View All Chicago IL 2-Flats Listings

8 Beds ⋅ 3 Baths ⋅ 12756650 MLS ⋅ NEW Status

Great investment opportunity !! Legal 3 flat located on quite cul-de-sac in sought after Albany Park, known for its strong rental market. Featuring 3 spacious unit. 1st and 2nd floor offers 3 bedrooms and 1 bath and garden apartment features 2 bedrooms and 1 bath. All units with separate utilities and HVAC system including first and second floor with central AC. Tenants are on a month to month basis, providing flexibility to increase rent. Each apartment is nicely updated and well maintained by long term tenants, featuring can lights, newer windows, hardwood floors, updated furnaces and modern kitchens. The fenced backyard offers tenants outdoor space for summer gatherings. Additional features include 2 car garage and parking pad for additional parking. An excellent opportunity for a savvy investor to increase rental income or for an owner occupant. Conveniently located walking distance to schools, bus stops, shopping, restaurants, El station and daily amenities. Washer and dryer not included

5038 N Harding Avenue, Chicago

$499,900

5 Beds ⋅ 2 Baths ⋅ 12753730 MLS ⋅ NEW Status

Fully occupied, renovated brick 2-flat with strong rental income and modern finishes. Each unit features open-concept layout, exposed brick accents, exposed ductwork, recessed lighting, updated kitchens and baths, in-unit laundry, and thoughtful design details throughout. Unit 1 is a 2 bed / 1 bath and Unit 2 is a 3 bed / 1 bath, providing a desirable rental mix for investors or future owner-occupants. Recent major renovation included updated kitchens, baths, mechanicals, electrical, plumbing, windows, exterior doors, concrete, and garage. The property features an unfinished walkout basement, fully fenced backyard, two rear open decks, and a detached 2-car garage. Property is currently tenant-occupied with existing leases in place. Convenient location near the Ogden/Cermak corridor with access to CTA Pink Line transportation, neighborhood retail, parks, restaurants, and major roadways. A turnkey multi-unit opportunity with modern finishes, garage parking, outdoor space, and immediate rental income. The property also features a full unfinished walkout basement, fully fenced backyard, two rear open decks, and a detached 2-car garage.

2103 S Christiana Avenue, Chicago

$1,349,000

6 Beds ⋅ 4 Baths ⋅ 12750888 MLS ⋅ NEW Status

Like brand new construction full brick 2-Flat BUT WITH 4-Legal units at the WORLD district of Devon Ave./California Ave., totally LIKE brand-new interior and exterior with quality work delivery including gourmet kitchens featuring granite counter-tops, quality cabinets with S.S. appliances, bathrooms, hardwood floors and beautiful brand-new decks out of the kitchen. High efficiency individual utilities include new central air, electric and plumbing including E.J. pump and sump pump. High basement ceiling with full 8'. Owned coin laundry room, 8-parking tandem spaces for additional income. Front and back security cameras along with all digital public entrance doors on electronic locks. Walking distance to public transportation, retailers, and restaurants, daily life necessities, minutes to major roads, Lake Shore Dr., northwest suburbs, and interstates. Strong investment area opportunity Fully leased.

6336 N Fairfield Avenue, Chicago

$549,900

5 Beds ⋅ 3 Baths ⋅ 12755567 MLS ⋅ NEW Status

Welcome to one of the largest residential 2-flat properties you'll find in the highly sought-after North Lawndale neighborhood! This property has been fully rehabbed, with the renovation completed in August 2026, offering buyers the opportunity to own a beautifully updated multi-unit property with modern finishes and extensive improvements. Situated on three city lots, this unique property offers an abundance of land and flexibility rarely found in a multi-unit setting. The property sits on one lot with an additional lot on each side, providing exceptional outdoor space and plenty of room for parking, recreation, expansion, or storage. Business owners with multiple vehicles, work trucks, equipment, or additional parking needs-this could be the ideal property for you! The expansive lot configuration provides valuable space that is difficult to find in the city. Inside, the property features two beautifully remodeled 2-bedroom units, each offering one full bath, a kitchen, and a modern open-concept layout. The second-floor unit is duplexed into the attic, creating additional living flexibility and making the space ideal for an in-law suite, extended family, guests, or other living arrangements. The attic includes its own kitchen and bathroom while sharing central heat with the second-floor unit. The first- and second-floor living spaces each feature their own individual furnace and central heating, providing separate heating systems for each unit. All living areas have been thoughtfully remodeled with modern finishes and an inviting open-concept design. Located in the rapidly developing North Lawndale community, this property offers convenient access to Chicago's Medical District, downtown Chicago, major highways, dining, entertainment, and nightlife. Approximately a 15-minute drive to the Medical District and 25 minutes to downtown, making this an excellent location for both residents and commuters. Whether you're an investor looking for a versatile multi-unit property, an owner-occupant seeking additional living space, or a business owner in need of substantial parking and land, this property offers possibilities that are hard to find. Three lots. Two remodeled units. Recently completed rehab. Exceptional flexibility and space. Don't miss this opportunity-schedule your showing today! This one won't last long!

