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Duplexes for Sale in Chicago, IL

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  • /29

    $850,000

    • 3 Beds
    • 3 Baths

    859 W Wrightwood Ave Unit 1, Chicago, IL 60614

    Located in sought-after Lincoln Park on picturesque Wrightwood Avenue, this expansive duplex condo has everything you need: 3 bedrooms, 3 full bathrooms, multiple living spaces, private outdoor space, and assigned parking. As you enter, you'll immediately notice the thoughtful layout that makes this home feel both spacious and polished. Natural light pours into the living room, which is centered

    Susan Pelletier Compass

    859 W Wrightwood Ave Unit 1, Chicago, IL 60614
  • /24

    $1,185,000

    Pending
    • 3 Beds
    • 3 Baths

    1510 N Dearborn Pkwy Unit 102, Chicago, IL 60610

    Gold Coast Refinement. Set within an intimate 18-unit elevator building, this completely renovated home offers exceptional attention to detail, timeless elegance, and modern luxury throughout. This expansive 3 bedroom & 3 bathroom duplex-down layout offers wonderful separation of living and sleeping spaces. The thoughtfully designed interiors showcase high-end finishes, refined craftsmanship, and

    Melinda Lawrence @properties Christie's International Real Estate

    1510 N Dearborn Pkwy Unit 102, Chicago, IL 60610
  • /5

    $130,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 600 Sq Ft

    4534 S Honore St, Chicago, IL 60609

    Investor special in Back of the Yards! This property has been fully demoed and is ready for your vision, ideal for rehabbers, builders, or seasoned investors looking for their next project. The interior has been cleared down to the studs, offering a true blank slate to design and customize to your specifications. Major exterior improvements have already been completed, including a new roof (tear

    Daisy Esparza United Real Estate - Chicago

    4534 S Honore St, Chicago, IL 60609
  • /30

    $1,399,000

    • 7 Beds
    • 6 Baths

    1327 W Walton St, Chicago, IL 60642

    BEAUTIFUL WEST TOWN/NOBLE SQUARE NEIGHBORHOOD 2-UNIT WITH 7 BEDROOMS / 5.5 BATHROOMS AND ENDLESS OPPORTUNITIES. NESTLED ON A QUIET TREE LINED STREET - UNIT 1 IS A 3 BED/2 BATH FULLY UPDATED UNIT WITH IN-UNIT LAUNDRY AND A LARGE PRIVATE PATIO SPACE. UNIT 2 IS A MASSIVE DUPLEX-UP 4 BEDROOM/3.5 BATH UNIT WITH 3 ENSUITES - IMMENSE PRIMARY SUITE WITH ITS OWN PRIVATE BALCONY - ZONED HVAC - AMAZING

    Robert Fleckenstein First In Realty, Inc.

    1327 W Walton St, Chicago, IL 60642
  • /24

    $399,900

    • 12 Beds
    • 5 Baths

    8239 S Colfax Ave, Chicago, IL 60617

    Fantastic investment opportunity in the heart of South Chicago! This solid brick 4-unit building offers 12 total bedrooms and 5 bathrooms, providing excellent potential for strong rental income. Each spacious unit includes a stove and refrigerator, and all utilities are separately metered for gas and electric, offering added convenience for management. A full finished basement provides additional

    Jose Martinez RE/MAX Mi Casa

    8239 S Colfax Ave, Chicago, IL 60617
  • /11

    $849,000

    • 7 Beds
    • 6 Baths

    6627 S Maryland Ave, Chicago, IL 60637

    Legal 3 fla.Total gut Rehab to the studs with new constructions permits, all mechanicals are brand new. New water lines B Box and meters, windows, insulations, GE appliances, sump pump & ejector pump. Everything you see is NEW. 3300 sqft living space.LUXURY-DESIGNED LAYOUT WITH THREE MASTER SUITES ON THE 2ND FLOOR DUPLEXED TO THE MAIN LEVEL WITH COMPLETE OPEN CONCEPT FLOOR PLAN!!! GREAT FOR OWNER

