View All Bridgeport Chicago IL 2-Flats Listings

$750,000
2 Beds 3 Baths 12749994 MLS ACTIVE Status
Fantastic investment opportunity in the highly desirable Bridgeport neighborhood, this meticulously maintained all-brick two-flat has been lovingly cared for by the same family for more than 30 years. Each spacious unit features 2 bedrooms and 1 full bath, with separate utilities and updated HVAC systems, while the first-floor unit offers the added convenience of in-unit laundry. The second-floor unit opens to a large private deck showcasing a spectacular Chicago skyline view, creating an exceptional space for entertaining or unwinding. A fully finished basement with an in-law kitchen and full bath adds valuable flexibility for extended family, guests, additional living space, or potential rental income. Outside, enjoy a full backyard and a two-car garage with a brand-new roof, along with new windows throughout the property. Above it all, the full unfinished attic offers exciting potential for future expansion. Located in the heart of Bridgeport, this property is just minutes from Chinatown, IIT, UIC, downtown Chicago, and major expressways. Enjoy convenient access to acclaimed restaurants, shopping, parks, public transportation, and the many new residential and mixed-use developments transforming the surrounding area. With its solid brick construction, prime location, skyline views, versatile finished basement, and substantial expansion potential, this property offers the perfect combination of income opportunity, long-term value, and Chicago lifestyle. A truly exceptional investment.

3039 S Lowe Avenue, Chicago

$565,000
5 Beds 3 Baths 12725191 MLS CONTINGENT Status
Welcome to 3623 S. Emerald Avenue - a beautifully updated brick two-flat in the heart of Bridgeport, showcasing a classic Chicago facade, bold yellow entry doors, and bright, modern interiors throughout. Thoughtfully renovated, this property is ideal for investors and owner-occupants alike, offering style, comfort, and income potential in one of the city's most walkable historic neighborhoods. Each of the two units offers a smart, modern layout with tall ceilings, hardwood floors, and oversized windows that fill the space with natural light. Kitchens are appointed with rich espresso cabinetry, granite countertops, and stainless steel appliances, while updated bathrooms feature contemporary finishes, sleek vanities, and walk-in showers for true turnkey appeal. Both units include central air conditioning for year-round comfort. The finished lower level adds valuable living space, including a flex room and full bathroom - perfect for a home office, guest suite, or recreation room. A shared laundry area adds everyday convenience, and a 2-car exterior parking pad provides rare off-street parking in the city. Located in one of Chicago's most vibrant and historic neighborhoods, you'll enjoy exceptional walkability to local dining, coffee shops, parks, and community hotspots. Stroll to Armour Square Park, catch a game at Guaranteed Rate Field, or hop on nearby CTA buses and the Sox-35th Red Line stop for an easy commute. Quick access to I-90/94 and I-55 makes getting around the city seamless. Whether you're looking to live in one unit and rent the other or expand your investment portfolio, 3623 S. Emerald Avenue delivers the perfect blend of location, character, and opportunity.

3623 S Emerald Avenue, Chicago

$900,000
4 Beds 3 Baths 12681989 MLS CLOSED Status
Exceptional investment and owner-occupant opportunity in the heart of Chicago's highly sought-after Bridgeport neighborhood! Situated on a rare double lot, this meticulously maintained all-brick 2-flat offers remarkable versatility, featuring two spacious units and a thoughtfully designed first floor duplex that extends into a beautifully finished lower level. With separate exterior entrances, the lower level presents an ideal opportunity for a private in-law arrangement or additional flexible living space. Designed with comfort in mind, the lower level showcases radiant heated floors, a luxurious Jacuzzi tub, and a steam shower, creating a true retreat within the home. Completing the property is a detached 4-car garage and an expansive side driveway and mechanical gate providing exceptional parking and storage rarely found in the city. Whether you're an investor seeking strong rental income, an owner occupant looking to house hack, a buyer interested in converting the property into a stunning single family residence, or someone looking to capitalize on the future potential of a rare double lot, this property offers endless possibilities. Perfectly positioned near Holden Elementary School, Tilden Career Community Academy, the CTA Orange Line, public transportation, and major expressways including I-55 and I-90/94, commuting to Downtown Chicago is effortless. Enjoy easy access to neighborhood parks, acclaimed restaurants, local shopping, and everything that makes Bridgeport one of Chicago's most vibrant, historic, and appreciating communities. A truly rare offering that combines location, flexibility, income potential, and long term value makes this is an opportunity you won't want to miss!

