Courtesy: Baird & Warner
312-242-1000
Exceptional investment opportunity in the heart of Logan Square! Situated on charming tree-lined Lyndale Street, this legal three-unit building offers the perfect blend of classic Chicago character and modern functionality in one of the city's most sought-after and rapidly growing neighborhoods. Just a short walk to Logan Boulevard, the Blue Line, parks, and a vibrant mix of restaurants, cafes, and nightlife. Two units features 3 bedrooms and 1 full bathroom & 1 unit 2 bedrooms and 1 full bathroom making the property ideal for both investors and owner-occupants. Updated kitchens and bathrooms complement the building's original charm, while three separate HVAC systems (gas forced heat and central air) provide comfort and efficiency for every unit. The first-floor apartment has been successfully operated as a longer-term Airbnb-style rental catering to working professionals. All indoor and outdoor furnishings shown are included, allowing a buyer to seamlessly continue this proven income model. The remaining units are unfurnished and well-suited for traditional long-term tenants, offering flexible rental strategies and strong income potential. Additional highlights include expansive rear decks, common area laundry in the lower level, and two exterior storage units located beneath the rear stairwells. The rear yard features a full concrete pad, pitched and engineered to support the future addition of an upper garage structure, along with an existing gated parking area accommodating two cars. The rental potential for the three units and parking is approximately $8,500-9,000 per month. Meticulously maintained and thoughtfully improved, this property delivers outstanding comfort, functionality, and long-term value - a rare turnkey multi-unit opportunity in one of Chicago's hottest neighborhoods. Unit 2 currently rented for $3,500 per month & unit 3 for $3,100 per month.
Courtesy: Pearson Realty Group
773-325-2800
NEW PRICE. Rare turnkey opportunity for an operator or investor seeking a fully renovated, PPA-licensed venue with uncommitted VGT potential in a prime Chicago corridor - includes Real Estate, Business, and Assets. Unlike standard restaurant offerings, this 4,055 SF freestanding corner asset includes a rare Public Place of Amusement (PPA), Liquor, and Food license, enabling the owner to collect cover charges or donations for ticketed events, raffles, live music, comedy, and more - creating multiple high-margin revenue streams beyond traditional food and beverage. The VGT-ready game room is currently uncommitted to any gaming operator, giving a new owner full leverage to negotiate their own terminal operator agreement and signing incentives. The restaurant was fully gut-rehabbed in late 2024, offering a new dining & bar space that seats 95 and a brand-new fully equipped commercial kitchen featuring pizza ovens, extended range, stove, prep areas, a walk-in cooler, and much more. The property functions as a clean, SBA-compliant operating shell primed for immediate occupancy - a true plug-and-play asset priced to bypass construction and permitting delays, minimize capital requirements, and facilitate a seamless acquisition of all existing licenses and FF&E. Situated on a 0.16-acre lot, the property features a 3,125 SF main level, a dedicated +15-car parking lot with ample street parking, and a 930 SF 3-bedroom residential unit for additional income. The site offers prime frontage on Irving Park Road near Harlem Avenue and the Harlem-Irving Plaza (HIP), capturing high visibility from over 26,000 vehicles per day (VPD) within a densely populated residential corridor. Contact Listing Agent for showings and details.
Courtesy: Equity Market Realty Inc.
773-743-7700
Brick 4 unit in Hot Humboldt Park location fully rehabbed in 2015. Rehab included new copper plumbing, new HVAC systems, new electrical systems, separate water tanks, new roof and tuck pointing. All work done with plans and permits. All 2 bedroom units consist of stainless steel appliances, granite countertops and hardwood floors. Private parking spaces, laundry room and storage space. 4th unit used to be a commercial space years ago. Very well maintained building with professional management.
