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Duplexes for Sale in Chicago, IL

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  • /35

    $2,199,000

    Pending
    • 7 Beds
    • 6 Baths

    1705 W Leland Ave, Chicago, IL 60640

    An exceptional opportunity awaits in the vibrant Ravenswood neighborhood. This handsome, historic residence combines elegant style, modern comfort, and rare investment potential. The property features a stunning luxury owner's duplex-up plus three well-appointed rental apartments, offering both refined living and multiple income streams. The owner's duplex-up is a true showpiece, with expansive

    Keith Goad Berkshire Hathaway HomeServices Chicago

    1705 W Leland Ave, Chicago, IL 60640
  • /23

    $450,000

    Pending
    • 3 Beds
    • 3 Baths

    3756 W Leland Ave Unit 1S, Chicago, IL 60625

    Situated in the heart of Albany Park, this thoughtfully laid-out 3 bed, 3 full bath duplex-down offers space, light, and flexibility across two distinct levels. The main floor is filled with natural light throughout the day and anchored by an open-concept living and dining area that flows into a spacious kitchen with granite countertops, stainless steel appliances, a breakfast bar, and a newer

    Tim McLoughlin @properties Christie's International Real Estate

    3756 W Leland Ave Unit 1S, Chicago, IL 60625
  • /23

    $1,850,000

    • 8,084 Sq Ft

    504 S Oakley Blvd, Chicago, IL 60612

    This exceptional investment opportunity offers the acquisition of a modern 6-unit multifamily asset ideally located in the rapidly growing Tri-Taylor neighborhood of Chicago. Constructed in 2014, the property features condominium-quality finishes, efficient building systems, and thoughtfully designed floor plans that continue to attract strong tenant demand and support premium rental rates. The

    Glynnis Johnson @properties Christie's International Real Estate

    504 S Oakley Blvd, Chicago, IL 60612
  • /21

    $289,900

    Pending
    • 5 Beds
    • 2 Baths

    5937 S Maplewood Ave, Chicago, IL 60629

    Discover the immense potential of this stately brick two-unit, perfectly positioned for a high-end restoration. The versatile first-floor layout features 2 bedrooms and 1 bath, offering the unique opportunity to duplex into the basement for a sprawling owner's suite. The second floor provides a generous 3-bedroom, 1-bath residence bathed in natural light. Set on a serene, tree-lined block within

    Elias Masud Compass

    5937 S Maplewood Ave, Chicago, IL 60629
  • /58

    $2,150,000

    New Construction $840K PRICE DROP
    • 11 Beds
    • 8 Baths

    Chicago, IL 60614

    Exceptional New Booth Hansen-Designed Three-Unit Residence on an Extra-Long Lot Built by legendary architect Booth Hansen and developer Ogden Partners. This stunning investment and/or live in investment property sits on an extra-long 25' x 150' lot, allowing for expansive layouts and extraordinary natural light throughout every home. This thoughtfully designed masonry brick and limestone building

    Linda Levin Jameson Sotheby's Intl Realty

    Chicago, IL 60614
  • /25

    $514,900

    • 2 Beds
    • 2 Baths

    2140 W Huron St Unit 2F, Chicago, IL 60612

    Located in Chicago's West Town neighborhood, this 2-bedroom, 2-bathroom home strikes the quintessential balance of vintage charm, style, and the kind of comfort that can only be found at home. This home will check all of your boxes: in-unit laundry, central AC/heat, and two private outdoor spaces. You don't have to look any further! Upon entering, you'll step through the front door and take note

    Melanie Everett Compass

    2140 W Huron St Unit 2F, Chicago, IL 60612
  • /24

    $245,000

    $15K PRICE DROP Pending Pre-Foreclosure
    • 7 Beds
    • 2 Baths

    7438 S Stewart Ave, Chicago, IL 60621

    Value-Add 2-Family Opportunity - Priced Well Below Market! Don't miss this excellent opportunity to own a 2-family property with strong upside potential. Property Highlights: Two-family layout with separate heating systems for each unit Cosmetic updates needed on both the first and second floors - perfect for investors or buyers looking to add value Full basement The first-floor unit offers the