2844 S Throop Street, Chicago

$735,000
6 Beds 3 Baths 12382559 MLS CLOSED Status
Legal Brick 3 Flat with Amazing Duplex Owner's Unit on Deep Lot in the Heart of Bridgeport. Whether you want to owner occupy, AirBnB or seek a solid investment property, there is finally a Bridgeport multi-unit that is move-in ready for all units! Electrical has been re-wired throughout the property so no typical cloth wiring issues. Each unit has its own forced air separate vent heating unit with updated CENTRAL AIR CONDITIONING. Separate power vented hot water heaters are smartly placed in common basement area. Tuckpointing has been professionally addressed with regular maintenance. Main sewer has been updated with front yard cleanout installed. Newer HEATED GARAGE has an extra tall door and is fully insulated with drop down stairs for additional storage. This creates the perfect opportunity for ADDITIONAL INCOME or an awesome workshop! The rear yard is deeper than average with both a grass yard section and a private patio with custom pavers creating two separate hangout areas so multiple people can enjoy at the same time. How about the units? The owner's unit is stunning with terrific southeast natural light, ORIGINAL WOODWORK throughout, custom high end kitchen with a separate dining area that looks out to the spacious backyard. There is also a delightful covered balcony tucked under the treetops. The unit has a second floor STUDIO with a separate entrance complete with custom oak stair rail allowing either exclusive use for Unit 3 or a separate rentable space. The top floor is a TRUE ESCAPE with unbelievable light from three massive skylights along w/ additional unfinished space to continue building out. Unit 2 features two bedrooms with another separate office area perched over the yard along with beautiful original woodwork & hardwood floors. First floor was fully remodeled in 2018 with an updated kitchen complete with stone counters and dishwasher, along with tasteful flooring and a private exterior vestibule. Building also features a laundry area, large workshop/storage area, and double pane aluminum windows. Location is superb, just a block from Halsted, surrounded by transit, restaurants, bars and of course, Sox park a few blocks away. This is truly a cut above most other multi-unit buildings as it was owner occupied by a detailed engineer for many years.

3458 S Lituanica Avenue, Chicago

$638,000
5 Beds 3 Baths 12366443 MLS CLOSED Status
***Rare opportunity to invest in a meticulously maintained, owner-occupied two-flat in a prime A+ Bridgeport location*** This classic brick building is surrounded by well landscaped front and back yards, offering outstanding curb appeal. Each of the units have separate utilities, individual forced air heat, central air conditioning, and their own laundry. At the top of the front steps, both units are entered through a charming 4 season foyer with preserved architectural details. Unit 1 is a 2 bedroom/1 bath home, and features bright natural light through numerous large windows, high ceilings, and oak floors. Upstairs, unit two is a 3 bedroom/1 bathroom apartment that also has high ceilings, bright natural light, and numerous large windows. It has been completely updated with oak flooring, appliances, granite countertops, bathroom, and in-unit washer/dryer. This is one of the nicest apartments in Bridgeport!! The basement is dry and has high ceilings, updated electrical, and its own half bathroom. Out back there is a sunny deck and a charming landscaped seating area with pavers. The two car brick garage in back adds further value and potential rental income. Located just steps from Halsted Street, Rate Field, the Red Line, major expressways, IIT, and the lakefront, this property is ideally positioned for both convenience and lifestyle. No existing leases mean you can rent at top-of-market rates from day one. Lovingly cared for by long-term owner-occupants, this is a turnkey investment or a perfect live-in opportunity ready for its next chapter.

3415 S Emerald Avenue, Chicago

$545,000
5 Beds 2 Baths 12342743 MLS CLOSED Status
Welcome to 2724 S Crowell Street, a beautifully updated and fully occupied two-flat nestled on a quiet, tree-lined street in the heart of Bridgeport-one of Chicago's most vibrant and fast-growing neighborhoods. Whether you're looking for a smart investment opportunity or the perfect chance to live in one unit and rent the other, this turn-key property delivers flexibility, comfort, and long-term value. The first-floor unit offers 3 spacious bedrooms and 1 full bathroom, featuring a stylishly renovated kitchen with quartz countertops, a freshly updated bathroom, new paint throughout, and direct access to a private deck overlooking a low-maintenance turf backyard-ideal for relaxing or entertaining. The second-floor unit includes 2 bedrooms and 1 bathroom, highlighted by vaulted ceilings, luxury vinyl plank flooring, brand-new stainless steel appliances, and a private deck that adds charm and livability. Key features include: New roof (2022) Updated mechanical systems Large unfinished basement with excellent storage or potential for additional living space Fully leased with strong rental income, but can also be delivered with one unit vacant for owner occupancy Located just minutes from parks, public transportation, restaurants, schools, and all that Bridgeport has to offer, this home is perfect for house hackers, multi-generational living, or those looking to generate supplemental rental income. Don't miss your chance to own a move-in ready and income-producing property in one of Chicago's most desirable neighborhoods-2724 S Crowell Street is the opportunity you've been waiting for!

2724 S Crowell Street, Chicago

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Bridgeport, Chicago IL · Curated MLS Search

2-Flats in Bridgeport, Chicago IL

An editorially curated view of every active 2-flats listing in Bridgeport, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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