Investment - Homes for Sale in Chicago, IL

• 

  

  

  /4

  $120,000

  $10K PRICE DROP

  • Land
  • 0 Sq Ft

  6415 S Drexel Ave, Chicago, IL 60637

  Adjacent lots also available: 6413 Drexel, 6411 Drexel & 6409 Drexel. Seize a premier development opportunity in the heart of Woodlawn, a high-velocity Chicago neighborhood experiencing a profound renaissance driven by massive institutional investment and the upcoming Obama Presidential Center. This prime, buildable lot offers a blank canvas for a luxury custom home or a high-density multi-unit

  Karen Fedyk Baird & Warner

  6415 S Drexel Ave, Chicago, IL 60637
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  /49

  $510,000

  • 9 Beds
  • 3 Baths

  7914 S Essex Ave, Chicago, IL 60617

  Recently updated 3-unit building in Chicago offering an excellent investment opportunity! Each spacious unit features 3 bedrooms and 1 bathroom with updated finishes throughout. The kitchens have been refreshed and include a refrigerator, microwave, and dishwasher in every unit. Washer/dryer hook up in each unit. The property is fully vacant, allowing investors to set market rents immediately or

  Frank Montro Keller Williams Preferred Rlty

  7914 S Essex Ave, Chicago, IL 60617
• 

  

  

  /22

  $149,900

  • 2 Beds
  • 1.5 Baths
  • 894 Sq Ft

  351 E 91st St Unit A, Chicago, IL 60619

  Welcome to this turnkey investment opportunity in the heart of Chatham! An income-producing property with a tenant already in place, offering immediate cash flow from day one!! This well-maintained home combines classic Chicago character with practical updates, making it an ideal addition to any investor's portfolio. The property features a spacious layout with bright living areas, generously

  Tuqoise Pender Real Broker LLC

  351 E 91st St Unit A, Chicago, IL 60619
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  /24

  $365,000

  • 5 Beds
  • 2 Baths

  6602 S Marquette Dr, Chicago, IL 60637

  Discover a beautifully proportioned two-flat in the heart of Chicago's historic Woodlawn neighborhood, offering a rare blend of architectural charm and modern potential. This classic Chicago two flat has strong investment appeal creating an ideal opportunity for owner-occupants or savvy investors seeking rental income. Each residence features generous living spaces filled with natural light, high

  Emily Connolly EXIT Strategy Realty

  6602 S Marquette Dr, Chicago, IL 60637
• 

  

  

  /23

  $365,000

  $5K PRICE DROP

  • 6 Beds
  • 2 Baths

  6624 S Rhodes Ave, Chicago, IL 60637

  Feel free to send your clients! recently renovated fully vacant, historic greystone 2-unit in the HOT Woodlawn neighborhood! 8 minutes from the Presidential Obama Center which opens in June of this year. This classic Chicago beauty is perfect for an owner-occupant "house hacker" or a savvy investor looking for strong rental potential in a rapidly appreciating area. Both floors offer a freshly

  Ugochinyere Akindele RE/MAX Premier

  6624 S Rhodes Ave, Chicago, IL 60637
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  /50

  $949,990

  Pending

  • 9 Beds
  • 6 Baths

  3755 N Kostner Ave, Chicago, IL 60641

  Extraordinary opportunity to both live, and earn income, in the heart of prime Old Irving! Beautiful, classic, legal 3 unit brick building. Units 1 & 3 were rehabbed in 2020, Unit 2 its in original condition. The property features 3 spacious bedrooms, 1.5 bath units with front balconies. Each unit offers generous living space, updated kitchens with granite countertops, newer appliances, renovated

  Rosy Beltran RE/MAX Premier

  3755 N Kostner Ave, Chicago, IL 60641
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  /19

  $459,900

  $20K PRICE DROP

  • Studio
  • 1 Bath
  • 907 Sq Ft

  401 N Wabash Ave Unit 2304, Chicago, IL 60611

  This expansive studio spans over 900 square feet, making it the perfect "pied-a-terre" or investment rental unit. Enjoy breathtaking east-facing views of Lake Michigan, the Chicago River, and iconic city landmarks. The studio is impeccably furnished and fully equipped, featuring a Snaidero-designed kitchen with Miele and Sub-Zero stainless steel appliances. The luxurious bathroom includes a

