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Duplexes for Sale in Chicago, IL

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  • /26

    $924,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    3236 N Seminary Ave Unit 1, Chicago, IL 60657

    Bright and beautifully appointed three-bedroom duplex-down in the heart of Lakeview, ideally situated on a picturesque, tree-lined street between Belmont and School. This thoughtfully designed home offers an exceptional floor plan with generous living space, beautiful finishes, abundant storage, and multiple private outdoor spaces. The main level features a welcoming front living room with a

    Stacey Dombar Redfin Corporation

    3236 N Seminary Ave Unit 1, Chicago, IL 60657
  • /31

    $1,450,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    2653 N Dayton St Unit 1, Chicago, IL 60614

    Welcome to a masterfully designed luxury duplex-down in the heart of Lincoln Park. This exceptional four bedroom, two and a half bath residence offers sophisticated design, impeccable craftsmanship, and seamless indoor-outdoor living. Thoughtfully curated with an effortless flow, every space has been designed for both elegant entertaining and comfortable everyday living.The impressive living and

    Susan Fichter @properties Christie's International Real Estate

    2653 N Dayton St Unit 1, Chicago, IL 60614
  • /35

    $815,000

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

    1445 N Mohawk St Unit 2, Chicago, IL 60610

    Experience the comfort and space of a single-family home in this expansive Old Town duplex, offering approximately 2,000 square feet of interior living space plus 350 square feet of private outdoor areas. Nestled within a charming, classic Chicago brick building, this exceptional residence combines timeless character with modern convenience. The thoughtfully designed floor plan features soaring

    Alexandre Stoykov Compass

    1445 N Mohawk St Unit 2, Chicago, IL 60610
  • /35

    $645,000

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,474 Sq Ft

    100 E Walton St Unit 41DE, Chicago, IL 60611

    Welcome home! Seller is offering 6 months of paid HOA monthly assessements! Enjoy lower upfront costs and extra breathing room to truly make this beautiful space your own from day one. This is a rare opportunity to own a truly distinctive corner duplex penthouse in one of the city's most coveted locations. Originally created as the developer's own residence, this architecturally distinctive

    Alexandra Bernardi Jameson Sotheby's Intl Realty

    100 E Walton St Unit 41DE, Chicago, IL 60611
  • /34

    $575,000

    $24K PRICE DROP
    • 4 Beds
    • 3 Baths

    5121 W Henderson St, Chicago, IL 60641

    Live in one, rent the other! This well-maintained brick two-flat in the heart of Portage Park is perfect for an owner-occupant looking to build wealth while enjoying the benefits of homeownership. The second floor unit is vacant and move-in ready, offering a blank slate to make it your own from day one while the first floor unit provides immediate rental income. Each unit features spacious rooms,

    Jon Ellingsen xr realty

    5121 W Henderson St, Chicago, IL 60641
  • /18

    $460,000

    Pending
    • 2 Beds
    • 1.5 Baths

    1033 N Wood St Unit 3, Chicago, IL 60622

    Flooded with natural light, this East Village duplex penthouse offers 2 bedrooms, 1.5 baths, and an ideal open layout. Spacious eat-in kitchen with granite countertops, 42" cabinetry, stainless steel appliances, and access to one of two private outdoor spaces. The airy living room features soaring ceilings and a wall of west-facing windows. The primary suite includes a walk-in closet and private

    Elizabeth Caya Redfin Corporation

    1033 N Wood St Unit 3, Chicago, IL 60622
  • /29

    $725,000

    Pending
    • 4 Beds
    • 3 Baths

    1311 W Columbia Ave, Chicago, IL 60626

    This is the 2-flat you've been looking for! This spacious building offers an incredible opportunity for an owner-occupant or investor in a prime location. The first-floor duplex-down unit features 3 bedrooms, and 2 full bathrooms, a chef's kitchen overlooking the backyard, formal living room and separate dining. As you go to the lower level, you will be surprised by 8-ft ceilings and even more