2248 S Kolin Avenue, Chicago

$159,900

5 Beds ⋅ 2 Baths ⋅ 12755439 MLS ⋅ NEW Status

Solid brick and stone 2-flat located in the West Garfield Park neighborhood. This property offers a total of 5 bedrooms and 2 bathrooms, providing spacious living arrangements across both units. Features include a full finished basement offering additional living or storage space and classic architectural details throughout. Property is being sold in AS IS condition, no surveys nor disclosures, taxes prorated. Excellent investment opportunity or rehab project with great potential. Conveniently located near schools, parks, public transportation and major expressways. SEE ATTACHED CITY OF CHICAGO LIST OF BUILDING VIOLATIONS Subject to prior offer cancellation.

925 S Springfield Avenue, Chicago

$599,900

5 Beds ⋅ 3 Baths ⋅ 12755079 MLS ⋅ NEW Status

JEFFERSON PARK GEM WITH A BACKYARD RETREAT LIKE NO OTHER! Meticulously maintained and exceptionally inviting, this charming 2 flat, within walking distance to Jefferson Park station, offers spacious living and dining rooms, beautiful hardwood floors, a newer kitchen, a 2nd floor rental unit and a fully finished basement ideal for extended family, guests, recreation, or additional living space. But the true heart of this home is the extraordinary two-level rear deck. Directly connected to the house and accessible from both the first and second levels, this expansive outdoor living space is an entertainer's dream. A covered gazebo, mature grapevines, warm wood decking, and a built-in hot tub create a private backyard oasis that feels more like a destination than an ordinary city backyard. It's the perfect setting for summer gatherings, quiet evenings, morning coffee, or relaxing in the hot tub surrounded by greenery. The oversized, fully fenced yard provides exceptional privacy and additional space for entertaining, gardening, or enjoying the outdoors. This is more than a very nice Jefferson Park home-it is a home with a truly special outdoor lifestyle.

5128 W Ainslie Street, Chicago

$22,500

4 Beds ⋅ 2 Baths ⋅ 12755234 MLS ⋅ NEW Status

***Attention all investors and rehabbers*** Add instant equity to this solid 2-flat in the heart of West Pullman. This property has tremendous potential and is just awaiting your design ideas. Prime location close to Metra and expressways. Sold strictly as-is. No survey. Must take subject to any violations/housing cases/code compliance requirements.

11940 S Wallace Street, Chicago

$500,000

6 Beds ⋅ 3 Baths ⋅ 12751332 MLS ⋅ NEW Status

Rare opportunity to own a multi-unit property in the heart of Mt Greenwood on a quiet residential street. This 2 Flat has lots of potential. 1st Floor Unit has 3 bedrooms, living room, kitchen, and full bath. The lower level in the basement is a studio with an open floor plan that can be related living. It includes a full bath and kitchenette. 2nd floor unit, has 4 bedrooms, living room, full sized kitchen with table area, full bath, and an open area that could function as an office. Laundry facilities are located in the basement and include a washing machine and gas dryer. Hot water heater in building is shared and is 1 year old. Water and garbage are also shared. Buiilding's yard has a concrete patio and 2 car garage. With 7 bedrooms across the two main units plus a versatile lower-level studio, this property provides multiple possibilities for rental income, owner occupancy, or related living. A great opportunity to bring your investment vision to Mt. Greenwood!

3310 W 114Th Street, Chicago

$675,000

8 Beds ⋅ 4 Baths ⋅ 12754882 MLS ⋅ NEW Status

Desirable Arcadia Terrace! Incredible investment opportunity with this all-brick 2-flat, including a non-conforming basement space, storage, laundry room and a 2-car garage. Units 1 & 2 feature hardwood flooring, 3-bedrooms / 1 bath. Unit 2 includes a FULLY updated kitchen & bath. The 2-Flat features recently updated electrical and tuck-pointing ( 5yrs). Age of roof is unknown and building is being sold as-is. Conveniently located near shopping, restaurants, parks, and public transportation. This property offers the perfect combination of space, location, and income potential.

5723 N Artesian Avenue, Chicago

$89,900

6 Beds ⋅ 2 Baths ⋅ 12754138 MLS ⋅ NEW Status

REHABBED 2 FLAT WITH FULL BASEMENT! IN-UNIT LAUNDRY PER UNIT! NEWER HVAC, FLOORING, KITCHEN & BATHS, WINDOWS AND MUCH MORE, MAKES GREAT INVESTMENT PROPERTY OR LIVE IN. Drive by only. Sold as is. No survey provided.

5610 S Throop Street, Chicago

$164,900

6 Beds ⋅ 3 Baths ⋅ 12754469 MLS ⋅ NEW Status

Large, Brick 2 flat near 115th and State with tremendous potential. This hidden gem features 3 bedrooms per unit, large kitchen, formal living and dining rooms, hard wood floors throughout and a 2-car garage. Unit 1 has 1.5 baths and is duplexed to the large, unfinished basement. Lot next door is not included. Property is V.A. owned & sold in "as is/where is" condition. Seller will make no repairs. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint potentially exists.

