Investment - Homes for Sale in Chicago, IL

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  /15

  $53,000

  $2K PRICE DROP

  • Studio
  • 1 Bath

  7854 S South Shore Dr Unit 306, Chicago, IL 60649

  Charming, studio condo ideally positioned along the vibrant South Shore corridor. This unit offers an excellent opportunity for investors seeking immediate cash flow, while still allowing flexibility for a future owner-occupant. Situated just steps from Lake Michigan, this location places you near the South Shore Cultural Center, Rainbow Beach, and ongoing neighborhood revitalization efforts. The

  Deja Blair Blue Door Dave Inc

  7854 S South Shore Dr Unit 306, Chicago, IL 60649
• 

  

  /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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  /9

  $325,000

  • 6 Beds
  • 2 Baths

  707 E 92nd Place, Chicago, IL 60619

  A well maintained 2flat offering a great opportunity for investors or owner occupants. Each unit features 3 bedrooms and 1 bath, a separate living room, formal dining room and eat-in kitchen. Both units are equipped with their own furnace, providing landlord convenience and control for each household. Recent interior upgrades add to the appeal and make this property a solid addition to any

  Perdure Carter Realty of America, LLC

  707 E 92nd Place, Chicago, IL 60619
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  /38

  $495,000

  $46K PRICE INCREASE Pending

  • 8 Beds
  • 3 Baths

  7049 S Vernon Ave, Chicago, IL 60637

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

  Rudy Gandy Premier Agent Network Illinois LLC

  7049 S Vernon Ave, Chicago, IL 60637
• 

  

  

  /21

  $825,000

  New Construction

  • 9 Beds
  • 6 Baths

  3109 W Polk St, Chicago, IL 60612

  Buyers can qualify for the Chicago Land Bank $20,000 Grant. Exceptional investment for an owner-occupant. October Delivery. New construction three-unit property featuring modern finishes and thoughtful design throughout. Each spacious unit offers 3 bedrooms and 2 full baths. Step inside to find open-concept layouts with abundant natural light, in-unit laundry, and stainless steel appliances in

  Lawrence Dunning Fulton Grace Realty

  3109 W Polk St, Chicago, IL 60612
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  /2

  $299,900

  • 12 Beds
  • 4 Baths

  1609 S Central Park Ave, Chicago, IL 60623

  ATTENTION INVESTORS, HOUSE HACKERS, AND SWEAT EQUITY SEEKERS! This all-brick 3-flat is a true cash-flow opportunity with 12 total bedrooms and 4 full bathrooms, a rare find with incredible income potential. The first unit is a spacious duplex featuring 5 bedrooms and 2 bathrooms, with 3 bedrooms above grade and 2 below. The second unit offers 4 bedrooms and 1 full bathroom, while the third unit

  Jorge Vega New Avenue Realty LLC

  1609 S Central Park Ave, Chicago, IL 60623
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  /20

  $185,900

  $14K PRICE DROP

  • 4 Beds
  • 2 Baths

  8220 S Houston Ave, Chicago, IL 60617

  This exceptional 2-flat is truly move-in ready and an outstanding investment opportunity! Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the other, property is a must-see!

  Salma Torres @properties Christie's International Real Estate

  8220 S Houston Ave, Chicago, IL 60617
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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
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  /34

  $799,900

  1206 W 83rd St, Chicago, IL 60620

  UNRIVALED 25-UNIT VALUE-ADD OPPORTUNITY IN THE HEART OF AUBURN GRESHAM Strike while the market is hot with this massive brick mixed-use powerhouse located at 1206-1210 W 83rd St. Positioned as the most competitive investment in the 60620 zip code, this asset is priced for a high-octane liquidation at just $799,000. This is a rare chance to secure a scale-level project at approximately $32,000 per

  Pete Chrysanthou Prime Real Estate Group Inc

  1206 W 83rd St, Chicago, IL 60620
• 

  

