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$519,900
7 Beds ⋅ 2 Baths ⋅ 12741386 MLS ⋅ PRICE CHANGE Status

4737 S Langley Avenue, Chicago
$200,000
4 Beds ⋅ 3 Baths ⋅ 12731934 MLS ⋅ CONTINGENT Status
Rare piece of Chicago history; built in 1887, likely the second property ever constructed on the South Shore, predating the area's annexation into the city. Owned and lovingly cared for by the same family for 120 years, this is a unique opportunity to own a true piece of the past. A legal 3-unit building offering flexible possibilities. Main level consists of a 2 bed, 1 bath, the second level has two one bed, one bath units, back to back. The third level contains a full attic with potential to finish and expand. The building features stunning original woodwork throughout and is in very solid structural condition, ready for its next chapter. The second-floor units have been unused for years and will need renovation, a blank canvas for a savvy investor or owner-occupant to add value. Recent neighborhood infrastructure upgrades include new streets, curbs, gutters, and LED street lights, enhancing this historic setting.

2714 E 93Rd Street, Chicago
$1,350,000
11 Beds ⋅ 5 Baths ⋅ 12741328 MLS ⋅ ACTIVE Status
Exceptionally rare opportunity to acquire one of only a handful of rental properties on Morgan Street directly across from the University of Illinois Chicago campus. This fully occupied brick three-flat contains 11 bedrooms and five full bathrooms across three units. Each unit features central heat and air conditioning, a refrigerator and range. The property also offers coin-operated laundry and rear tandem parking for up to six vehicles, providing additional income potential. Located in the heart of Little Italy/University Village with convenient access to UIC, public transportation, expressways, dining and neighborhood amenities. Do not disturb tenants. Financial information and offering materials are available from the listing broker.

836 S Morgan Street, Chicago
$625,000
5 Beds ⋅ 3 Baths ⋅ 12660589 MLS ⋅ CONTINGENT Status
Large, well-maintained all-brick 2-flat with a non-conforming garden unit on a 30' wide lot in Belmont Cragin. Very generous room sizes make living here a delight, along with hardwood floors and great light throughout. The top floor has a kitchen with a large pantry, an updated bathroom, and can be two or three bedrooms depending on the use of the back room as a family room/dining room/or primary bedroom. The first floor is two bedroom with the updated kitchen opening up to a dining room. The finished lower level has three bedrooms and a full bathroom with two egress. Shared laundry. Upper units are separately metered. Also includes a hardie board clad 2 car garage and spacious back patio.

5051 W Montana Street, Chicago
$609,000
5 Beds ⋅ 3 Baths ⋅ 12741864 MLS ⋅ ACTIVE Status
Incredible opportunity to own a well-maintained legal two-flat with an additional garden unit! Each spacious unit features hardwood flooring, generous living rooms, formal dining areas, large kitchens, ample closet space, and wide enclosed porches. The first-floor unit offers two bedrooms plus a versatile den-perfect for a home office, guest room, or additional living space. Major improvements include a newer roof and water heater (2016), HVAC upgrades completed in 2021, and updated plumbing within the past two years. Situated on a wide lot with a side driveway and one-car garage, this property is conveniently located near restaurants, theaters, shopping, and public transportation. An excellent opportunity for an owner-occupant or investor!

5005 W Eddy Street, Chicago
$699,000
5 Beds ⋅ 4 Baths ⋅ 12740618 MLS ⋅ ACTIVE Status
Live large, live green, and let your investment work for you. As the first of its kind ever built in North Lawndale, this two-unit marks the dawn of the next generation of housing in the neighborhood - a solar-powered building designed for an owner who wants the space and feel of a single-family home with the built-in cash flow of a rental unit. The Owner's Duplex-Up: Spanning two full floors, this 3-bedroom, 2.5-bath duplex-up lives like a detached single-family home. Soaring 9' ceilings and an open, light-filled layout set the stage for the elegant chef's kitchen with floor-to-ceiling cabinetry, quartz countertops, and a sleek induction range, anchored by a massive 10' island and glass herringbone backsplash. The living room centers around a fireplace framed by built-in glass shelving, while crown molding with LED up-lighting adds a refined finishing touch throughout. Just off the living room, the dining area is made for hosting - a dry bar, wine cooler, and floating shelves make every gathering effortless. Custom built-in mudroom cabinetry keeps everyday life organized as you walk in the door. This is a home designed for how people actually live - spacious, efficient, and thoughtful. The Garden Investment Unit: A 2-bedroom, 1-bath garden unit offers immediate rental income potential, finished to the same high standard as the owner's unit - quartz countertops, custom cabinetry, and an induction range. Whether you're offsetting your mortgage or building a rental portfolio, this unit delivers flexibility from day one. Solar-Powered & All-Electric Efficiency: Every system in this home runs on electricity, powered by on-site solar - meaning lower utility costs, a smaller carbon footprint, and a home built for the future of energy. High-performance construction is evident throughout, with triple-pane windows, Broan ERVs for continuous fresh air, and staggered stud framing with continuous spray foam insulation for a tight, comfortable building envelope year-round. Outdoor Space & Parking: A completely fenced, extra-large lot offers privacy and outdoor space rarely available with new construction in the city. The future-proof, EV-ready 2-car garage means your electric vehicle charging needs are already covered. The North Lawndale Opportunity: Positioned in one of Chicago's most dynamic West Side neighborhoods, this property puts owners close to Douglas Park, growing neighborhood investment, and easy access to downtown - all while offering the rare combination of single-family living and rental income in one address. All Electric. All New. All Yours.

