Investment - Homes for Sale in Chicago, IL

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  /44

  $1,550,000

  $50K PRICE DROP Pending

  • 7 Beds
  • 7 Baths

  1337 W Barry Ave, Chicago, IL 60657

  Exceptional investment opportunity in the heart of Lakeview! This 4-unit property offers a versatile mix ideal for both investors and owner-occupants. The front building features two units, including a stunning duplex-up that lives like a single-family home. The top unit offers 3 bedrooms and 2.5 baths, complete with in-unit laundry and individual HVAC-perfect for an owner-occupant seeking

  Matthew Liss Mark Allen Realty ERA Powered

  1337 W Barry Ave, Chicago, IL 60657
• 

  

  

  /11

  $460,000

  Pending

  • 7 Beds
  • 3 Baths

  7232 S Union Ave, Chicago, IL 60621

  Step inside and fall in love with the soaring 10-foot ceilings, open-concept floor plan, recessed lighting, and sleek designer finishes throughout. The kitchens are a true showstopper, featuring quartz countertops, 42-inch custom cabinetry, and bold black fixtures that bring the perfect touch of modern elegance. The first-floor unit offers a spacious duplex-down layout with four bedrooms and two

  Candice Payne 5th Group Corp

  7232 S Union Ave, Chicago, IL 60621
• 

  

  /2

  $25,000

  • Land
  • 0 Sq Ft

  7249 S Harvard Ave, Chicago, IL 60621

  This vacant land is located in Greater Grand Crossing neighborhood. The owner has four additional lots on this street. Great investment opportunity for a developer looking to build in this area.

  Rockeya Wilson Berkshire Hathaway HomeServices Chicago

  7249 S Harvard Ave, Chicago, IL 60621
• 

  

  

  /13

  $475,900

  Pending

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  1541 N Artesian Ave Unit 2, Chicago, IL 60622

  SOLD BEFORE PRINT. Bright, spacious, and ready to call home, this 2-bedroom, 2-bath home offers the ideal blend of comfort and convenience in the heart of Chicago's thriving West Side. Freshly painted throughout and ready to welcome its new owners, the open-concept layout is filled with natural light and features hardwood floors, generous living and dining spaces, and a functional floor plan

  Peter Kozera Eras Brokerage and Realty LLC

  1541 N Artesian Ave Unit 2, Chicago, IL 60622
• 

  

  /2

  $35,000

  • Land
  • 0 Sq Ft

  4023 W 16th St, Chicago, IL 60623

  vacant lot ideal for new construction or investment. Located in a growing area with strong redevelopment activity. Motivated seller and open to project collaboration. Drive by and bring your vision.

  Bridget Johnson House of Real Estate

  4023 W 16th St, Chicago, IL 60623
• 

  

  /4

  $199,900

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  9515 S Woodlawn Ave, Chicago, IL 60628

  Investment Opportunity! This property at 9515 S Woodlawn in Chicago is occupied and being sold as-is at auction, presenting a great opportunity for investors seeking a value-add asset. The home offers immediate rental income potential. Located on a residential street with convenient access to shopping, dining, schools, and public transportation, this property is ideal for investors looking for

  Anthony Disano Parkvue Realty Corporation

  9515 S Woodlawn Ave, Chicago, IL 60628
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  /83

  $4,995,000

  • 6 Beds
  • 8 Baths

  1019 N Wolcott Ave, Chicago, IL 60622

  The Lincoln Street Bath House is one of Chicago's most extraordinary and versatile residential offerings. This historical masterpiece seamlessly blends modern luxury with iconic neoclassical architecture. Spanning approximately 10,000 square feet across two-and-a-half city lots, this one-of-a-kind, highly adaptable property presents a rare opportunity for multi-generational living, live/work

  Melanie Carlson @properties Christie's International Real Estate

  1019 N Wolcott Ave, Chicago, IL 60622
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  /4

  $23,000

  $2K PRICE DROP Pending

  • Land
  • 0 Sq Ft

  7149 S Champlain Ave, Chicago, IL 60619

  VACANT LOT - Greater Grand Crossing, Chicago Fantastic investment opportunity in the growing Greater Grand Crossing neighborhood! This RS-3 zoned vacant lot is ideal for building a single-family home or two-unit property. The land is ready for development. Enjoy easy access to the Dan Ryan Expressway, Chicago Skyway, and public transportation, making this a prime location for commuters and future

  Petru Amarei Chicagoland Brokers, Inc.