    Crystal Smith, REALTOR® ERA Partners

    7438 S Stewart Ave, Chicago, IL 60621
  • /27

    $499,000

    • 7 Beds
    • 3 Baths

    11127 S Homewood Ave, Chicago, IL 60643

    Presenting a rare and one of kind architecturally designed French brick 2 unit residential building. Gut-renovated in 2000 (and updated between 2012-2014), this well-maintained 2-flat is ready for a new owner! Currently configured with a large (+/- 1,600 sf) 3/1 + den first floor simplex and a massive (+/- 2,700 sf) 4/2 + den duplex up. Both apartments feature hardwood floors, wood burning

    Scott Siegel Chicago Real Estate Authority

    11127 S Homewood Ave, Chicago, IL 60643
  • /19

    $699,000

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

    1931 N Damen Ave Unit 1S, Chicago, IL 60647

    OH 5/23 CANCELED. Welcome to 1931 N Damen Unit 1S, a duplex down in a boutique elevator building ideally located in the heart of Bucktown at Damen and Armitage. With over 31 feet of living and dining space, soaring 11.5-foot ceilings, and an incredibly functional layout, this 3 bed, 2.1 bath home lives like a single family and offers the flexibility of a true 4 bedroom floor plan. One of the most

    Michael Glickman @properties Christie's International Real Estate

    1931 N Damen Ave Unit 1S, Chicago, IL 60647
  • /19

    $230,000

    • 2 Beds
    • 1 Bath

    3005 N Kolmar Ave Unit 1, Chicago, IL 60641

    Gorgeous 2/Bed 1/Bath Condo property, Features refinished hardwood floors, living room, formal dining room, nice sized foyer, updated kitchen w/S.S. appliances and lots of countertop and storage space. The unit has washer and dryer in unit, A/C, and beautifully bathroom. New sump pump in basement. " Full Unfinished Basement that can be converted into duplex down". Perfectly located just minutes

    Gabriel Abarca Elite Realty Network LLC

    3005 N Kolmar Ave Unit 1, Chicago, IL 60641
  • /46

    $8,400,000

    $500K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 7,880 Sq Ft

    159 E Walton Place Unit PH, Chicago, IL 60611

    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

    Brian Loomis Jameson Sotheby's Intl Realty

    159 E Walton Place Unit PH, Chicago, IL 60611
  • /21

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 1,436 Sq Ft

    735 E 50th St Unit 2, Chicago, IL 60615

    Stunning Bronzeville Duplex-Down 3-Bed, 2.5-Bath with garage parking included. Beautifully updated and move-in ready, this Bronzeville gem features hardwood floors, soaring ceilings, and natural light throughout. The sleek kitchen boasts quartz countertops and backsplash, white cabinetry, and brand-new stainless appliances plus an extra nook perfect for a coffee or wet bar. The primary suite

    Omor Eguasa Baird & Warner

    735 E 50th St Unit 2, Chicago, IL 60615
  • /33

    $989,000

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 1,983 Sq Ft

    1406 W Cuyler Ave Unit 3, Chicago, IL 60613

    Experience elevated living at 1406 W. Cuyler Ave in UNIT 3, an exceptional brand-new duplex-up offering approximately 2,000 square feet of expansive indoor and outdoor living space. Thoughtfully designed with sleek sophistication and timeless finishes, this residence features engineered white oak hardwood flooring throughout, oversized windows, soaring airy spaces, and premium Kohler and

    DOROTA MOSKAL Dorota Moskal

    1406 W Cuyler Ave Unit 3, Chicago, IL 60613
  • /21

    $8,495,000

    4742 S Michigan Ave, Chicago, IL 60615

    Unbelievable trophy-piece opportunity, three 8 unit boutique buildings, 24 Units fully stabilized, condo-quality and developed in 2025 in the Heart of Bronzeville. Each building features TWO front and back 3 bed 3 bath duplex units and SIX front and back 2 bed/2 bath simplex units. Many high-design details, from hallway accents to primary suite wall details meant to set this apart. Highlights

    Karen Biazar North Clybourn Group, Inc.