3256 W Douglas Boulevard, Chicago
$650,000
6 Beds ⋅ 3 Baths ⋅ 12732536 MLS ⋅ ACTIVE Status
Location, Location, Location !! Highly sought-after neighborhood California and Armitage. Walk to Blue line on Milwaukee Ave. Solid large tall handsome 3 apartment Brick building with an English garden unit with 2 entrances. Lots of woodwork. Hardwood floors. Good size apartments. Formal living Room and Dining Room. Plenty of closets. Spacious garden apartment . Enclosed Porch. Wide backyard. Front iron fence. Beautiful three lined street . Walking distance to new stores, restaurants, parks and entertainment. Close to Logan, Bucktown and Humboldt Park . Easy Transportation : CTA on Armitage Ave and California. Walking distance to the blue line on Milwaukee Ave. Long term tenants. Rehab needed. Renovate and the value will increase. Great investment. An excellent opportunity with multiple options: live in one unit while generating income from the other 2 apartments, operate as a fully rented investment, or convert to a duplex or a single-family home.

1949 N Francisco Avenue, Chicago
$359,000
6 Beds ⋅ 2 Baths ⋅ 12741839 MLS ⋅ ACTIVE Status
Prepare to be captivated by this stunning reimagined BRICK two flat that perfectly balances modern sophistication with incredible income potential. From the moment you step inside 9015 S Muskegon Ave, you will notice the sun drenched rooms and the pristine, high quality finishes that elevate every square foot. Each unit serves as a pristine, move in ready sanctuary, boasting expansive layouts that feel open and airy. Whether you are an investor looking to secure a lucrative gem for your portfolio or an owner occupant eager to live luxuriously while generating effortless passive income, this beautifully transformed multi family property stands out as a true neighborhood showstopper.

9015 S Muskegon Avenue, Chicago
$545,000
6 Beds ⋅ 3 Baths ⋅ 12741729 MLS ⋅ ACTIVE Status

7419 S Stewart Avenue, Chicago
$790,000
8 Beds ⋅ 5 Baths ⋅ 12740081 MLS ⋅ ACTIVE Status
Amazing investment opportunty to own an updated legal 2-flat with a finished English Garden Unit with HIGH ceilings in Jefferson Park. This property offers generous living space, strong rental income, and excellent flexibility for an investor, owner-occupant, or multi-generational household. Both Unit 1 and Unit 2 feature 3 bedrooms and 1.5 bathrooms with thoughtfully redesigned floor plans that provide larger bedrooms than typically found in vintage Chicago buildings. Each unit offers bright living spaces, recessed lighting, updated kitchens with quartz countertops, stainless steel appliances, and ample cabinetry, plus one full bathroom and a convenient powder room. Unit 1 is currently leased at $2,650 per month, including electricity, gas/heat, water, trash removal, landscaping, and one garage parking space. Unit 2 is currently leased at $2,400 per month, including electricity and water. Together, the two legal units currently generate $5,050 in monthly rental revenue, or $60,600 annually. The finished basement is currently vacant but can provide additional flexible living space with 2 bedrooms and 1 full bathroom and an estimated rental potential of approximately $2,300 per month (MLS Comparable#: 12616160), subject to applicable laws, zoning, approvals, and permitted use. If legally approved for rental use, the property's potential combined gross income could reach approximately $7,250 per month or $87,000 annually. Additional features include an oversized deck above the garage, shared outdoor space, rear decks, and coin-operated washer and dryer, providing added convenience and potential supplemental income. Conveniently located near shopping, dining, transportation, parks, and neighborhood amenities, this is a versatile income-producing property with updated interiors, spacious layouts, and excellent long-term potential. Schedule your private showing today and explore everything this unique Chicago 2-flat has to offer.

5759 N Elston Avenue, Chicago
$299,950
5 Beds ⋅ 2 Baths ⋅ 12741766 MLS ⋅ RE-ACTIVATED Status
Chicago two-flat opportunity in the West Garfield Park area, delivered vacant at closing. The property offers a spacious two-unit layout with a three-bedroom unit and a two-bedroom unit, providing flexibility for an investor looking to renovate, lease, or reposition the property. The owner has already completed several cosmetic updates including newer kitchen cabinets, updated countertops, and laminate flooring throughout.

4352 W Monroe Street, Chicago
$200,000
4 Beds ⋅ 2 Baths ⋅ 12740658 MLS ⋅ ACTIVE Status
Opportunity awaits! This brick 2-flat offers two units, each with 2 bedrooms and 1 bathroom, plus an unfinished basement and an enclosed rear porch. Water heaters are approximately two years old. Conveniently located near transportation, shopping, and neighborhood amenities. The property is sold AS-IS and needs repairs and updates, making it a great opportunity for an investor or buyer looking to add value. Sale is pursuant to lender approval of a short sale. Buyer to verify all information, room sizes, zoning, and property details. Schedule your showing and explore the possibilities!

