Courtesy: Keller Williams ONEChicago
312-216-2422
With its red brick facade and architectural cornice detailing, this classic Chicago two-flat has the character that makes these buildings so timeless. With one residence ready for its next chapter and another already generating income, it also offers the kind of flexibility that makes multi-unit ownership so appealing. Rehabbed in 2019, the property offers 7 bedrooms across two spacious residences, with hardwood floors, updated kitchens and baths, generous living spaces, and separate gas forced-air heat. The vacant first-floor residence features 3 bedrooms and 1 bath with separate living and dining rooms, a spacious kitchen, covered rear deck, and access to the full, partially finished basement. Upstairs, the 4-bedroom, 1-bath residence offers an expansive living and dining space and is currently leased, with the tenant paying gas, electric, and heat. Two off-alley parking spaces add everyday function and value. Ideally situated just blocks from Garfield Park and the Conservatory, with convenient access to public transportation and downtown. With the second floor already generating rental income, the next owner has the freedom to move right in and house hack or select their own tenant for the first floor and operate the property as an investment. This property can be purchased as a package with nearby buildings 5315 W Monroe (MLS#12748904); 4319 W Jackson (MLS#12749441) or purchased separately. MULTIPLE OFFERS RECEIVED - Highest & best Due by Tuesday 9/8 at 2PM
Courtesy: EXIT Strategy Realty
312-554-5478
Positioned in the heart of Chicago's historic Woodlawn neighborhood, this classic two flat presents an attractive opportunity for investors, owner occupants, and buyers seeking long-term value in an evolving South Side market. The property combines the enduring appeal of a traditional Chicago multifamily with multiple avenues to enhance income, improve value, and build equity. The building features two residential units: a 2 bed /1 bath first floor unit and a 3 bed /1 bath second floor unit. Both apartments offer generous living areas, abundant natural light, high ceilings, and the architectural character associated with Chicago's classic two flats. A full basement provides valuable storage and potential for future expansion or additional usable space, while on site parking adds convenience and enhances tenant appeal. From an investment perspective, the property offers several compelling strategies, including buy and hold, value add renovation, rental income optimization, and owner occupant house hacking. Investors have the opportunity to capitalize on the property's existing two units while exploring improvements that could increase rents, strengthen tenant demand, and enhance long term asset value. The property is situated near the University of Chicago, Jackson Park, and the Obama Presidential Center, as well as the ongoing redevelopment and investment throughout the Woodlawn corridor. Continued neighborhood revitalization, proximity to major institutions, transportation, parks, and cultural amenities provide a strong foundation for future demand and potential appreciation. For investors looking to acquire a multifamily asset in a neighborhood undergoing significant transformation, this Woodlawn two flat offers a compelling combination of income potential, value add upside, and long term appreciation prospects. Tenant on 1st floor pays $1650/month for rent plus utilities.
Courtesy: Chicago Real Estate Authority
773-968-1110
Fabulous LEGAL Cape Cod-Style 3-flat with a non-conforming 4th unit AND adjacent vacant lot in Chicago's rapidly appreciating West Pullman neighborhood! Configured as follows: 1st Floor Front, 1st Floor Rear and 2nd Floor. Don't forget about the CTA Red Line extension and their upcoming station around the corner at 115th & Michigan. TLC is required throughout and a new roof is in order, but tuned-up and stabilized, this property has a potential GPI of over 5K+per month and an ARV over 350K!
Courtesy: Coldwell Banker Realty
312-266-7000
Excellent opportunity in Galewood! This legal 3-unit building sits on an oversized lot and offers spacious units with nice, functional layouts and plenty of potential. The property needs some TLC and updating, making it a great opportunity for an owner-occupant or investor looking to add value. Conveniently located near shopping, dining, transportation, and neighborhood amenities. Three legal units, an oversized lot, a great location, and tons of upside potential. Sold As-Is.
Courtesy: HomeSmart Connect LLC
847-495-5000
Versatility, space, and opportunity come together in this well-maintained multi-level property! Offering a unique layout with two apartments each with 2-bedroom, 1-bath, this property provides flexibility for investors, extended families, or buyers looking for additional living arrangements. The added value is the basement in-law suite, featuring a bedroom, living area, and kitchenette. Whether used as a private space for parents or extended family, a guest suite, or additional flexible living space, this area adds tremendous value and versatility. Outside, enjoy a spacious backyard and private 3-car carport, offering plenty of parking and outdoor space-an uncommon and highly desirable combination. Conveniently located near shopping, restaurants, Metra, major expressways, and key intersections. Whether you're looking to house multiple generations under one roof, create additional private living space, or expand your investment portfolio, this property offers options that are hard to find.