  /22

  $849,000

  New Construction Pending

  • 9 Beds
  • 6 Baths

  3119 W Flournoy St, Chicago, IL 60612

  Exceptional investment or owner-occupant opportunity with this coming soon new construction three-unit property featuring modern finishes and thoughtful design throughout. Each spacious unit offers 3 bedrooms and 2 full baths. Step inside to find open-concept layouts with abundant natural light, in-unit laundry, and stainless steel appliances in every kitchen. A rear parking pad provides

  Lawrence Dunning Fulton Grace Realty

  3119 W Flournoy St, Chicago, IL 60612
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  /78

  $445,000

  • 5 Beds
  • 3 Baths
  • 2,821 Sq Ft

  543 N Leclaire Ave, Chicago, IL 60644

  An exceptional opportunity to own a spacious four-level home offering approximately 2,821 square feet in one of Chicago's fastest-growing neighborhoods. Designed for today's lifestyle, this stunning residence features 5 generously sized bedrooms, 3 full bathrooms, expansive living and entertaining spaces, and quality craftsmanship throughout. The beautifully appointed kitchen showcases white

  Michael Applegate Straight-A Realty, LLC

  543 N Leclaire Ave, Chicago, IL 60644
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  /31

  $550,000

  Open Sun 12PM - 2PM

  • 5 Beds
  • 2 Baths

  2923 N Neenah Ave, Chicago, IL 60634

  Don't miss this excellent investment opportunity in the desirable Dunning neighborhood! This well-maintained two-flat offers a spacious first-floor unit featuring three bedrooms, beautiful hardwood floors, and a sunroom off the primary bedroom-perfect for a home office, reading nook, or flex space. The second-floor unit was extensively remodeled in 2024 and features new luxury vinyl flooring, a

  Crystal Burgos Realty of America, LLC

  2923 N Neenah Ave, Chicago, IL 60634
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  /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 currently leased, but good opportunity to become an owner occupant. Tenants pay their own electric and gas. All units updated with newer kitchens and baths. Two units with washer/dryer in unit. 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
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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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  /20

  $400,000

  Pending

  • 9 Beds
  • 5 Baths

  8305 S Throop St, Chicago, IL 60620

  If you know you KNOW, Auburn Gresham is EVOLVING! Owner-Occupant or Investor Opportunity | 4 Unit + 1 more income producing basement unit that has two entrances! Solid brick 4 flat building featuring 9 bedrooms and 5 bathrooms, offering exceptional flexibility and income opportunity. Property is currently tenant-occupied; however, the 1st-floor unit will be delivered vacant at closing, creating

  Dana Jones Century 21 IMPACT

  8305 S Throop St, Chicago, IL 60620
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  /28

  $310,000

  • 5 Beds
  • 2 Baths

  4141 W Monroe St, Chicago, IL 60624

  Opportunity awaits in this spacious Chicago two-flat-ideal for an owner-occupant or investor looking to build equity and generate rental income. The first-floor unit offers 2 bedrooms and 1 bathroom and is ready for your renovation ideas. The updated second-floor unit features 3 bedrooms, 1 bathroom, attractive flooring, a spacious living and dining area, and a comfortable, move-in-ready layout.

  Luis Perez Realty of America, LLC

  4141 W Monroe St, Chicago, IL 60624
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  /9

  $479,900

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  2130 W Highland Ave, Chicago, IL 60659

  Opportunity awaits in this classic brick home offering a spacious and versatile layout with plenty of potential to make it your own. The interior features hardwood flooring, generous living and dining areas, a functional kitchen, multiple bedrooms, and additional basement space for storage, laundry, or future possibilities. Outside, the property offers a fenced yard with room for outdoor

  Christopher Lobrillo Grandview Realty, LLC

  2130 W Highland Ave, Chicago, IL 60659
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  /33

  $229,900

  Pending

  • 6 Beds
  • 3 Baths

  1 E 114th St, Chicago, IL 60628

  Welcome to your new home! This spacious brick corner-lot property offers plenty of room for a large family and is packed with updates and investment potential. The home features 6 generously sized bedrooms, 3 full bathrooms, and a dedicated office/study. Enjoy a comfortable living room with a fireplace, a beautifully updated kitchen with granite countertops and new stainless steel appliances, and

  Ola Sanni Century 21 S.G.R., Inc.