11748 S Wentworth Avenue, Chicago
$785,000
8 Beds ⋅ 3 Baths ⋅ 12741671 MLS ⋅ ACTIVE Status
Excellent income-producing opportunity in the desirable Arcadia Terrace neighborhood of West Ridge. This beautifully updated all-brick 2-unit building offers exceptional flexibility for investors and owner-occupants alike, with two spacious 3-bedroom, 1-bathroom main units plus additional garden-level living space featuring 2 bedrooms and 1 bathroom. An owner-occupant can live comfortably in one main unit while renting the other, with additional rental potential from the garden-level space, subject to applicable use and occupancy requirements. A full cosmetic renovation was completed in 2019, including modern kitchens with stainless steel appliances and quartz countertops, updated bathrooms, and hardwood floors throughout the main units. The second-floor unit includes convenient in-unit laundry, while additional coin-operated laundry is available on the garden level. Enjoy a shared outdoor courtyard, perfect for relaxing or entertaining. Parking is a standout advantage, with a detached 2-car garage plus an exterior parking space for a third vehicle. Ideally located near West Ridge Nature Park, shopping, restaurants, schools, and public transportation, this well-maintained property combines flexible living arrangements, strong rental potential, valuable parking, and shared outdoor space in a highly desirable neighborhood.

5653 N Talman Avenue, Chicago
$1,369,000
14 Beds ⋅ 8 Baths ⋅ 12741726 MLS ⋅ PRICE CHANGE Status
EXCEPTIONAL, MASSIVE, EXTRA WIDE, ARCHITECTURALLY SIGNIFICANT 4 UNITS BUILDING ON A DOUBLE LOT AND IN MOST HOT, DESIRABLE LOCATION. IT WAS CONVERTED FROM 8 SMALLER UNITS TO HUGE 4 UNITS. ALL NEW ROOF, WINDOWS, PLUMBING, ELECTRIC, MECHANICALS, ETC. 4TH SMALL BEDROOM IS OPTIONAL OFF LIVING ROOM. IN UNIT LAUNDRY. 2 CAR GARAGE, 3 EXTERIOR PARKING SPOTS OFF ALLEY AND 3 EXTERIOR SPOTS ON SIDE DRIVE. TONS OF NEW CONSTRUCTION AND REHABS ON THE BLOCK. UNBEATABLE LOCATION. VERY CLOSE TO GREEN LINE AND ALL PUBLIC TRANSPORTATION. ACT NOW !!!

6418 S Vernon Avenue, Chicago
$470,000
8 Beds ⋅ 3 Baths ⋅ 12741619 MLS ⋅ ACTIVE Status
Fantastic opportunity to own a 3-unit building in the heart of North Lawndale! Whether you're an investor looking to maximize rental income or an owner-occupant seeking additional income potential, this property offers incredible flexibility and long-term value. Unit 1 features 2 bedrooms and 1 bathroom, while Units 2 and 3 each offer spacious 3-bedroom, 1-bath layouts with bright living spaces and functional floor plans. The property also includes a convenient coin-operated laundry area, a 4-car parking slab in the rear, and one unit is currently vacant, allowing the new owner to set market rents immediately or move right in. The other two units are tenant-occupied, providing immediate rental income. Conveniently located near schools, parks, shopping, restaurants, public transportation, and major expressways, this is an excellent opportunity to add a turnkey multi-unit property to your portfolio.

1622 S Karlov Avenue, Chicago
$329,999
6 Beds ⋅ 3 Baths ⋅ 12741705 MLS ⋅ ACTIVE Status
This property is an excellent opportunity for first time homebuyers who want an affordable path to homeownership. This three unit flat is located in a steadily improving neighborhood on the Southeast Side of Chicago and offers strong long term potential. Each unit includes appliances and features a comfortable two bedroom one bathroom layout. For first time buyers, this is an ideal chance to live in one unit and use the rental income from the other two units to help lower your mortgage. All three units are currently occupied by dependable tenants, which also makes this a solid option for investors seeking immediate rental income. The building provides spacious units and there is consistent rental demand in this area. As the neighborhood continues to improve, the property is well positioned for future appreciation. Whether you are purchasing your first home or looking to expand your real estate portfolio, this turn key three flat offers value, stability, and long term opportunity.

8632 S Escanaba Avenue, Chicago
$549,999
4 Beds ⋅ 3 Baths ⋅ 12732399 MLS ⋅ CONTINGENT Status
Rare opportunity to own a beautifully maintained two-flat in the heart of Gladstone Park! Owned by the same family for over 60 years, this pride-of-ownership property combines classic Chicago charm with numerous updates and strong income potential. Property being sold as-as. Both units have been thoughtfully refreshed, making this a truly turnkey opportunity for investors and owner-occupants alike. Major improvements include newer windows, roof, siding, gutters, downspouts, furnace, central air, updated kitchens, and recent interior paint. The second-floor unit was extensively updated in 2022 with new flooring, cabinetry, carpeting, and fresh paint, while the first-floor unit was repainted in 2025. The property features two well maintained units with tenants already in place, providing immediate rental income from day one. Both leases are currently month-to-month, offering future owners flexibility while benefiting from an established income stream. The first-floor unit has use of a finished rec room and bathroom, currently enjoyed as a comfortable space to relax, entertain, and watch the game. Located in highly desirable Gladstone Park, residents enjoy tree-lined streets, a strong neighborhood feel, and convenient access to the Kennedy Expressway, Metra, parks, restaurants, shopping, and everyday conveniences. This Northwest Side community is known for its welcoming atmosphere, excellent connectivity, and balance of city living with a more residential feel. Whether you're looking to expand your investment portfolio, live in one unit while generating rental income from the other, or acquire a well cared for multi-unit property in a prime location, this exceptional two-flat checks all the boxes. Don't miss the opportunity to own a turnkey building in one of Chicago's most established and sought-after neighborhoods.