Courtesy: Real Broker LLC
217-960-8605
BIG PRICE IMPROVEMENT With this Great looking Old Irving Park (3 Unit) Multi-family! ((POTENTIAL FOR OVER 50K IN INCOME PER YEAR!)) The property is a legal 2 flat for disclosure purposes but lives and breathes like a (3 unit). The property consists of the 1st and 2nd floor being (2) bed (1) bath units and the attic is a one bed one bath unit. The basement has one large storage area and two private storage units that can be locked off. The property is located on a beautiful and quiet Tree Line Street. The building has been updated with Hardwood Floors, Laminate Floors, Stainless Steel Appliances and Updated Kitchens. There is some VALUE ADD if you wanted to ADD dishwashers to each of the units and install AC units for the first and second floors. Currently the first and second floors have HVAC, furnaces but no AC units. The attic unit has a Furnace and AC for that space. All (3) units have electric and gas that are separated out for each unit. ((ALL UTILITIES ARE SEPERATE FOR EACH UNIT)) There is a privacy fence that goes all around the entire yard. The building currently has two long-term tenants on the second floor and attic and the first floor is currently vacant. This would make for a perfect opportunity for someone to purchase the property and live in the first floor and collect rent from the other two. Super easy street parking although you are landlocked and there is NO garage. The property is super close to Kilbourne park, shopping, restaurants, public transportation and super quick access to the highway.
Courtesy: Pearson Realty Group
773-325-2800
This solid all-brick two-flat is a rare find-perfect for savvy investors or owner-occupants seeking rental income! Each spacious unit features 2 bedrooms and 1 bath, complemented by newer windows that enhance energy efficiency and curb appeal. The property includes a detached 2-car garage and a full basement offering additional storage or expansion potential.
Courtesy: Re/Max Cityview
773-631-8260
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 finished basement adds valuable space for recreation, a home office or storage. Ideally located with convenient access to the multiple CTA bus routes, and the Kennedy Expressway (I-90/94), commuting throughout the city is simple. Enjoy nearby neighborhood favorites including Riis Park, along with a growing collection of local restaurants, coffee shops, breweries, and boutiques that continue to make this area one of Chicago's most desirable neighborhoods. Whether you're looking for rental income, or expand your investment portfolio, this well-located property presents an outstanding opportunity in a thriving Chicago community.
Courtesy: EXIT Strategy Realty
312-554-5478
Excellent investment or owner-occupant opportunity! This solid brick 3-unit property offers immediate income with two occupied units generating $1,528 and $1,620 per month, while the third unit is vacant and ready for a new tenant or perfect for house hacking. The property also features a detached brick garage, generous outdoor space, and is conveniently located near the Cottage Grove shopping plaza, restaurants, public transportation, and everyday amenities. Whether you're looking to expand your portfolio or this property offers strong cash flow potential in a convenient South Side location. Outside pictures may be slightly enhanced! Schedule your private showing today!
Courtesy: @properties Christie's International Real Estate
773-472-0200
Move right into this beautifully updated East Woodlawn two-unit offering the perfect blend of immediate income potential and comfortable owner-occupancy. The spacious first-floor duplex features 4 bedrooms, 2 full baths, two separate living areas, an updated kitchen with stainless steel appliances and a dishwasher, private laundry with storage, and a private entrance-ideal for related living, guests, or a short-term rental opportunity. Two of the bedrooms easily accommodate king-size beds with nightstands. The second-floor simplex offers 3 bedrooms, 1 bath, an L-shaped kitchen, in-unit laundry, and a spacious primary bedroom that comfortably fits a king-size bed. A rare find in Chicago multifamily homes, each unit has separate utilities, generous closets, and individual laundry. Step outside to enjoy a spacious rear deck, backyard, and a 2-car brick garage. Live in one unit and rent the other, or add a turnkey investment to your portfolio. Ideally located just minutes from the University of Chicago, the Obama Presidential Center, Jackson Park, Lake Michigan, public transportation, neighborhood restaurants, coffee shops, and the vibrant Hyde Park corridor. Surrounded by historic architecture, tree-lined streets, and ongoing redevelopment, this property is perfectly positioned for long-term appreciation in one of Chicago's most sought-after investment neighborhoods. Whether you're an investor seeking strong cash flow or an owner-occupant looking to offset your mortgage with rental income, this is an exceptional opportunity in the heart of Woodlawn.
