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Duplexes for Sale in Chicago, IL

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  • /38

    $150,000

    • 4 Beds
    • 3 Baths

    9905 S Yale Ave, Chicago, IL 60628

    Calling all savvy owner-occupants and investors! This spacious 1.5-story duplex offers incredible potential to renovate and occupy, fix & flip, or hold as an income-producing rental. Previously used by the owner as a single-family residence, the property features newer roof, 4 bedrooms, 3 bathrooms, a full finished basement with 2 additional family rooms, and a stylish interior staircase

    Tyrone Cotton T Cotton & Associates Realty, LLC

    9905 S Yale Ave, Chicago, IL 60628
  • /22

    $890,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,450 Sq Ft

    3713 N Ashland Ave Unit 1N, Chicago, IL 60613

    OVERSIZED 3 bedrooms, 3 baths duplex down with two large private outdoor spaces (over 500 sq ft deck and balcony) in the Southport corridor. Recently renovated, spacious open floor plan. The kitchen boasts granite countertops and backsplash, 42'' tall cabinets, stainless steel appliances and a long breakfast bay. Western exposure allows for enviable natural light in both the dining and living

    Sari Levy Lucid Realty, Inc.

    3713 N Ashland Ave Unit 1N, Chicago, IL 60613
  • /26

    $895,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,770 Sq Ft

    505 N Mcclurg Ct Unit 204, Chicago, IL 60611

    This is the one you have been waiting for! the perfect duplex (one of only 6 townhomes) at Parkview. Truly one of a kind. Two very large terraces...one off of the livingroom facing East overlooking beautiful Bennett Park and the other off of the 2nd level...facing West overlooking the pool. Outdoor living at its best. Beautifully updated kitchen. Livingroom, kitchen and powder room on the main

    Lisa McGuirt Baird & Warner

    505 N Mcclurg Ct Unit 204, Chicago, IL 60611
  • /25

    $1,499,000

    • 6 Beds
    • 4 Baths

    3405 N Seminary Ave, Chicago, IL 60657

    Prime Wrigleyville/East Lakeview Investment Opportunity! This meticulously maintained and updated 3-unit building offers an exceptional opportunity for investors or owner-occupants looking to capitalize on strong rental demand in one of Chicago's most desirable neighborhoods. Situated on an oversized 35' x 125' lot and zoned RM-5, the property offers excellent current income with additional

    Laura Ziccardi Realty One Group Excel

    3405 N Seminary Ave, Chicago, IL 60657
  • /20

    $219,900

    $10K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,241 Sq Ft

    6651 S Maryland Ave Unit 1E, Chicago, IL 60637

    Welcome home to this awesome 2-bedroom, 2-bath duplex-up condo in the heart of Woodlawn. This home features hardwood floors throughout the main level, an open layout, and exposed brick that adds character and warmth. The primary suite includes an ensuite bathroom, offering comfort and privacy. Kitchen features stainless steel refrigerator and other appliances will be upgraded to stainless steel

    Sheree Bradley Kale Realty

    6651 S Maryland Ave Unit 1E, Chicago, IL 60637
  • /57

    $1,495,000

    • 5 Beds
    • 5 Baths
    • 3,400 Sq Ft

    310 S Michigan Ave Unit 1500, Chicago, IL 60604

    Owner Financing Available | Flexible 3BR/3BA + 2BR/2BA Configuration Available furnished and the owner is open to dividing the residence into two separate units: a 3-bedroom, 3-bathroom residence and a 2-bedroom, 2-bathroom residence. Combined as they are now, they offer a single-family home on one level with breathtaking views of Lake Michigan, Grant Park, and Chicago's iconic skyline. Sprawling