5641 N Austin Avenue, Chicago
$580,000
5 Beds ⋅ 3 Baths ⋅ 12741656 MLS ⋅ ACTIVE Status
Seize the day with this Updated, Versatile two-flat in Portage Park offering Cash Flow and Value-add upside. The property features one duplex-down unit with 3 bedrooms and 2 baths, plus a 2nd floor Simplex apartment with 2-bedroom/1-bath. Separate utilities and private laundry for each unit add convenience and investor appeal. Fully fenced yard, plus a 2-car garage with potential for additional income. Ideally located near historic 38-acre Portage Park, with access to nature walks, Olympic-size pool with aquatics, team & individual sports, gymnasium facilities, and fieldhouses. Walk to neighborhood favorites including Binny's, Target, PetSmart, Jewel-Osco, Ross, restaurants, shopping, and everyday conveniences. Enjoy easy access to I-90/94, CTA, Metra, O'Hare Airport, and Downtown Chicago. Make your appointment today!

4817 W Dakin Street, Chicago
$310,000
5 Beds ⋅ 3 Baths ⋅ 12741209 MLS ⋅ CONTINGENT Status
Welcome to 4943 S Hoyne Ave! This well-maintained family-owned 2-flat will be delivered vacant at closing with no outside tenants or leases. Each unit features 2 bedrooms plus a small office, granite countertops, custom wood flooring, and quality finishes. The finished attic includes its own washroom and can be duplexed with the second-floor unit. Separate utilities serve each main unit, with the second floor and attic serviced together. Low taxes, tankless water heater, detached garage, and move-in-ready condition make this a great option for owner-occupants or investors. Bring your FHA buyers! Conveniently located near Back of the Yards College Prep, Orange Line CTA access, and multiple grocery stores. move-in ready, low taxes, great opportunity 2 flats like these don't come around often

4943 S Hoyne Avenue, Chicago
$489,000
9 Beds ⋅ 7 Baths ⋅ 12740698 MLS ⋅ CONTINGENT Status
TURNKEY + VALUE-ADD opportunity in South Shore! REHAB/RENOVATION FINANCING REQUIRED due to the remaining work in the legal garden unit. This is a LEGAL 4-UNIT. Three spacious 3-bedroom, 1.1-bath units have been fully rehabbed with updated mechanicals, new bathrooms, kitchens, flooring and light fixtures. All three units are VACANT and ready to lease at current market rents, allowing the next owner to select their own tenants and start generating rental income immediately. The legal 4th garden unit is a 1-bedroom, 1-bath offering even more rental income once the remaining improvements are completed. The three large upper units are ready to rent and can help support the property's expenses while the final unit is completed. A 3-car garage plus basement common area offer additional income potential through garage parking and coin laundry. An excellent opportunity for an investor or owner-occupant. FHA 203(k), Fannie Mae HomeStyle or other qualifying renovation financing required. Sold As-Is.

8010 S Phillips Avenue, Chicago
$505,000
6 Beds ⋅ 3 Baths ⋅ 12735226 MLS ⋅ ACTIVE Status
Bring your family or your future tenants with you to view this solid and clean 2 flat brick property with added living space in the basement. Located in the heart of the Belmont-Cragin Community. Highlights include updated kitchens and baths on 1st and 2nd floors.1st flr. unit has room right off living room that can be used as office or 3rd bedroom. Finished basement has living room, kitchen, full bath and 2 bedrooms. Large enclosed porches can provide more room to enjoy. 2 car garage and a spacious yard. Multi generational living and multi generational wealth awaits you.

2025 N Lawler Avenue, Chicago
$540,000
12 Beds ⋅ 4 Baths ⋅ 12741395 MLS ⋅ PRICE CHANGE Status
Well-located mixed-use building on high-traffic Pulaski Road - a hard corner with steady visibility in North Lawndale - offering three residential units above ground-floor commercial space. Excellent access to public transit, the Illinois Medical District, and the I-290 corridor, in a submarket drawing continued public and private investment along the Pulaski and Ogden corridors. The property suits an investor seeking diversified income or an owner-operator who wants to activate the ground-floor commercial space while leasing the units above. Strong value-add potential for a buyer who restores the storefront to commercial use or pursues the appropriate approvals for its current configuration. Unit configuration / use disclosure: Building comprises three residential units plus a ground-floor commercial unit (four total). The ground-floor commercial space is currently being used residentially, which is a non-conforming use. Buyer to independently verify unit count, zoning, permitted use, and legal occupancy with the City of Chicago and to satisfy itself as to any steps required to conform or continue the current use. Tax advantage: The 2025 assessment was successfully appealed at the Cook County Board of Review, reducing the assessed value from 48,063 to 32,013 - roughly a 33 pct reduction and an estimated annual savings of about $3,100. Post-appeal real estate taxes are projected in the ~$6,100-$6,400 range, meaningfully improving NOI and buyer returns. A rare mixed-use hold in an appreciating West Side submarket. Financials and lease summary available on request.

