd Aquarium and Field Museum. Spanning 3350 square feet, this

    Joy Larkin @properties Christie's International Real Estate

    310 S Michigan Ave Unit 1100, Chicago, IL 60604
  • /44

    $2,795,000

    • 6 Beds
    • 7 Baths
    • 5,800 Sq Ft

    1246 W George St, Chicago, IL 60657

    This truly one-of-a-kind 5,800 sq ft warehouse conversion captures the essence of a SoHo loft, reimagined with warm Chicago elegance in the heart of Lakeview. A thoughtfully executed gut renovation showcases an extra-wide 23-foot floor plan, soaring 12-foot ceilings, and exposed brick, creating a sense of scale, warmth, and architectural presence that cannot be replicated. Designed for both

    Jeffrey Lowe Compass

    1246 W George St, Chicago, IL 60657
  • /25

    $715,000

    • 2 Beds
    • 2.5 Baths
    • 1,820 Sq Ft

    161 E Chicago Ave Unit 38C, Chicago, IL 60611

    Gorgeous, sweeping views of Lake Michigan and the city skyline from sunrise to sunset through an abundance of oversized windows! This elegant & sophisticated home is beautifully appointed and offers the ideal floor plan. From the gracious entry foyer, your eyes are drawn to the spectacular views as you walk through to the large living and dining rooms. The kitchen features updated, stainless

    Debra Dobbs Compass

    161 E Chicago Ave Unit 38C, Chicago, IL 60611
  • /40

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    362 W Huron St Unit B, Chicago, IL 60654

    Look no further, your outdoor rooftop oasis awaits! Extra wide sun-drenched River North townhome in Tuxedo Park that lives like a single-family home with an attached garage. First floor includes plantation shutters throughout, living room with fireplace and dining area that leads into an upgraded kitchen and breakfast room with granite counters and cabinets. Off the kitchen is your first outdoor

    Brandon Renner-re Kale Realty

    362 W Huron St Unit B, Chicago, IL 60654
  • /21

    $329,000

    • 1 Bed
    • 1 Bath
    • 725 Sq Ft

    300 N State St Unit 4512, Chicago, IL 60654

    Iconic city living meets modern luxury in this fully gut-rehabbed residence at Marina Towers. Completely renovated from top to bottom, this one-bedroom offers stunning, unobstructed views of the Chicago River, Lake Michigan, and the downtown skyline. The open-concept living and dining area features brand-new kitchen is outfitted with warm wood cabinetry, stainless steel appliances, generous

    Nitasha Kassam @properties Christie's International Real Estate

    300 N State St Unit 4512, Chicago, IL 60654
  • /26

    $155,000

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft

    6301 N Sheridan Rd Unit 23N, Chicago, IL 60660

    Overlooking Lake Michigan, Close to LOYOLA .. Very cool unit on higher floor with awesome views (east & north). Extremely sunny and bright unit. This spacious unit has been freshly painted with neutral colors! Amazing kitchen with contemporary designer cabinets! Cool splash guard and stainless-steel appliances including dishwasher and Microwave. GRANITE Countertop open concept, the kitchen was

    Misael Chacon Beycome brokerage realty LLC

    6301 N Sheridan Rd Unit 23N, Chicago, IL 60660
  • /43

    $1,175,000

    • 4 Beds
    • 4 Baths
    • 2,898 Sq Ft

    836 E 52nd St, Chicago, IL 60615

    A truly rare opportunity has arrived-this exceptional twostory bungalow in the heart of Hyde Park is ready to welcome its next chapter. From the moment you step through the striking doubleentry vestibule, you're greeted by an expansive main level boasting tenfoot ceilings, vintage hardwood floors, and oversized windows that flood every room with radiant natural light. Exquisite balustrades and

    Silvia Miner RE/MAX Plaza

    836 E 52nd St, Chicago, IL 60615
  • /19

    $569,000

    • 2 Beds
    • 2 Baths
    • 1,359 Sq Ft

    737 W Washington Blvd Unit 1110, Chicago, IL 60661

    PERFECTION IN HOT WEST LOOP - SKYBRIDGE! Completely renovated from top to bottom a few years ago, this stunning 2-bedroom, 2-bath residence offers sophisticated city living with spectacular west-facing sunset views. The beautiful kitchen and baths showcase high-end finishes and thoughtful design throughout. Gorgeous hardwood floors flow seamlessly through the living and dining areas, highlighted

    Sharon O'Hara @properties Christie's International Real Estate

    737 W Washington Blvd Unit 1110, Chicago, IL 60661
  • /29

    $475,000

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    680 N Green St Unit 702, Chicago, IL 60642