  1 E 114th St, Chicago, IL 60628
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  /16

  $124,900

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  5205 W Drummond Place Unit 1, Chicago, IL 60639

  This 600-square-foot condo offers 1 bedroom and 1 bathroom, featuring hardwood floors and a kitchen with granite countertops. The property includes desirable amenities such as an on-site fitness center, and coin-operated laundry facilities. With no rental cap, this unit presents a great investment opportunity for investors!

  Julianna Gil Gil & Gil Group Corp.

  5205 W Drummond Place Unit 1, Chicago, IL 60639
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  /20

  $325,000

  • 4 Beds
  • 2 Baths

  3425 W 63rd Place, Chicago, IL 60629

  TWO UNIT FRAME BUILDING IN GOOD CONDITION ! SOME UPDATING THROUGH OUT THE ENTIRE BUILDING NEWER TWO CAR GARAGE AND NEWER BRICK PATIO WITH BEAUTIFUL GARDEN ! EVERYTHING YOU NEED IS NEAR BY SCHOOLS, PUBLIC TRANSPORTATION, SHOPPING AND THE PARK. DON'T MISS THIS ONE GREAT INVESTMENT OPPORTUNITY !!

  Felicitas Gonzalez Century 21 Circle

  3425 W 63rd Place, Chicago, IL 60629
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  /13

  $210,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 969 Sq Ft

  2133 W 49th Place, Chicago, IL 60609

  Welcome to this charming and inviting ranch-style home, featuring 3 bedrooms, 2 full bathrooms, a full basement, and a detached 2-car garage. Original hardwood flooring that runs throughout the living room and all three bedrooms. The full basement provides valuable additional space, perfect for a recreation room or home office. Whether you are a first-time homebuyer or looking for an excellent

  Christine Medina Mathewson Coldwell Banker Realty

  2133 W 49th Place, Chicago, IL 60609
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  /13

  $1,125,000

  • 8,766 Sq Ft

  4723 S Vincennes Ave, Chicago, IL 60615

  4723-25 S. Vincennes Avenue is a six-unit plus one non- conforming multifamily investment opportunity located in the heart of Bronzeville, one of Chicago's most historic and rapidly evolving neighborhoods. Comprised of exceptionally large apartment layouts, the property features three 2-bedroom/1- bathroom units, three 3-bedroom + den/1-bathroom units, and one non-conforming garden unit

  Quinn Evans Essex 312, LLC

  4723 S Vincennes Ave, Chicago, IL 60615
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  /45

  $650,000

  Pending

  • 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
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  /16

  $489,000

  $11K PRICE DROP

  • 5 Beds
  • 4 Baths

  2341 N Merrimac Ave, Chicago, IL 60639

  Classic Chicago bungalow offering the versatility of a legal 2-unit plus a finished basement, providing exceptional flexibility for owner-occupants, multigenerational living, or investors alike. This home blends the timeless appeal of a classic Chicago bungalow with the practical layout of a multi-unit property. Each unit offers comfortable living space filled with natural light, while the

  Corina Flores-Moradi Re/Max Cityview

  2341 N Merrimac Ave, Chicago, IL 60639
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  /9

  $69,990

  $9K PRICE DROP

  • 7 Beds
  • 3 Baths

  7137 S Carpenter St, Chicago, IL 60621

  GREYSTONE TWO UNIT ready for rehab. Two bedroom apartment previously in the basement. First floor 2 bedroom and second floor 3 bedroom. Property in need a lot of work, but will be a good investment/flip. Sold as is. No survey provided.