2008 S Pulaski Road, Chicago
$725,000
6 Beds ⋅ 3 Baths ⋅ 12738604 MLS ⋅ CONTINGENT Status
Step into a piece of Bridgeport history with this meticulously maintained, legal three-flat situated in Bridgeport, one of Chicago's most vibrant and rapidly evolving neighborhoods. All-brick masonry building has been lovingly cared for by long-time owners, offering a rare blend of pristine vintage character and essential modern updates. Each of the three units is located above grade, flooded with natural light that highlights the incredible original craftsmanship. Stunning hardwood floors run throughout each unit, as well as intricate moldings, built-ins, and original doors and windows that tell the story of a bygone era. While the vintage soul remains intact, the heavy lifting has already been done with updated electrical and plumbing systems throughout. The second and third-floor units feature the modern convenience of gas forced air and central AC, while the first floor retains the cozy warmth of radiator heating. The massive unfinished basement is a standout feature, boasting high ceilings, individual storage rooms for each unit, and tenant laundry facilities that provide an easy stream of additional income. Find true yard space out back, plus a dedicated parking pad providing three spaces-one for every unit-a premium commodity in this neighborhood. Located in the heart of a charming historic neighborhood, surrounded by creative energy and a wave of new restaurants, coffee shops, and bars that are making Bridgeport a top destination for renters and homeowners alike. Whether you're looking to add a turnkey gem to your portfolio or live in one unit while the others pay your mortgage, this building is a standout opportunity that you won't want to miss!

925 W 31St Place, Chicago
$399,500
9 Beds ⋅ 3 Baths ⋅ 12741251 MLS ⋅ ACTIVE Status
Exceptional opportunity for both owner-occupants and investors to acquire a solid brick 3-flat in the rapidly evolving East Garfield Park/Illinois Medical District corridor. The property consists of three spacious 3-bedroom, 1-bathroom units with separately metered utilities, allowing tenants to have their own gas and electric. Property to be sold occupied. Each unit includes a stove and refrigerator, while the unfinished basement offers additional potential and flexibility for a future owner. Whether you're looking to owner-occupy or add a strong multi-unit asset to your portfolio, this property offers a variety of possibilities and long-term upside. Ideally located just minutes from I-290, CTA public transportation, the United Center, the University of Illinois Chicago, and the Illinois Medical District (IMD), one of the largest urban medical districts in the United States. The area continues to benefit from ongoing investment, redevelopment, healthcare expansion, and economic growth. 3046 W Polk presents an excellent opportunity to acquire a well-maintained multi-unit property in one of Chicago's most rapidly developing neighborhoods. Property to be sold occupied. Seller will not provide notice to vacate. Units 1 and 2 are month-to-month; Unit 3 lease expires 12/2026.

3046 W Polk Street, Chicago
$575,000
9 Beds ⋅ 3 Baths ⋅ 12740640 MLS ⋅ ACTIVE Status
This classic all-brick 3-flat in the desirable Hyde Park/South Shore area. Each of the three spacious, units features, 3 bedrooms and 1 updated full bathroom, an oversized living room with a decorative fireplace, a Formal Dining room ideal for entertaining, and a newly updated kitchen with an efficient layout and ample cabinet space. All units have been freshly painted The enclosed rear porches provide valuable year-round living space, while the full unfinished basement offers excellent potential for additional storage or future development. Recent improvements include a new roof and parapet, new heating systems, a completely rebuilt 3-car garage with a new floor, roof, and doors, a gated front yard, a new rear patio, and new tuckpointing. With spacious units, significant recent improvements, and strong income potential, this property is truly an investor's dream and a fantastic opportunity in a desirable Chicago neighborhood.

7730 S Essex Avenue, Chicago
$575,000
8 Beds ⋅ 3 Baths ⋅ 12741013 MLS ⋅ ACTIVE Status
This spacious 8-bedroom, 3-bath multi-unit offers incredible space and major updates throughout! The first-floor unit features a duplex-down layout, plus the property boasts central air (2021), 200-amp electrical (2024), roof and siding (2020), oversized gutters, tankless water heater (2020), tuck pointing (2024), newer windows (2020/2024), and a new sump pump and support pillars. Enjoy the added bonus of being the only multi-unit on the block with a balcony! Located in a rapidly developing neighborhood surrounded by new construction, this is a great opportunity for an owner-occupant or investor looking to get into an area with exciting growth. Long term tenants and income-producing property generating approximately $4,700 in monthly cash flow. In October applications will open up to potentially buy the double lot right next door for ONLY 10% of purchase price which is $8,000. THIS COULD BE AN AMAZING OPPORTUNITY for an INVESTOR or owner occupy!