    Bryan Eugenio @properties Christie's International Real Estate

    310 S Michigan Ave Unit 1500, Chicago, IL 60604
  • /10

    $220,000

    $30K PRICE DROP
    • 6 Beds
    • 2 Baths

    3109 W Lexington St, Chicago, IL 60612

    ATTENTION ALL INVESTORS OR REHABBERS! This is your chance to finish off your way and make a big profit. Whole building has been gutted to the studs and cleaned up, basement has been dug out but no floor has been pored yet. New roof was put on in 2020, all new windows in 2019, whole building was tuck pointed, and all the stone has been freshly capped in 2023. Solid building to turn this into a 3

    Martyna Tos Northwest Real Estate Group

    3109 W Lexington St, Chicago, IL 60612
  • /15

    $1,525,000

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    1443 W Roscoe St Unit 1, Chicago, IL 60657

    Welcome to 1443 W. Roscoe! ****UNDER CONSTRUCTION -DELIVERY LATE 2026***Model units next door. This spacious 4 bed 3.1 bath duplex is set in an intimate all masonry new construction 2 unit building on a beautiful, quiet tree lined street in prime Southport Corridor. The main level encompases open concept living spaces and 9'+ ceiling height. The front of the home features the living room and

    Sam Jenkins Jameson Sotheby's Intl Realty

    1443 W Roscoe St Unit 1, Chicago, IL 60657
  • /38

    $995,000

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

    33 W Ontario St Unit 14B, Chicago, IL 60654

    Luxury Duplex Living in the Heart of River North | Expansive Terrace + Private Hot Tub. Discover the pinnacle of urban sophistication in this exceptional 2-level duplex residence, ideally located in Chicago's coveted River North neighborhood. Spanning approximately 2,600 square feet, this meticulously designed home offers 3 bedrooms and 3 bathrooms, blending refined elegance with contemporary

    Amir Fouad @properties Christie's International Real Estate

    33 W Ontario St Unit 14B, Chicago, IL 60654
  • /5

    $2,000,000

    New Construction
    • 3 Beds
    • 2.5 Baths

    1839 N Dayton St Unit 101, 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 101, Chicago, IL 60614
  • /20

    $460,000

    • 10 Beds
    • 3 Baths

    3056 E 87th St, Chicago, IL 60617

    Don't miss this exceptional income-producing property featuring two apartments plus a coach house offering multiple streams of rental income. First floor offers 3 bedrooms and one bathroom. Second unit is a duplex and offers five bedrooms and one bathroom. The coach house has 2 bedrooms and one bathroom. The unfinished basement offers additional potential living space. Whether you are first time

    Lorena Ramirez-Carrillo YUB Realty Inc

    3056 E 87th St, Chicago, IL 60617
  • /48

    $364,999

    Pending
    • 8 Beds
    • 2 Baths

    1418 S Saint Louis Ave, Chicago, IL 60623

    Step into 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-Inside, both units offer a layout with formal living room and dining room, hardwood floors. The first-floor unit features 4 Bedrooms and is currently rented month to month. Upstairs, the

    Phillip Younan Fulton Grace Realty

    1418 S Saint Louis Ave, Chicago, IL 60623
  • /73

    $799,000

    • 6 Beds
    • 4 Baths

    2839 W Monroe St, Chicago, IL 60612

    Welcome to this absolutely stunning & unique 2-unit home nestled on a quiet tree-lined street in prime East Garfield Park, less than a block from the $42M newly announced Madison Street Athletic & Cultural Complex. Must see to really appreciate this a fully reimagined frame/brick home showcasing meticulous craftsmanship and high-end designer finishes throughout. Unlike in most multi-unit

    Ben Staker Certified Realty Group LLC

    2839 W Monroe St, Chicago, IL 60612
  • /43

    $799,000

    $31K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,904 Sq Ft

    310 S Michigan Ave Unit 1700, Chicago, IL 60604

    Forever views from this 3bed/3bath NE corner home! 1900+ square feet with protected city, lake and park views. great natural light and windows in all rooms. Home is approximately 1900 SF with 8 windows along the north and east sides of this home. Home sits on the 17th floor of 20 in this tier and perched above Michigan avenue over-looking Grant park and north-east corner of Millenium park.