    Step into this extra-wide, light-filled east-facing corner penthouse offering unobstructed city skyline views and private roof rights. Wake up to sun-drenched living spaces and step onto your balcony for morning coffee with the skyline as your backdrop. The expansive, functional layout is designed for both everyday comfort and effortless entertaining, with generous room for formal dining, a

    Joel Holland Keller Williams ONEChicago

    680 N Green St Unit 702, Chicago, IL 60642
  • /19

    $479,900

    • Studio
    • 1 Bath
    • 907 Sq Ft

    401 N Wabash Ave Unit 2304, Chicago, IL 60611

    This expansive studio spans over 900 square feet, making it the perfect "pied-a-terre" or investment rental unit. Enjoy breathtaking east-facing views of Lake Michigan, the Chicago River, and iconic city landmarks. The studio is impeccably furnished and fully equipped, featuring a Snaidero-designed kitchen with Miele and Sub-Zero stainless steel appliances. The luxurious bathroom includes a

    James Qiu Kale Realty

    401 N Wabash Ave Unit 2304, Chicago, IL 60611
  • /17

    $2,575,000 Open Sun 11AM - 3PM

    • 5 Beds
    • 4.5 Baths
    • 4,560 Sq Ft

    4442 N Greenview Ave, Chicago, IL 60640

    This beautiful house has a great street appeal, it is featuring five bedrooms, third floor spacious sixty five feet deck with pergola, open first floor porch and three car garage. The house is located in well acclaimed Ravenswood elementary School District, it features 10-foot ceilings on every level and high-end finishes throughout. The main level boasts custom millwork, crown moldings, and

    Milena Birov @properties Christie's International Real Estate

    4442 N Greenview Ave, Chicago, IL 60640
  • /13

    $315,000

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft

    2800 N Lake Shore Dr Unit 712, Chicago, IL 60657

    This south-facing one-bedroom offers unobstructed views of Lincoln Park, the city skyline, Navy Pier, and Diversey Harbor-views that never get old, no matter the season or time of day. Morning light fills the unit, sunsets are spectacular, and the constant presence of the lake and park creates a sense of calm that's hard to find in the city. At 900 square feet, the unit feels comfortable, open,

    Nathan Wolf John Haderlein & Son, Inc.

    2800 N Lake Shore Dr Unit 712, Chicago, IL 60657
  • /87

    $8,995,000

    • 7 Beds
    • 5.5 Baths
    • 8,691 Sq Ft

    1853 N Burling St, Chicago, IL 60614

    Set on an expansive 44-ft-wide lot on the most coveted block of one of Chicago's most prestigious streets, 1853 N Burling is an exceptional custom-built estate. Situated in the heart of Lincoln Park, this architectural tour de force seamlessly combines masterful craftsmanship & refined modern living. Designed for extraordinary living, every element of this home has been carefully curated to

    Carrie McCormick @properties Christie's International Real Estate

    1853 N Burling St, Chicago, IL 60614
  • /18

    $1,600,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,269 Sq Ft

    2235 W Oakdale Ave Unit 25-D, Chicago, IL 60618

    NOW UNDER CONSTRUCTION! Introducing RiverWard - a collection of 35 new construction, extra-wide row homes tucked along the north branch of the Chicago River in west Lakeview. Perfectly situated in an idyllic location and with access to Southport, Roscoe Village, and the expressway, this exclusive offering will deliver contemporary new construction row homes never before available in the

    Cory Robertson Jameson Sotheby's Intl Realty

    2235 W Oakdale Ave Unit 25-D, Chicago, IL 60618
  • /24

    $1,049,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    2341 W Belden Ave Unit 1, Chicago, IL 60647

    New construction duplex-down condominium offering 3 bedrooms and 2.5 bathrooms with high-end finishes and thoughtful design throughout. This spacious home blends indoor and outdoor living and includes a private garage rooftop deck with privacy fence and built-in speaker system, providing a rare outdoor extension ideal for everyday living and entertaining. The main level features an open-concept

    Damian Wojcik Chicagoland Brokers, Inc.

    2341 W Belden Ave Unit 1, Chicago, IL 60647
  • /51

    $1,600,000

    • 4 Beds
    • 4.5 Baths
    • 4,924 Sq Ft

    600 N Kingsbury St Unit 506, Chicago, IL 60654

    This three-story penthouse at 600 N Kingsbury is a rare opportunity to own one of River North's most dramatic and spacious residences. With four bedrooms, four-and-a-half bathrooms, a private four-car attached garage, and nearly 1,800 square feet of exclusive outdoor space, this home blends the scale of a single-family residence with the convenience of full-amenity condominium living. Inside,

    Grigory Pekarsky Vesta Preferred LLC

    600 N Kingsbury St Unit 506, Chicago, IL 60654

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