1121 N Lawndale Avenue, Chicago
$1,049,914
12 Beds ⋅ 6 Baths ⋅ 12740995 MLS ⋅ ACTIVE Status

3432 W Cortland Street, Chicago
$539,900
4 Beds ⋅ 2 Baths ⋅ 12740981 MLS ⋅ ACTIVE Status
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.

5848 W Catalpa Avenue, Chicago
$599,000
12 Beds ⋅ 4 Baths ⋅ 12740833 MLS ⋅ ACTIVE Status
LARGE updated legal four in rapidly appreciating North Lawndale. 1301 S Christiana boasts updated units with modern efficiencies like in-unit washers and dryers, individual furnaces and central air in EVERY UNIT, and updated kitchens with beautiful granite countertops. The property was built big extending to the sidewalk to create above standard units with plenty of sunlight since it is on the end of the street. This makes it the ideal investment for a house hacker looking to use FHA financing or any owner-occupy loan, or for any savvy investor wanting to invest in North Lawndale. In addition to the unit updates, the property received a 400 amp electrical service installation, newer windows, and a roof tear-off in 2017. Leases are below market value because the owner wanted to keep the great long term tenants. Parking is available in the back with easy street parking for any occupant. 1301 S Christiana is an excellent addition to any portfolio.

1301 S Christiana Avenue, Chicago
$289,999
6 Beds ⋅ 3 Baths ⋅ 12721545 MLS ⋅ ACTIVE Status
This lovely 2-unit building with an additional finished studio/attic space in West Englewood is a must-see! A spacious property offering two generous apartments, a full basement, finished attic space, and a detached 2-car garage. The first-floor unit features 2 bedrooms and 1 bathroom, while the recently renovated second-floor unit offers 3 bedrooms and 1 bathroom. The finished attic provides additional living space, including a bedroom, living area, and full bathroom, offering excellent flexibility for additional living or recreational space. Both main units feature bright, open living areas, hardwood floors, and plenty of natural light. With some cosmetic updates, there is significant potential to further enhance the property's appeal and value. The full basement provides ample storage space and includes a dedicated laundry area. The property also features separate utilities, new water heaters, and a newer roof that is only a few years old. Outside, the large backyard provides plenty of space for outdoor entertaining and gatherings, while the detached 2-car garage offers convenient parking and additional storage. Whether you're an investor looking for strong rental income potential or an owner-occupant seeking a spacious multi-unit property, this property offers an excellent opportunity in West Englewood. Conveniently located near public transportation, schools, parks, and shopping. The property is being sold AS-IS. Don't miss this opportunity to own a spacious and versatile investment property with excellent potential. Schedule your showing today!

1516 W 72Nd Street, Chicago
$625,000
6 Beds ⋅ 3 Baths ⋅ 12740704 MLS ⋅ ACTIVE Status
Fully rehabbed and turn-key brick 3-flat in North Lawndale, featuring three spacious 2-bedroom, 1-bathroom units. This property has undergone an extensive renovation with improvements throughout the entire building. Updates include new kitchens, new bathrooms, new HVAC systems, new water heaters, new flooring, fresh paint and finishes, roof improvements, tuckpointing, and much more. The major capital improvements have been addressed, offering a tremendous opportunity for an investor or owner-occupant seeking a low maintenance, income producing property. Each unit offers a functional 2BR/1BA layout, providing comfortable living space along with updated kitchens and bathrooms. Each unit has individual furnace and water heater with separate utilities. The building also features rear porches and a full unfinished walk-out basement, providing additional storage and future potential, subject to zoning and permitting. Ideally situated in Chicago's North Lawndale neighborhood, with convenient access to public transportation, neighborhood shopping, restaurants, parks and everyday amenities. The property is also conveniently located near CTA transportation and the I-290 Eisenhower Expressway, providing easy access to downtown Chicago and surrounding areas. Schedule your showing today and see the extensive improvements for yourself!

1222 S Karlov Avenue, Chicago
$80,000
4 Beds ⋅ 1 Baths ⋅ 12740427 MLS ⋅ ACTIVE Status
Great investment opportunity with plenty of potential. This multi-level property features a spacious layout, new rear porch & convenient location. New rear porch. Each unit has living room, kitchen & 2 bedrooms. Basement & attic open unfinished. Sold "as-is".

321 E 116Th Street, Chicago
$240,000
5 Beds ⋅ 2 Baths ⋅ 12740648 MLS ⋅ ACTIVE Status

7213 S Green Street, Chicago
$625,000
8 Beds ⋅ 2 Baths ⋅ 12740513 MLS ⋅ CONTINGENT Status
Brookline Real Estate is pleased to present 823 S. Carpenter Street, a fully leased two-unit investment property in Chicago's Little Italy/University Village neighborhood. The property contains two four-bedroom, one-bath apartments and totals approximately 2,656 square feet. Located within the UIC campus and near the Illinois Medical District, Taylor Street, public transportation and downtown Chicago. The property offers immediate income in a highly desirable, supply-constrained rental market. Additional financial and property information is available in the sales brochure. Proof of funds and pre-approval required. Showing to start Friday afternoon at 12 PM. There may be overlap in showings.