  James Qiu Kale Realty

  401 N Wabash Ave Unit 2304, Chicago, IL 60611
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  /27

  $599,999

  Pending

  • 6 Beds
  • 4 Baths

  63 E 56th St, Chicago, IL 60637

  Exceptional Greystone opportunity in Chicago's evolving Washington Park community-ideal for investors and owner-occupants seeking versatility and long-term value. This property features a finished basement with a private 1-bedroom, 1-bathroom mother-in-law suite complete with a full kitchen, creating the perfect setup for multi-generational living, guest accommodations, or potential rental

  Dishenda Mock Mock Realty LLC

  63 E 56th St, Chicago, IL 60637
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  /47

  $5,880,000

  1025 - 49 W Vermont St, Calumet Park, IL 60827

  Pleased to present the exclusive offering of Vermont Street Apartments, a 60-unit multifamily community located at 1025-1049 W. Vermont St, Calumet Park, IL 60827. This investment opportunity consists of 3 contiguous, 20-unit yellow brick flexicore buildings totaling 60,459 SF and offering a desirable unit mix, strong in-place income, and significant upside potential through a light value-add

  Tony Hardy Keller Williams ONEChicago

  1025 - 49 W Vermont St, Calumet Park, IL 60827
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  /24

  $385,000

  • 6 Beds
  • 3 Baths

  2627 W Montgomery Ave, Chicago, IL 60632

  Great investment opportunity in Brighton Park! This 3 unit property features a 2-bedroom, 1-bath unit on the first floor and a 2-bedroom, 1-bath unit on the upper level. Recent updates include electrical work, a newer furnace, hot water tank, and an updated second-floor kitchen. The first-floor unit still needs finishing touches, offering a great opportunity to add value and build equity. A 2-car

  Luz Gutierrez Garcia RE/MAX LOYALTY

  2627 W Montgomery Ave, Chicago, IL 60632
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  /55

  $926,000

  $10K 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
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  /20

  $150,000

  $25K PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 2,496 Sq Ft

  Unlisted Address

  This custom-built home presents a unique opportunity for buyers seeking a home with plenty of space and potential. Home features three spacious bedrooms, three bathrooms, and an expansive three-car garage, enclosed walk-In porch: The home w entryway that connects directly to the garage, living room, bedrooms, three bathrooms, and a well-appointed kitchen, downstairs to a family room, from there

  Johnnie Martin JMAR Realty Group

  Unlisted Address
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  /25

  $270,000

  Pending

  • 5 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  11315 S Stewart Ave, Chicago, IL 60628

  Welcome home! This move-in ready single-family property is perfect whether you're buying your first home or adding to your investment portfolio. Recently renovated with a modern touch, it features an open and airy layout filled with natural light, complemented by crisp white cabinetry and elegant quartz countertops. Enjoy 5 spacious bedrooms, 2 full baths, and a convenient half bath in the

  Irene Perez Coldwell Banker Realty

  11315 S Stewart Ave, Chicago, IL 60628
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  /4

  $259,000

  Pending

  • 6 Beds
  • 3 Baths

  5410 S Winchester Ave, Chicago, IL 60609

  Spacious legal 2-unit property offering strong income potential and flexible living arrangements. This move in ready investment features a 3-bedroom, 1-bath unit on the main level along with a 2-bedroom, 1-bath second floor unit. Property also includes an additional finished attic living space with 1 bedroom and 1 bath. Separate gas and electric utilities with 2 meters already in place. Property

  Landon Kelly Real Broker, LLC

  5410 S Winchester Ave, Chicago, IL 60609
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  /14

  $550,000

  Pending

  • 7 Beds
  • 4 Baths

  6840 W Diversey Ave, Chicago, IL 60707

  ***Multiple offers received***Great Investment Opportunity in the desirable Montclare neighborhood! This legal 3 -flat features two spacious 3-bedroom, 1-bath units and one 1-bedroom, 1-bath unit, offering excellent income potential. The property includes a 2-car detached garage with a new floor and a large fenced backyard. Major building improvements include three newer boilers (approximately 5,

  Dorota Dynak Coldwell Banker Residential

  6840 W Diversey Ave, Chicago, IL 60707
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  /27

  $324,999

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

  6123 S Kimbark Ave Unit 1S, Chicago, IL 60637

  Spacious and move-in-ready 3-bedroom, 2-bath condo ideally situated on a high first floor in a well-maintained brick building! This bright and inviting home features an open-concept floor plan with generous living and dining spaces, perfect for everyday living and entertaining. The upgraded kitchen offers granite countertops, stainless steel appliances, 42-inch cabinetry, and a large center