    Michael Gentile @properties Christie's International Real Estate

    310 S Michigan Ave Unit 1700, Chicago, IL 60604
  • /31

    $799,000

    $30K PRICE DROP
    • 4 Beds
    • 3 Baths

    1017 W Dakin St Unit 1, Chicago, IL 60613

    This expansive duplex down offers a well-designed floor plan featuring 10-foot ceilings, Hunter Douglas blinds, and hardwood floors throughout the main level. The bright living room centers around a fireplace and flows into a kitchen equipped with stainless steel appliances, granite countertops, maple cabinetry, and an island with dining space. The main level also houses a dedicated laundry room

    Daniel Cruz Westward360 RM

    1017 W Dakin St Unit 1, Chicago, IL 60613
  • /25

    $549,999

    New Construction
    • 5 Beds
    • 5 Baths

    1433 S Trumbull Ave, Chicago, IL 60623

    Thoughtfully composed for modern ownership, 1433 S. Trumbull introduces a new-construction two-flat where refined design and income-producing flexibility share one cohesive address. Anticipated for October 2026 delivery, the property pairs a contemporary brick-and-Hardie exterior with two independently functional residences, a two-car garage, rear deck, fenced backyard, and approximately 2,900

    Danielle Dowell Berkshire Hathaway HomeServices Chicago

    1433 S Trumbull Ave, Chicago, IL 60623
  • /7

    $819,900

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 1,775 Sq Ft

    4317 N Paulina St Unit 102, Chicago, IL 60613

    ONLY 3 LEFT!! Titan Development presents extra wide, new construction homes! This spacious duplex down features 3 bedrooms / 2.1 bathrooms, a stunning kitchen with an enormous island, separate dining area, a large front deck finished in porcelain tile decking & rear garage roof deck and garage parking. Professionally designed finishes include White Oak cabinetry, Bosch Professional appliances,

    Tim Sheahan Compass

    4317 N Paulina St Unit 102, Chicago, IL 60613
  • /36

    $800,000

    $25K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,223 Sq Ft

    1500 W Monroe St Unit 727, Chicago, IL 60607

    Welcome to a true statement piece in the heart of the West Loop-a rare, updated duplex penthouse that delivers the space of a single-family home with the energy of one of Chicago's most sought-after neighborhoods. This 3-bedroom, 2.1-bath, 2,200+ sq ft residence is the largest unit in the building, flooded with natural southern light and designed for both elevated everyday living and

    Jack Michalkiewicz Coldwell Banker Realty

    1500 W Monroe St Unit 727, Chicago, IL 60607
  • /36

    $1,300,000

    • 10,118 Sq Ft

    724 E 50th Place, Chicago, IL 60615

    Presenting 724 East 50th Place, a six-unit multifamily asset in Bronzeville priced at $$216,667/unit which is below active comps and in line with recent trades. The building is comprised of two 4BD/3BA duplex units and four 3BD/2BA units, plus 5 exterior parking spaces, and received a comprehensive 2005 renovation covering the roof, masonry, windows, plumbing, electrical, and HVAC. Year 1 NOI is

    Kevin Rocio @properties Commercial

    724 E 50th Place, Chicago, IL 60615
  • /48

    $1,499,900

    • 3 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    2640 N Bosworth Ave Unit PHS, Chicago, IL 60614

    Welcome to this exceptional Lincoln Park penthouse duplex-up, combining stylish interiors, incredible private outdoor space, and a prime location. Only three years old and meticulously maintained, this designer-finished home shows like new. The bright and open main level features oversized windows, a spacious family room & dining area with fireplace, & a beautiful chef's kitchen with Wolf and

    Yongjing Murphy HomeSmart Connect LLC

    2640 N Bosworth Ave Unit PHS, Chicago, IL 60614
  • /22

    $750,000

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

    5830 N Lincoln Ave Unit 1E, Chicago, IL 60659

    Experience refined city living in this stunning new construction duplex-down condominium, ideally located just west of Lincoln Square in the highly desirable Peterson Park neighborhood. This expansive approximately 3600-square-foot residence offers luxurious finishes throughout, including beautiful hardwood flooring and soaring ceilings complemented by dramatic floor-to-ceiling windows that fill

