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Duplexes for Sale in Chicago, IL

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  • /33

    $350,000

    Pending
    • 1 Bed
    • 1 Bath
    • 900 Sq Ft

    2343 N Greenview Ave Unit 211, Chicago, IL 60614

    Rarely available, spacious duplex loft in the heart of Lincoln Park! Soaring 10-foot ceilings, dramatic oversized windows, rich hardwood floors, and a cozy fireplace create an inviting and light-filled living space that feels both expansive and warm. The open concept layout is ideal for everyday living and entertaining, while the private deck provides the perfect spot to enjoy your morning coffee

    Ashley Cox Compass

    2343 N Greenview Ave Unit 211, Chicago, IL 60614
  • /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
  • /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
  • /13

    $264,500

    • 1 Bed
    • 1.5 Baths
    • 1,073 Sq Ft

    1727 S Indiana Ave Unit 110, Chicago, IL 60616

    Rare duplex loft in the iconic Prairie District Lofts - the former Kodak Building. This 1-bedroom, 1 1/2 bathroom, two-story home delivers 1,073 sq ft of dramatic living space with 14' ceilings, 9' windows, exposed brick, timber beams, hardwood floors, and a gas fireplace. The open kitchen features a granite island, custom cabinetry, and stainless steel appliances. Two walk-in closets and in-unit

    Rachel Montel EXIT Strategy Realty

    1727 S Indiana Ave Unit 110, Chicago, IL 60616
  • /27

    $1,875,000

    New Construction Pending
    • 5 Beds
    • 4 Baths

    3923 N Janssen Ave Unit 1E, Chicago, IL 60613

    New construction 5BR / 4BA duplex-down in a great part of Lakeview, offering single-family-style living with high-end finishes throughout. The main level features an open-concept living and dining space and a chef's kitchen with custom cabinetry, walk-in pantry, Sub-Zero & Wolf appliances, and oversized island. Enjoy a separate wet bar area with beverage center outdoor living with a massive

    William Goldberg Fulton Grace Realty

    3923 N Janssen Ave Unit 1E, Chicago, IL 60613
  • /7

    $674,900

    New Construction Open Sun 12PM - 2PM
    • 2 Beds
    • 2.5 Baths
    • 1,375 Sq Ft

    4317 N Paulina St Unit 103, Chicago, IL 60613

    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, light oak

    Tim Sheahan Compass

    4317 N Paulina St Unit 103, Chicago, IL 60613
  • /21

    $1,250,000

    • 7 Beds
    • 4 Baths

    1446 W Catalpa Ave, Chicago, IL 60640

    Classic Chicago two-flat in the heart of Andersonville, thoughtfully updated in 2025 to blend modern amenities with timeless vintage charm. An exceptional investment opportunity, this property is ideal as a live-in, owner-occupied home with rental income or as a fully leased, income-producing asset. The second-floor two-bedroom apartment features central A/C, in-unit laundry, and a beautifully

    Philip Skowron Compass

    1446 W Catalpa Ave, Chicago, IL 60640
  • /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
  • /29

    $1,549,000

    • 7 Beds
    • 7 Baths

    Unlisted Address

    Newer Construction Passive Home 3 Unit building right on Harrison Park- Full Masonry Perfect Wall, All Electric energy-efficient and intelligently engineered for optimal living conditions. Three Bedroom/2.1 Bath Duplex, 2nd floor 2 bed/2 bath & Penthouse 2 bed/2 bath with interior stair to penthouse room and full finished rooftop deck. Excellent views of Harrison Park, the City and abundant

    Karen Biazar North Clybourn Group, Inc.

    Unlisted Address
  • /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
  • /30

    $260,000

    Pending
    • 3 Beds
    • 3 Baths

    3657 W Ohio St, Chicago, IL 60624

    Discover the potential in this solid all-brick 2-flat located in the up-and-coming West Humboldt Park neighborhood! This fully vacant property offers a rare opportunity for investors or owner-occupants to bring their vision to life and select their own tenants from day one. The first unit features 1 bedroom, with the first-floor unit offering a finished bathroom and direct access to the

    Cherilyn Williams eXp Realty

    3657 W Ohio St, Chicago, IL 60624
  • /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
  • /13

    $545,000

    $5K PRICE DROP
    • 7 Beds
    • 3 Baths

    651 N Long Ave, Chicago, IL 60644

    Beautifully updated two-flat with a duplexed first unit! Featuring modern kitchens with quartz countertops and stylish backsplashes, recessed lighting, new fixtures, attractive flooring, and panel doors throughout. Unit 1 offers a spacious duplex layout with four bedrooms and two full baths. Unit 2 includes three large bedrooms, a full bath, and a sunroom. Bathrooms feature ceramic tile, new