  David Williamson Choice Realty Group Inc.

  7137 S Carpenter St, Chicago, IL 60621
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  /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
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  /26

  $490,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  2935 W Howard St, Chicago, IL 60645

  Solid 3-bed, 2-bath West Ridge home with a full finished basement featuring a bonus room, second kitchen, and second full bath-perfect for related living! Outside features a concrete parking slab for 2 cars. Currently tenant-occupied on a month-to-month lease paying $2,500/mo. Tenant wishes to stay, making this a seamless turn-key investment or a great home for owner occupants. Excellent location

  Elyahu Herszberg Kale Realty

  2935 W Howard St, Chicago, IL 60645
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  /2

  $9,999

  • Land
  • 0 Sq Ft

  7354 S Marshfield Ave, Chicago, IL 60636

  Development Opportunity in West Englewood! This location is ideal for those seeking a strategic investment in a rapidly developing area. A mix of modern and newly renovated homes, with continued growth in the area. The Chicago neighborhood is seeing increasing development and revitalization, making this an excellent opportunity to invest in an area with great potential for future appreciation.

  Chanee Roby Coldwell Banker Real Estate Group

  7354 S Marshfield Ave, Chicago, IL 60636
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  /14

  $199,000

  Pending

  • 5 Beds
  • 2 Baths

  11633 S Parnell Ave, Chicago, IL 60628

  Fully occupied 2-flat ready for a new owner. This property generates $3,350/mo in total monthly rents and offers multiple investment strategies: buy-and-hold, value add, or owner occupy / house hack. Both units feature hardwood floors, spacious living/dining areas and functional layouts. A full unfinished basement provides expansion potential, plus a detached 2-car garage. Conveniently located

  Michael Scanlon eXp Realty

  11633 S Parnell Ave, Chicago, IL 60628
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  /22

  $575,000

  Open Sun 1PM - 4PM $75K PRICE DROP

  • 7 Beds
  • 2 Baths

  4339 S Indiana Ave, Chicago, IL 60653

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

  Henry Torn ListWithFreedom.com

  4339 S Indiana Ave, Chicago, IL 60653
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  /20

  $120,000

  • 3 Beds
  • 1 Bath
  • 722 Sq Ft

  3921 W Huron St Unit 5, Chicago, IL 60624

  Whether you're looking for an affordable place to call home or a smart investment opportunity, this updated 3-bedroom condo is worth a look! The bright, functional layout features hardwood floors, abundant natural light, French doors, and an updated kitchen with stainless steel appliances. Enjoy a private balcony, a rear deck, and the convenience of an assigned parking space. Offering a great

  Donald Capshaw Fulton Grace Realty

  3921 W Huron St Unit 5, Chicago, IL 60624
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  /2

  $9,999

  • Land
  • 0 Sq Ft

  7316 S Marshfield Ave, Chicago, IL 60636

  Development Opportunity in West Englewood! This location is ideal for those seeking a strategic investment in a rapidly developing area. A mix of modern and newly renovated homes, with continued growth in the area. The Chicago neighborhood is seeing increasing development and revitalization, making this an excellent opportunity to invest in an area with great potential for future appreciation.

  Chanee Roby Coldwell Banker Real Estate Group

  7316 S Marshfield Ave, Chicago, IL 60636
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  /36

  $450,000

  Pending

  • 5 Beds
  • 3 Baths

  3014 W Walnut St, Chicago, IL 60612

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

  Scott Newman Keller Williams ONEChicago

  3014 W Walnut St, Chicago, IL 60612
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  /47

  $549,900

  Pending

  • 5 Beds
  • 3 Baths

  4823 W Grace St, Chicago, IL 60641

  ** Multiple Offers ** Highest & Best due Tuesday @ 8pm *** Your Portage Park investment is ready for you to call home sweet home as you collect the rents or keep as the perfect arm chair investment! Don't miss your opportunity to invest in this well maintained legal 2 unit plus in-law near 6 corners! 1-2 blocks away! Nice size units with tall ceilings. 1st floor unit is spacious and bright with 2