Courtesy: Second City Real Estate
312-392-1650
Bring your vision to 5753 N Washtenaw Ave! This property presents an excellent opportunity for an owner-occupant, investor, or developer looking to create value in a desirable Chicago neighborhood. The property offers tremendous potential for renovation, redevelopment, or customization to suit the buyer's needs. Located on a residential block with convenient access to neighborhood amenities, restaurants, shopping, parks, transportation, and major thoroughfares, this property provides a great opportunity to invest in a sought-after area of Chicago. The property is being offered AS IS, WHERE IS, with the seller making no representations or warranties regarding the condition, zoning, permitted uses, existing improvements, code compliance, violations, permits, or future development potential. Seller will not make repairs or provide credits based on property condition, violations, permits, zoning, or other due diligence matters.
Courtesy: Su Familia Real Estate Inc
773-581-9600
Welcome to 4833 W Gladys Ave, a stunning brick two unit property full of incredible potential and classic Chicago charm! Featuring generous multilevel layouts, rich architectural character and abundant natural light throughout each unit, this building offers solid fundamentals ready for personal design updates or steady rental income. Live comfortably in one unit while renting the other! Situated on a quiet residential block just steps from Columbus Park, local schools and neighborhood retail. The home also boasts excellent transit connectivity with quick access to the CTA Blue Line, multiple bus routes, and interstate 290 just minutes from downtown. Seller will provide a 2% credit to buyer's closing costs!
Courtesy: @properties Christie's International Real Estate
312-682-8500
A rare opportunity to own a beautifully updated Greystone. 3 legal units (basement ADU) in one of Chicago's most exciting growth corridors. This stately building commands immediate attention. With freshly tuckpointed stonework, stonewashed exterior, and updated landscaping, it delivers curb appeal that stands apart on the block. Brand new kitchens, bathrooms, and flooring throughout, complemented by fresh paint and newer windows that flood each space with natural light. The fully permitted garden-level ADU adds a legal 3rd income stream and significantly boosts overall yield. Live in one, rent two, or maximize all three. Woodlawn is in the midst of a remarkable transformation. With a wave of new construction in the pipeline and steadily climbing rental rates, savvy investors are moving in early. This property puts you ahead of the curve. Secured in a neighborhood whose trajectory is unmistakably upward, with the bones, the beauty, and the bottom line to match.
Courtesy: Fathom Realty IL
708-543-1106
Family owned 30+ years, Legal 3-Unit Opportunity in Albany Park reflecting current family owned rental amounts and outstanding long-term upside. In ADU district , where Chicago's permanent Additional Dwelling Unit ordinance (effective April 2026). Buyers may have a path to explore building additional coach house in rear for additional living space as a conforming ADU, adding a possible additional income stream. First and Second floor with spacious units featuring desirable 3-bedroom layouts, creating strong tenant demand and premium rental potential. Full 2 bedroom 2 bath legal unit in lower level. Red Hot Albany Park that Investors will appreciate. Owner-occupants will also love the opportunity to live in one unit while generating income from the others. May also be an excellent condo conversion project. Tenants pay their own utilities, helping keep expenses low and returns strong. The property also includes a 2-car garage plus additional space on side of garage, adding convenience and value for residents. Ideally located near the Brown Line, shopping, dining, and all that Albany Park has to offer. This property combines convenience, quality, and strong upside rental demand. Whether you're expanding your portfolio or looking for a live-in investment, this is a rare opportunity to own a legal 3 with possible added ADU potential in a highly desirable neighborhood.
Courtesy: eXp Realty
888-574-9405
Bring your vision to life with this substantial investment opportunity, fully demoed to the studs and ready for redevelopment. Plans were previously submitted to the City and are available upon request. A newer roof is in place. The property offers an impressive amount of space and income potential, with 2-bedroom, 1-bath layouts on both the first and second floors, plus a 1-bedroom attic apartment with two separate points of entry/exit. Adding a finished basement to this already massive property further elevates its potential. The surrounding block has seen significant reinvestment. Numerous distressed properties brought back to life and with this continued redevelopment throughout the area, this oversized property presents an exciting opportunity for an investor looking to capitalize on the neighborhood's momentum. Conveniently located directly across from a STEM high school, approximately a 12-minute walk to CTA train service, and just a 3-minute drive to I-90/94. Property is being sold AS-IS. No survey will be provided. Buyer's agent to verify room count, zoning, permitted use, and all property information.