  Michael Zapart Compass

  6123 S Kimbark Ave Unit 1S, Chicago, IL 60637
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  /12

  $1,050,000

  4821 W Cornelia Ave, Chicago, IL 60641

  Here is your opportunity to purchase a fully updated Courtyard Brick Apartment Building with 4 large units and a 5th non-conforming garden unit. Located on the city's Northwest Side, this Portage Park multi unit investment generates income of $107,894 annually. Rare, L-Shaped All Brick Building on oversized (40ftx133ft). Built in 1921, and freshly updated in 2020, all units feature white shaker

  Kelly Angelopoulos Jameson Sotheby's Intl Realty

  4821 W Cornelia Ave, Chicago, IL 60641
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  /23

  $164,000

  $5K PRICE DROP

  • 8 Beds
  • 3 Baths

  5338 S Wood St, Chicago, IL 60609

  Great investment opportunity in the New City / Back of the Yards area! This legal 3-flat offers strong potential for investors looking to add value and generate future income. The 2nd and 3rd floor units are in livable condition, while the 1st floor unit is ready for a full renovation, providing an excellent opportunity to customize and increase equity. The property features a 2-car detached

  Maria Castillo RE/MAX Mi Casa

  5338 S Wood St, Chicago, IL 60609
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  /10

  $322,000

  • 6 Beds
  • 2 Baths

  7940 S Evans Ave, Chicago, IL 60619

  INVESTMENT OPPORTUNITY! Welcome to a versatile and income-generating multi-family townhouse nestled in the heart of Chatham. Whether you're seeking a live-in owner opportunity or landlord investment, this residence is poised for rental income or owner-occupancy with solid upside potential. Don't miss your chance to own a piece of historic character in a vibrant South Side community. Unit 2 is

  Michael Fisher M Property Group LLC

  7940 S Evans Ave, Chicago, IL 60619
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  /9

  $215,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  4537 S Drexel Blvd Unit 203, Chicago, IL 60653

  Excellent investment opportunity in the beautiful and historic Drexel Boulevard corridor. This spacious 1-bedroom, 1-bath condominium features wood-finish flooring throughout, a cozy fireplace, fresh paint, and a large bathroom with dual vanities. The well-maintained building offers secure fob entry, an included exterior parking space, and low HOA dues. Currently tenant-occupied with an excellent

  Chavez Carter LPT Realty LLC

  4537 S Drexel Blvd Unit 203, Chicago, IL 60653
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  /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
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  /2

  $149,900

  $10K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  5352 S Paulina St, Chicago, IL 60609

  Introducing 5352 S Paulina Street, a solid 4-bedroom, 2-bath brick single-family home located in Chicago's New City community. This property offers immediate livability with the opportunity to add significant value through updates and improvements, making it ideal for an owner-occupant or an investor seeking their next portfolio addition. The main level includes two bedrooms (one smaller and

  Cassandra Sneed EXIT Strategy Realty

  5352 S Paulina St, Chicago, IL 60609
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  /38

  $515,000

  Pending

  • 5 Beds
  • 3 Baths

  3134 W 42nd St, Chicago, IL 60632

  Beautifully rehabbed multi-unit property, fully updated in 2025, offering excellent income potential and versatile living space throughout. This well-maintained building features 2 residential units, each offering 2 bedrooms, comfortable living areas, and kitchens with brand-new appliances, along with an additional spacious attic level that provides extra usable space and flexibility. The attic

  Wing Ho Chi Real Estate Group LLC

  3134 W 42nd St, Chicago, IL 60632
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  /52

  $343,900

  • 2 Beds
  • 2 Baths

  3234 N Central Ave Unit 304, Chicago, IL 60634

  An apartment you'll be eager to step into-and never want to leave. A bright, fully renovated 2-bedroom, 2-bath apartment where everything has already been taken care of: the renovation, the details, and the comfort. Simply move in and start living from day one-with no further investment, waiting periods, or added hassles. This highly sought-after property is situated on the 3rd floor, facing

  Brenda Sarmiento 606 Brokers LLC

  3234 N Central Ave Unit 304, Chicago, IL 60634
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  /24

  $599,900

  • 8 Beds
  • 4 Baths

  8153 S South Shore Dr, Chicago, IL 60617

  Beautifully maintained and recently updated 4-unit investment property located in the rapidly developing South Shore neighborhood! This solid brick building features four spacious 2-bedroom, 1-bathroom units, offering an excellent opportunity for both investors and owner-occupants seeking strong rental potential and long-term appreciation. Each unit offers hardwood floors, forced heating and

  Britney Davis Consumer Realty Group, Inc.