Chicago

$235,000

4 Beds ⋅ 2 Baths ⋅ 12754451 MLS ⋅ NEW Status

Welcome to 8233 S Escanaba Ave: a two-unit property offering versatility, space, and an excellent South Side location near Lake Michigan! Each unit features 2 bedrooms and 1 bathroom, providing a practical layout for rental income, owner occupancy, or multi-generational living. The property offers a spacious unfinished basement with excellent potential for additional storage, a workshop, recreation space, or future expansion. A detached 2-car garage adds valuable parking and storage. Location is where this property truly shines. Enjoy easy access to Lake Michigan, nearby beaches, parks, and the lakefront, including Rainbow Beach Park, a nearly 61-acre lakefront destination featuring a beach, fitness facilities, sports courts, playgrounds, a community garden, and beautiful views of the Chicago skyline. Commuters will appreciate convenient access to Lake Shore Drive and major South Side thoroughfares, making trips to downtown Chicago and surrounding neighborhoods more accessible. The area also offers a variety of local restaurants, shops, parks, recreational opportunities, and cultural attractions. Whether you're looking to house-hack, build your rental portfolio, live in one unit while generating income from the other, or accommodate extended family, 8233 S Escanaba Ave offers an opportunity to make the most of a two-flat in a location surrounded by Chicago's lakefront amenities. Bring your vision and explore the possibilities this property has to offer! *BROKER/AGENT IS RELATED TO THE SELLER.

8233 S Escanaba Avenue, Chicago

$875,000

6 Beds ⋅ 3 Baths ⋅ 12753851 MLS ⋅ NEW Status

Exceptional opportunity to own a beautifully updated 3-flat in the highly sought-after Logan Square neighborhood! This well-maintained, income-generating property offers a perfect blend of modern updates and classic charm, making it ideal for both investors and owner-occupants. Each unit features gleaming hardwood floors throughout, thoughtfully updated kitchens with stainless steel appliances, and stylishly renovated bathrooms complete with ceramic tile finishes. High ceilings and oversized windows create bright, airy living spaces filled with natural light, while all bedrooms are generously sized to comfortably accommodate a variety of living arrangements. The building is designed for convenience and privacy, offering separate entrances for each unit along with individually metered utilities-allowing tenants to pay their own gas, electric, and other services. Outdoor amenities include a rear patio, private backyard, and balcony/deck space-perfect for relaxing, entertaining, or enjoying Chicago's warmer months. A 2-car garage adds even more value, with one parking space already rented for $100/month, presenting an additional stream of income. Situated in a prime Logan Square location, this property is just steps away from a vibrant mix of local shops, popular restaurants, cafes, and nightlife. Enjoy easy access to the 606 Trail for walking, running, and biking. Commuting is a breeze with nearby public transportation options and quick access to major expressways. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the others, this property checks all the boxes-location, condition, and income potential.

3041 W Fullerton Avenue, Chicago

$749,000

7 Beds ⋅ 3 Baths ⋅ 12749582 MLS ⋅ NEW Status

JUMBO BRICK LEGAL 3-FLAT on an EXTRA-WIDE 31' x 126' LOT! An exceptional opportunity for both investors and owner-occupants, this well-maintained three-unit property offers 7 total bedrooms and 3 bathrooms with generously sized interiors throughout. The building features a 1-bedroom/1-bath garden unit and two spacious 3-bedroom/1-bath residences on the first and second floors. All three units underwent extensive renovations in late 2020, including remodeled kitchens and bathrooms and updated appliances, creating move-in-ready spaces while maintaining the building's original character and woodwork. Each residence offers an extra-wide floor plan, spacious rooms and large eat-in kitchens. Three separate HVAC systems allow tenants to control their own gas and electric, while water, sewer and garbage are included. Additional features include coin-operated laundry, basement and rear-stairwell storage, a fenced backyard with patio space, and a 2-car garage with covered parking. Ideally located just three blocks from the Addison Blue Line with convenient access to I-90/94, shopping, dining and neighborhood amenities. With strong rental appeal, potential for increased rents, an extra-wide lot and substantial updates already completed, this is a compelling opportunity to live in one unit while generating income from the others or add a turnkey multi-unit property to an investment portfolio. All units are currently tenant-occupied; therefore, the property is not available for immediate owner occupancy. Lease dates posted.

3344 N Monticello Avenue, Chicago

$999,999

7 Beds ⋅ 4 Baths ⋅ 12749567 MLS ⋅ NEW Status

Fantastic investment opportunity in highly sought-after Noble Square/East Village! This solid brick 4-flat offers a full basement with laundry, 2-car garage plus an additional parking pad, and four fully occupied units with month-to-month tenants. The property features one 1-bedroom/1-bath unit and three spacious 1-bedroom + den/1-bath units. Tenants pay their own utilities, with each unit featuring individual gas heat, window A/C units, and a dedicated hot water tank located in the basement. Currently 100% occupied with rents below market, offering excellent potential for increased rental income. Units have historically rented quickly, making this a great opportunity for investors looking to add a well-located, income-producing property to their portfolio!

1433 W Superior Street, Chicago

$129,900

4 Beds ⋅ 2 Baths ⋅ 12751933 MLS ⋅ NEW Status

Fantastic opportunity for investors or owner occupants. This classic 2 Flat brick property in the heart of Englewood features two spacious, well maintained units. Each unit offers a functional layout with 2 generous bedrooms, 1 full bathroom, bright living and dining areas, and ample natural light throughout. The building includes a full unfinished basement providing substantial space for storage, laundry set up, or potential expansion. Solid structure with endless potential. Conveniently located near schools, parks, shopping and public transportation. Property being sold in AS IS condition, no surveys nor disclosures, taxes prorated.

