Courtesy: Serene Realty, Inc.
312-650-7940
Welcome to 9731 S Michigan Ave, a well-maintained three-unit property located in a highly sought-after South Side area of Rosemoor. This property offers an excellent owner-occupant or investment opportunity, with the ability to live in one unit while collecting rental income from the other two units. Well maintained and thoughtfully positioned, this property provides the flexibility of homeownership with the added benefit of income-producing units. Conveniently located near neighborhood amenities, Chicago State University, shopping, dining, transportation, and schools. This also a great opportunity to expand your investment portfolio. This property offers versatility and opportunity in a highly sought-after Chicago location.
Courtesy: Fulton Grace Realty
773-698-6648
Excellent investment opportunity in the heart of West Town! This fully occupied 4-unit property features two units in the front building and two additional units in the rear coach house. Each spacious unit offers a functional 2-bedroom layout, along with granite countertops, stainless steel appliances, generous room sizes, and convenient in-unit laundry. Ideally located near public transportation and surrounded by West Town's restaurants, shopping, and neighborhood amenities. With all four units currently occupied, the property offers immediate rental income while also presenting a great future opportunity for an owner-occupant looking to live on-site while generating income from the remaining units. A versatile addition to any investment portfolio in a highly desirable Chicago neighborhood.
Courtesy: Century 21 Circle
708-424-1199
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 !!
Courtesy: Coldwell Banker Realty
773-631-8300
Great opportunity to own a legal 3-unit corner building situated between Chicago's Hermosa and Humboldt Park neighborhoods. 1st floor and 2nd floor feature 2 bedrooms plus a den, providing additional flexible space for an office, sitting area, or other use. The property features separate gas and electric meters for each unit, along with individual central air conditioning and furnaces that are approximately 3 years old. The roof is approximately 6 years old. The ground-floor unit is only a few steps below grade and offers good ceiling height, with laundry hookups conveniently located nearby. Parking is a major plus with a 2-car garage, additional carport, and permit street parking. With three legal units, separate utilities, newer mechanicals, flexible layouts, and multiple parking options, this property is well suited for an investor or owner-occupant. Sold As-Is.
Courtesy: North Clybourn Group, Inc.
773-252-0600
Magazine Caliber Simply Stunning, Massive Expansive footprint, with 3 car garage New Construction 3 flat all 3 bedroom 2 baths set on over sized 152 deep lot. Exceptional, Elegant, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Full Back splash, Fireplace with Custom Mill Work and indirect Lighting, Mud Rooms, Wide Plank Engineered Flooring, Accent Wall Cohesive Design offering relief from ordinary, sequestered primary suite, lifestyles primary bathroom offer Opulent over sized Shower w/ Frame less Glass, & Custom Mirrors and designer plumbing fixtures. Professional closet organizers throughout, 3 car Garage. Urban Intimacy w/ Hyper Convenience Experience excellence. Veteran developers of 25 + years, 1 year warranty included. Hyper Convenient, AAA Trophy Piece Perfect Turn key, Owner Occupied, Investor or 1031.This is exceptional property and location. IMMEDIATE Delivery. Pictures are from actual project. Actual* Monthly Income $8950/ $105,000 Annual/7.5 CAP Move in ready Ask about preferred lender incentives *Unit 3 at value
Courtesy: North Clybourn Group, Inc.
773-252-0600
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 natural light. Hardwood floors, Modern Kitchens designed for entertaining with Gray shaker cabinets with quartz countertops, island, full backsplash, and stainless-steel appliances. All bedrooms generously sized to accommodate king sized beds and the bathrooms are finished in Carrera porcelains and brushed nickel. Thoughtful storage and walk-in closets throughout. Rear deck system and washer/dryer in each unit. 3 car Outdoor secured parking. Amazing location, very short walk to the Pink Line and 18th Street with all its vibrancy; Thalia Hall, Canton Regio, Brew Brew PLUS Harrison Park with tennis courts, full gym, indoor swimming pool soccer pitch and all Pilsen has to offer! Builder built for himself and spared no expense- top floor will be vacant at close, perfect for owner-occupant! Grss Annual Income $124,740. NOI $96,555. 6.2 Cap Rate
Courtesy: Serene Realty, Inc.