    Katerina Pavlova Pavlova Properties

    6627 S Maryland Ave, Chicago, IL 60637
  • /40

    $674,000

    $1K PRICE DROP
    • 3 Beds
    • 3 Baths

    3033 N Racine Ave Unit 3, Chicago, IL 60657

    3 Bed / 3 Bath duplex-up condo for sale in south central Lakeview. Sunny, light filled top floor duplex up featuring hardwood floors throughout, open kitchen, gas fireplace, in-unit washer and dryer, central heat and air. Main floor has 2 BR, 2BA. Top floor has private suite including separate living space, bedroom, full bathroom and private outdoor deck with fantastic city views! 1 garage space

    Gene Hart 33 Realty

    3033 N Racine Ave Unit 3, Chicago, IL 60657
  • /34

    $799,000

    • 3 Beds
    • 3 Baths
    • 1,950 Sq Ft

    1938 N Francisco Ave Unit 1S, Chicago, IL 60647

    Space, separation and a rare townhome-style layout set this nearly 2,000-square-foot, 3-bedroom, 3-full-bath duplex apart. Two bedrooms and two full baths, including the primary suite, are conveniently located together on the main level, while the lower level offers an expansive second living space with a wet bar, third bedroom and third full bath. The main level features an open-concept living

    Mitch Masia Percent One, LLC

    1938 N Francisco Ave Unit 1S, Chicago, IL 60647
  • /9

    $264,999

    $31K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 640 Sq Ft

    2862 W 22nd Place, Chicago, IL 60623

    Great Opportunity to buy that starter single family home in Little Village. Possibilities are endless with this cottage home. Home does need work. Main floor has 2 bedrooms, office, kitchen, full-bath and living room. Basement in-law unit finished with full bath, kitchen and one bedroom. Lower unit rented $950, expires 7/31/2027. (non-conforming) Attic unfinished with ability to build up and

    Benjamin Sanford Durante & Rich Real Estate

    2862 W 22nd Place, Chicago, IL 60623
  • /31

    $405,000

    $10K PRICE DROP Pending
    • 5 Beds
    • 2 Baths

    5228 W Quincy St, Chicago, IL 60644

    Check out this well-maintained two-unit property in Chicago's Austin neighborhood! Each unit offers three bedrooms, one bathroom, hardwood floors throughout, and spacious living and dining rooms. Enjoy beautifully renovated, spa-inspired bathrooms and radiant heat-perfect for Chicago winters. The first floor also provides an excellent opportunity to duplex down and create additional living space.

    Amanda Stapleton Blue Door Dave Inc

    5228 W Quincy St, Chicago, IL 60644
  • /33

    $638,000

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

    2710 W Haddon Ave Unit 1, Chicago, IL 60622

    Stunningly renovated 4-bedroom/3 bath duplex-down in the heart of Humboldt Park! This thoughtfully designed home features a spacious split layout, two living areas, and beautiful hardwood floors. The chef's kitchen boasts a large custom island, quartz countertops, and GE Cafe appliances, opening to bright living and dining spaces with an updated fireplace and designer finishes. The expansive

    Ben Lalez Compass

    2710 W Haddon Ave Unit 1, Chicago, IL 60622
  • /28

    $1,050,000

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

    1938 N Sawyer Ave Unit 1, Chicago, IL 60647

    Like-new construction built just 2 years ago, this exceptional 4 bed/3.5 bath duplex-down lives like a true single-family home with a private front entrance, expansive outdoor spaces, and designer finishes throughout. Situated on an oversized, 177ft deep lot in the heart of Logan Square, this home offers the perfect blend of luxury, functionality, and indoor/outdoor living. The thoughtfully

    Kelsey Mayher Jameson Sotheby's Intl Realty

    1938 N Sawyer Ave Unit 1, Chicago, IL 60647
  • /22

    $799,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    1719 W George St Unit 55, Chicago, IL 60657