6237 S Ada Street, Chicago

$365,000

6 Beds ⋅ 2 Baths ⋅ 12753109 MLS ⋅ NEW Status

Rarely Available Greystone 2-Flat! This Gem has the original wood work thru-out along with gorgeous hardwood flooring. The built-in on the first level adds character that blends with the remodeled upgrades perfectly. All units feature remodeled kitchen and baths with stainless steel appliances, dishwasher and granite countertops with ceramic style modern flooring and new vinyl windows (2022)Newer roof with silver coating. Seperate heat in all units. First floor has 3 bedrooms and Second floor has 3 bedrooms. Partially finished basement with laundry and storage. Detached 2 Car Garage and conveniently located near transportation and the Obama Presidential Library.

6525 S Vernon Avenue, Chicago

$1,450,000

6 Beds ⋅ 5 Baths ⋅ 12748897 MLS ⋅ NEW Status

Simply the best 2-Flat! Unique 2023 full gut rehab created 2 duplex units, each with the feel of a single-family home. Property boasts two, 3-bedroom 2.5 & 2.0 bath luxury apartments. Corner lot provides incredible natural light via casement windows with top-down blinds for privacy. Welcoming Living Rooms have gas fireplaces. Large modern Kitchens have sizable islands, high-end Samsung appliances, hot water taps, and an extraordinary amount of storage space. Custom marble-tiled bathrooms with Grohe fixtures. Full-size front-loading washers and dryers. Primary Bedrooms have large walk-in closets and double vanity ensuite Bathrooms. LED lighting, Central heat and Air conditioning, Smart thermostats and door locks. Two car Garage parking with 240 EV charging and extra parking on driveway apron. Beautifully landscaped front and back yard with patios and a huge front porch. Solid lease, in Unit 2, may allow buyers to qualify for more than you think; check with your lender! This is a turn-key property; move in or lease Unit 1. Excellent location: Near Metra, CTA Brown + Red Line stations, and multiple dining & shopping districts. Walk to highly ranked/exemplary public schools (Chappell, Amundsen) or several excellent private schools: Lycee Francais de Chicago, Rogers Park Montessori, Chicago Waldorf, North Park Elementary. Close to Winnemac Park, West Ridge Nature Park, and beautiful city and lake-front parks. Enjoy Bowmanville's tranquility while being close to Andersonville/Lincoln Square.

1901 W Berwyn Avenue, Chicago

$435,000

5 Beds ⋅ 3 Baths ⋅ 12696590 MLS ⋅ NEW Status

2 Flat on a beautiful street in Albany Park! Perfect opportunity to owner occupy with income, or possible rehab to a single family home. Larger unit is a duplex up consisting of a 2 bedrooms on the main floor, family room, dining room, kitchen that leads out to a generous deck. 2nd floor has a large bedroom with ensuite bathroom. Garden/1st floor is a 2 bedroom with family room, proper dining room, workable size kitchen and bath. Interior door leads to a shared laundry room. Great backyard and 2 car garage.

4602 N Karlov Avenue, Chicago

$599,900

7 Beds ⋅ 3 Baths ⋅ 12721240 MLS ⋅ NEW Status

Attention rehabbers, flippers or move-in ready! The main floor is a 3/1; the 2nd floor is a 4/2, duplexed up. The duplex-up can also be a separate in-law unit with its own separate egresses; it is a legal 2-flat. There's a great rooftop deck accessible from the 2nd-floor unit. Main and 2nd floors have 3/bedrooms, 1/bath each. 2nd floor is duplexed up and upper level has 1/br, 1/bath. Main floor has gas forced air heat and window air conditioners. 2nd floor HVAC and is shared with upper level. Roof 20 years old [complete tear-off with new gutters]. Check out the roof deck built over garage in '92 with a catwalk from the main house. Windows are 15 years old [except laundry/utility room], 3 - 100 amp circuit breaker panels, copper plumbing approximately 5 years old, H2o heaters main floor approximately 2 years old, the main floor and attic heaters 3-4 years old. Sold as-is. Legal 2 unit - buyer and buyers agent to verify.

2423 N Lawndale Avenue, Chicago

$655,000

4 Beds ⋅ 2 Baths ⋅ 12751659 MLS ⋅ NEW Status

EXCEPTIONAL 2-FLAT | UPDATED UNITS | FLEXIBLE LIVING | INCOME POTENTIAL Beautifully maintained and thoughtfully updated, this versatile 2-flat offers an excellent opportunity for an owner-occupant, multi-generational household, or investor. Situated on a quiet residential street, the property features two, 2-bedroom, 1-bathroom units, each with updated kitchens, modern fixtures, comfortable living spaces, and the convenience of in-unit laundry. The enclosed rear stairwell leads to a well-maintained backyard, providing an outdoor space for entertaining, relaxing, gardening, or enjoying the outdoors. The basement offers additional flexibility with an in-law-style living area that can be used for extended family, guests, a home office, or potentially additional rental use, subject to applicable zoning and municipal requirements. Conveniently located near bus transportation with connections toward the Blue Line and close to a forest preserve offering walking trails, green space, and outdoor recreation. Whether you're looking to live in one unit and rent the other, accommodate extended family, or add a versatile property to your investment portfolio, this 2-flat offers updated living spaces, separate laundry, outdoor space, and multiple possibilities. A well-maintained multi-unit property with the flexibility today's buyers are looking for. Schedule your showing today!