    Leopoldo Gutierrez Redfin Corporation

    1311 W Columbia Ave, Chicago, IL 60626
  • /21

    $264,900

    Pending
    • 1 Bed
    • 1 Bath
    • 800 Sq Ft

    1221 N Dearborn St Unit 812N, Chicago, IL 60610

    Sleek, stylish, and updated, this Gold Coast duplex one-bedroom lives like a private retreat in the heart of the city. Two levels of living space with beautiful red oak hardwood floors in a natural finish, complemented by a rebuilt hardwood staircase and modern lighting that gives the home a clean, contemporary feel. The redesigned kitchen features quartz countertops, stainless steel appliances,

    Camie Cirrincione Redfin Corporation

    1221 N Dearborn St Unit 812N, Chicago, IL 60610
  • /27

    $579,900

    • 6 Beds
    • 3 Baths

    5353 N Spaulding Ave, Chicago, IL 60625

    Multiple Offers Received. Highest & Best due Monday 9/14/2026 5PMCST An incredible find! Nothing is more classic than the 1921 Craftsman brick two-flat in Chicago and this one, on an extra-wide city lot, is not to be missed. Designed for comfortable and affordable multi-family living, this model has withstood the test of time for a reason. Two, 2BR+TANDEM units with formal living and dining room

    Anthony Rodriguez Coldwell Banker Realty

    5353 N Spaulding Ave, Chicago, IL 60625
  • /26

    $999,000

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

    611 N Noble St Unit 3, Chicago, IL 60642

    Rare full-floor duplex penthouse in West Town, crowned by an expansive private rooftop deck with spectacular unobstructed Chicago skyline views! Designed for indoor/outdoor living and effortless entertaining, this three-bedroom home offers FIVE distinct outdoor spaces, including a spacious balcony directly off the open-concept kitchen, dining, and living area. Upstairs, the east-facing primary

    Ryan Templeton Keller Williams ONEChicago

    611 N Noble St Unit 3, Chicago, IL 60642
  • /29

    $549,900

    Pending
    • 2 Beds
    • 2 Baths

    Unlisted Address

    Welcome to this beautifully designed duplex-up that lives like a single-family home. Featuring soaring cathedral ceilings, abundant natural light, and a thoughtfully designed floor plan, this home offers a spacious kitchen with a large walk-in pantry, granite counters, coffee bar, a separate dining room, a generous living room, and a full bath on the main level. Upstairs, you'll find two

    Laura Topp Berkshire Hathaway HomeServices Chicago

    Unlisted Address
  • /34

    $999,995

    Pending
    • 3 Beds
    • 2.5 Baths
    • 3,100 Sq Ft

    1366 W Walton St Unit 1E, Chicago, IL 60642

    Experience an extraordinary level of design, craftsmanship, and outdoor living in this stunning extra-wide, south-facing duplex by award-winning Noah Properties and Axios Architects. Offering the comfort and scale of a single-family home with the convenience of condominium living, this exceptional 3-bedroom, 2.1-bath residence is filled with designer finishes, cutting-edge smart home technology,

    Matt Laricy Americorp, Ltd

    1366 W Walton St Unit 1E, Chicago, IL 60642
  • /30

    $245,000

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

    738 S Kedzie Ave Unit 2, Chicago, IL 60612

    Welcome to 738 S Kedzie Ave, Unit 2! This beautiful 3-bedroom, 2-full-bath duplex-up condo offers spacious living, modern comfort, and a layout designed for both everyday living and entertaining. Enjoy generous living spaces across two levels, well-sized bedrooms, two full baths, and the added convenience of garage parking. One of the home's standout features is rooftop access-perfect for

    Tameka McClellon Tameka McClellon

    738 S Kedzie Ave Unit 2, Chicago, IL 60612
  • /46

    $4,995,000

    • 5 Beds
    • 4.5 Baths
    • 5,110 Sq Ft

    1109 W Washington Blvd Unit PH8D, Chicago, IL 60607

    Welcome to the crown jewel of the iconic Hayden boutique building in the heart of the West Loop! Featured in Interiors Magazine, this extraordinary duplex-up penthouse is one of the largest floor plans in the building, spanning two breathtaking levels with over 5,000 square feet of living space, with private dual-elevator access, soaring ceilings, and walls of windows that flood every inch of the