    4742 S Michigan Ave, Chicago, IL 60615
  • /18

    $300,000

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    1108 E Marquette Rd Unit 207, Chicago, IL 60637

    Experience elevated living in the heart of Woodlawn at 1108 E Marquette Rd, Unit 207; a luxury duplex-up residence surrounded by new development and just minutes from the future Obama Presidential Library, University of Chicago, Jackson Park, and the lakefront. This stunning home features real hardwood floors throughout and an open-concept main level designed for both everyday comfort and stylish

    Whitney Hampton Keller Williams ONEChicago

    1108 E Marquette Rd Unit 207, Chicago, IL 60637
  • /28

    $425,000

    • 4 Beds
    • 2 Baths

    3517 S Lowe Ave, Chicago, IL 60609

    Multiple Offers Received. Requesting Highest & Best by 7/28/2026 Tuesday 3 p.m. Prime Bridgeport Location! Don't miss this solid 2-flat nestled on one of Bridgeport's most desirable tree-lined streets. Whether you're an owner-occupant, investor, or someone looking for a property with future potential, this is an exceptional opportunity in one of Chicago's most sought-after neighborhoods. Both the

    Sheila Messer Bridgeport Realty Group, LLC

    3517 S Lowe Ave, Chicago, IL 60609
  • /13

    $260,000

    $90K PRICE DROP

    2911 W 25th St, Chicago, IL 60623

    Property was originally 4 Flat but has been gutted to the studs. Next door Lot at 2909 W. 25th St MLS#12461803 is included which has separate pin number. Seller will include Architectural Plans he had for rebuilt on each lot of 2 Duplex 2 units. Cash or Reno loan needed to purchase. Seller will not separate both lots must be sold together.

    Gloria Ortiz Real People Realty

    2911 W 25th St, Chicago, IL 60623
  • /27

    $449,900

    $50K PRICE DROP Pending
    • 5 Beds
    • 2 Baths

    8018 S Harvard Ave, Chicago, IL 60620

    Own your home while your tenant helps with the mortgage! Beautifully renovated brick 2-flat with each unit boasting new white shaker cabinets, quartz countertops, new stainless steel appliances, new bathrooms, and a washer & dryer in the building; Fresh new concrete slab carport in the rear. Spacious duplex owner's unit plus a income-producing second floor already occupied. Smart living and

    Nicholas Hansen Home One Realty

    8018 S Harvard Ave, Chicago, IL 60620
  • /46

    $950,000

    Pending
    • 8 Beds
    • 5 Baths

    2909 N Ridgeway Ave, Chicago, IL 60618

    Multiple offers. Highest and best due 6/28 by 6 pm. Large 3 unit, fully rented, (Unit 1: $2000, Unit 2: $3000, Coach House: $1900) Prime Logan-dale location, on border of the popular Logan Square and Avondale neighborhoods. Perfectly located right off Milwaukee ave on a tree-lined residential street, steps to all Avondale/Logan have to offer! Enjoy this solid, Beautifully renovated, MONEY- MAKING

    Rose Toma @properties Christie's International Real Estate

    2909 N Ridgeway Ave, Chicago, IL 60618
  • /29

    $595,000

    Open Sat 12PM - 1:30PM $5K PRICE DROP
    • 3 Beds
    • 2 Baths

    1429 W Fillmore St Unit 3, Chicago, IL 60607

    This extra bright, super spacious three bed/two bath duplex up is situated in the heart of Little Italy/Univ Village. The wide floor plan, vaulted ceilings, and skylights make living in this home a dream. The unit features hardwood floors, 15-year LED bulbs throughout, an open concept on-trend white kitchen with stainless steel appliances including new refrigerator and microwave from 2025 and