5631 N Parkside Avenue, Chicago

$450,000

7 Beds ⋅ 5 Baths ⋅ 12733872 MLS ⋅ CLOSED Status

Welcome to 7018 S Rhodes Avenue, a full gut rehab legal 2-flat offering the rare combination of turnkey condition, flexible living space, rental income potential, and permitted improvements in the Greater Grand Crossing neighborhood. Completed as a full gut rehab with City of Chicago permits, this approximately 3,404 sq. ft. brick two-unit has been thoughtfully redesigned from top to bottom. The 1st floor apartment is an expansive 5-bedroom, 3-bath duplex-down spanning approximately 2,230 sq. ft., giving an owner-occupant an impressive amount of private living space while retaining the income-producing benefits of a multi-unit property. The 2nd floor apartment offers approximately 1,174 sq. ft. with 4 bedrooms and 2 full baths. Both units feature bright open-concept living spaces, modern kitchens with quartz countertops and full-height backsplash, stainless steel appliances, shaker-style cabinetry, contemporary lighting, and clean modern finishes throughout. Beautifully renovated bathrooms feature floor-to-ceiling tile, upgraded vanities, LED mirrors, and designer fixtures. Central heating and air conditioning add year-round comfort. The duplex-down provides even more flexibility with a spacious finished lower level, additional bedrooms and baths, and a striking illuminated staircase connecting the two levels. Outside, enjoy newly constructed rear porches, a fenced yard, and a two-car concrete parking pad. For buyers searching for a renovated Chicago 2-flat, owner-occupied investment, or house-hack opportunity, 7018 S Rhodes delivers the space and finish of a newly renovated home with the added advantage of a separate income-producing residence. This property is eligible for the Cook County Land Bank Grant. Qualified buyers may receive up to $20,000 in purchase assistance, subject to buyer eligibility and program requirements.

7018 S Rhodes Avenue, Chicago

$269,900

4 Beds ⋅ 2 Baths ⋅ 12746183 MLS ⋅ ACTIVE Status

Opportunity awaits with this oversized brick 2-flat, ideally situated on a well-kept Chicago block. Each spacious unit offers 2 generous bedrooms, 1 full bath, a separate formal dining room, hardwood floors throughout, and an abundance of natural light. The property boasts great curb appeal, a functional layout, and the added benefit of tenants paying their own utilities-helping to keep operating expenses low. With its attractive price point and manageable maintenance, this property is an excellent option for both an owner-occupant and an investor seeking a solid addition to their portfolio. Two-flats in the surrounding area have experienced strong appreciation, making this an excellent opportunity to purchase a quality property with equity potential and promising long-term value. Don't miss your chance to own a classic Chicago brick 2-flat with both immediate appeal and future upside.

1316 W 77Th Street, Chicago

4 Beds ⋅ 3 Baths ⋅ 12751017 MLS ⋅ AUCTION Status

Excellent opportunity for investors or owner-occupants! This classic brick 2-flat in Englewood features two spacious units, each offering 2 generous bedrooms and 1 full bathroom. First floor living extends outdoors with a charming back deck off the unit, perfect for morning coffee or relaxing in the evening. Enjoy a large yard with ample green space for outdoor gatherings and gardening, along with a secure 2-car detached garage. Conveniently located near public transportation, major expressways, parks, and local amenities. Bring your ideas and capitalize on great rental potential or live in one unit and rent out the other. Property being sold in AS IS condition, no surveys nor disclosures, taxes prorated.

6336 S Ada Street, Chicago

$295,000

6 Beds ⋅ 4 Baths ⋅ 12751086 MLS ⋅ ACTIVE Status

Excellent opportunity to own a solid brick 2-flat offering space, versatility, and long-term potential! This move in ready property features some updates, a finished attic and full finished basement, providing additional living space and potential income opportunities. Ideal for an owner-occupant or investor, with plenty of possibilities for the next owner to further enhance and add value. Major improvements include a roof approximately 5 years old, along with boilers and furnaces approximately 5 years old. Property is being sold strictly AS-IS. Seller will not make repairs. AS-IS Rider required.

5160 S Damen Avenue, Chicago

$350,000

5 Beds ⋅ 2 Baths ⋅ 12749441 MLS ⋅ ACTIVE Status

Greystone architecture and original details give this early 1900s two-flat a character that's distinctly Chicago. Projecting bays, tall windows, hardwood floors and original millwork bring warmth and architectural interest throughout two well laid out residences. The first-floor unit offers 2 bedrooms and 1 bath with separate living and dining rooms, an updated kitchen with granite countertops and stainless steel appliances, in-unit laundry hookup, and a primary bedroom with walk-in closet. Upstairs, the 3-bedroom, 1-bath residence features an expansive living and dining space, updated kitchen and bath, hardwood floors, and in-unit laundry hookup. A full unfinished basement offers additional storage and utility, while generous outdoor space and parking for up to four vehicles are valuable additions. With two distinct residences, the property lends itself equally well to owner-occupancy or a fully income-producing investment. Located near Garfield Park, just east of the Conservatory, with convenient access to public transportation and downtown, this is an opportunity to own an architecturally rich piece of Chicago in a prime location. This property can be purchased as a package with nearby buildings 5315 W Monroe (MLS#12748904); 3344 W Fulton (MLS#12748759) or purchased separately. MULTIPLE OFFERS RECEIVED - Highest & best Due by Tuesday 9/8 at 2PM

4319 W Jackson Boulevard, Chicago

$375,000

5 Beds ⋅ 2 Baths ⋅ 12748904 MLS ⋅ ACTIVE Status

With an inviting stucco facade, wide windows and sun-filled interiors, this two-flat feels bright and spacious from the moment you step inside. Hardwood floors run throughout generous living and dining spaces, with flexible layouts across both residences. The vacant first-floor unit offers 2 bedrooms and 1 bath, creating an easy opportunity for an owner-occupant or a new tenant. Upstairs, the 3-bedroom, 1-bath residence is currently rented month-to-month, providing immediate rental income. A full unfinished basement adds valuable additional space to expand, while rear decks, a yard and detached 2-car garage bring even more function to the property. Conveniently located near the Oak Park border with easy access to I-290, public transportation and nearby shopping, this two-flat offers a perfect balance of space, income and flexibility for its next owner. This property can be purchased as a package with nearby buildings 3344 W Fulton (MLS#12748759); 4319 W Jackson (MLS#12749441) or purchased separately.

