Courtesy: Keller Williams ONEChicago
312-216-2422
City-certified two-flat in the heart of Gladstone Park offering exceptional flexibility for investors, owner-occupants, or multi-generational living. Thoughtfully updated over the years, this well-maintained property features remodeled kitchens and bathrooms on both the first and second floors, along with an updated first-floor primary bedroom. Each unit offers comfortable living space, while the second-floor apartment features two private entrances and an expanded rear deck overlooking the beautifully landscaped yard. A partially finished basement includes an in-law suite, providing additional flexible living space. Outside, you'll find a true urban oasis with raised garden beds, fruit trees, a patio, and mature landscaping that creates a private retreat. The insulated 2.5-car garage was fully rehabbed in 2023 and offers excellent storage or workshop potential. Additional improvements include newer windows, hardwood floors, and numerous updates throughout. Interior stairs connecting the first and second floors remain behind the dining room wall, offering the potential for a future single-family conversion if desired. This versatile property combines income potential, beautifully maintained outdoor space, and a prime Gladstone Park location. Property is being sold As-Is.
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: 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: Raider Realty LLC.
847-347-3293
Vintage two flat, with spacious duplex apartments. Located in booming Avondale, with new construction, residential and commercial development all around. Convenient location, offers easy access to downtown, O'Hare, Logan Square and beyond via the Blue Line and highway. Rents are below market value, representing long tenants. Please note: 1) Property As-Is. 2) Exterior and interior dimensions and square footage are estimates. 3) Property is within the jurisdiction of the Northwest Side Preservation Ordinance; tenants may exercise the right of first refusal. 4) Trust Owner Property. 5) Best and final offer on or before 7-28-2026.
Courtesy: Keller Williams Infinity
630-778-5800
Exceptional, fully leased legal 3-unit brick building in hot West Town near Fulton Market, situated on a peaceful, tree-lined block. Offers over 3,650 sq ft of above-grade living space plus an expansive finished basement. Perfect for turn-key investors or owner-occupants. Unit 1 is a massive 3BR/3BA duplex down. Units 2 & 3 feature identical, spacious 3BR/2BA layouts. All units boast in-unit W/D, sun-drenched living spaces, private rear decks, hardwood floors, updated kitchens/baths, fireplaces, plus recent furnaces, A/C units, and tankless water heaters. Secure perimeter fencing with electronic lock door. Fully leased with a strong day-one cash flow of almost $10k/month and stable leases at below-market rents. Massive upside to transition to market rates in 2027. Built in 1993, it features copper plumbing, high grade electrical systems, panels, and a modern architectural layout. Newer Roof (2022) Ultra-low owner overhead: tenants pay separate utilities via individual gas/electric meters and dedicated HVAC systems. Rear 3-car parking footprint offers prime value-add potential: monetize for monthly revenue with lease renewals, build a private 2-car garage, or construct a coach house/ADU for a lucrative fourth income stream (buyer to verify zoning/ADU compliance with the City). Unmatched location central to major upcoming neighborhood developments: Bally's Casino (0.6mi), Fulton Market Expansion (0.5mi), $7B United Center Expansion (2mi), and Grand/Chicago Ave commercial upgrades (0.3mi). A commuter's dream with effortless access to the city and suburbs: 5-min walk to CTA train, 2-min walk to bus, 0.4 mi to I-90, and 1.2 mi to I-290. Minutes from world-class Michelin-starred dining, trendy cocktail lounges, vibrant nightlife, and premier sports hubs. Walking distance to reputed Noble Charter Golder College Prep school.
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: 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: 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: 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: @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: Keller Williams Premiere Properties
630-545-9860
Exceptional investment opportunity in Chicago's desirable South Shore neighborhood! This jumbo 3-flat features spacious, move-in-ready units with similar layouts, each offering 3 bedrooms, 2 full baths - including a primary suite with private ensuite bath - hardwood floors, formal dining room, and a bright living room with classic bay window. A defined foyer entry, walk-in pantry space, and generous room sizes throughout add to the appeal. Ideally located near Lake Michigan, Rainbow Beach, South Shore Cultural Center, Jackson Park, and neighborhood parks, offering easy access to recreation and outdoor amenities. Close to shopping, dining, schools, and public transportation - including CTA bus routes and Metra Electric - for a quick commute to Hyde Park, the University of Chicago, and Downtown Chicago. Whether you're expanding your portfolio or planning to owner-occupy while collecting rental income from the remaining units, this well-maintained multi-unit building offers strong long-term potential in one of Chicago's historic lakefront communities. Don't miss this rare opportunity in a location that continues to attract both residents and investors.
Courtesy: Baird & Warner
773-775-1855
NORWOOD PARK Beautiful, well-maintained brick 2-flat with a STUNNING nonconforming garden apartment. The first and second floor units feature newer kitchens and baths, updated appliances and mechanicals, separate heating systems, spacious dining rooms, and breakfast nooks. Quiet residential location just a short distance from Rosedale Park and close to shopping, restaurants, public transportation, and expressways. Property taxes do not reflect any exemptions. Seller and broker make no representation as to the legality of the garden apartment. Strong rents and always on time tenants! A great opportunity for owner-occupants or investors. Seller nor broker make no representation as to the legality of the garden unit.
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: 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: 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: @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: RE/MAX Mi Casa
773-767-1616
Great opportunity in the North Lawndale area! This solid brick 2-flat offers a versatile layout ideal for both investors and owner-occupants. The property features two spacious units: 1st floor unit has 2-bedrooms, 1-bath, living room, kitchen, and laundry; 2nd floor unit has 3-bedroom, 1-bath, living room, kitchen, and laundry. Both units each with comfortable living space and functional layouts. Both units are vacant, making it easy to move forward with rental plans or owner occupancy. Each unit includes a kitchen equipped with stove, refrigerator, and microwave, and tenants pay their own gas and electric, helping to reduce operating expenses. The property also includes a full unfinished basement, offering potential for additional storage or future expansion. Conveniently located near major streets, public transportation, schools, and local amenities. A great opportunity to build equity and generate income in a growing area.**One of the LLC members is an Illinois licensed Realtor (Not Listing Brokers)**
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. Owner does not warranty that garden unit is conforming.
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: 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.
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.