    Matt Laricy Americorp, Ltd

    5830 N Lincoln Ave Unit 1E, Chicago, IL 60659
  • /55

    $925,000

    $11K PRICE DROP
    • 6 Beds
    • 4 Baths

    948 N California Ave, Chicago, IL 60622

    Great investment opportunity a true legal fully leased 3 story apartment building rents below market. Great for rental income or live in owner by booming West Town area on 'California Corridor' features 3 impressive units for a total of 6 bedrooms & 4 bathrooms with a first floor duplex down & 3 remote controlls for the gated parking with 3 spots. unit features include hardwood floors, in unit

    Kelly Wong Coldwell Banker Realty

    948 N California Ave, Chicago, IL 60622
  • /34

    $859,999

    • 6 Beds
    • 4 Baths

    1019 W 18th St, Chicago, IL 60608

    East Pilsen four-unit building with unfinished full basement currently collecting $76,800/year in rental income. Basement under back half currently used for common storage and laundry, with the basement under the front half ready to be duplexed. Brand new wooden deck and staircase between the units, new front gate and doors in front of property. Rear units 1R and 2R were both upgraded with new

    Eric Sporinsky Realty of America, LLC

    1019 W 18th St, Chicago, IL 60608
  • /26

    $489,900

    • 9 Beds
    • 3 Baths

    6433 S Sangamon St, Chicago, IL 60621

    Fully rehabbed 2-unit building coming soon at 6433 S Sangamon Street in Chicago. The current owner is actively completing the renovation and the property will be delivered fully rehabbed upon completion. Permits have been issued and inspections have already passed as construction continues. The first-floor unit will be a duplex-down featuring 5 bedrooms, 2 full bathrooms, an in-unit laundry

    Doris E Rivera Coldwell Banker Realty

    6433 S Sangamon St, Chicago, IL 60621
  • /18

    $2,100,000

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    2679 N Orchard St Unit 1S, Chicago, IL 60614

    We are pleased to introduce 2679 N Orchard, East Lincoln Park's newest boutique luxury development. Ideally situated on an oversized lot within the highly sought-after Alcott Elementary and Lincoln Park School Districts these oversized duplex homes are a must see. This exclusive offering features expansive duplex residences, each thoughtfully designed with four bedrooms and three-and-a-half

    Andrew Thurston Meridian Real Estate Chicago LLC

    2679 N Orchard St Unit 1S, Chicago, IL 60614
  • /22

    $310,000

    Pending
    • 2 Beds
    • 1 Bath

    6232 W Byron St, Chicago, IL 60634

    AFFORDABLE HOME ALERT! Welcome to 6232 W Byron! This beautiful brick 2 story duplex boasts a sun drenched living room, separate dining room, eat in kitchen, two large bedrooms, full size washer and dryer, gleaming hardwood floors throughout, and the only duplex home in the neighborhood with a 2.5 car garage. There is also room to grow here with a full unfinished basement. Smyser school district,

    Melanie Giglio-Vakos Compass

    6232 W Byron St, Chicago, IL 60634
  • /49

    $273,000

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft

    313 E 60th St Unit 1, Chicago, IL 60637

    Motivated Seller !! A great opportunity to own a spacious and beautifully updated duplex down, offering 3 bedrooms, 2 bathrooms, a dedicated office, and parking. This unique residence features nearly 2,000 square feet of living space across two levels, thoughtfully updated with modern, neutral finishes. Expansive rooms with rich hardwood flooring create a warm and inviting atmosphere throughout.