  7149 S Champlain Ave, Chicago, IL 60619
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  /38

  $750,000

  • 9 Beds
  • 3 Baths

  2833 W Polk St, Chicago, IL 60612

  Turnkey investment opportunity with strong income potential! This well-maintained 3-unit building features an additional basement unit, offering even more rental revenue. Each spacious unit boasts 3 bedrooms and 1 bathroom, designed with modern finishes and thoughtful layouts. All units showcase open-concept living with large, elongated windows that flood the space with natural light. Kitchens

  Mayra Keating Results Realty ERA Powered

  2833 W Polk St, Chicago, IL 60612
• 

  

  /13

  $115,000

  $20K PRICE DROP Pending

  • 4 Beds
  • 1 Bath
  • 1,298 Sq Ft

  9021 S Exchange Ave, Chicago, IL 60617

  Single Family 4 bedrooms, 1 bath home. Updates in 2026 include kitchen, baths, - ceramic tile floors, cabinets, sinks, laminate countertops, vanity and lighting. Laminate hardwood floors in living room and carpet in bedrooms. MOVE IN READY!!! SOLD AS IS!! READY FOR YOU OR FOR YOUR PORTFOLIO INVESTMENT!!! THIS IS A HOT ONE, DON'T MISS OUT!!!!

  Damaris Santiago Manage Chicago, Inc.

  9021 S Exchange Ave, Chicago, IL 60617
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  /34

  $1,095,000

  Pending

  • 7,548 Sq Ft

  6037 S Champlain Ave, Chicago, IL 60637

  Prime 8-Unit Income Property in Woodlawn just steps from University of Chicago. Invest in one of Woodlawn's most desirable locations with this well-maintained 8-unit building, just three blocks from the University of Chicago Hospital and approximately one mile from the Obama Presidential Center. Strong, consistent rental demand makes this an exceptional income-generating opportunity. The property

  Christina Horne Chicagoland Realty & Associates Inc

  6037 S Champlain Ave, Chicago, IL 60637
• 

  

  /22

  $250,000

  $15K PRICE DROP

  • Studio
  • 1 Bath
  • 640 Sq Ft

  474 N Lake Shore Dr Unit 5207, Chicago, IL 60611

  Welcome to your perch in the clouds! This jumbo studio unit in the heart of Streeterville/Gold Coast is calling your name. 640 sqft of comfortable, updated, move-in condition living space with sweeping western city views is perfect for a first purchase, portfolio addition, or as a pied-a-terre investment. Unit was rehabbed in 2018, including new kitchen and appliances (aside from refrigerator,

  Kirk Hudson Baird & Warner

  474 N Lake Shore Dr Unit 5207, Chicago, IL 60611
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  /4

  $329,000

  • 1 Bed
  • 1 Bath
  • 960 Sq Ft

  175 E Delaware Place Unit 4901, Chicago, IL 60611

  ONE-BEDROOM FACING EAST THAT'S IN ORIGINAL CONDITION. THIS HAS BEEN AN INVESTMENT PROPERTY FOREVERAND THE CURRENT TENANT IS GOLD STANDARD WHOSE LEASE EXPIRES ON OCTOBER 2026, HOWEVER, IS WILLING TO CONTINUE TO STAY. ENDLESS AMENITIES WITHIN THE BUILDING, SUCH AS; INDOOR POOL, FULLSERVICE GROCERY STORE POTASH, FITNESS CENTER, TWO HOSPITALITY ROOMS, ETC. OVER 23 MILLION IN RESERVES AND NEVER HAD A

  Pat Cohen Baird & Warner

  175 E Delaware Place Unit 4901, Chicago, IL 60611
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  /3

  $145,000

  • Land
  • 0 Sq Ft

  5226 S Loomis St, Chicago, IL 60609

  Opportunity Knocks! Prime lot located directly across from Sherman Park-ideal for a multi-unit development and a strong investment opportunity. Situated in an up-and-coming area with low taxes and within walking distance to Sherman School of Excellence. Commuter-friendly location close to restaurants, shopping, and major expressways. Don't miss this chance to build in a growing neighborhood!