5315 W Monroe Street, Chicago

$519,000

4 Beds ⋅ 3 Baths ⋅ 12750822 MLS ⋅ ACTIVE Status

Welcome to this classic 2-flat brick home in the desirable Belmont Cragin area! This solid multi-unit property offers a great opportunity for an owner-occupant, extended family, or investor looking to add value in a well-established Chicago neighborhood. Each unit offers a functional layout with comfortable living spaces, bedrooms, and kitchens, providing flexibility for rental income or multi-generational living. The full brick exterior offers classic Chicago character and durability, while the property's generous layout provides plenty of potential to make it your own. Conveniently located near neighborhood shopping, restaurants, schools, parks, public transportation, and major roadways, this property offers easy access to everything Belmont Cragin and surrounding neighborhoods have to offer. Whether you're looking to live in one unit and rent the other or add a solid property to your investment portfolio, this 2-flat is an opportunity worth exploring.

5036 W Wrightwood Avenue, Chicago

$554,900

6 Beds ⋅ 2 Baths ⋅ 12750850 MLS ⋅ ACTIVE Status

An exceptional and rare find along the vibrant Ogden corridor, this stunning, completely updated 2-flat property perfectly blends classic architectural character with high-end modern finishes. Every inch of both units has been thoughtfully renovated to deliver modern comfort and timeless style. Interior Highlights: Gleaming, restored hardwood flooring stretching throughout the primary living spaces. Chef-inspired kitchens featuring premium granite countertops, extensive cabinetry, and top-of-the-line stainless steel appliances. Generous floor plans in both units, each boasting 3 super-large bedrooms, expansive formal living rooms, and separate dining rooms. Charming architectural details throughout, including delightful nooks and crannies ideal for home offices, reading corners, or extra storage. Exterior & Location Benefits: Dedicated off-street parking accommodating 2 vehicles in the rear of the building. Unbeatable convenience with a local park and hospital located within easy walking distance. Exceptional transit-oriented location featuring seamless downtown access via the Ogden bus corridor and a rail station just a few blocks away. Whether you are an investor looking for a high-performing income generator or an owner-occupant seeking a spacious home with rental assistance, this turn-key 2-flat presents an extraordinary opportunity.

1656 S Troy Street, Chicago

$359,000

6 Beds ⋅ 2 Baths ⋅ 12738504 MLS ⋅ ACTIVE Status

Welcome to this beautifully recently remodeled, all-brick 2-flat offering an excellent opportunity for investors or owner-occupants! Both units feature 3 bedrooms and 1 bathroom, with generously sized living rooms, formal dining areas, hardwood flooring, and contemporary kitchens featuring European-style cabinetry, quartz countertops, full glass-tile backsplashes, and newer appliances. The updated bathrooms feature stylish finishes, including floor-to-ceiling tile, a rain shower, a newer vanity, and elegant fixtures. Each unit also offers in-unit washer/dryer and central heat/air. Enjoy a deck overlooking the fully fenced backyard and paved patio, providing great outdoor space for relaxing or entertaining. Outdoor parking spaces. Ideally located just off Ashland Avenue, close to shops, restaurants, parks, CTA Bus #9/#47, downtown, Chinatown, lakefront and more. Whether you're looking to add an income-producing property to your portfolio or live in one unit while generating rental income from the other, this property offers modern updates, spacious living areas, and excellent investment potential. Sold AS IS.

4505 S Justine Street, Chicago

$585,000

6 Beds ⋅ 2 Baths ⋅ 12738628 MLS ⋅ CONTINGENT Status

Solid brick 2 flat in coveted Avondale/Belmont Garden area on quiet tree lined street. The building offers two spacious units each with living room, separate dining room, kitchen and 3 bedrooms, as well as storage in enclosed porches. Each unit also has large bathroom, separate GFA heat, electric and water heaters. The full basement is semi finished with drywalled ceiling and walls, as well as a roughed in bathroom. Owner has maintained and made recent improvements such as newer furnaces & hallway painting. Both 1st and 2nd floor units are tenant occupied with leases ending at end of 2026. Current rents are below market with room for increase with capital improvements such as kitchen and bath updates. This is a great opportunity for investors or owner occupants in a fast appreciating area.