  8153 S South Shore Dr, Chicago, IL 60617
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  /11

  $126,000

  Pending

  • 2 Beds
  • 1 Bath
  • 842 Sq Ft

  742 E 105th St, Chicago, IL 60628

  Cash-Flowing Investment Opportunity in the Pullman Area! Townhouse-style home offering strong investment potential and immediate rental income. This brick property features a functional layout with a spacious Living Room, Dining Room, Kitchen, 2 Bedrooms, 1 Full Bath, plus an additional basement room currently being used as a bedroom. The property is tenant-occupied on a month-to-month lease at

  Jermaine McGee Premier Midwest Realty, INC

  742 E 105th St, Chicago, IL 60628
• 

  /2

  $23,000

  $4K PRICE INCREASE

  • Land
  • 0 Sq Ft

  4904 S Princeton Ave, Chicago, IL 60609

  Exceptional Opportunity for Investors and Home Builders This is a rare chance to purchase a buildable lot in Chicago's Fuller Park neighborhood, just minutes from downtown. In addition to this parcel, the same owners are also offering six other nearby lots, each with its own Property Identification Number (PIN) and separate price. These additional lots are not included in the price of the

  Spasoje Bjelica City Realtor INC.

  4904 S Princeton Ave, Chicago, IL 60609
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  /25

  $140,000

  Pending

  • Studio
  • 1 Bath

  4240 N Clarendon Ave Unit 312S, Chicago, IL 60613

  Phenomenal Location! Outstanding Value! Nestled in the heart of Buena Park, surrounded by some of the city's most beautiful homes, this freshly painted studio condo is an exceptional alternative to renting and a fantastic investment opportunity. Located in a charming former hotel building, residents are welcomed by a dramatic entry corridor that evokes the elegance and character of a bygone era.

  David Zwarycz @properties Christie's International Real Estate

  4240 N Clarendon Ave Unit 312S, Chicago, IL 60613
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  /21

  $1,100,000

  • 6,225 Sq Ft

  2435 S California Blvd, Chicago, IL 60608

  Large brick 6-unit overlooking California Boulevard. In place 7% CAP rate with rental upside. Plus potential to add 2 more garden units with existing city approved plans conveyed in price. Great corner building with 3 full floor units, plus a coach house with 3 additional units. The property was gut renovated in 2017 and still has a great value add opportunity through bringing rents to market.

  Michael Scanlon eXp Realty

  2435 S California Blvd, Chicago, IL 60608
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  /58

  $399,999

  • 10 Beds
  • 4 Baths

  2243 S Sawyer Ave, Chicago, IL 60623

  Turnkey investment opportunity in the heart of the vibrant South Lawndale neighborhood! This well-maintained and updated 4-unit building is perfect for investors looking to generate strong rental income from day one. Each unit features updated kitchens with granite countertops, offering modern finishes that tenants love. The property has been thoughtfully improved with major updates completed

  Luis Ortiz RE/MAX Partners

  2243 S Sawyer Ave, Chicago, IL 60623
• 

  

  /35

  $565,000

  $15K PRICE DROP Pending

  • 6 Beds
  • 2 Baths

  2017 W Norwood St, Chicago, IL 60659

  Calling all investors! This fully-occupied 2-unit has everything you need to start your home-hacking journey, or add as a valuable addition to your current portfolio. Both units are 3bed/1bath, updated/remodeled in 2018, and feature hardwood floors throughout (second floor under carpet), with ceramic tile in the kitchens. Classic Chicago-sized bedrooms all have closets, and will fit queen-size

  Kirk Hudson Baird & Warner

  2017 W Norwood St, Chicago, IL 60659
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  /27

  $475,000

  $25K PRICE DROP

  • 5 Beds
  • 3 Baths

  2320 S Albany Ave, Chicago, IL 60623

  This stunning two-unit multifamily property boasts spacious and beautiful interiors. It features a new roof, siding, and several interior updates. With a total of 5 bedrooms and 3 full bathrooms, each unit comes with its own laundry space. It's the ideal investment opportunity!