    Reggie Eaton Park Place Realty Group LLC

    651 N Long Ave, Chicago, IL 60644
  • /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 by PLD Homes, 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

    Hayley Westhoff Compass

    914 W Fletcher St Unit PH, Chicago, IL 60657
  • /29

    $475,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 2 Baths

    4950 W Gunnison St, Chicago, IL 60630

    Situated on an extra wide lot in a premier location of Jefferson Park, this turnkey 2 flat presents an extraordinary opportunity for investors, multi-generational living, or house hackers - live in one unit and generate income leasing the other unit! Both bright and airy apartments feature 2 bedrooms with walk-in closets, 1 bath, tall ceilings, formal living and dining rooms, charming breakfast

    Tiffany Razo Compass

    4950 W Gunnison St, Chicago, IL 60630
  • /28

    $650,000

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

    2455 W Walton St Unit 1, Chicago, IL 60622

    Duplex-down living at its best on a tree-lined street in the heart of Ukrainian Village. Walk in the front door to coffered 10-ft ceilings, 8-ft doors, hardwood floors throughout, and a gas fireplace anchoring a wide-open living and dining layout. Custom window treatments and first-floor surround sound. The spacious kitchen is perfect for entertaining: granite counters, espresso cabinetry,

    Mike Rasmussen @properties Christie's International Real Estate

    2455 W Walton St Unit 1, Chicago, IL 60622
  • /22

    $605,000

    $45K PRICE DROP
    • 7 Beds
    • 1 Bath

    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
  • /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
  • /46

    $1,850,000

    $50K PRICE DROP Pending
    • 8 Beds
    • 6 Baths

    1053 N Damen Ave, Chicago, IL 60622

    Completely rehabbed in 2022. Brick 2-flat plus a fantastic updated coach house above a 2-car garage. The owner's duplex-down features 4 bedrooms and 3.5 bathrooms. High end finishes and vintage touches throughout. The large kitchen with an island opens up to a living/dining area with a fireplace. Gorgeous powder room off the main living area with a vessel sink and venetian plaster wall. En-suite

    Lucas Blahnik @properties Christie's International Real Estate

    1053 N Damen Ave, Chicago, IL 60622
  • /17

    $270,000

    Pre-Foreclosure
    • 5 Beds
    • 3 Baths

    10044 S La Salle St, Chicago, IL 60628

    This well-maintained two-unit property on a quiet, tree-lined street in the heart of Roseland offers an excellent opportunity for both homeowners and investors. The first-floor duplex-down unit features four bedrooms, two full baths, a spacious living room, separate dining room, and a den in the walk-out basement. The second-floor unit includes a large one-bedroom layout with a full bath,

    Israel Dominguez Realty of America, LLC

    10044 S La Salle St, Chicago, IL 60628
  • /19

    $500,000

    • 5 Beds
    • 4 Baths

    6552 S Evans Ave, Chicago, IL 60637

    Rare Opportunity: Anyone INCLUDING Non-Veterans Can Assume This 2.487% VA Mortgage & Save Over $418,000 in Interest! Save $1,373 Every Month by Locking In This Historically Low, Fixed-Rate Loan Instead of Today's ~7.25% Market Rate! Ideal for Owner-Occupants or Savvy Investors - Only a Handful of Multi-Units in All of Illinois Qualify for a Rate This Good! This New Construction (Built 2021)

    Ryan Widerberg eXp Realty - Chicago North Ave

    6552 S Evans Ave, Chicago, IL 60637
  • /60

    $850,000

    Pending
    • 6 Beds
    • 6 Baths

    5707 N Rockwell St, Chicago, IL 60659

    Rarely available and impeccably updated, this condo-quality two-unit building in sought-after Arcadia Terrace offers an exceptional opportunity for both investors and owner-occupants. Each expansive duplex lives like a single-family home, featuring 3 bedrooms, 2.5 bathrooms, and thoughtfully designed open-concept living spaces. Both units boast spacious kitchens, abundant natural light, hardwood

    Jeffrey Frcka Baird & Warner

    5707 N Rockwell St, Chicago, IL 60659
  • /44

    $525,000

    Pending
    • 8 Beds
    • 5 Baths

    4162 S Wells St, Chicago, IL 60609

    Welcome to Bronzeville! This new two-unit building which was fully renovated in 2023 offers not only a blend of modern luxury but such a large amount of space that anyone can call it home. The first floor unit is very large duplex-down. With 5 bedrooms and 3 full bathrooms, this unit will make anyone feel as if they are in a single family home! With its inviting atmosphere with its thoughtfully