  Antonio Sarmiento 606 Brokers LLC

  4823 W Grace St, Chicago, IL 60641
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  /3

  $10,000

  $5K PRICE DROP

  • Land
  • 0 Sq Ft

  6507 S Marshfield Ave, Chicago, IL 60636

  Attention builders, developers, and investors! Fantastic opportunity to acquire this 25x123 lot zoned RS-3 in an area experiencing continued residential growth and redevelopment. Perfect opportunity for new construction or long-term investment potential. Conveniently located near schools, parks, public transportation, shopping, and major roadways.Drive by and explore the possibilities this

  Christopher Anthony Keller Williams ONEChicago

  6507 S Marshfield Ave, Chicago, IL 60636
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  /2

  $659,000

  $90K PRICE INCREASE

  • Land
  • 0 Sq Ft

  2613-2633 N Cicero Ave, Chicago, IL 60641

  On a busy Cicero Aveneue between Diversy and Fullerton, this 9,375 square foot parcel is available for sale. The land could be developed for a wide variety of retail uses. The site has low taxes for the area with substantial frontage on Cicero Avenue with easy access to bustling Six Corners. Great opportunity for a user or developer. The Belmont Cragin community has benefited from steady growth

  Daniel Hyman Millennium Properties RE, Inc.

  2613-2633 N Cicero Ave, Chicago, IL 60641
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  /28

  $559,900

  Pending

  • 7 Beds
  • 4 Baths

  2924 S Princeton Ave, Chicago, IL 60616

  Prime investment opportunity in Chicago's sought-after south-side corridor. This well-maintained 4-unit building at 2924 S Princeton Ave offers strong cash flow with upside, just minutes away from vibrant neighborhoods, transit, and everyday conveniences. The property comprises four spacious units totaling 7 bedrooms, 4 bathrooms, and a detached 2.5 car garage. Brick exterior, solid mechanicals,

  Bernardo Casas Duarte Realty Company

  2924 S Princeton Ave, Chicago, IL 60616
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  /44

  $335,000

  Pending

  • 5 Beds
  • 2 Baths

  4912 W Fulton St, Chicago, IL 60644

  Great investment opportunity in the Austin neighborhood! This property needs some TLC and offers strong potential for renovation, rental income, or value-add investment. Buyer and buyer's agent to conduct their own due diligence prior to submitting an offer. Located on Chicago's West Side, the property has convenient access to public transit (CTA Green Line & buses), parks and recreation nearby

  Karolina Bak KOMAR

  4912 W Fulton St, Chicago, IL 60644
• 

  

  /3

  $679,000

  • Land
  • 0 Sq Ft

  7216 N Western Ave, Chicago, IL 60645

  Prime commercial vacant land investment and development opportunity on Western Ave, just north of Touhy Ave., on the west side of the street in Chicago's West Ridge/Rogers Park area. between Touhy Ave. and Howard St. approximately 7,400 Sq. ft., positioned along a major commercial corridor with high daily traffic, the property offers excellent visibility and convenient access to surrounding

  Mark Ahmad Century 21 Circle

  7216 N Western Ave, Chicago, IL 60645
• 

  

  /40

  $439,000

  Pending

  • 6 Beds
  • 3 Baths

  3005 S Pulaski Rd, Chicago, IL 60623

  Excellent opportunity to own this updated multi-unit property in a prime location and lots of updates! The building features two, 2-bedroom units, each offering a comfortable layout with bright living areas, eat-in kitchens, and generous room sizes. The garden level offers additional living space with 2 bedrooms. Newer flooring, utilities including a brand new central HVAC system, brand new

  Maggie Antillon Realty of America, LLC

  3005 S Pulaski Rd, Chicago, IL 60623

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