    Like-new, fully renovated duplex up in the coveted Columbia Place development. Located in the heart of West Lakeview and within the highly sought-after Burley School District, this turnkey residence offers over 2,300 square feet of beautifully renovated living space with two bedrooms, two and a half bathrooms, and the rare convenience of a private attached one-car garage with a dedicated mudroom

    Nancy Tassone Jameson Sotheby's Intl Realty

    1719 W George St Unit 55, Chicago, IL 60657
  • /19

    $3,500,000

    • 5 Beds
    • 8 Baths
    • 6,860 Sq Ft

    270 E Pearson St Unit 701-801, Chicago, IL 60611

    Introducing a truly one-of-a-kind duplex in one of the city's premiere boutique buildings with endless opportunities to create your dream home. Located across from Lakeshore Park and steps from the lakefront, this homes offers spectacular views of the city, park, lake, and Navy Pier. Enjoy over 6800 sq. ft. of expansive living and entertaining spaces along with 3 terraces, five en-suite bedrooms,

    Caroline Druker Baird & Warner

    270 E Pearson St Unit 701-801, Chicago, IL 60611
  • /2

    $1,475,000

    New Construction Pending
    • 4 Beds
    • 2.5 Baths

    2341 W Saint Paul Ave Unit 2East, Chicago, IL 60647

    Sold Before Print. New Construction, duplex up penthouse designed by Studio Group.

    Michael Yeagle @properties Christie's International Real Estate

    2341 W Saint Paul Ave Unit 2East, Chicago, IL 60647
  • /22

    $799,900

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

    853 N Wood St Unit 1, Chicago, IL 60622

    3 bedroom, 3 bath home that lives like a single-family residence. Duplex down in intimate building. Filled with natural light, this home features an open layout, excellent privacy, one garage parking space, and two private outdoor spaces plus a shared yard. 1 garage spot included, located in a small, low-maintenance, self-managed building with low assessments. The building was sealed in 2025.

    Nancy Leflar eXp Realty

    853 N Wood St Unit 1, Chicago, IL 60622
  • /11

    $161,500

    $9K PRICE DROP Pending
    • 6 Beds
    • 2 Baths

    8130 S Ada St, Chicago, IL 60620

    Exceptional value-add opportunity in the heart of Auburn Gresham! This solid all-brick two-flat is a rare find, offering incredible potential for investors and owner-occupants alike. Each spacious unit features a bright formal living room with an adjoining sunroom, a separate formal dining room, and three generously sized bedrooms, providing an ideal layout for comfortable living. Whether you're

    Ryan Smith Smith Partners & Associates

    8130 S Ada St, Chicago, IL 60620
  • /40

    $1,500,000

    New Construction
    • 4 Beds
    • 3.5 Baths

    3739 N Clifton Ave Unit 1, Chicago, IL 60613

    Brand-new luxury construction meets timeless design in this exceptional four-bedroom duplex-down, offering expansive living spaces, refined finishes, and a floor plan designed for the way you live today. The open-concept main level is flooded with natural light through dramatic floor-to-ceiling windows and anchored by a beautiful fireplace that creates a warm, inviting focal point. The chef's

    Carrie McCormick @properties Christie's International Real Estate

    3739 N Clifton Ave Unit 1, Chicago, IL 60613
  • /10

    $298,000

    Pending
    • 4 Beds
    • 2 Baths

    9710 S Genoa Ave, Chicago, IL 60643

    Investor special! Fully occupied 2-flat sits on a quiet, desirable block; start generating income from day one. The basement offers additional upside with duplex-down opportunity. Conveniently located near Beverly, shopping, and expressway.