    Rosa Sanchez-Fryer @properties Christie's International Real Estate

    313 E 60th St Unit 1, Chicago, IL 60637
  • /38

    $449,000

    Pending
    • 8 Beds
    • 3 Baths

    7049 S Vernon Ave, Chicago, IL 60637

    Discover a distinctive renovated multi-family residence offering two generously scaled units refined with contemporary updates and elevated finishes. Ideal for buyers seeking space, flexibility, and sophisticated design in a multi-unit setting. The First floor home features five bedrooms, two baths, set up with 2 bedrooms on first floor and 3 bedrooms downstair and the duplex layout extending

    Rudy Gandy Premier Agent Network Illinois LLC

    7049 S Vernon Ave, Chicago, IL 60637
  • /7

    $674,900

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,375 Sq Ft

    4317 N Paulina St Unit 103, Chicago, IL 60613

    ONLY 3 LEFT! Titan Development presents extra wide, new construction homes! This spacious duplex down features 2 bedrooms / 2.1 bathrooms, a stunning kitchen with an enormous peninsula breakfast bar, separate dining area, an attached garage roof deck finished in porcelain tile decking and garage parking. Professionally designed finishes include White Oak cabinetry, Bosch Professional appliances,

    Tim Sheahan Compass

    4317 N Paulina St Unit 103, Chicago, IL 60613
  • /14

    $624,999

    • 2 Beds
    • 2 Baths

    1760 W Wrightwood Ave Unit 305, Chicago, IL 60614

    SELLER OFFERING INTEREST RATE BUYDOWN - Ask for Details! Extremely large and cool top floor light-filled 18 foot ceiling penthouse loft Duplex-up in Lincoln Park. 1,625 square feet on two levels. This 2 bedroom 2 bath loft has great natural light. Is totally updated. New Anderson Sliding doors on main floor automatic roll down blinds. Has in unit W/D. New Trex deck. Pergola. Gated parking

    Jeff Beck @properties Christie's International Real Estate

    1760 W Wrightwood Ave Unit 305, Chicago, IL 60614
  • /34

    $1,175,000

    • 7 Beds
    • 5 Baths

    2115 W Wellington Ave, Chicago, IL 60618

    Great investment opportunity in Roscoe Village on an oversized lot! All units updated with newer kitchens and baths, central A/C and washer/dryer in unit. Tenants pay their own electric and gas. All units currently leased, but easy opportunity to become an owner occupant. Second floor front unit is a spacious duplex up that makes a wonderful owner's unit. Total current annual rent income of

    Barbara Allen Metru Real Estate LLC

    2115 W Wellington Ave, Chicago, IL 60618
  • /18

    $1,525,000

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    1502 W School St Unit 1, Chicago, IL 60657

    New Construction, duplex down designed by Studio Group, delivering winter 2026. Offering 4 bedrooms, 3.5 bathrooms, two incredible private outdoor spaces at a premiere Southport Corridor location, this one of kind home blends bold design, elite craftsmanship at an unbeatable location. The main floor is anchored by a showpiece kitchen with Wolf and Sub-Zero appliances, bespoke Amish cabinetry, a

    Michael Yeagle @properties Christie's International Real Estate

    1502 W School St Unit 1, Chicago, IL 60657
  • /45

    $899,000

    New Construction Pending
    • 4 Beds
    • 3 Baths
    • 3,944 Sq Ft

    4353 N Richmond St Unit 1N, Chicago, IL 60618

    Located in Irving Park, this expansive 4-bedroom, 3.5-bath duplex with over 3,800 sq ft offers the space and comfort of a single-family home. Featuring 10.5-ft ceilings, 8-ft solid core doors, and hardwood floors throughout. Walk into the large open concept living and dining room complemented by a large west-facing balcony. The chef's kitchen boasts custom cabinetry, quartz countertops, a vented

    Hadley Rue Baird & Warner

    4353 N Richmond St Unit 1N, Chicago, IL 60618
  • /28

    $350,000

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

    614 S Loomis St Unit 1, Chicago, IL 60607

    Set within a beautiful building on a tree-lined Tri-Taylor block, close to shopping, dining, the medical district, and the Blue Line. A rare, oversized 5-bedroom, 2-bathroom duplex-down offering significant space and rental upside, projected at $3,300/month market rent. Recent updates include fresh paint, a brand-new central air conditioning system (completed May 2026), all-new light fixtures,