    Feras Abbas Jameson Sotheby's Intl Realty

    4162 S Wells St, Chicago, IL 60609
  • /51

    $639,900

    Pending
    • 5 Beds
    • 3 Baths

    3761 S Lake Park Ave, Chicago, IL 60653

    Rarely available Lake Park Avenue duplex! This property offers exceptional flexibility for owner-occupants, multigenerational living, or investors in a sought-after Bronzeville location near the lakefront and downtown. The property features a 3-bedroom, 1.5-bath owner's duplex and a private 2-bedroom, 1-bath garden unit with strong rental potential. The main duplex boasts hardwood floors

    Benita Cathey The Margie Smigel Group, LLC

    3761 S Lake Park Ave, Chicago, IL 60653
  • /21

    $375,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,475 Sq Ft

    2146 N Lawndale Ave Unit 1, Chicago, IL 60647

    Contemporary duplex living with the space of a townhome in Logan Square! This bright 2 bed, 1.5 bath home offers an open floor plan with hardwood floors, oversized windows, high ceilings, a generous granite kitchen with stainless steel appliances, and an oversized island perfect for entertaining. Both bedrooms provide privacy from the main living area, including a spacious primary suite with a

    Katherine Paris Compass

    2146 N Lawndale Ave Unit 1, Chicago, IL 60647
  • /13

    $1,750,000

    Pending
    • 6 Beds
    • 7 Baths

    1442 W Melrose St, Chicago, IL 60657

    Turnkey investment opportunity in fantastic Lakeview location! This is a well maintained 3 unit building with a non-conforming garden unit. Well maintained building features recently updated units with central air/heat, newer kitchens and baths, dishwashers, hardwood floors and outdoor decks. Cathedral ceilings on the 3rd floor. Each unit has its own laundry allowing for premium rents. Tenants

    Barbara Allen Metru Real Estate LLC

    1442 W Melrose St, Chicago, IL 60657
  • /54

    $949,000

    New Construction Pending
    • 3 Beds
    • 4 Baths
    • 2,300 Sq Ft

    505 W Elm St Unit 1, Chicago, IL 60610

    Just 2 units left! Seven on Elm Residences. We are thrilled to introduce a rare opportunity to own a piece of Chicago history: seven luxury residences within a stunning church conversion in the Historic Old Town neighborhood. This project masterfully blends timeless architectural character with modern sophistication, offering truly one-of-a-kind homes designed for elevated urban living. This

    Joanna Olszynska Compass

    505 W Elm St Unit 1, Chicago, IL 60610
  • /19

    $369,900

    • 2 Beds
    • 2 Baths
    • 1,661 Sq Ft

    3512 W Leland Ave Unit 1, Chicago, IL 60625

    Charming duplex condo in Amazing location! Enjoy sunny south-facing living room, spacious rooms, amenities such as new Central AC, hardwood floors, large eat-in kitchen, custom blinds, gas fireplace, private deck. Lower level has full sized windows for maximum light, tall ceilings, an amazing master suite with enormous bedroom and bath plus a den/family room. Front loading washer and dryer in

    Loyda Paredes ProCasa Realty, Ltd.

    3512 W Leland Ave Unit 1, Chicago, IL 60625
  • /41

    $900,000

    Pending
    • 7 Beds
    • 4 Baths

    3859 N Whipple St, Chicago, IL 60618

    Great Investment Opportunity for New Home Buyers to Have Their Mortgage Paid by Their Renters and live Rent/ Mortgage Free!! 4 Unit Building in a Great Location in Irving Park East!! 3 Units currently rented with One 2 Bed/ 2 Bath Duplex Up Available for Immediate Move in!! Close to the Hi-Way and Public Transportation!! Off Street Parking Available! Each Units Has it's Own In-Unit Washer/ Dryer

    Adam Antonucci Fulton Grace Realty

    3859 N Whipple St, Chicago, IL 60618
  • /17

    $695,000

    $104K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft

    257 E Delaware Place Unit 1A2A, Chicago, IL 60611

    This is the opportunity you have been waiting for! Rare duplex in the heart of Streeterville now available! Unit features 3 bedrooms, 3.5 baths, separate dining and generous closet space. Unbeatable location! Near Michigan Ave, Lake Michigan, shopping, restaurants, parks, museums, entertainment, and so much more. Don't miss your chance to experience city living at its finest.