Courtesy: Realty of America, LLC
708-788-1900
Don't miss out on this SOLID BRICK 4-UNIT in the heart of LITTLE VILLAGE, an area known for its STRONG RENTAL DEMAND and CONSISTENT TENANT POOL! This CASH-FLOWING property features a SPACIOUS 3-BEDROOM UNIT with a RECENTLY UPDATED BATHROOM, offering modern comfort and added appeal. The three additional units each feature 2 BEDROOMS and 1 BATHROOM, providing excellent RENTAL POTENTIAL. The property also includes an UNFINISHED BASEMENT for TENANT STORAGE and a 2-CAR GARAGE with RECENTLY REPLACED SIDING. Conveniently located near I-55, the CTA PINK LINE, and MULTIPLE BUS ROUTES, this property offers EASY ACCESS for COMMUTERS, STUDENTS, and EVERYDAY RENTERS. Whether you're looking to GROW YOUR PORTFOLIO or purchase your FIRST INVESTMENT PROPERTY, this is a fantastic opportunity to own a TURNKEY, INCOME-PRODUCING property with STRONG CASH FLOW and LONG-TERM UPSIDE!
Courtesy: Keller Williams Preferred Rlty
708-798-1111
Excellent investment opportunity! This well-maintained, three-unit building was constructed in 2007. Each unit offers 3 bedrooms and 2 full bathrooms with a master suite. Units 1 and 2 are currently occupied by month-to-month tenants, Unit 3 is vacant features stainless steel appliances, including a stove, refrigerator, dishwasher, and microwave, to be installed before closing. Each tenant pays their own gas and electric,. The owner pays for water and trash. The roof and exterior are maintained annually. A great opportunity for an investor or owner-occupant!
Courtesy: @properties Christie's International Real Estate
312-254-0200
Don't miss this beautifully renovated all-brick 4-unit building in Chicago's desirable Chatham neighborhood. Extensively rehabbed over the past two years, this income-producing property offers the perfect combination of modern updates and long-term value. Each unit has been thoughtfully updated and features brand-new appliances, while major mechanical improvements include new furnaces and new water heaters, providing peace of mind for years to come. The roof is approximately 10 years old, further minimizing future maintenance expenses. Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the others, this property is truly move-in ready. Conveniently located near public transportation, shopping, schools, parks, and major expressways, this is an exceptional opportunity to own a low-maintenance multifamily asset in one of Chicago's established South Side neighborhoods. Schedule your private showing today and discover the potential this turnkey property has to offer! Similar units have rented in the area from $1050 to $1150 per month.
Courtesy: Century 21 Circle
847-336-7333
Two unit frame stucco building. Two car garage with patio. Open exterior wood rear porch,
Courtesy: Chicagoland Brokers, Inc.
773-745-1000
Fantastic investment opportunity in the desirable Jefferson Park neighborhood-a well-maintained and updated 2-flat that offers both turnkey investment potential and the option for owner-occupancy. Each unit features 2 bedrooms and 1 bathroom, complemented by beautiful hardwood floors, central HVAC, and a bonus back porch. The main floor unit boasts modern upgrades, including stainless steel appliances, maple cabinetry, and new light fixtures. Both units have separate utilities, ensuring convenience and privacy. The unfinished lower level provides dedicated laundry spaces, mechanical systems, and open storage for each unit. Additionally, there is a detached 2.5 garage currently leased to a neighbor, adding extra income potential. Situated on a quiet, tree-lined street, this property is within walking distance to the Gladstone Park Metra station, offers quick highway access, and is close to schools, parks, restaurants, and shopping. Current tenant leases expire in December 2026 and June 2027.
Courtesy: Safe Harbor Realty LLC
312-337-7384
Fully rehabbed and rented. Excellent investment property. Rent Roll attached and T-12 income statement. Please email listing agent if you are attending. Two CHA tenants and one market. Building is legal 2 unit with one non-conforming unit. Seller may apply to legalize unit under ADU ordinance. Only one unit will be shown on one scheduled day, next showing date to be scheduled week of 8.24 and posted here. Please note that property is not suitable for owner occupant buyer with FHA or VA loans due to tenants rights. Current owner will not vacate any units therefore any 90 day occupancy requirement not feasible.