    Kevin Little @properties Christie's International Real Estate

    614 S Loomis St Unit 1, Chicago, IL 60607
  • /4

    $1,650,000

    New Construction
    • 4 Beds
    • 3.5 Baths

    914 W Fletcher St Unit PH, Chicago, IL 60657

    A beautifully executed brand-new construction 4 bedroom duplex-up residence, this home delivers a refined blend of design, scale, and everyday livability in the heart of Lakeview. From the moment you enter, the attention to detail is unmistakable. The main level is flooded with natural light and anchored by white oak hardwood floors, soaring 10' ceilings, and 8-inch doors, all enhanced by

    Hayley Westhoff Compass

    914 W Fletcher St Unit PH, Chicago, IL 60657
  • /25

    $534,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 3 Baths
    • 2,200 Sq Ft

    2645 W Haddon Ave Unit 1, Chicago, IL 60622

    Spacious 2,200 sq. ft. duplex-down offering the space of a single-family home with the convenience of condo living! This freshly painted, beautifully designed 3-bedroom, 3-bath residence features two levels of thoughtfully designed living space, perfect for entertaining and everyday comfort. The main level showcases rich maple hardwood floors with elegant cherry inlays, a gas fireplace, and an

    Arden Fowler CHICAGO HANDSHAKE LLC

    2645 W Haddon Ave Unit 1, Chicago, IL 60622
  • /22

    $575,000

    $75K PRICE DROP
    • 7 Beds
    • 2 Baths

    4339 S Indiana Ave, Chicago, IL 60653

    Welcome to a spacious vintage home with all the amenities of luxurious city living. Located In up and coming historic Bronzeville, just south of downtown, this gem boasts two generous units with high ceilings and spacious living and dining areas. This exceptional property blends classic Chicago character with all the modern comforts of a home. Whether you seek a strong investment opportunity or a

    Henry Torn ListWithFreedom.com

    4339 S Indiana Ave, Chicago, IL 60653
  • /36

    $450,000

    Pending
    • 5 Beds
    • 3 Baths

    3014 W Walnut St, Chicago, IL 60612

    Fantastic investment opportunity in fast-appreciating East Garfield Park! This charming and beautifully updated two-unit building offers high-end finishes, modern updates, and an ideal layout for an owner-occupant or investor. The first-floor duplex-down features 3 bedrooms and 2 baths, while the second-floor simplex offers 2 bedrooms and 1 bath. Both units showcase hardwood floors throughout,

    Scott Newman Keller Williams ONEChicago

    3014 W Walnut St, Chicago, IL 60612
  • /29

    $515,000

    Pending
    • 6 Beds
    • 5 Baths

    4419 W Gladys Ave, Chicago, IL 60624

    Stunning fully renovated brick 2-flat featuring a 3 bed/2 bath second-floor unit and an expansive 3 bed/3 bath duplex-down owner's unit, BOTH with Master Suites. Thoughtfully redesigned with luxury finishes throughout, including hardwood floors, quartz countertops, custom cabinetry, stainless steel appliances, recessed lighting, and beautifully updated bathrooms. Major improvements include

    Hakeem Sisney MNK Realty Professionals LLC

    4419 W Gladys Ave, Chicago, IL 60624
  • /41

    $1,400,000

    Pending
    • 6 Beds
    • 3 Baths

    3719 N Janssen Ave, Chicago, IL 60613

    Stunning and well-maintained two-flat in the heart of the Southport Corridor/ Blaine School. The owner's duplex-up spans the second and third floors with four bedrooms, two updated baths, and two bedrooms on each level. The bright main floor features a generous living room with high ceilings and a sunny kitchen with an island, gas cooking, and newer appliances. Two private decks and exclusive use

    Jim Buczynski Compass

    3719 N Janssen Ave, Chicago, IL 60613

Showing Results 161 - 200, Page 5 of 13

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