312-650-7940
Welcome to 9731 S Michigan Ave, a well-maintained three-unit property located in a highly sought-after South Side area of Rosemoor. This property offers an excellent owner-occupant or investment opportunity, with the ability to live in one unit while collecting rental income from the other two units. Well maintained and thoughtfully positioned, this property provides the flexibility of homeownership with the added benefit of income-producing units. Conveniently located near neighborhood amenities, Chicago State University, shopping, dining, transportation, and schools. This also a great opportunity to expand your investment portfolio. This property offers versatility and opportunity in a highly sought-after Chicago location. Property is being sold as-is.
Courtesy: @properties Christie's International Real Estate
708-971-0060
Exceptional investment opportunity in prime Loyola University location generating over $105,000 in annual rental income! This classic brick two-flat features two bright and spacious 3-bedroom, 1.5-bath apartments, plus a beautifully renovated 2-bedroom, 1-bath garden unit. The upper apartments offer generous room sizes, hardwood floors, abundant natural light, updated kitchens and baths, and charming front and rear sunrooms. The garden level was recently renovated with a modern kitchen, stainless-steel appliances, stylish bath, updated flooring, and recessed lighting. Fully rented with leases extending through May and June 2027. The building has a history of exceptional tenant demand with zero vacancy due to its proximity to Loyola University. Additional highlights include a two-car garage, flood-control system, new boiler and water heater, numerous capital improvements, and potential to add a fourth bedroom to the upper apartments for additional income. Ideally located near Loyola University, the Red Line, lakefront, restaurants, shopping and neighborhood conveniences. Garden unit is non-conforming; seller makes no representation regarding its legality. Licensed Illinois real estate broker has ownership interest in the property.
Courtesy: Golden Enterprise Realty Inc
773-523-8000
STRONG POSITIVE CASH FLOW IN THE HEART OF BACK OF THE YARDS Welcome to 4504 S Paulina St, a solid and well-maintained legal 3-unit building offering an excellent investment opportunity with positive cash flow. The property features three separate apartment units: First Floor Front Unit: Spacious apartment First Floor Rear Unit: Separate apartment Second Floor: Full-floor unit extending from front to rear All three units are legally configured as a 3-unit property. An additional benefit for investors is that tenants pay their own gas and electric, helping keep operating expenses lower and supporting strong cash flow. This is an excellent opportunity for an investor or owner occupant looking for a cash-flowing multifamily property in Back of the Yards, with multiple rental units and tenant-paid utilities. Property Highlights: Legal 3-unit building 2 units on the first floor 1 full-unit apartment on the second floor Positive cash flow Tenants pay gas and electric Strong investment opportunity Located in Back of the Yards
Courtesy: Coldwell Banker Realty
773-451-1200
Cool, affordable, and move-in ready, this exceptional two-flat offers a rare opportunity for both owner-occupants and investors alike. Both units are in excellent condition and ready for immediate occupancy, whether you're looking to live in one unit and generate rental income from the other or add a turnkey property to your portfolio. Ideally located just blocks from the 550-acre Jackson Park, featuring lakefront access, a golf course, harbor, and the Obama Presidential Center campus, this property also offers a short walk to Metra service for an easy commute. Each unit features 2 spacious bedrooms and 1 full bath, providing comfortable, efficient living with strong rental appeal. With its desirable location, move-in-ready condition, and attractive price point, this is an outstanding value you won't want to miss.
Courtesy: Essex 312, LLC
773-305-4858
2418 N Western Avenue is a well-configured four-unit property located in the heart of Bucktown. The property features three units in the front building plus a detached coach house in the rear, offering four separate 1-bedroom/1-bathroom units. Each unit is separately equipped with its own HVAC system, hot water tank, and electric panel. The property also features common-area laundry located in the basement of the rear coach house, along with one exterior parking space accessible from the alley. Rents are currently below market, providing meaningful upside for a new owner. The four units currently generate an average rent of $1,756 per month compared to an estimated market average of $2,300 per month. Unit 2F is currently in the process of moving out, creating an opportunity for an owner-occupant or investor seeking flexibility. Ideally situated at the convergence of Bucktown, Logan Square, and West Lakeview, 2418 N Western Avenue offers convenient access to the Western Blue Line station, expressway, and multiple bus routes. The property combines strong neighborhood connectivity with immediate rental upside and a flexible four-unit configuration.