Courtesy: ExaRealty LLC
312-525-0910
Exceptional opportunity to own a solid four-unit building in the heart of Chicago's vibrant Back of the Yards neighborhood. Whether you're an investor seeking strong income potential or an owner-occupant looking to live in one unit while the other three help pay your mortgage, this property offers incredible value and long-term upside. Each of the four units features two bedrooms, one full bathroom, comfortable living areas, and layouts designed for everyday living. Additional highlights include a walk-up attic with a washer and dryer, a two-car garage, and excellent storage space. Ideally located at 4318 S. Hermitage Ave., this property is just minutes from Downtown Chicago with easy access to I-90/94, I-55, CTA bus routes, and the Orange Line. Enjoy being close to UIC, Pilsen, Chinatown, Guaranteed Rate Field, McKinley Park, schools, shopping, restaurants, and countless neighborhood amenities. This is a rare opportunity to own a versatile, income-producing property in a location with strong rental demand and continued growth. Whether you're expanding your investment portfolio or purchasing your first multifamily property, this one checks all the boxes. Don't miss your chance to secure this outstanding investment-schedule your private showing today!
Courtesy: ExaRealty LLC
312-525-0910
Rare opportunity to own a spacious 2-unit building with incredible income potential in a prime Chicago location ON A HUGE TRIPLE LOT! First time on the market in over a decade, this well-maintained property is perfect for investors or owner-occupants looking to build generational wealth. The first-floor unit offers 2 bedrooms and 1 bathroom, while the second-floor unit features 3 bedrooms and 1 bathroom, both with spacious living rooms, dining rooms, and functional kitchens designed for comfortable living. Ideal opportunity to live in one unit while collecting rental income from the other, or maximize cash flow by renting both units. Conveniently located across from the schools, parks, public transportation, shopping, dining, and entertainment with everything you need just minutes away. Properties with this much space, flexibility, and investment potential do not come around often. Add this gem to your portfolio and secure your future today-schedule your showing before it's gone!
Courtesy: Mayorga Realty Inc
773-434-0903
***COME SEE THIS 2 UNIT BUILDING*** FEATURES RELATED LIVING HAS LOTS OF SPACE*** 2 CAR GARAGE*** NEEDS SOME TLC*** READY FOR ALL YOUR WONDERFUL IDEAS*** SOLD AS-IS!!!
Courtesy: Century 21 S.G.R., Inc.
312-326-2121
Investor opportunity! Solid-brick multi-family building featuring 2 oversized residential units, an occupied income-producing garden apartment, detached 2-car garage, separate utilities, and a full basement with exterior access. Offering significant value-add potential, this property is ideal for investors seeking a rehab project, BRRRR strategy, long-term hold, or owner-occupants looking to build equity while generating rental income. Spacious floorplans, classic Chicago architecture, and multiple exit strategies make this an outstanding investment opportunity. Buyer information package available with estimated renovation costs, projected market rents, ARV analysis, and investment highlights. Property is being sold "as-is."
Courtesy: Keller Williams Premiere Properties
630-545-9860
Two unit brick building on a spacious corner double lot! 2 car garage with driveway. Each unit has 2 bedrooms, 1 bathroom with hardwood floors and central HVAC. The building has a finished attic in-law arrangement with a kitchenette, 1 bedroom and 1 bathroom. Property needs work!! sold AS IS. Cash or Hard-money only, this is a Short Sale.
Courtesy: @properties Christie's International Real Estate
312-682-8500
Exceptional legal 3-unit greystone in the heart of rapidly growing Woodlawn! This beautifully updated investment property features two spacious 2-bedroom units, each with a bonus room ideal for a home office, den, or flex space, plus a large 1-bedroom garden unit. Additional highlights include on-site coin laundry, a 2-car garage, and a finished enclosed porch. Ideally located just minutes from the Obama Presidential Center, the University of Chicago and public transportation. Perfect for an owner-occupant looking to house hack or an investor seeking a strong addition to their portfolio. Don't miss this outstanding cash flowing opportunity in one of Chicago's most dynamic neighborhoods!
Courtesy: RE/MAX LOYALTY
773-772-6969
Don't miss this excellent opportunity to own a 3-unit property in the heart of Brighton Park! The building features a 2-bedroom, 1-bath unit on the first floor and a 2-bedroom, 1-bath unit on the second floor. Recent improvements include updated electrical work, a newer furnace, a newer hot water tank, and a renovated second-floor kitchen.The first-floor unit still needs finishing touches, great candidate for an FHA 203(k) Renovation Loan.Currently generating rental income of $1,400 per month, offering immediate cash flow.Additional features include a 2-car garage and a fantastic location just four houses from the neighborhood park and only a few blocks from Kelly High School. Enjoy convenient access to I-55, public transportation, shopping, restaurants, gyms, and other everyday amenities.