    Jason Shapiro RISING REALTY LLC

    257 E Delaware Place Unit 1A2A, Chicago, IL 60611
  • /49

    $344,900

    • 3 Beds
    • 3 Baths

    4105 S Drexel Blvd Unit 1SR, Chicago, IL 60653

    Welcome to this marvelous over-sized duplex condo in the picturesque sought after neighborhood of historic Bronzeville. Featuring 3 bedrooms and 3 full bathrooms, this beautifully updated duplex offers an abundance of space that is drenched with natural light. The gleaming luxury hardwood floors welcome you in the spacious living room with a grandiose patio door that offers wonderful views of the

    Arturo Olivares Premier Choice Realty Inc

    4105 S Drexel Blvd Unit 1SR, Chicago, IL 60653
  • /21

    $730,000

    New Construction $5K PRICE INCREASE Pending
    • 6 Beds
    • 5 Baths

    5027 S Indiana Ave, Chicago, IL 60615

    Owner-occupied buyers will qualify for 20,000 grant from the Cook County. This gorgeous 2-unit new construction features 4 bedrooms and 3 bathrooms in the duplex down first floor unit with white shaker designer kitchen cabinets, a large peninsula, quartz counters, stainless steel appliances and hardwood floors throughout. The second-floor unit has 2 bedrooms and 2 baths. There is a brand new

    Marika Kakhiani Pedestal Realty LLC

    5027 S Indiana Ave, Chicago, IL 60615
  • /11

    $1,649,000

    New Construction Pending
    • 3 Beds
    • 3.5 Baths

    1443 W Roscoe St Unit PH, Chicago, IL 60657

    NEW, UNDER-CONSTRUCTION DUPLEX UP PENTHOUSE. Welcome to 1443 W. Roscoe St. ***DELIVERING NOVEMBER 2026***This INTIMATE all masonry luxury new construction 2-unit building is Located in the heart of THE Southport corridor. This incredible 3 bed 3.1 bath PENTHOUSE DUPLEX-UP home with FULLY PAVED AND BUILT OUT PRIVATE ROOF TERRACE. Built with luxury transitional finishes, A spacious open floor plan,

    Sam Jenkins Jameson Sotheby's Intl Realty

    1443 W Roscoe St Unit PH, Chicago, IL 60657
  • /31

    $1,725,000

    New Construction Pending
    • 4 Beds
    • 4.5 Baths

    3617 N Magnolia Ave Unit 1, Chicago, IL 60613

    We're excited to present this incredibly rare opportunity to completely customize your own 30ft wide duplex down in the heart of Southport Corridor. Nestled on picturesque Magnolia and situated in the Top Rated Blaine school district, this home will offer four bedrooms, four and 1/2 baths, exceptional private outdoor space and an expansive open floor plan with designer finishes throughout. Buyers

    James Sheehan Meridian Real Estate Chicago LLC

    3617 N Magnolia Ave Unit 1, Chicago, IL 60613
  • /38

    $1,185,000

    $65K PRICE DROP
    • 8 Beds
    • 5 Baths

    4988 N Elston Ave, Chicago, IL 60630

    First time to market! This extra large Mayfair three-flat is not only in pristine condition, but it also has an amazing two-floor owner's suite complete with a private rooftop deck! These owners did the legwork to change the zoning to "mixed-use" for the most income potential! As a result, the well-appointed garden unit can either be a business or residential unit, but it is perfectly equipped to

    Jennifer Delaney Kale Realty

    4988 N Elston Ave, Chicago, IL 60630
  • /23

    $650,000

    • 5 Beds
    • 4 Baths

    1132 E 44th St, Chicago, IL 60653

    Value & Location: "Stunning Duplex with Dedicated Property Easement next to Kennicott Park!" Discover an incredible investment or house-hacking opportunity in Chicago's Historic Kenwood neighborhood. Priced to sell, this unique, townhouse-style two-unit building spans multi-level living space. Situated directly across from the scenic Kennicott Park and minutes from DuSable Lake Shore Drive, this

    Henry Torn ListWithFreedom.com

    1132 E 44th St, Chicago, IL 60653
  • /16

    $679,999

    Pending
    • 2 Beds
    • 2.5 Baths

    1350 W Belmont Ave Unit A, Chicago, IL 60657

    Highly sought after southport Corridor location! Bright, extra wide, south facing duplex up with 2 bedrooms, 2.5 baths, and a private two car garage that lives like a single family home. Located on the second and third floors, this spacious home features soaring 11-foot ceilings, a 23' front Trex balcony perfect for grilling, and generously sized bedrooms. The primary suite offers a walk in

    Bethany Baltutat @properties Christie's International Real Estate

    1350 W Belmont Ave Unit A, Chicago, IL 60657
  • /33

    $535,000

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

    4355 S Lake Park Ave Unit 2N, Chicago, IL 60653

    Welcome to The Windsor, an exceptional duplex-up penthouse residence in the heart of North Kenwood offering approximately 2,600 square feet of sophisticated living space. This expansive 3-bedroom plus loft (optional 4th bedroom), 3.5-bath home combines elegant design, modern finishes, and breathtaking city and lake views. The main living area showcases rich hardwood flooring, crown molding,

    Robin Conner Keller Williams Preferred Rlty

    4355 S Lake Park Ave Unit 2N, Chicago, IL 60653

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