  Janet Vilchez EXIT Strategy Realty

  5226 S Loomis St, Chicago, IL 60609
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  /33

  $134,900

  • 5 Beds
  • 2 Baths

  4734 S Racine Ave, Chicago, IL 60609

  Located in the highly sought after back of the yards community this jumbo two-unit building offers a pivot opportunity to a savvy buyer! Renovate the building, add value and live in one unit while renting the other out or use this as a straight investment property by renting both units while adding value, either way this is a win win situation! The building offers great size in both units with

  Ryan Smith RE/MAX Premier

  4734 S Racine Ave, Chicago, IL 60609
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  /6

  $89,999

  Pending

  • 7 Beds
  • 4 Baths

  645 E 113th St, Chicago, IL 60628

  Price Improvement and Prime Investment Opportunity in Historic Pullman. For the savvy investor/discerning buyer, unlock the full potential of this 2-unit located in the rapidly revitalizing Pullman district. With a ton of square footage plus a full, unfinished basement, this property offers a rare opportunity to add significant value through renovation, reconfiguration, or redevelopment. Whether

  Sharial Howard @properties Christie's International Real Estate

  645 E 113th St, Chicago, IL 60628
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  /2

  $60,000

  • 5 Beds
  • 2 Baths

  5802 S May St, Chicago, IL 60621

  Come and view this excellent investment and renovation project. This 2 flat offers a spacious 2br 1bth unit and a 3br 1bth unit. Full basement. Property Sold AS/WHERE-IS. Buyer responsible for all liens, taxes, judgments, closing costs, totaling $40K. No tax prorations.

  Edrick Salomon Select a Fee RE System

  5802 S May St, Chicago, IL 60621
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  /46

  $150,000

  $104K PRICE DROP Pending

  • 6 Beds
  • 2 Baths

  10002 S Torrence Ave, Chicago, IL 60617

  Huge Price Reduction. Rare Bundle Sale! Buy 2 Amazing Properties. Cash offer or investment loan only, reading about zoning in agent remarks . Huge Price Reduction - Homeowner, House Hacker & Investor's Dream! Welcome to 10002 & 10004 S Torrence Ave, Chicago, IL 60617 - yes, two houses with two separate PINs, right next door to each other! This rare opportunity offers low taxes and an unbeatable

  Olga Kaminska Core Realty & Investments Inc.

  10002 S Torrence Ave, Chicago, IL 60617
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  /27

  $659,900

  • 5 Beds
  • 3 Baths

  5008 W Strong St, Chicago, IL 60630

  Fantastic investment opportunity on a quite tree lined street of Jefferson Park. Legal 3 flat perfect for an investor or live in owner looking to invest in themselves. Get the best of both worlds with a wonderful mix of vintage charm and modern conveniences. Kitchens and baths have been remodeled a while ago but very nice. Two 2-bedroom 1 bath units plus a large 4 room one bedroom on top floor.

  Matthew Mika Compass

  5008 W Strong St, Chicago, IL 60630
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  /14

  $699,000

  $1K PRICE DROP Pending

  4459 W Jackson Blvd, Chicago, IL 60624

  4459 W Jackson Blvd is a solid brick 9-unit building located in the West Garfield Park neighborhood. The building features three tiers of units with a mix of 2 bed / 1 bath and 1 bed / 1 bath unit apartments. They include hardwood floors, gas forced-air heat, and individually metered electric for all units. The kitchens include ranges and refrigerators. The building has a strong rental history

  Davis Edgerly 33 Realty

  4459 W Jackson Blvd, Chicago, IL 60624
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  /4

  $95,000

  $15K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  9918 S Hoxie Ave, Chicago, IL 60617

  Income producing brick beauty in Chicago!! Solid 2-bedroom, 1 bath brick single family home, tenant occupied and generating income from day one! This is the kind of smart investment Chicago buyers are looking for: steady cash flow, strong structure, and long-term upside. Whether you're building your portfolio or purchasing your first rental, this is your opportunity to start earning more and

  Damaris Santiago Manage Chicago, Inc.