Courtesy: Realty of America, LLC
708-788-1900
***** CASH OR RENOVATIONS LOANS ONLY ***** Approved Legal 3 unit!! Building consists of a total of 5 bedrooms and 3 bathrooms. On the first floor unit you will find an open concept kitchen/living room area along with 2 bedrooms, huge pantry, and 1 full bath.On the second level unit, you find another 2 bedrooms, 1 bath, with a full kitchen and living room. Downstairs in the ground unit you will find 1 huge bedroom, 1 full bath annd open layout kitchen/ living room Combined. Each unit has its own high efficiency furnace along with their own individual entrance and exits. There is an ample front yard, private balcony, and gated throughout! Located in highly incoming New city! Potential to earn 4K plus in monthly cash flow! LOW TAXES! PROPERTY WAS REHABBED IN 2022 WITH NEW KITCHENS, BATHROOMS, CENTRAL AIR SYSTEMS. Schedule your showing today! ***** CASH OR REHAB LOANS ONLY AS THERE ARE SOME CITY VIOLATIONS THAT WILL NEED TO GET ADRESSED*****
Courtesy: RE/MAX LOYALTY
773-772-6969
Classic brick 3-unit in the highly sought-after Heart of Chicago neighborhood of Pilsen, offering an exceptional opportunity for investors or owner-occupants. The property features two 2 bedroom, 1 bath apartments on the first floor, front and rear units, plus an expansive 5-bedroom, 2-bath top-floor residence with outstanding potential. The top-floor unit offers interior access to a large unfinished attic, creating an exciting opportunity to duplex up and add additional living space, value, and rental income. Both the top-floor apartment and rear first-floor unit are currently occupied. The unfinished basement offers even more potential, with roughed-in plumbing for a bathroom, rear egress, and a common laundry area. Situated in one of Pilsen's most vibrant areas. Surrounded by restaurants, cafes, and neighborhood favorites. Enjoy convenient access to the Pink Line and short drive to expressways.
Courtesy: Real Broker LLC
217-960-8605
BACK ON MARKET, NO FAULT OF SELLER! Previous buyer's financing fell through after they were unable to obtain their anticipated grant. Don't miss another opportunity to own this spacious brick 2-flat in Chicago's Chatham community. Offering 6 bedrooms and 2 full bathrooms, each unit features 3 bedrooms and 1 bath, making this a great option for an owner-occupant or investor. The finished basement provides additional flexible living and recreational space.The property has received numerous improvements in 2026, including a newly resealed roof (July 2026), fresh interior paint (July 2026), new bathroom sinks in both units (July 2026), front, side and rear tuckpointing, chimney tuckpointing and repairs, newly stained and sealed second-floor hardwood floors (March 2026), repaired and reinforced hallway stairs, water heater repairs with new hardware, plumbing repairs including resolution of basement leaks, and drywall repairs with fresh paint.Rear parking provides space for 2 vehicles. Conveniently located near public transportation, neighborhood schools, shopping and everyday amenities. The 79th Street Chatham Metra Electric station is nearby, providing rail service toward downtown Chicago, while neighborhood grocery options include ALDI. Schedule your showing today and take another look at everything this property has to offer!
Courtesy: eXp Realty
888-574-9405
Beautifully renovated brick two-flat in Greater Grand Crossing, fully rehabbed in 2026 with new major systems, updated kitchens and baths, and fresh finishes throughout. The first unit offers two bedrooms and two full bathrooms across the main and lower levels, plus a finished basement with two additional rooms. The second-floor unit features two bedrooms and one full bathroom. A great opportunity for investors looking to expand their portfolio or buyers who want rental income. Conveniently located near Hamilton Park, 75th Street bus service, the 79th Street Red Line and the Dan Ryan Expressway. Schedule your showing today!