Courtesy: IRPINO Real Estate, Inc.
773-525-0900
Excellent Investment or Owner-Occupant Opportunity in Chicago! This Well-Maintained Two-flat offers Two Spacious Residences plus a versatile In-law Garden Unit. The Main-Level Unit features a Large Living Room and Adjoining Family Room, Separate Dining Room, Updated Kitchen with Granite Counters, Tiled Backsplash and Stainless-Steel Appliances, Two Bedrooms, One Full Bathroom and an Entry Area with Stairs that lead to the One Bedroom, One Bathroom In-Law Garden Unit with Family Room and Kitchen. The Upper-Level Unit features a Living Room, Dining Room that opens to the Updated Kitchen, Two Bedrooms, One Full Bathroom and a Sunroom. With Flexible Accommodations across Three Levels, this Property offers Outstanding Potential for Multigenerational Living and/or Rental Income with a Fantastic Opportunity to live in one unit while generating income from the others! Enjoy the Outdoors on the Patio that Overlooks the Landscaped Backyard and the Two Car Garage! The Prime Location is Moments to: CTA Bus Stops, Northeastern IL University, Loyola University, Kathy Osterman Beach, Local Parks, Tons of Dining Options, Shopping and Nightlife. This is an Estate Sale and Property is sold As-Is and Hold Harmless. Sellers does not provide survey or disclosures - please verify all details on your own.
Courtesy: Davison Realty
773-892-1500
This two-unit property located in the West Garfield area presents a unique investment opportunity. New construction is just one block away. The Garden unit features 2 bedrooms, 1 bathroom, and a kitchen. Unit #2 comprises 3 bedrooms, 1 bathroom, a living room, and a dining room, with hardwood floors beneath the carpet and a large eat-in kitchen. An enclosed back porch adds to the charm. While the property requires updating and repairs, it offers the potential for instant equity. It is being sold as-is. Please call today to schedule your appointment.
Courtesy: Keller Williams ONEChicago
312-216-2422
Money-making brick three-unit investment opportunity with full basement and three-car garage! This solid, income-producing property features three spacious units, each offering two bedrooms and one full bathroom. Each unit has individual furnaces and water heaters, with tenants responsible for their own gas and electric-an attractive setup for operating efficiency. The full unfinished basement provides additional storage and future value-add potential, while the three-car garage adds valuable off-street parking. Perfect for investors seeking existing cash flow or an owner-occupant looking to house hack by living in one unit while generating income from the others. Unit 1 is currently month-to-month, offering added flexibility for an owner-occupant. Income-producing, well-positioned, and ready for its next owner-don't miss this Chatham opportunity!
Courtesy: Baird & Warner
773-549-1855
Nestled in the heart of West Town, this incredible 4-flat property is ready for its new owner's ideas! Four, 2bed/1bath units (2 units front and rear), each roughly 900 sq.ft., featuring central air/heat already installed, some light interior updates to kitchens and bathrooms, lots of original woodwork and doors, these would be excellent income-generating apartments when comparably finished/updated to surrounding market standard. Long-time private owner is sad to see this wonderful property go, but has decided it is time to move on. Schedule your tour today!
Courtesy: Kale Realty
312-939-5253
Beautiful and well maintained 2 flat updated within the last 5 years + partially finished garden unit. This property offers spacious living areas, modern finishes and a functional layout throughout. Three car brick garage and plenty of backyard space. Ideal for an owner-occupant or investor looking to add a solid multi-unit property to their portfolio. Conveniently located near public transportation and e-way. Schedule your showings today.
Courtesy: Coldwell Banker Realty
708-352-4840
Great opportunity to own a classic Chicago brick two-flat, each unit features 3 bedrooms, 2 bathrooms, providing comfortable living space updating and personalizing
Courtesy: Coldwell Banker Realty
708-352-4840
The property showcases timeless Chicago architecture with an attractive brick exterior, distinctive windows, and separate living spaces. Generously sized rooms and abundant natural light provide a solid foundation for updating and personalizing each unit
Courtesy: Pearson Realty Group
773-325-2800
Logan Square Multi-Unit Brick Building with 1,700 Sq Ft units on the 1st & 2nd floor levels. Large Spacious units with no small rooms at all, Living Room, Kitchen, Dining Room, 2 Bedrooms, Rear heated Sunroom which can possibly be turned into a 3rd Bedroom to maximize use and rental income. Basement Unit fully renovated: Living Room, Kitchen, One Bedroom, plus an additional room at the rear of the building for laundry room potential. All utilities are separate: 3 Boilers (Base-Board Heating), 3 Water Heaters, 3 Electrical Panels. Good sized rear yard and a 2 Car Garage. Walking distance to a Super Market, Restaurants, Shops & Retail. Healy Metra Train Station a short distance away. Blue Line Train Station 1.2 miles.