823 S Carpenter Street, Chicago
$464,500
6 Beds ⋅ 4 Baths ⋅ 12731701 MLS ⋅ CONTINGENT Status
Experience a rare opportunity to own an **oversized** two-flat in the highly sought-after Pill Hill community, offering remarkable space, versatility, and comfort. Each unit boasts more than 1900 sq feet of living area, designed with an open-concept layout that's perfect for modern living and entertaining. Step into expansive living and dining rooms that flow seamlessly together, complemented by a generous family room in each unit for added relaxation and gathering space. Both residences feature 3 well-appointed bedrooms and 2 full bathrooms, providing ideal accommodations for owner-occupants, extended families, or savvy investors seeking strong rental potential. The property also includes an attached 2-car garage, a desirable convenience rarely found in the area. A finished basement with a large recreation room and private entry adds even more flexibility-perfect for a home gym, media room, workspace, or additional entertaining zone. Situated in the established Pill Hill neighborhood, this unique oversized two-flat blends space, function, and location-an exceptional opportunity that doesn't come to market often.

1630 E 92Nd Place, Chicago
$365,000
6 Beds ⋅ 3 Baths ⋅ 12740252 MLS ⋅ CONTINGENT Status
Wow!!! Beautiful red brick 2 unit with updated 3 bedrooms 1 bath in each unit. Huge eat in kitchens with newer cabinets. Beautiful vinyl plank flooring throughout both units. Tenants pay all utilities. Ready for new owners!!!

3949 W Monroe Street, Chicago
$649,900
5 Beds ⋅ 3 Baths ⋅ 12738930 MLS ⋅ CONTINGENT Status
Classic brick Chicago two-flat offering two spacious 2-bedroom, 1-bath residences plus a finished non-conforming lower level that adds exceptional flexibility and potential. An excellent opportunity for an owner-occupant or investor, the property provides the ability to live in one unit while generating rental income from the other, with the lower level offering additional potential for supplemental income or extended living arrangements, subject to applicable zoning and legal-use requirements. Both conforming units feature generous living and dining spaces, hardwood flooring, abundant natural light, private kitchens, and well-proportioned bedrooms. The upper residence offers a comfortable, open flow with a spacious kitchen, expansive living and dining areas, and additional enclosed porch space. The main-level residence provides equally flexible living space with its own kitchen and private accommodations. The finished basement includes one bedroom, one full bathroom, a full kitchen, and both interior and exterior access. Additional features throughout the property include multiple enclosed porch and bonus spaces, laundry, storage, and plenty of opportunity to update or personalize over time. Outside, the solid brick exterior is complemented by a fenced front yard, mature landscaping, rear patio and green space, creating additional room to enjoy the property beyond the interior. Conveniently located near neighborhood favorites along Kedzie, Irving Park, and Montrose, with easy access to Independence Park, Horner Park, the Brown and Blue Lines, and notable area schools including Lane Tech College Prep, Northside College Prep, and DePaul College Prep. Whether you're looking to house-hack, expand your investment portfolio, or create a flexible multi-generational living arrangement, this two-flat offers space, versatility, and compelling income potential in a well-connected Chicago neighborhood.

4252 N Whipple Street, Chicago
$347,900
6 Beds ⋅ 4 Baths ⋅ 12740190 MLS ⋅ ACTIVE Status

3311 W Monroe Street, Chicago
$649,000
4 Beds ⋅ 2 Baths ⋅ 12733369 MLS ⋅ ACTIVE Status
This rare 1 story style duplex has been completely renovated from top to bottom, inside and out! The exterior features an all new torch-down roof, windows, doors, siding, gutters, vents, mailboxes, light fixtures, and all of the brick has been properly tuck-pointed. Inside, both units have undergone a total transformation into truly turnkey condition, ready for immediate occupancy. All new engineered hardwood flooring, oversized 7" baseboards, doors/hardware, blinds, closet shelving, and wooden railings with metal balusters throughout. Both bathrooms are tastefully remodeled including professionally installed tile work. Both kitchens boast gorgeous white shaker cabinets, quartz countertops, and stainless steel appliances. The basement provides ample storage space and houses the two new high efficiency furnaces along with two new air conditioners outside. The home's zero-front setback allows for a nice large back yard. This location in desirable Norwood Park is only .5 miles from the Metra station and 1 mile from both the CTA Blue Line station and I-90 tollway for easy commuting. See the 3D virtual tour!

7120 W Highland Avenue, Chicago
$420,000
4 Beds ⋅ 2 Baths ⋅ 12740079 MLS ⋅ PENDING Status
Great opportunity to own a classic brick 2-flat in Chicago! Each unit offers 2 bedrooms, 1 full bath, a separate sitting room and approximately 1,000 square feet of living space. The property underwent extensive renovations in 2020, including updates to the kitchens, bathrooms, roof and interior finishes. Both units feature open kitchen and dining areas, quartz countertops, glass tile backsplashes, stainless steel appliances and hardwood flooring. The sitting room in each unit provides flexible additional living space and is ideal for a home office, den or reading room. The full unfinished basement provides plenty of additional storage, and separate utilities add convenience for both owner-occupants and investors. Exterior features include a fenced yard and detached 2.5-car brick garage. An excellent opportunity to live in one unit while generating income from the other or add a solid 2-flat to your investment portfolio. Conveniently located near shopping, dining, transportation and neighborhood amenities. Schedule your showing today!