    Hayley Westhoff Compass

    1109 W Washington Blvd Unit PH8D, Chicago, IL 60607
  • /19

    $475,000

    • 10 Beds
    • 4 Baths

    2518 S Claremont Ave, Chicago, IL 60608

    INVESTMENT OPPORTUNIYT! This huge brick two flat building located in the heart of Pilsen. Featuring two updated units, has plenty space and bedrooms in each unit, four full bathrooms and a full walk-up attic equipped with a bedroom and a bath for extra living space or duplex up with second floor unit. Two car garage! Located in a rapidly growing area for investment. Preferable cash or

    Ana Ramirez REMAX Legends

    2518 S Claremont Ave, Chicago, IL 60608
  • /15

    $360,000

    Pending
    • 6 Beds
    • 2 Baths

    8722 S Kingston Ave, Chicago, IL 60617

    Cash flowing from day one! This fully occupied, rehabbed (2022) two-story brick duplex is the definition of turn-key. Both units are 3BR/1BA with modern finishes and all appliances included - tenants in place, rent coming in; however, the second-floor unit is MTM. Basement laundry includes electronically operated machines, which adds even more to the bottom line. 48-hour notice required for

    Vanessa Matthews Keller Williams Preferred Rlty

    8722 S Kingston Ave, Chicago, IL 60617
  • /20

    $657,000

    New Construction $43K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,285 Sq Ft

    2847 N Damen Ave Unit 2, Chicago, IL 60618

    Penthouse and duplex units coming soon. BRAND NEW CONSTRUCTION | 2 BED, 2 BATH | PRIVATE BALCONY & ROOFTOP DECK | GARAGE PARKING INCLUDED Be the first to call this stunning new-construction residence home in Hamlin Park. Unit 2 pairs sophisticated, contemporary finishes with exceptional outdoor space in one of the neighborhood's most sought-after locations, just steps from Roscoe Village. A

    Colleen Berg Berg Properties

    2847 N Damen Ave Unit 2, Chicago, IL 60618
  • /35

    $650,000

    $90K PRICE DROP
    • 6 Beds
    • 3 Baths

    1949 N Francisco Ave, Chicago, IL 60647

    Location, Location, Location !! Highly sought-after neighborhood California and Armitage. Walk to Blue line on Milwaukee Ave. Solid large tall handsome 3 apartment Brick building with an English garden unit with 2 entrances. Lots of woodwork. Hardwood floors. Good size apartments. Formal living Room and Dining Room. Plenty of closets. Spacious garden apartment . Enclosed Porch. Wide backyard.

    Ernesto Escalante Charles Rutenberg Realty

    1949 N Francisco Ave, Chicago, IL 60647
  • /29

    $799,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    17 N Loomis St Unit 1J, Chicago, IL 60607

    Welcome to this beautifully updated duplex-down loft in the heart of the highly sought-after West Loop. Offering 3 bedrooms and 2.5 bathrooms, this unique floor plan features a desirable main-level primary suite and two spacious bedrooms on the lower level. The open-concept living and dining area showcases soaring ceilings, refinished hardwood floors, abundant natural light, and a stylish

    Joey Tanzillo Baird & Warner

    17 N Loomis St Unit 1J, Chicago, IL 60607
  • /26

    $799,000

    • 2 Beds
    • 2 Baths

    520 W Huron St Unit 609, Chicago, IL 60654

    The River North home you've been waiting for! This stunning two bedroom, two bath penthouse duplex loft delivers dramatic architectural character, an expansive open floor plan and two outdoor spaces with gorgeous skyline views day & night. Soaring ceilings, exposed brick, timber beams, oversized windows and hardwood floors capture that authentic city feel. The open living space is built for