Courtesy: AiHome Realty Group LLC
312-508-8581
Courtesy: Keller Williams ONEChicago
312-216-2422
Beautifully rehabbed two-unit multi-family property, completed in 2026, offering a total of 8 bedrooms and 3 full bathrooms throughout the building. Both units feature spacious living and dining areas, hardwood flooring, updated kitchens with abundant cabinetry and modern tile backsplashes, and well-appointed bathrooms. Additional highlights include an enclosed porch, finished basement with expansive recreational space, home gym area, laundry, ample storage, and a 3-car garage. Great opportunity for an owner occupant or investor seeking a move-in-ready multi-unit property in Chicago's West Lawn neighborhood.
Courtesy: RE/MAX Top Performers
847-295-0800
Exceptional investment opportunity in the heart of historic Bronzeville. Welcome to 4040 S. Calumet Ave, a distinctive property offering classic Chicago architecture, beautifully updated interiors, outdoor space, and an outstanding location just minutes from downtown Chicago and the lakefront. Units are currently occupied, giving an investor the opportunity to acquire an established multifamily property with existing tenancy. The building features spacious living areas, contemporary kitchens, stainless steel appliances, modern cabinetry, hardwood flooring, updated baths, multiple rear decks, and a gated entry. The location adds tremendous appeal with convenient access to downtown Chicago, the Lake Michigan lakefront, McCormick Place, the Obama Presidential Center, Washington Park, the DuSable Black History Museum and Education Center, public transportation, major expressways, and the many cultural, dining, and recreational destinations surrounding historic Bronzeville. 4040 S. Calumet brings together the features investors want most: location, character, updated interiors, existing occupancy, outdoor space, and multifamily income potential. Opportunities like this deserve a closer look. Schedule your private showing and come see what 4040 S. Calumet has to offer.
Courtesy: Chicagoland Brokers, Inc.
773-745-1000
NICE JEFFERSON PARK 2 FLAT WITH FINISHED BASEMENT! 2 OVERSIZE UNITS WITH CENTRAL AIR, THREE SEPARATE FURNACES AND HOT WATER TANKS, COPPER PLUMBING. BOTH UNITS HAVE FORMAL DINING ROOM, DEN AND SLIDING DOOR TO THE DECK! NEWER WIDOWS, NEWER 1ST FLOOR AC UNIT,TWO FURNACES AND WATER TANKS ARE NEWER TOO. 2 CAR GARAGE AND ADDITIONAL PARKING SPOT. COIN LAUNDRY. GREAT RES BLOCK! THE PROPERTY IS IN A GREAT SHAPE BUT SELLER WANTS TO SELL IT AS IS.
Courtesy: Berkshire Hathaway HomeServices Chicago
312-944-8900
Don't wait to view this update interior rehabbed classic Chicago architecture two-unit design brick multi-unit. In-eat kitchen and dining room. Each unit has a rear back enclosed multi-purpose room. It also has a basement unit for opportunity to expand to a 3-unit in the future. 3 electrical panels, instant cost savings. The property is located near public transportation, schools, parks and shopping with easy access to Downtown. Immediate cash flow with established great paying tenants. You can walk into an income producing property or property can be delivered vacant.
Courtesy: Golden Key Realty
773-276-6222
Excellent Investment opportunity in Logan Square area! Just North of Central Park & Altgeld intersection. Two nice size 3-bedroom units. Please note the extra wide lot size, per city records it is 44' wide. Close to shopping, public transportation & more. Very nice front porch to enjoy your evenings. Extra wide yard for enjoyment. Full Basement has a half a bath and an additional room that could be used as another bedroom or an office. Bring your own ideas to make it into additional living spaces. 2 car garage & additional Parking spaces next to the garage. Long term ownership. Selling in AS - IS condition.
Courtesy: RE/MAX 10
708-857-1500
Great investment opportunity in Chicago's North Lawndale neighborhood! Newer-construction, legal 3-flat built in 2007 and fully occupied, offering immediate rental income from day one. Each spacious unit features 3 bedrooms, 2 full bathrooms, in-unit laundry, and nicely updated interiors. All three units have separate utilities, with tenants responsible for heat, gas, and electricity; owner pays water only. A solid opportunity for investors looking for an income-producing property with established tenants and minimal work needed. Take ownership and start enjoying the cash flow!
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.