  9918 S Hoxie Ave, Chicago, IL 60617
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  /21

  $799,000

  $50K PRICE DROP

  • 8 Beds
  • 4 Baths

  4040 S Calumet Ave, Chicago, IL 60653

  Exceptional investment opportunity in the heart of historic Bronzeville. This fully renovated three-unit building at 4040 S. Calumet Ave offers investors a rare turn-key asset with strong income and long-term appreciation potential. The property has undergone a complete rehabilitation in recent years, with significant updates throughout the building. Each unit is currently rented at above-market

  Sophie Beaudoin RE/MAX Top Performers

  4040 S Calumet Ave, Chicago, IL 60653
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  /36

  $755,000

  Pending

  • 14 Beds
  • 8 Baths

  5319 S Indiana Ave, Chicago, IL 60615

  Calling all investors and owner-occupants to this rare Washington Park Greystone opportunity! This massive 4-unit property features an impressive 14 bedrooms and 8 bathrooms, offering size, flexibility, and income potential that is rarely available in today's market. Truly nothing else like it around. Located 5 miles from downtown, just 1.5 miles from the University of Chicago and within biking

  Darnisha Holliday EXIT Strategy Realty

  5319 S Indiana Ave, Chicago, IL 60615
• 

  

  /20

  $260,000

  $35K PRICE INCREASE Pending

  • 6 Beds
  • 2 Baths

  2922 E 97th St, Chicago, IL 60617

  Looking to acquire a rental investment or a property in which you are able to live and rent out another unit? This is definitley that opportunity. This property has two units with 3 beds/1 bath with a 2 car detached garage and fenced in yard. Close to the skyway, local retail, park, etc.

  Mercedes Pomales New Chapter Real Estate

  2922 E 97th St, Chicago, IL 60617
• 

  /2

  $474,500

  Pending

  • 16 Beds
  • 4 Baths

  7256 S Lowe Ave, Chicago, IL 60621

  This 4 unit is an amazing investment! Come and get it!

  Sean Cochran eXp Realty

  7256 S Lowe Ave, Chicago, IL 60621
• 

  

  /20

  $320,000

  Pending

  • 5 Beds
  • 3 Baths

  3017 E 83rd St, Chicago, IL 60617

  Excellent investment opportunity in Chicago! This well-maintained two-unit property offers incredible versatility for investors or owner-occupants looking to generate rental income. The main building features two spacious units with bright living areas, updated flooring, generous room sizes, and functional layouts designed for comfortable living. A standout feature of this property is the

  Dione Branch eXp Realty

  3017 E 83rd St, Chicago, IL 60617
• 

  

  /10

  $875,000

  $25K PRICE DROP

  • 8,118 Sq Ft

  8001 S Maryland Ave, Chicago, IL 60619

  12-unit brick walk-up building located in Chicago's East Chatham neighborhood. The property features a well-balanced unit mix of six (6) one-bedroom / one-bath apartments and six (6) two-bedroom / one-bath apartments, catering to strong and consistent tenant demand in the submarket. The building has undergone significant recent capital improvements, positioning it as a turnkey investment

  Quinn Evans Essex 312, LLC

  8001 S Maryland Ave, Chicago, IL 60619
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  /2

  $40,000

  • Land
  • 0 Sq Ft

  5647 S Peoria St, Chicago, IL 60621

  Prime South Side Development Opportunity: Unlock the potential at 5647 S. Peoria. This 4,500 sq ft vacant lot offers a rare opportunity for builders, developers, and forward-thinking investors ready to capitalize on Chicago's ongoing growth and revitalization. Positioned in an established South Side corridor, this parcel provides the flexibility to bring new construction to life-whether you're

  Elijah Reese Serene Realty, Inc.