    Scott Petcov Keller Williams ONEChicago

    1429 W Fillmore St Unit 3, Chicago, IL 60607
  • /17

    $600,000

    Pending
    • 4 Beds
    • 3 Baths

    1034 N Drake Ave, Chicago, IL 60651

    Beautiful home located in Hot West Humboldt Park Neighborhood is awaiting its new owner. Completely rehabbed in 2024 with stunning condo quality finishes in both units and a new built garage. This luxury property features a 1 bedroom top floor apartment currently rented, and a 3 bedrooms and 2 bathrooms in the duplex down first floor with a family room on the lower level. New hardwood floors in

    Silva Jelebinkov Jam Realty Co

    1034 N Drake Ave, Chicago, IL 60651
  • /32

    $799,000

    Pending
    • 5 Beds
    • 3 Baths

    2621 W Haddon Ave, Chicago, IL 60622

    Located in the heart of East Humboldt Park, just steps from the energy of Wicker Park and Bucktown, this well-maintained brick two-flat offers an exceptional opportunity for both investors and owner-occupants. The property features a spacious duplex-down owner's unit with 3 bedrooms and 2 full baths along with a bright and functional second-floor simplex offering 2 bedrooms and 1 bath. Both units

    Tim McLoughlin @properties Christie's International Real Estate

    2621 W Haddon Ave, Chicago, IL 60622
  • /45

    $2,650,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    2207 N Orchard St Unit 1, Chicago, IL 60614

    This is what you've been waiting for! Gorgeous newer-construction duplex down set on an extra-wide lot directly across from Oz Park with tree and park views. An amazing East Lincoln Park location! You have never seen this layout and floor plan before - only possible on an oversized lot. Thoughtfully designed, this highly upgraded home is defined by its three exceptional outdoor living spaces,

    Susan Miner Premier Relocation, Inc.

    2207 N Orchard St Unit 1, Chicago, IL 60614
  • /24

    $725,000

    Open Sat 11AM - 12:30PM
    • 3 Beds
    • 2.5 Baths

    1523 N Fairfield Ave Unit 1, Chicago, IL 60622

    Welcome to this bright and spacious three bedroom, two-and-a-half bathroom duplex-down in the heart of Humboldt Park. This move-in ready home features floor-to-ceiling windows, beautiful hardwood floors, and a generously sized living room anchored by a fireplace. The kitchen offers quartz countertops, high-end stainless steel appliances, a tile backsplash, gas cooking with a vented range hood,

    Axel Cohen Compass

    1523 N Fairfield Ave Unit 1, Chicago, IL 60622
  • /5

    $190,000

    Pending
    • 7 Beds
    • 3 Baths

    6732 S Michigan Ave, Chicago, IL 60637

    Investment Opportunity! This 2-unit building offers a blend of comfort, value, and income potential. The current owner purchased as an investment property and it has severed is purpose. The building features updated electrical and plumbing, hardwood floors throughout, eat-in kitchens, with bathrooms. The first-floor unit is a duplex with the finished basement, providing a spacious 2-bedroom,

    Deborah Peoples Keller Williams ONEChicago

    6732 S Michigan Ave, Chicago, IL 60637
  • /18

    $900,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    2226 N Racine Ave Unit 15, Chicago, IL 60614

    This beautifully rehabbed and unique timber loft duplex is located at the back of a quiet courtyard setting across the street from highly rated Oscar Mayer School and Trebes Park! Open floor plan is flooded with light and showcases a large family room with 12+ ft ceilings, generous windows throughout and exposed brick. A dual-sided gas fireplace is centered perfectly to create a cozy living room

    Ian Schwartz Coldwell Banker Realty

    2226 N Racine Ave Unit 15, Chicago, IL 60614
  • /18

    $450,000

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths

    5400 S Hyde Park Blvd Unit B12, Chicago, IL 60615

    Bright and spacious two level, top floor townhome in the highly desirable Hedgerow Community. This beautifully updated duplex up is peacefully situated in a gated courtyard community with elevator access and garage parking included. This thoughtful home features a beautifully updated kitchen and baths with gorgeous tile work. Additionally, there are hardwood floors, in-unit washer and dryer,