Courtesy: Keller Williams Preferred Rlty
708-798-1111
Beautiful greystone multi-unit building in Chicago's Washington Park neighborhood. Plumbing, electrical and hvac rough- ins completed. Roof in good condition free of leaks. Floors 1 through 3 are designed to accommodate spacious 4-bedroom layouts. Plans approved. Bathtubs and shower bodies are installed on floors 1 through 3. Excavated basement features an approximately 7'6" ceiling height, four new columns, two replacement support beams, drain tile, and poured concrete. Proposed four-unit plans are available under Additional Information. An excellent opportunity for an investor or developer to complete this substantial renovation.
Courtesy: @properties Christie's International Real Estate
773-472-0200
Prime McKinley Park location overlooking the park. This clean, well-maintained, all-brick 2-flat offers an excellent opportunity for an owner-occupant, multigenerational household or investor seeking a solid property in one of McKinley Park's most desirable and convenient locations. The first-floor apartment features 2 bedrooms and 1 bath, while the second-floor apartment offers 3 bedrooms and 1 bath. Both apartments feature comfortable layouts and eat-in kitchens. The second-floor unit has been nicely updated with stainless steel appliances, forced-air furnace and central air conditioning. A full unfinished basement provides abundant storage and utility space. Outside, the property continues to deliver. A fenced rear yard provides valuable private green space for gardening, pets, outdoor entertaining or future landscaping enhancements. A concrete walkway leads to the all-brick detached 2-car garage with alley access, providing highly desirable off-street parking and additional storage potential. The location is truly the standout feature. Directly across from McKinley Park-an approximately 69-acre "oasis in the city"-residents can enjoy expansive green space, recreation and neighborhood amenities right outside their door. The property is also just one block from Archer Avenue and the Orange Line station, providing convenient access to public transportation, shopping, dining and downtown Chicago. A rare opportunity to own a well-maintained brick 2-flat with a 2-car garage in a prime park-facing location. Whether you're looking to live in one unit while generating rental income from the other or add a solid asset to your investment portfolio, this property offers an outstanding combination of location, flexibility and long-term potential. Building is in excellent condition and will be conveyed As-Is. Buyer pre-approval and disclosures to accompany offers.
Courtesy: A.R.E. Partners Inc.
312-300-7237
Great opportunity to own 2-unit property located in Chicago's Portage Park neighborhood minutes from Jefferson Park and Mayfair. Both units are currently occupied with leases in place through May 2027. Tenants pay electric and gas. Interiors feature vintage character, including woodwork and built-in hutches, with spacious kitchens and formal dining rooms. The property also includes enclosed back porch, unfinished basement with storage and laundry space, unfinished attic, and a detached two-car garage. Conveniently located less than a mile from two CTA Blue Line stations and the Jefferson Park Metra station, with easy access to I-90 and Milwaukee Avenue, shopping, dining, parks, and other neighborhood amenities.
Courtesy: Bloom/Sanchez Realty, Inc.
773-221-3244
Exceptional investment opportunity! Legal 4-unit building with an additional non-conforming owner suite unit, potentially offering 5 total income streams. Ideal for investors or owner-occupants seeking strong cash flow with value-added potential. This property has so much potential for overall income and cap rate. Property features a full unfinished basement, brick 4-car garage, and a concrete car pad secured by a wrought iron gate for additional parking or storage. Two adjacent lots included in the sale. The fenced in lots features an open green space-perfect for outdoor enjoyment today with long-term potential for development, expansion, or additional income opportunities. Ideally located just minutes from the Illinois Quantum and Microelectronics Park, positioning the property for long-term growth and increased demand. Sold as-is.
Courtesy: Century 21 S.G.R., Inc.
312-326-2121
Welcome to this 4-unit investment opportunity in prime Bridgeport! Oversized corner property with approximately 3,818 sq ft, 9 bedrooms, 5 bathrooms, 4 legal units plus a bonus unit. Flexible unit mix includes 1 three-bedroom, 2 two-bedroom, and 2 one-bedroom layouts - ideal for investors or owner-occupants looking to house-hack. Features include 10'+ ceilings, open-concept kitchens, private porches, 6 gas meters, 6 electric meters, and coin-operated laundry provides an additional source of income. Expansive unfinished basement, newer tear-off roof (about 5-6 years new), newer porch, some newer windows, and detached 2-car garage. Rents are currently below market, offering potential upside. Projected annual income of approximately $88,800. Conveniently located near I-55, Archer Ave, CTA Bus #62, Orange Line, Palmisano Park, Morgan and Halsted dining/entertainment, Cermak Produce, Mariano's, Chinatown, Downtown, Guaranteed Rate Field, lakefront, and more. Excellent opportunity to add a multi-unit property to your Bridgeport portfolio!