    Marshon Sutton Coldwell Banker Realty

    9710 S Genoa Ave, Chicago, IL 60643
  • /12

    $1,450,000

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    1404 W George St Unit 1, Chicago, IL 60657

    NEW, UNDER-CONSTRUCTION 4 BEDROOM DUPLEX . Welcome to 1404 W. George St. ***DELIVERING FALL 2026*** Intimate all masonry new construction 2-unit building located in the heart of the Southport corridor. This wonderful 4 bed 3.1 bath home is built with luxury transitional finishes, a spacious open floor plan, and wonderful outdoor space including a large covered terrace off the family room, and

    Sam Jenkins Jameson Sotheby's Intl Realty

    1404 W George St Unit 1, Chicago, IL 60657
  • /48

    $575,000

    $114K PRICE DROP
    • 6 Beds
    • 5 Baths

    2407 S Albany Ave, Chicago, IL 60623

    NEW PRICE - $575,000! Seller offering up to $10,000 toward buyer's allowable closing costs and prepaid expenses with an acceptable offer. Rarely available side-by-side duplex in the heart of Little Village! This updated 2-flat offers two spacious bi-level units with a unique layout that's hard to find-an excellent opportunity for investors, multi-generational living, or an owner-occupant looking

    Roberto Hernandez Command Realty Group LLC

    2407 S Albany Ave, Chicago, IL 60623
  • /28

    $699,900

    Pending
    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2919 N Burling St Unit E, Chicago, IL 60657

    Perfectly positioned on one of Chicago's most coveted, picturesque tree-lined streets in the heart of Lincoln Park. This beautifully maintained 2 Bedroom 2 Bathroom Duplex-Up offers something increasingly hard to find-over 1,600 square feet of living space with a true sense of openness, privacy, and separation across two thoughtfully designed levels. The bright and inviting main floor features

    Zachary Koran Baird & Warner

    2919 N Burling St Unit E, Chicago, IL 60657
  • /12

    $3,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,725 Sq Ft

    1447 N Dearborn St Unit 1S, Chicago, IL 60610

    Eight new construction, exclusive, full-floor residences offer a refined lifestyle that blends eclectic interiors with unparalleled luxury and an estimated delivery date of December 2026. Discover an extraordinary opportunity to live boldly at 1447 N. Dearborn, an enduring Gold Coast icon. Nestled on a quiet street, these residences overlook treelined and courtyard views, offering a sense of

    Carrie McCormick @properties Christie's International Real Estate

    1447 N Dearborn St Unit 1S, Chicago, IL 60610
  • /16

    $649,900

    Pending
    • 6 Beds
    • 3 Baths

    1101 N Lawndale Ave, Chicago, IL 60651

    Welcome to 1101 N Lawndale, a newer construction two-flat built in late 2023 that gives you income and a place to live all in one. The first floor is a duplex down unit with 4 bedrooms and 2 bathrooms, currently rented at $3,000 a month, so you have a tenant helping cover your mortgage from day one. The second floor is a 2 bed, 1 bath simplex, ready for you to move right in and live above your

    James Shin @properties Christie's International Real Estate

    1101 N Lawndale Ave, Chicago, IL 60651
  • /24

    $875,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    877 N Hermitage Ave Unit 1, Chicago, IL 60622

    Enjoy the best of city living in this expansive 3-bedroom, 2.1-bathroom duplex down, ideally situated on a quiet, tree-lined street just steps from everything Wicker Park has to offer. With soaring ceilings, high-end finishes, abundant natural light, and a thoughtful layout that lives like a single-family home, this residence offers an exceptional blend of space, style, and location. Upon entry,

    Lindsey Dickinson Baird & Warner

    877 N Hermitage Ave Unit 1, Chicago, IL 60622
  • /54

    $1,050,000

    Pending
    • 7 Beds
    • 3 Baths

    2434 N Albany Ave, Chicago, IL 60647

    Beautifully renovated 2-flat with additional non-conforming garden unit on a tree-lined street just steps from Logan Square's thriving Milwaukee Avenue corridor. Meticulously maintained and thoughtfully updated with over $40,000 in recent capital improvements, this classic all-brick building blends timeless Chicago character with modern functionality, smart-home features, and strong rental