    Stuart Schwartz Compass

    5400 S Hyde Park Blvd Unit B12, Chicago, IL 60615
  • /12

    $459,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    6755 N Hermitage Ave Unit 3, Chicago, IL 60626

    LAST UNIT AVAILABLE - DUPLEX-UP! Introducing beautiful, quality-built new construction residences in an intimate eight-unit building in the heart of Rogers Park. There are six thoughtfully designed duplexes and two simplexes, creating a true boutique residential feel. This spacious and light-filled 3 bedroom/2.1 bath duplex-up showcases modern design and expert craftsmanship throughout. The homes

    Natasha Motev Jameson Sotheby's Intl Realty

    6755 N Hermitage Ave Unit 3, Chicago, IL 60626
  • /11

    $460,000

    Pending
    • 7 Beds
    • 3 Baths

    7232 S Union Ave, Chicago, IL 60621

    Step inside and fall in love with the soaring 10-foot ceilings, open-concept floor plan, recessed lighting, and sleek designer finishes throughout. The kitchens are a true showstopper, featuring quartz countertops, 42-inch custom cabinetry, and bold black fixtures that bring the perfect touch of modern elegance. The first-floor unit offers a spacious duplex-down layout with four bedrooms and two

    Candice Payne 5th Group Corp

    7232 S Union Ave, Chicago, IL 60621
  • /26

    $2,150,000

    New Construction
    • 3 Beds
    • 3.5 Baths

    1942 N Orchard St Unit 1N, Chicago, IL 60614

    ONLY TWO LEFT. Rare opportunity to live on one of the most prestigious streets and nestled among the iconic mansions of Chicago in a new construction condo. This new construction project blends in with a timeless brick and limestone facade. Separating itself from other new construction, this home offers a custom kitchen with Ceruse Oak cabinets, natural quartzite countertops, professional grade

    Jeffrey Lowe Compass

    1942 N Orchard St Unit 1N, Chicago, IL 60614
  • /43

    $569,999

    Open Sat 11AM - 12:30PM
    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    1033 W 14th Place Unit 318, Chicago, IL 60608

    Welcome to one of the largest and most impressive duplex penthouses in the sought-after University Commons community. This exceptional residence offers a rare combination of space, luxury, and outdoor living with an expansive open floor plan, soaring 12-foot ceilings, and a massive private terrace showcasing picturesque treetop views by day and stunning Chicago skyline views by night. Designed

    Cory Tanzer Option Premier LLC

    1033 W 14th Place Unit 318, Chicago, IL 60608
  • /25

    $674,900

    • 3 Beds
    • 3 Baths

    4662 N Winthrop Ave Unit 1S, Chicago, IL 60640

    Eclectic, historic, exciting and appreciating Uptown! 3 bedrooms/3 bathrooms -yes rarely available 3bds/3bths! in gorgeous architectural building in the heart of this vibrant community. This duplex down offers tall ceilings, bright rooms and space to roam and grow into. The top level has a generous open floor plan offering: a beautiful kitchen with large breakfast bar peninsula, living

    Maribel Selva Coldwell Banker Realty

    4662 N Winthrop Ave Unit 1S, Chicago, IL 60640
  • /5

    $1,450,000

    New Construction
    • 3 Beds
    • 2 Baths

    1839 N Dayton St Unit 204, Chicago, IL 60614

    1839 North Dayton Street: The Pinnacle of Lincoln Park Luxury Introducing a highly anticipated, exclusive collection of new-construction luxury residences situated on a prestigious residential block in the heart of Lincoln Park. This boutique development brings sophisticated, modern living to one of Chicago's most desirable streets /blocks of Lincoln Park, Designed for ultimate privacy and

    Sabina Szura Mark Allen Realty ERA Powered

    1839 N Dayton St Unit 204, Chicago, IL 60614
  • /20

    $639,000

    $6K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    645 W Bittersweet Place Unit 1, Chicago, IL 60613