  5647 S Peoria St, Chicago, IL 60621
• 

  

  /14

  $349,999

  $145K PRICE DROP

  • 9 Beds
  • 3 Baths

  3018 W Flournoy St, Chicago, IL 60612

  Large brick 3-unit investment opportunity with major upside potential. Property previously underwent extensive renovation work including updated kitchens, bathrooms, refinished hardwood floors, recessed lighting, newer HVAC systems, updated mechanicals, newer appliances, and exterior improvements. Spacious layouts with strong rental and value-add potential. Interior photos reflect prior

  Jeffrey Sklar Beycome Brokerage Realty LLC

  3018 W Flournoy St, Chicago, IL 60612
• 

  

  /24

  $525,000

  • 1 Bed
  • 2 Baths
  • 1,220 Sq Ft

  401 N Wabash Ave Unit 2222, Chicago, IL 60611

  Rare opportunity to own an expansive 1-bedroom, 2-bath residence in one of Chicago's premier luxury buildings. Offered impeccably furnished, this sophisticated home showcases breathtaking city views complemented by refined, high-end finishes throughout. The spacious living and dining areas flow seamlessly into a separate kitchen, creating an ideal layout for both everyday living and entertaining.

  Julie Zwick Premier Relocation, Inc.

  401 N Wabash Ave Unit 2222, Chicago, IL 60611
• 

  

  /26

  $384,900

  $35K PRICE DROP Pending

  • 8 Beds
  • 3 Baths

  5029 S Racine Ave, Chicago, IL 60609

  Fantastic opportunity to build equity and expand your portfolio with this spacious multi-unit property in the Back of the Yards neighborhood! This property features 3 units: The first-floor unit boasts high ceilings, 4 generously sized bedrooms, a full bath, an eat-in kitchen, a spacious living room and a month-to-month tenant. The second-floor front unit includes 2 bedrooms, a full bath, a

  Jose Leon RE/MAX Partners

  5029 S Racine Ave, Chicago, IL 60609
• 

  

  /28

  $135,000

  • 8 Beds
  • 5 Baths

  8711 S Exchange Ave, Chicago, IL 60617

  Exceptional Investment Opportunity in this 4-Unit building in South Chicago neighborhood ! This high-potential property presents a rare opportunity for savvy investors. Additional in-law arrangement garden unit plus large and high attic . The building spans approximately 3,050 square feet and features 10 bedrooms, 5 bathrooms and a detached 2-car garage. Prime location close to parks, stores, and

  Grazyna Przybysz Chicago Area Realty Inc

  8711 S Exchange Ave, Chicago, IL 60617
• 

  

  /25

  $649,900

  • 4 Beds
  • 3 Baths

  4155 N Francisco Ave, Chicago, IL 60618

  Charming oversized lot Multi-Family Opportunity in Irving Park / Rose Park! Recently renovated 2-Unit Building, | Oversized 4,000 Sq Ft Lot | Incredible Location Welcome to your next great investment or the perfect live-in income property! Nestled within the highly sought-after Rose Park subdivision of Chicago's vibrant Irving Park neighborhood, this beautifully recently updated two-unit

  Paulo Diaz Real People Realty

  4155 N Francisco Ave, Chicago, IL 60618
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  /2

  $50,000

  • Land
  • 0 Sq Ft

  403 W 62nd St, Chicago, IL 60621

  Bring your vision to life on this vacant lot with exciting potential for future development. Whether you are a builder, investor, or buyer looking to create from the ground up, this parcel offers a blank canvas in an established neighborhood with ongoing growth and opportunity. Explore the possibilities for new construction, a long-term investment hold, or a custom project designed to fit your