4140 W Barry Avenue, Chicago

$499,900

12 Beds ⋅ 4 Baths ⋅ 12750409 MLS ⋅ ACTIVE Status

Frame 2 Flat with Basement Apartment and Coach House / Occupied / Property being sold occupied / Property being sold in AS IS condition, no surveys nor disclosures, taxes prorated / Seller will review offers after the property has been on the market for 7 days. (Room counts/sizes are estimates) First Floor Unit has 4 Bedrooms /1 Bathroom, Second Floor Unit has 3 Bedrooms /1 Bathroom, Basement Unit has 3 Bedrooms /1 Bathroom, Coach house has 2 Bedrooms / 1 Bathroom

644 N Albany Avenue, Chicago

$325,000

5 Beds ⋅ 2 Baths ⋅ 12748855 MLS ⋅ ACTIVE Status

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.

6602 S Marquette Road, Chicago

$585,000

4 Beds ⋅ 3 Baths ⋅ 12748911 MLS ⋅ CONTINGENT Status

Amazing brick 2-flat opportunity in Portage Park, situated on an oversized 35' x 125' lot. This property offers excellent upside potential by duplexing the first-floor unit into the lower level, which features good ceiling height and an existing bathroom. The front stairwell is configured to allow for a straightforward entryway modification, seamlessly connecting the two levels. Once completed, the duplex-down unit could offer either 3 beds / 2 baths or 4 beds / 2 baths. Both units are currently configured with 2 bedrooms and 1 bathroom. The second-floor unit features an enclosed rear porch that has been incorporated into the living space and works perfectly as an office or den. Additional highlights include basement laundry, a two-car detached garage, and a separate parking pad for a third vehicle. This property is an excellent alternative to a single-family home, with the added benefit of rental income to help balance ownership costs. The first-floor tenant will vacate at the end of September. Please refer to the showing schedule for prearranged showing times.

5051 W Berenice Avenue, Chicago

$499,000

6 Beds ⋅ 2 Baths ⋅ 12748816 MLS ⋅ ACTIVE Status

Welcome to this fully rehabbed all brick Austin 2 FLAT. 6 Bedrooms, 2 Baths each floor with a 3/1 layout. Large open concept;1000 sq feet per unit. You must see this beautiful two flat to appreciate the value; 2 similar units with their own unique style. Convenient to Austin Bus, walk to train, shopping, parks and school. Your chance to own an income producing property. Owner occupy or rent out both units for even more income. Finishing touches are happening NOW.

1051 N Massasoit Avenue, Chicago

$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

$399,700

6 Beds ⋅ 2 Baths ⋅ 12748493 MLS ⋅ ACTIVE Status

Fully renovated two-flat offering incredible flexibility for an owner-occupant or investor. Both units have been completely updated with new flooring, new kitchens, and new bathrooms throughout - a true turn-key opportunity. This 6-bedroom, 2-bathroom building offers approximately 2,124 square feet of living space across two spacious 3-bedroom units, plus a full basement ready for storage or future finish. Live in one unit and rent the other, or hold both as a fully renovated income property. Located in a South Side Chicago neighborhood convenient to transit, schools, and shopping. Financing available through Conventional, FHA, and Investor loan programs. Schedule your showing today!

6955 S Honore Street, Chicago

$999,000

8 Beds ⋅ 4 Baths ⋅ 12749788 MLS ⋅ ACTIVE Status

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!

2343 W Cortez Street, Chicago

$410,000

5 Beds ⋅ 3 Baths ⋅ 12749674 MLS ⋅ ACTIVE Status

Beautiful and well maintained 2 flat with an additional garden unit updated within the last 5 years. This property offers spacious living areas, modern finishes and a functional layout throughout. Two 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.

7605 S Calumet Avenue, Chicago

$725,000

4 Beds ⋅ 3 Baths ⋅ 12703740 MLS ⋅ PRICE CHANGE Status

Hot investment opportunity in Avondale! Beautifully maintained and spacious 2-flat offering a fantastic opportunity for investors or owner-occupants looking to generate rental income. Both units feature the same desirable floor plan with expansive living and dining rooms, large kitchens with walk-in pantries, two bedrooms and a full bath. Unit 1's bathroom has been recently updated with modern finishes. The finished basement adds even more potential featuring a large recreation room, two additional bedrooms, a full bath, and laundry area, making it ideal for an in-law arrangement. Recent updates: fresh paint 2026, new carpet on main level 2026, newer kitchens and baths, water heater 2025, furnace 2019, newer garage, hardwood floors under carpet. Outside, enjoy a spacious deck, veggie garden, and a newer extra tall 2.5-car garage. Whether you choose to rent both units or live in one and rent the other, this property offers excellent versatility. Ideally located just minutes from I-90/94, grocery stores, restaurants and CTA Blue line. Avondale was recently named one of the Coolest Neighborhoods!

3445 N Monticello Avenue, Chicago

$429,900

7 Beds ⋅ 3 Baths ⋅ 12747390 MLS ⋅ ACTIVE Status

Welcome to this spacious brick 2-flat in the Englewood area, offering excellent space and flexibility with 7 bedrooms and 3 full baths across two units. Each unit features a 3-bedroom layout, comfortable living spaces, and a kitchen equipped with a stove, refrigerator, and microwave. The finished basement provides additional space for storage, recreation, or other possibilities. Both units are currently vacant, offering a great opportunity for an owner occupant or investor. Conveniently located near public transportation, shopping, dining, parks, and neighborhood amenities. Don't miss the opportunity to make this versatile 2-flat your own!