    Christine Sullivan Baird & Warner

    2434 N Albany Ave, Chicago, IL 60647
  • /25

    $339,000

    • 3 Beds
    • 2 Baths

    3105 W Argyle St Unit 1, Chicago, IL 60625

    Bright and spacious 3-bedroom, 2-bathroom duplex-down condo directly across from River Park! Sun-filled main level features hardwood floors, granite countertops, stainless steel appliances, and an inviting layout. Spacious lower level offers a full bath and side-by-side washer/dryer. Great location just steps from the dog park and a short walk to the Brown Line. Building completely rehabbed in

    Kip Thang Real 1 Realty

    3105 W Argyle St Unit 1, Chicago, IL 60625
  • /2

    $599,000

    • 6 Beds
    • 5 Baths

    440 N Hamlin Ave, Chicago, IL 60624

    Exceptional opportunity to own this beautifully renovated 2-story brick multi-unit building featuring a spacious duplex-down first unit and a newly constructed 2-story rear wood porch. Unit 1 offers a duplex layout with 3 bedrooms and 2.5 bathrooms, an open-concept living room with a fireplace, a modern kitchen equipped with stainless steel appliances, a large center island, and an in-unit washer

    Stephanie Sotelo @properties Christie's International Real Estate

    440 N Hamlin Ave, Chicago, IL 60624
  • /19

    $289,000

    Pending
    • 5 Beds
    • 2 Baths

    Unlisted Address

    Gorgeous 5 BR 2-Flat home nestled on a Roseland cul-de-sac street, each unit with SS kitchen appliances, hardwood floors, updated bathrooms, fantastic light fixtures, recessed lights, chandeliers and ceiling fans, and bright two-tone paint throughout w/chair rail. The full basement has a W/D and is awaiting your storage, duplex down or ADU vision and creativity. Enclosed back porch leads to the

    Chris Davis ARD Real Estate PLLC

    Unlisted Address
  • /39

    $1,250,000

    Pending
    • 7 Beds
    • 5 Baths

    1507 W Hollywood Ave, Chicago, IL 60660

    Beautifully updated two-flat in the heart of Andersonville! The vacant first-floor duplex-down offers 4 bedrooms, 3 baths, a spacious open layout, enclosed sunroom, finished lower level with a wet bar, and abundant storage. The second-floor 3-bedroom, 2-bath unit is leased through next year, providing immediate rental income. Both units feature separate utilities, central heat and air, in-unit

    Diane Zavala Keller Williams ONEChicago

    1507 W Hollywood Ave, Chicago, IL 60660
  • /18

    $925,000

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    841 W Buckingham Place Unit 1, Chicago, IL 60657

    Rarely available! Very spacious duplex down on beautiful treelined street in prime east Lakeview location! Main floor has a living room with fireplace, dining room, kitchen open to large family room with fireplace, and a 1/2 bath. Lower level has 3 bedrooms and 2 full baths. The primary bedroom is very large and has direct access to a patio area. There is a deck off the main floor family room and

    Nick Powers Baird & Warner

    841 W Buckingham Place Unit 1, Chicago, IL 60657
  • /7

    $819,900

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

    4317 N Paulina St Unit 101, 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 101, Chicago, IL 60613
  • /31

    $1,295,000

    • 3 Beds
    • 3.5 Baths
    • 2,706 Sq Ft

    310 S Michigan Ave Unit 1705, Chicago, IL 60604

    Welcome to the Historic Metropolitan Tower on Michigan Ave. Stunning SE corner inventory at 310 S Michigan just steps away from The Art Institute and the CSO! Ideal combination unit with SE corner views from 17th floor, over 2700 square feet with 3 bed/3.5 bath. Flooded with natural light, this home's 10 windows and Juliet balcony overlook Grant Park, Lake Michigan, and Museum Campus! Extremely

    Michael Gentile @properties Christie's International Real Estate

    310 S Michigan Ave Unit 1705, Chicago, IL 60604
  • /26

    $499,900

    New Construction
    • 3 Beds
    • 2.5 Baths

    6414 N Francisco Ave Unit 102, Chicago, IL 60645

    This stunning duplex residence is a brand-new 3-bedroom, 2.5-bathroom home thoughtfully designed for modern living and comfortable entertaining. The main level features an open, inviting layout ideal for hosting, while the lower level offers a quiet, private retreat with well-appointed bedrooms. Flooded with natural light, the home showcases luxury modern finishes throughout, including engineered