  Andres Olaez Keller Williams ONEChicago

  2320 S Albany Ave, Chicago, IL 60623
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  /37

  $325,000

  $25K PRICE DROP Pending

  • 8 Beds
  • 3 Baths

  6230 S Langley Ave, Chicago, IL 60637

  Nestled in the vibrant Woodlawn neighborhood, this classic greystone 2-unit property with the possibility of an ADU offers a perfect blend of historic charm and modern investment appeal. With Woodlawn experiencing impressive property appreciation in recent years-driven by new development initiatives and steady demand-this smartly positioned building promises solid long-term value. Just steps from

  Asya Muhammad Coldwell Banker Realty

  6230 S Langley Ave, Chicago, IL 60637
• 

  

  /13

  $549,000

  • 15 Beds
  • 4 Baths

  1311 S Harding Ave, Chicago, IL 60623

  Turnkey investment opportunity in the heart of North Lawndale! This recently remodeled 4-unit brick building sits on a well-kept block and offers strong income potential for both seasoned investors and owner-occupants alike. Each unit features its own separate furnace and hot water tank, providing efficiency, convenience, and reduced operating expenses. The property has been thoughtfully updated,

  Alexander Summers Triton Realty Group LLC

  1311 S Harding Ave, Chicago, IL 60623
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  /32

  $699,999

  • 4 Beds
  • 2 Baths

  2846 N Elston Ave, Chicago, IL 60618

  Located in the heart of Avondale, this well-maintained 2-flat with a non-conforming garden unit offers an ideal blend of investment potential and owner-occupant appeal. Just steps from popular coffee shops, craft breweries, restaurants, and multiple grocery options, the location continues to attract strong tenant demand. The spacious first-floor unit features soaring 10-foot ceilings and an open

  Elias Masud Compass

  2846 N Elston Ave, Chicago, IL 60618
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  /45

  $650,000

  • 4,943 Sq Ft

  6058 S Massasoit Ave, Chicago, IL 60638

  6058 S Massasoit Ave is a solid, all-brick 6-unit apartment building located in the highly desirable Midway Clearing/Garfield Ridge area neighborhood. This property offers a reliable investment opportunity with a strong rent roll, generating $5,975 in monthly income and a total of $71,700 annually. The building consists of 3 one bedroom apartments - and 3 two-bedroom apartments. On-site

  Sergio Hernandez Keller Williams Premiere Properties

  6058 S Massasoit Ave, Chicago, IL 60638
• 

  

  /21

  $489,000

  $24K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  600 N Kingsbury St Unit 906, Chicago, IL 60654

  An exceptional investment opportunity in the heart of River North, a spacious 2-bedroom, 2-bath home can deliver immediate rental income and the kind of consistent demand investors love with a lease that extends through June 30, 2027. The unit showcases sweeping skyline views through floor-to-ceiling windows and opens onto a generous balcony-an inviting place to pause, breathe, and take in the

  Erin Booker Engel & Voelkers Chicago North Shore

  600 N Kingsbury St Unit 906, Chicago, IL 60654
• 

  

  /25

  $875,000

  • 4 Beds
  • 3 Baths

  1520 N Campbell Ave, Chicago, IL 60622

  **$12,500 buyer closing credit** Prime investment opportunity or multi-generational home in Chicago's vibrant West Town/East Humboldt neighborhood. This recently renovated light filled 2-unit building offers 3 bedrooms 2 bathrooms on the main level in addition to laundry room, dining/ living, and pantry, glass slider, and steel deck perfect for parties and entertaining. The ground level unit

  Anthony White EXIT Strategy Realty

  1520 N Campbell Ave, Chicago, IL 60622
• 

  

  /27

  $1,100,000

  • 10 Beds
  • 3 Baths

  1657 N Artesian Ave, Chicago, IL 60647

  Welcome to 1657 N Artesian in Chicago this is a classic two-flat featuring a solid brick coach house at the rear of the property, offering a rare and versatile investment opportunity. Situated on a single PIN, the property is ideal for developers or investors looking to convert the buildings into condominiums or undertake a unique redevelopment project. Schedule your appointment today!!

  Monica Morales Extreme Realty LLC

  1657 N Artesian Ave, Chicago, IL 60647
• 

  

  /15

  $290,000

  Pending

  • 12 Beds
  • 4 Baths

  7321 S Stewart Ave, Chicago, IL 60621

  GREAT INVESTMENT OPPORTUNITY!!! 2 units are vacant and 2 units are rented month 2 month 12 bds, 4 bth, 4908 sqft Year built 1900 Condition per the seller Plumbing & Electrical: Owner states there are no issues with the plumbing or electrical systems. Foundation: Owner confirmed there are no foundation issues. General Painting: At least one apartment needs a full paint job. Drywall Work: One unit

  Airreca Weaver Coldwell Banker Real Estate Group

  7321 S Stewart Ave, Chicago, IL 60621

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