    Steps from the lakefront, this sun-filled 3-bedroom, 2 bath home offers the best of East Lakeview living in an intimate 3-unit building. The south-facing living room with gas fireplace and hardwood floors throughout creates a warm, light-filled space ideal for both everyday living and entertaining. The thoughtfully designed floor plan features generously sized rooms, stainless steel appliances,

    Andrea Granias Compass

    645 W Bittersweet Place Unit 1, Chicago, IL 60613
  • /21

    $799,000

    New Construction Pending
    • 3 Beds
    • 2.5 Baths

    5428 N Winthrop Ave Unit 103, Chicago, IL 60640

    **Under Construction and delivering in June 2026. 30% pre-sold before completion. Secure your unit now at pre-construction pricing through the month of May only. Prices will increase after May. Don't miss this limited opportunity. This brand-new 3-bedroom, 2.5-bathroom duplex in a boutique 12-unit ELEVATOR building in the heart of Edgewater offers an expansive open layout with a spacious living

    Svitlana Creadon Compass

    5428 N Winthrop Ave Unit 103, Chicago, IL 60640
  • /6

    $649,000

    Pending
    • 4 Beds
    • 2 Baths

    2852 W Polk St, Chicago, IL 60612

    East Garfield Park Brick 2 Unit near The United Center 1901 Redevelopment. Each unit features an impressive 1,500 sq ft of living space, large open concepts with Kitchen(s) overlooking a spacious Dining & Living Room area, 2 Bedrooms, 1 full Bathroom Walk-in Showers with Benches for a Spa-Like Experience. Full unfinished basement ideal for a third unit conversion with front & rear entrances or

    Eduardo Padro Pearson Realty Group

    2852 W Polk St, Chicago, IL 60612
  • /9

    $449,999

    • 5 Beds
    • 2 Baths

    7254 S Lafayette Ave, Chicago, IL 60621

    Brick 2 unit in The Greater Grand Crossing Community Of Chicago with large apartments. 1st floor unit: 2 bedroom, 1 bath, living room, dining room & kitchen open concept with potential to duplex into the basement. 2nd floor unit 3 bedroom, 1 bath, living room, dining room & kitchen open concept. *** PLEASE NOTE: Basement third unit potential with separate front, rear entrances and adequate

    Eduardo Padro Pearson Realty Group

    7254 S Lafayette Ave, Chicago, IL 60621
  • /20

    $325,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,411 Sq Ft

    5252 S Drexel Ave Unit 52521A, Chicago, IL 60615

    Beautiful duplex condominium offering 2 bedrooms and 2.5 bathrooms in the heart of Hyde Park. This thoughtfully designed home features an open-concept living, dining, and kitchen area, creating a spacious and functional layout with abundant natural light from south- and east-facing windows. The main level includes a generously sized primary suite with ample closet space and a large en-suite bath

    Colleen Berg Berg Properties

    5252 S Drexel Ave Unit 52521A, Chicago, IL 60615
  • /10

    $250,000

    Pending
    • 5 Beds
    • 3 Baths
    • 2,000 Sq Ft

    6328 S Drexel Ave Unit 1, Chicago, IL 60637

    Spacious and beautifully updated 5-bedroom, 3-bath duplex-down in the highly sought-after Woodlawn neighborhood, just minutes from public transportation, the University of Chicago, and the future Obama Presidential Center. Offering exceptional space and flexibility, this home is ideal for homeowners, multigenerational living, or investors seeking additional income potential. The main level

    Nikki Kimsey Keller Williams Preferred Rlty

    6328 S Drexel Ave Unit 1, Chicago, IL 60637
  • /38

    $2,950,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 3,692 Sq Ft

    21 N May St Unit 305, Chicago, IL 60607

    Introducing the first duplex resale at the Embry! Welcome to Unit 305, an exceptionally rare four-bedroom, four-and-a-half-bath duplex residence in the heart of the West Loop. One of only four duplex homes built in this celebrated luxury development, this home at almost 3,700 sq ft offers impeccable features including elegant herringbone hardwood floor in the foyer and living room along with

    Sarah Marsh @properties Christie's International Real Estate

    21 N May St Unit 305, Chicago, IL 60607

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