  Bridget Johnson House of Real Estate

  403 W 62nd St, Chicago, IL 60621
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  /5

  $140,000

  $37K PRICE DROP Pending

  • 4 Beds
  • 3 Baths

  5350 S Winchester Ave, Chicago, IL 60609

  QUIET BLOCK IN UPCOMING NEW CITY NEIGHBORHOOD! Seller is motivated yet comps in area show lots of room to make this *vacant* BRICK 2 flat with 4 beds and 3 bath (yet a very large living room to add a third bedroom in one of the apartments) a basic rental or a splendid work of art at whatever level of creativity you desire! GREAT POSSIBILITIES!!!!. Turn this in to a wonderful investment property

  Dana Jones Century 21 IMPACT

  5350 S Winchester Ave, Chicago, IL 60609
• 

  

  /22

  $669,900

  Pending

  • 5 Beds
  • 3 Baths

  6430 N Hoyne Ave, Chicago, IL 60645

  GREAT INVESTMENT OPPORTUNITY! SOLID BRICK 3-UNIT BUILDING IN A GREAT NEIGHBORHOOD. 1ST FL & 2ND FL EACH HAS 2 SPACIOUS BEDROOMS, 1 BATH, LARGE, SUNNY LIVING ROOM & DINING ROOM, NICE KITCHEN. GARDEN UNIT HAS 1 BEDROOM, 1 BATH, KITCHEN, NICE LIVING ROOM. SEPARATE UTILITIES. COIN LAUNDRY, STORAGE IN LOWER LEVEL. 2 CAR GARAGE. LONG TIME TENANTS. GOOD FOR LIVE IN AND INVESTMENT. PRE-APPROVED BUYER,

  Ngocmai Huynh VNT Realty

  6430 N Hoyne Ave, Chicago, IL 60645
• 

  

  /24

  $65,000

  $5K PRICE DROP Pending

  • 5 Beds
  • 3 Baths

  8405 S Baltimore Ave, Chicago, IL 60617

  Solid investment opportunity with strong upside potential. This frame 2-flat includes two spacious 2-bedroom units and an additional 1-bedroom garden unit, offering multiple income streams. The property features individual heating systems for each unit, improving efficiency and tenant appeal. While the building requires rehabilitation, it presents a prime value-add opportunity for investors

  Brenda Molina HomeSmart Connect LLC

  8405 S Baltimore Ave, Chicago, IL 60617
• 

  

  /8

  $299,900

  Pending

  • 6 Beds
  • 3 Baths

  8236 S May St, Chicago, IL 60620

  Excellent Investment Opportunity in Auburn Gresham. Discover the potential in this solid all-brick 2-unit property located in the Auburn Gresham neighborhood. Each unit offers 3 bedrooms and 1 bathroom with functional layouts, well-maintained, providing a strong foundation for rental income or owner-occupant use. The property also features a full basement, offering additional possibilities for

  Deonte Barbee Real Broker LLC

  8236 S May St, Chicago, IL 60620
• 

  

  /4

  $224,900

  $12K PRICE DROP

  • 6 Beds
  • 2 Baths

  1806 S Homan Ave, Chicago, IL 60623

  *Attention investors!* This is an opportunity for buyers seeking a project or investment property. This property is being sold as-is via Xome auction and is currently occupied. No access will be provided to the property, do not disturb occupants. The sale is subject to auction terms and conditions. Seller does not provide survey. Buyer to verify zoning and take subject to any municipal

  Anthony Disano Parkvue Realty Corporation

  1806 S Homan Ave, Chicago, IL 60623
• 

  

  /11

  $849,000

  Pending

  • 8 Beds
  • 4 Baths

  1347 W Flournoy St, Chicago, IL 60607

  RARE CHANCE to own a huge solid brick 2 flat on oversized lot (24 x 150) with enourmous 1300 square 6 car garage in PRIME Little Italy location steps to Arrigo Park, UIC/Rush Medical District, UIC East Campus, CTA Blue Line, Taylor Street and so much more. Both apartments are 4 bed 2 baths currently leased thru July 2026 and positioned in an area with incredible rent demand. Corner building

  Peter Gordon C. Gallucci Realty, Inc.

  1347 W Flournoy St, Chicago, IL 60607

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