    Jodi Slutzky Jameson Sotheby's Intl Realty

    520 W Huron St Unit 609, Chicago, IL 60654
  • /27

    $715,000

    $44K PRICE DROP
    • 7 Beds
    • 7 Baths

    5318 S Kenneth Ave, Chicago, IL 60632

    PASSED ALL CITY INSPECTIONS! COME AND APPLY FINANCING LIVE IN ONE AND RENT OTHER TWO UNITS. FHA CONVENTIONAL APPROVED BUILDING! Recently completed updates and a complete transformation make this turn-key 3-unit building feel almost brand new and completely move-in ready. Major improvements include a brand-new electrical system (2026), first floor furnace and A/C (2024), all new copper plumbing

    Mina Nikolic Baird & Warner

    5318 S Kenneth Ave, Chicago, IL 60632
  • /48

    $420,000

    $50K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,500 Sq Ft

    4839 S Vincennes Ave Unit 1, Chicago, IL 60615

    Gorgeous, well-maintained 4 beds/3 full baths duplex down grey-stone avail now in Historic Grand Boulevard! Main level has hardwood floors in living/dining/kitchen, stainless steel appliances, granite countertops, recessed lighting and ceiling fans throughout. Living area has electric fireplace w/mantle and beautiful bay windows for plenty of sunlight. 2 nice-sized carpeted bedrooms on main level

    Marjorie Tatum Keller Williams ONEChicago

    4839 S Vincennes Ave Unit 1, Chicago, IL 60615
  • /12

    $899,000

    • 7,947 Sq Ft

    8035 S Essex Ave, Chicago, IL 60617

    Yellow Brick Octagon 6 Unit. Ideal building to turn into an 8 unit or duplex the 1st floor units into the unfinished basement with high ceiling height for some massive units. All units come with separate utilities, large living rooms & dining rooms. Four car brick garage. Close proximity to a city park, an 8 - 10 min drive to Route 41 Jean-Baptiste Pointe DuSable Lake Shore Drive, an 10 - 15 min

    Eduardo Padro Pearson Realty Group

    8035 S Essex Ave, Chicago, IL 60617
  • /23

    $275,000

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths

    7707 S Peoria St, Chicago, IL 60620

    Exceptional investment opportunity in Chicago's Auburn Gresham neighborhood! This well-maintained brick two-unit building offers strong cash-flow potential with two long-term tenants currently in place on month-to-month leases, providing flexibility for investors and owner-occupants alike. The first-floor unit includes direct access to the basement, offering potential for a duplex-down

    Adrian Perez Avenue Properties Chicago

    7707 S Peoria St, Chicago, IL 60620
  • /24

    $315,000

    $5K PRICE INCREASE Pending
    • 4 Beds
    • 2 Baths

    1117 W 57th St, Chicago, IL 60621

    The first-floor unit offers a 211bed 1 bath spacious duplex-down layout featuring a generous family room and has opportunity to create a 3rd bedroom or office , convenient laundry hookups in both units spa-inspired bathrooms, an electric heat fireplace, and abundant natural light-perfect for an owner-occupant. The second-floor unit includes 2 bedrooms and 1 bathroom nice size bedrooms . 2nd floor

    Amanda Stapleton Blue Door Dave Inc

    1117 W 57th St, Chicago, IL 60621
  • /20

    $529,000

    Pending
    • 2 Beds
    • 2 Baths

    2851 N Southport Ave Unit B, Chicago, IL 60657

    Southport corridor duplex up, featuring two bedrooms, two full baths, real hardwood flooring, fireplace, in-unit laundry & dedicated parking. Beautifully maintained with new carpet, paint, light fixtures & 2023 SS fridge. Private patio area for grilling. Investor & pet friendly. Worry free with a 2024 furnace & AC. Strong reserves and NO planned special assessments. Conveniently located near

    Nina McDaniel Baird & Warner

    2851 N Southport Ave Unit B, Chicago, IL 60657
  • /50

    $874,900

    • 6 Beds
    • 4 Baths

    4111 N Francisco Ave, Chicago, IL 60618

    Rare opportunity to own a beautifully maintained brick two-flat in highly desirable East Irving Park, just steps from Horner Park. With one apartment currently vacant, this property presents an exceptional opportunity for an owner-occupant, house hacker, or investor looking for a substantially updated building with many of the major capital improvements already completed. Extensive improvements