Courtesy: Extreme Realty LLC
773-875-2400
Turnkey investment opportunity! 3-unit building with extra-large apartments. 1st & 2nd floor units have hardwood floors. 2nd floor unit has washer & dryer hook-up. All units have separate utilities. Close to I-290 & Metra station. Units are currently rented MTM.
Courtesy: Realty of America, LLC
708-788-1900
Discover the potential of 7844 S Greenwood Ave, a spacious Chicago 2-flat in the Greater Grand Crossing area offering an ideal opportunity for owner-occupants, house hackers, and real estate investors looking for rental income, long-term appreciation, and value-add potential. Each unit offers 3 bedrooms and nearly 1,000 square feet of living space with bright, sun-filled living rooms, attractive flooring, and the convenience of in-unit laundry, creating a functional layout for both tenants and multi-generational living. Recent improvements add even more value, including a partially repaired roof in 2026, a rear deck replaced in 2026, replaced in 2026, and a basement furnace that is approximately one year old. Additional features include a private backyard, two dedicated exterior parking spaces, ample free street parking, and an unfinished basement with separate exterior access that provides useful storage and future value-add potential, subject to applicable zoning and permitting requirements. Commuters will appreciate the convenient location near the 79th St./Chatham Metra Electric station, CTA bus routes, I-90, and the Chicago Skyway, while nearby destinations such as Grand Crossing Park, the South Shore Cultural Center, the University of Chicago, local shopping, dining, and everyday neighborhood amenities add to the property's appeal. Whether you're searching for a Chicago 2-flat for sale, a Greater Grand Crossing multi-family home, an income-producing property, a house hacking opportunity, or a South Side Chicago investment property, 7844 S Greenwood Ave delivers a compelling combination of space, location, recent updates, rental potential, and future upside. Schedule your private showing today and explore everything this well-positioned Chicago multi-unit property has to offer.
Courtesy: Baird & Warner
773-549-1855
Vintage 2 flat with a finished basement. Property needs work but is livable. All units are vacant. 1st floor is a 2 bed 1bath with an updated kitchen and central air. 2nd floor is a large 1 bed 1 bath with forced air heat no AC. The basement is finished as an additional apartment but shares utilities with the 1st floor. Laundry in the basement. Building sits on an oversized lot with a nice yard and 2 car garage. Bring your fun renovations to this property.
Courtesy: Geary's Realty LLC
847-234-2040
Attention savvy buyers/investors-this 1908 brick two-flat has been waiting for the right owner. Real East Humboldt Park bones - two units (basement legal status not represented), 5BR/2BA legal, full basement, brick garage - steps from the 606 Trail and Wicker Park. Vacant, sold as-is. Receivership sale; contracts subject to court approval. Multiple offers received - highest and best due Monday September 28th by 5PM. Will submit to the court for approval the following day.
Courtesy: New Avenue Realty LLC
312-444-0981
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 includes 3 bedrooms and 1 bathroom. All utilities are separate, making this an investor's dream. Located directly across from Dvorak Elementary School and just minutes from the Pink Line and bus stop, this property is in a high-demand rental area. Easy access to the Medical District, Douglass Park, and shopping adds to its appeal. The property needs work and is being sold as-is, with no warranties or repairs. *Recent Roof** Agent-owned interest applies. Agents read broker private remarks. Don't miss this incredible investment opportunity! It will be Your Smartest Move!
Chicago is located in Illinois. Chicago, Illinois has a population of 2,742,119. Chicago is less family-centric than the surrounding county with 27.11% of the households containing married families with children. The county average for households married with children is 29.73%.
The median household income in Chicago, Illinois is $65,781. The median household income for the surrounding county is $72,121 compared to the national median of $69,021. The median age of people living in Chicago is 35.1 years.
The average high temperature in July is 83.9 degrees, with an average low temperature in January of 19.2 degrees. The average rainfall is approximately 38.2 inches per year, with 35.1 inches of snow per year.