7131 S Normal Boulevard, Chicago

$439,900

8 Beds ⋅ 3 Baths ⋅ 12749070 MLS ⋅ ACTIVE Status

Recently updated extra large 2 flat Gray-stone on a quiet block. Modern finishes include - new white kitchen cabinets, granite counter tops, ceramic tile backsplash, new SS appliances new light fixtures, mirrors, faucets...... 2 bedrooms on first floor and 4 bedrooms on the second. Finished basement duplexed to the first floor with additional 2 bedrooms and 1 bath creates extended living space. This house is perfect for a live-in owner or investor. Call for your appointment.

6946 S May Street, Chicago

$310,000

6 Beds ⋅ 2 Baths ⋅ 12748907 MLS ⋅ CONTINGENT Status

Great opportunity to own a classic Chicago brick two-flat, each unit features 3 bedrooms, 2 bathrooms, providing comfortable living space updating and personalizing

1140 N Waller Avenue, Chicago

$249,000

5 Beds ⋅ 2 Baths ⋅ 12741326 MLS ⋅ CONTINGENT Status

Now available at 5524 S Wells St, Chicago, IL 60621. This newly rehabbed, turnkey 2-flat is being offered at $249,000 and features a 3-bedroom, 1-bath first-floor unit and a legal 2-bedroom, 1-bath garden unit. Both units are currently vacant and move-in ready, making this a great opportunity for either an owner-occupant or investor. The property has separate furnaces, separate water heaters, separate electric meters, and separate gas service for each unit. The first-floor water heater was newly installed in 2026. The property also includes a 2-car garage that was built from the ground up with permits in 2022, along with a fenced yard and updated kitchens and bathrooms throughout. This property is ideal for someone looking to live in one unit and rent the other, or for an investor looking for a turnkey 2-unit property with separate utilities. FHA, VA, and conventional financing are accepted. Serious buyers and agents may reach out for additional information or to schedule a showing.

5524 S Wells Street, Chicago

$635,900

5 Beds ⋅ 3 Baths ⋅ 12748438 MLS ⋅ ACTIVE Status

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.

5475 N Monitor Avenue, Chicago

$383,000

5 Beds ⋅ 3 Baths ⋅ 12740447 MLS ⋅ ACTIVE Status

Discover an outstanding opportunity in this beautifully maintained Chicago two-flat! Each unit offers 2 bedrooms, 1 bathroom, and a functional layout designed for comfortable everyday living. The fully finished basement provides additional space with 2 bedrooms and 1 bathroom. With fully finished basement also adds even more value. Conveniently located near schools, parks, shopping, dining, and major expressways, this property is ideal for both owner-occupants and investors. Schedule your showing today opportunities like this don't last long! Property is being sold as-is.

6641 S Fairfield Avenue, Chicago

$450,000

4 Beds ⋅ 3 Baths ⋅ 12748178 MLS ⋅ ACTIVE Status

All-brick 2-flat building, fully updated and completely move-in ready! Each spacious unit features two generous bedrooms, a formal dining room, an inviting living room with a cozy fireplace, fully remodeled kitchen and bathroom, and a bright enclosed porch-complete with separate utilities for maximum convenience. The full basement offers fantastic added versatility with an extra 1-bedroom space and ample storage. Don't miss out on this incredible turnkey opportunity-schedule your showing today!

5948 S Washtenaw Avenue, Chicago

$419,000

4 Beds ⋅ 3 Baths ⋅ 12748064 MLS ⋅ PRICE CHANGE Status

Welcome to this well-maintained classic Chicago brick Two Flat in the highly desirable North Austin neighborhood, offering an outstanding opportunity for both investors and owner-occupants. The 1st and 2nd floor provide spacious units that features 2 bedrooms, 1 bathroom, generous living and dining rooms, large kitchens, hardwood floors throughout, and an additional flex room that can serve as a sunroom, walk-in closet, home office, or extra living space, while the finished basement is a studio style unit w/ a kitchen, living area, full bath and front/rear entry and exit. The property also includes a rear deck, private two car garage parking, and separately metered utilities with individual furnaces, water heaters, and utility billing for each unit. The building is fully occupied with Unit 1 leased month-to-month at $1,250, Unit 2 will be vacant upon closing, and the garden unit leased through 3/2027 at $800. Electrical for the entire building was updated in 2025. Austin continues to emerge as one of Chicago's most promising investment corridors, offering affordability, strong rental demand, and convenient access to CTA buses, Metra, parks, schools, shopping, grocery stores, Walmart, Galewood Theatre, fitness centers, and more. Whether you're seeking immediate cash flow with future upside or looking to supplement your mortgage through rental income, this property delivers exceptional long-term potential. Seller and broker do not represent the legality of the garden unit. Don't miss this opportunity to invest in one of Chicago's rapidly appreciating neighborhoods. Selling "As Is"

1810 N Linder Avenue, Chicago

$599,000

9 Beds ⋅ 6 Baths ⋅ 12746844 MLS ⋅ ACTIVE Status

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!

1632 S Homan Avenue, Chicago

$394,900

6 Beds ⋅ 3 Baths ⋅ 12747736 MLS ⋅ CONTINGENT Status

Excellent opportunity to own this solid brick 2-flat with a finished basement. Each apartment offers 6 rooms, 2 bedrooms and 1 bath. The finished basement includes 2 additional bedrooms, a family room, and a full bath, providing valuable extra living space. The 1st floor and basement feature boiler heat, while the 2nd floor is equipped with gas space heaters. Separate utilities throughout. The building has been recently tuckpointed. Property is being sold AS-IS

1634 N Kildare Avenue, Chicago

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