    Joel Halperin Compass

    6414 N Francisco Ave Unit 102, Chicago, IL 60645
  • /26

    $260,000

    Pending
    • 6 Beds
    • 3 Baths

    6020 S Vernon Ave, Chicago, IL 60637

    Located in the highly desirable Woodlawn neighborhood, just steps from Washington Park, this classic all-brick two-flat offers exceptional value, flexibility, and investment potential. The first and second-floor units feature nearly identical layouts, each with a spacious living room, two bedrooms, and a galley-style kitchen. The second-floor unit is move-in ready, showcasing newer flooring, an

    Ryan Smith Smith Partners & Associates

    6020 S Vernon Ave, Chicago, IL 60637
  • /34

    $1,247,500

    • 7 Beds
    • 4 Baths

    4937 N Bell Ave, Chicago, IL 60625

    SECOND CHANCE AT AN EXCEPTIONAL LINCOLN SQUARE PROPERTY! Back on the market after the previous buyers were unable to move forward. This beautifully maintained 2-unit property features a rare DUPLEX-UP + DUPLEX-DOWN configuration with 7 BEDROOMS, 4 FULL BATHS AND A 2-CAR GARAGE. The 4-bedroom duplex-up is NOW VACANT AND EASY TO SHOW, offering excellent upside potential for an owner-occupant or

    Michelle Quan Coldwell Banker Realty

    4937 N Bell Ave, Chicago, IL 60625
  • /29

    $675,000

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

    6816 N Lakewood Ave Unit 2, Chicago, IL 60626

    Rarely available top-floor 2nd & 3rd floor duplex-up offering over 3,000 square feet of beautifully restored vintage elegance in the heart of Rogers Park. This sun-filled 4-bedroom, 2-bath residence seamlessly blends timeless architectural character with thoughtfully curated modern updates, creating a home that is both sophisticated and move-in ready. Recent improvements include beautifully

    Joseph Perez Landstar Realty Group, Inc.

    6816 N Lakewood Ave Unit 2, Chicago, IL 60626
  • /36

    $599,000

    • 5 Beds
    • 3 Baths

    4542 N Long Ave, Chicago, IL 60630

    Rare opportunity to own a well-maintained brick two-flat in the highly desirable Jefferson Park neighborhood, offering flexibility for owner-occupants, house hackers, and investors alike. Situated on a quiet residential block, this property combines spacious living, quality updates, and exceptional access to transportation, shopping, and neighborhood amenities. The first-floor unit is a spacious

    Michael McCoy @properties Christie's International Real Estate

    4542 N Long Ave, Chicago, IL 60630
  • /20

    $299,900

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

    4731 S Ingleside Ave Unit D1, Chicago, IL 60615

    Welcome to this beautifully appointed 2-bedroom, 2.5-bath duplex that lives like a townhome, offering an exceptional combination of space, comfort, and modern convenience. Designed with both comfort and functionality in mind, this expansive home features hardwood flooring throughout the upper level, abundant natural light, and an open, inviting floor plan. The contemporary kitchen is appointed

    Paulette Hollingsworth Baird & Warner

    4731 S Ingleside Ave Unit D1, Chicago, IL 60615
  • /16

    $650,000

    $50K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths

    946 W Sheridan Rd Unit 2, Chicago, IL 60613

    Lakeview's best vintage DUPLEX-UP with 3bd 2 1/2 baths that's flooded with light and close to Lake Michigan, parks, shopping, dining, and transportation. HWD floors and 10ft ceilings will impress along with a professional kitchen, white shaker cabinets, quartz counters, and SS appliances. The first level features a spacious dining, kitchen, family and living rooms, 1/2 bath, and laundry. The top

    Greg Alvarado @properties Christie's International Real Estate

    946 W Sheridan Rd Unit 2, Chicago, IL 60613

Showing Results 401 - 440, Page 11 of 13

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