Courtesy: Coldwell Banker Realty
847-724-5800
ALL BRICK 2-FLAT WITH A GARDEN UNIT AND HUGE FENCED IN YARD. 1ST AND 2ND FLOOR HAVE IDENTICAL LAYOUTS WITH HARDWOOD FLOORS THROUGH-OUT WITH SEPARATE LIVING ROOM, DINING ROOM AND 3 LARGE BEDROOMS, UPDATED 1.1 BATHS, EAT-IN KITCHEN WITH SHAKER WHITE CABINETRY, STAINLESS STEEL APPLIANCES. BASEMENT COMES WITH 2 BEDS, 1 BATHROOM, CHERRY RED CABINETRY AND STAINLESS-STEEL APPLIANCES. ENTIRE BUILDING HAS FORCED AIR AND HEAT. UPDATES IN 2026 INCLUDE NEW ROOF, FULL EXTERIOR PAINT AND INTERIOR PAINT, BUILDING EXTERIOR DOORS, ENTIRE BUILDING HAS NEW FLOORS, APT 1 AND APT 2 NEW BATHS, NEW KITCHEN, ALL NEW LIGHT FIXTURES, DUCT CLEANING, DECK PAINTED, BASEMENT KITCHEN UPGRADED
Courtesy: xr realty
773-234-8155
Beautiful, Legal 2 Flat with in-law arrangement in the heart of Jefferson Park. Excellent building includes top floor unit 2 Bed 1 Bath. First floor unit 2 Bed 1 Bath and in-law down for an additional Bed and Bath. Bright open units each equipped with private rear porches. Pictures only reflect second floor unit but first floor is even bigger and more updated. Long time owner, solid and well maintained building. Excellent locations, located on a quiet street close to restaurants, shopping, parks, schools, train and highway! This home has it all! Don't miss out! HURRY!!
Courtesy: Compass
312-206-3787
Prime Bucktown Renovation or Conversion Opportunity!Seize a rare chance to own a possible 3-unit building or keep as single family this home sits on a spacious 23x125 lot in the heart of Bucktown. Zoned RT-4, this 1919 classic boasts 5 bedrooms (including a studio garden unit), 3 full baths, and an all-brick 1.5-car garage, and a huge backyard space. Sold AS-IS as this is an Estate Sale. This is the ultimate canvas for a complete modern rehab or a spectacular single-family home conversion. Unmatched Walkability & Local Amenities: Transit: Steps to the Clybourn Metra station, Damen/Western Blue Line CTA, and minutes to I-90/94. Parks & Play: Easy access to the elevated 606 Trail and the swimming pool/sports courts at Holstein Park. Enjoy Bucktown's vibrant lifestyle with renowned dining, craft coffee houses, and boutique retail right outside your door. Bring your contractor and design ideas! The Zoning is RT-4 and single-family conversion potential draws in premium buyers who want custom homes, not just multi-unit investors.Transit Trifecta, Explicitly mentions Clybourn Metra, Blue Line, and Highway access.Bucktown Icons:The 606 Trail and Holstein Park
Courtesy: Redfin Corporation
312-836-4263
Discover this promising legal 3-unit building located in the vibrant Humboldt Park neighborhood. Each of the three units features two bedrooms and one bathroom, with the first and second-floor residences offering separate living rooms, dining rooms, and kitchens. Tenants enjoy individual control over their own boilers and water heaters, and the second-floor boiler was recently replaced in 2025. The property includes a shared common area with free laundry facilities, a large backyard, and a 1.5-car garage. While the roof is estimated to be 15-20 years old and most appliances are original, the first-floor stove and range were updated in 2025. Currently, all tenants are on month-to-month leases, providing flexibility for new ownership. Situated in the northwest corner of Humboldt Park, residents are just a short drive from the park's extensive amenities, including tennis courts, the beach and lagoon, the National Museum of Puerto Rican Arts & Culture, and various sports fields, while also benefiting from proximity to local grocery options, public transportation, and popular dining spots.
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.