    Kieran Fahy Fahy Real Estate Inc

    4111 N Francisco Ave, Chicago, IL 60618
  • /20

    $350,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    2539 W Warren Blvd Unit 1, Chicago, IL 60612

    Welcome home to your 3 bed, 2 1/2 bath stunning duplex condo with 2,600 square feet of living space near the upcoming 1901 Project! Cozy up to your wood burning fireplace with a custom paint design while enjoying your spacious kitchen with 42" cherry cabinets, granite counters and an impressive travertine stone backsplash. Brand new refrigerator with newer appliances. Home features refinished

    Adam Antonucci Fulton Grace Realty

    2539 W Warren Blvd Unit 1, Chicago, IL 60612
  • /53

    $1,199,000

    $100K PRICE DROP
    • 6 Beds
    • 4 Baths

    2215 W Arthur Ave, Chicago, IL 60645

    Rarely available, fully renovated jumbo 3-flat on an extra-wide lot in the heart of West Ridge (West Rogers Park), just moments from Warren Park and situated on a quiet one-way street that is minutes to Rogers Park Amenities. This exceptional investment or owner-occupant opportunity features a spacious first-floor duplex-down offering 2 bedrooms and 2 full baths, along with two additional

    Alexander Tzallas RE/MAX 10 Lincoln Park

    2215 W Arthur Ave, Chicago, IL 60645
  • /10

    $1,399,000

    New Construction
    • 3 Beds
    • 2.5 Baths

    1951 W Dickens Ave Unit 1, Chicago, IL 60614

    1951 W Dickens, Bucktown - an extra-wide duplex-down unit with 3 bedrooms and 2.5 bathrooms. The main level includes a living room, separate dining room, and kitchen with a large island and built-in pantry, opening to a family room at the rear. The lower level features a primary suite with walk-in closet and en-suite bath with dual vanities, two additional bedrooms, a second full bathroom, and

    William Goldberg Fulton Grace Realty

    1951 W Dickens Ave Unit 1, Chicago, IL 60614
  • /39

    $825,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,255 Sq Ft

    1522 W Cortez St Unit 1, Chicago, IL 60642

    Life is too short not to live in a turnkey home like this in Chicago! Welcome to this impeccably designed 4 bedroom, 3 bathroom duplex down in the heart of West Town/Noble Square/Wicker Park. The dramatic main level boasts 13-foot ceilings, hardwood oak floors, a beautiful gas fireplace, oversized south-facing windows, and abundant natural light throughout. The modern kitchen is fully equipped

    Stephanie Spenner Compass

    1522 W Cortez St Unit 1, Chicago, IL 60642
  • /25

    $330,000

    Pending
    • 5 Beds
    • 2 Baths

    1317 S Homan Ave, Chicago, IL 60623

    Step into the charm of a classic 1898 Chicago Greystone, ideally situated in the evolving North Lawndale neighborhood just west of Douglas Park, between Roosevelt and Douglas Blvd. This area is seeing exciting revitalization-take a look around and you'll notice the steady stream of beautifully restored homes adding to the neighborhood's appeal. Inside, both units offer a timeless layout with

    Juan Espinosa E-Professional Realty

    1317 S Homan Ave, Chicago, IL 60623
  • /18

    $349,000

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft

    5017 S Prairie Ave Unit 1N, Chicago, IL 60615

    Fantastic opportunity to own your own duplex in the Hot Bronzeville/Washington Park!! Its a huge unit and has 4 spacious bedrooms, 3 bathrooms and a parking space in the rear. Freshly painted, the unit is in great condition! It features maple kitchen cabinets, granite tops, stainless steel appliances, and hardwood floors. Located in a good neighborhood close to schools, shopping, restaurants, and

    Ryan Banks HomeSmart Realty Group

    5017 S Prairie Ave Unit 1N, Chicago, IL 60615
  • /25

    $850,000

    Pending
    • 9 Beds
    • 3 Baths

    5117 N Western Ave, Chicago, IL 60625

    Turnkey legal 3-unit building in the heart of desirable Lincoln Square. This fully leased property features three spacious 3-bedroom, 1-bath units, each with central heat and air conditioning, in-unit laundry, and strong rental demand. The building currently generates over $75,000 in annual income, with tenants responsible for all their own utilities. Additional highlights include usable attic

    Luke Wojcik Triton Realty Group LLC

    5117 N Western Ave, Chicago, IL 60625
  • /25

    $439,900

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,000 Sq Ft

    435 E 42nd St Unit 1, Chicago, IL 60653

    At nearly 3,000 square feet, this spacious duplex-down condo offers the comfort and feel of a single-family home in the heart of Bronzeville. The home reflects normal wear and presents a wonderful opportunity for the next owner to add their own style through a few cosmetic updates. This 4 bedroom, 3 bath open-concept condo welcomes you with hardwood floors throughout the main floor and a

    Tambra Chadwell Tambra Chadwell

    435 E 42nd St Unit 1, Chicago, IL 60653
  • /16

    $245,000

    Pending
    • 2 Beds
    • 2 Baths
    • 992 Sq Ft

    5184 W 64th Place, Chicago, IL 60638

    Brick, 2 bed, 2 bath half duplex with finished basement (could easily be 3rd bed!), garage & fenced yard with deck on large corner lot!! Freshly painted in 2025, white trim, & tons of natural light! Main level hosts a cozy living room, spacious kitchen with stainless steel appliances & wood look tile! Upstairs is home to 2 large bedrooms and a full bath. The finished walk out basement provides

    Jacob Kilts HomeSmart Realty Group

    5184 W 64th Place, Chicago, IL 60638
  • /27

    $525,000

    • 3 Beds
    • 2 Baths

    1427 W Superior St Unit 2F, Chicago, IL 60642

    Don't miss this opportunity during low-inventory days to grab this cute and cozy duplex in hot Noble Square! Located on a quiet street with mature trees, this is what you picture when you envision your first home in Chicago. This duplex up has all the modern touches (quartz countertops, stainless appliances) and the classic touch of a fully brick structure to ease your mind. With 3 spacious

    Laura Renaldo Look With Laura

    1427 W Superior St Unit 2F, Chicago, IL 60642
  • /38

    $1,299,000

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

    161 E Chicago Ave Unit 24-02, Chicago, IL 60611

    RARELY available two-story duplex in the iconic Olympia Centre, one of Chicago's most prestigious luxury residences. Soaring 25-foot floor-to-ceiling picture windows create a dramatic architectural statement while framing breathtaking panoramic views of Michigan Avenue, Lake Michigan, the historic Water Tower, and the John Hancock Center. Bathed in natural light, this extraordinary home offers an

    Ornit Mandell Ornit Mandell

    161 E Chicago Ave Unit 24-02, Chicago, IL 60611
  • /25

    $499,900

    Pending
    • 7 Beds
    • 3 Baths

    6520 S Ellis Ave, Chicago, IL 60637

    Why pay a full mortgage when tenants can cover it? Turnkey East Woodlawn 2-flat with massive income potential. Unit 1: 4BD/2BA duplex with 2 living areas, stainless steel appliances, and in-unit laundry/storage. King-sized beds fit easily, making it ideal for short-term rentals, house hacking, or related living. Unit 2: Bright 3BD/1BA with L-shaped kitchen, in-unit W/D, and a primary bedroom that

    Naja Morris @properties Christie's International Real Estate

    6520 S Ellis Ave, Chicago, IL 60637
  • /35

    $1,780,000

    • 9 Beds
    • 6 Baths

    1415 W Augusta Blvd, Chicago, IL 60642

    Location! location! Location! Large updated 3 unit building located in central noble square walking distance to wicker park and Ukrainian village with rare high ceilings in the 2 upper units and 3 single car separate covered garage spaces. Top floor penthouse unit features large 4 bedroom, 3 bath duplex with high ceilings. First floor unit also has high ceilings is 2 bed, 1 bath unit. Garden unit

    Kyle Olszewski Kale Realty

    1415 W Augusta Blvd, Chicago, IL 60642

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