1749 N Meade Avenue, Chicago
$365,000
6 Beds ⋅ 2 Baths ⋅ 12740054 MLS ⋅ ACTIVE Status
Don't miss this exceptional opportunity to own a versatile two-unit property with endless potential. Live in one unit while generating rental income from the other, or add this solid investment to your portfolio. The unfinished basement offers a blank canvas for your creative vision and the brand new garage adds even more value. Whether you're an owner-occupant or an investor, this property is ready for its next chapter.

530 N Lawler Avenue, Chicago
$550,000
9 Beds ⋅ 6 Baths ⋅ 12740010 MLS ⋅ CONTINGENT Status
**Exceptional South Shore 3-flat offering immediate rental income, long-term equity potential, and an outstanding opportunity for an investor OR an owner-occupant looking to HOUSE HACK!** Offered at **$550,000**, this well-maintained brick building features **three jumbo approximately 1,700 SF apartments, each with 3 bedrooms and 2 full bathrooms-9 bedrooms and 6 full baths total.** Each unit offers large living rooms and bedrooms, formal dining rooms, beautiful hardwood floors and generous layouts that are increasingly difficult to find. The building is fully occupied by established, long-term residents who have demonstrated consistent payment history, currently carry **$0 tenant balances**, and take pride in caring for their homes. Current scheduled rent is **$3,912 per month/$46,944 per year**, giving a buyer income from day one, while **all three tenancies are currently month-to-month**, providing valuable future flexibility subject to applicable tenant rights and notice requirements. For a **first-time buyer or owner-occupant**, this is a compelling house-hacking opportunity: live in one of the three large 3-bedroom/2-bath units when legally available while collecting rent from the other two to help offset the cost of ownership. For an investor, the rental-growth potential is substantial. Current rents remain well below the approximately **$2,037/month average identified by the property's rental comparable analysis for similar 3-bedroom apartments within one mile**; at that benchmark, three units would generate approximately **$6,111/month or $73,332/year**, representing approximately **$2,199/month/$26,388 per year of potential additional gross rental income-about 56% above today's scheduled rent roll-if all three units ultimately achieved that benchmark.** Unit 2 currently rents for **$1,287/month**, and a **CHA rent increase to $2,000/month has already been submitted and is pending approval**, which alone would add **$713/month or $8,556/year** if approved. The building was designed with income-property ownership in mind: **tenants pay their own gas, heat and electricity**, each unit has **separate forced-air heating and individual controls**, and the property includes a **full basement with tenant storage, landlord storage, natural-gas basement heat and coin-laundry facilities as reported in the prior listing.** The full basement's size, ceiling height, layout and access may also offer an exciting opportunity to investigate future additional living/income-producing space or a garden/ADU configuration, **subject to City of Chicago approval, zoning, permits and buyer due diligence.** Outside, the property includes a valuable **owned detached 3-car garage**; the prior listing also reported a newer tear-off roof on the main building with a transferable warranty and a **2020 tear-off garage roof**, which buyers should independently verify. The equity story is equally exciting: comparable-market analysis reviewed during the listing process included renovated multifamily product with finished garden space selling in the **$700,000+ range**. Against the **$550,000 asking price**, that illustrates a **$150,000+ gross valuation spread** and the potential opportunity to build substantial equity through thoughtful improvements, increasing below-market rents and maximizing the property's existing space; comparable properties differ and future value is not guaranteed. Located in **South Shore**, one of Chicago's established lakefront communities, the property offers convenient access to the lakefront, beaches, schools, shopping and the recreational and cultural amenities surrounding the neighborhood. Whether you're a seasoned investor seeking a stabilized building with significant room to increase income, or a **first-time owner-occupant who wants to live in a spacious unit while tenants help pay the mortgage**, this property offers something increasingly difficult to find: **a clean and proven rent roll, $46,944 in current annual

7414 S Chappel Avenue, Chicago
$189,000
5 Beds ⋅ 2 Baths ⋅ 12739761 MLS ⋅ ACTIVE Status
Related living 2 units, 5 bedrooms, 2 kitchens, 2 bathrooms, basement for storage. NEW ROOF. 3 beds on the main 2 beds in the upstairs unit. Tenant on 2nd floor is month to month. freshly painted, floors on the main finished last year.

911 W 84Th Street, Chicago
$585,000
5 Beds ⋅ 3 Baths ⋅ 12728618 MLS ⋅ ACTIVE Status

2706 W Jackson Boulevard, Chicago
$550,000
3 Beds ⋅ 3 Baths ⋅ 12739310 MLS ⋅ CONTINGENT Status
This well maintained legal 2 unit building featuring a full basement and 2 car garage! The first floor unit offers 2 bedrooms, a comfortable living room, and an eat-in kitchen. The second floor unit features 1 bedroom, a spacious living room, and an eat-in kitchen. Each unit also includes its own porch, providing a great space to relax and enjoy the outdoors. The partially finished basement offers additional space for storage, recreation, or future use. A 2 car garage completes the property. Great opportunity for an owner occupant or investor looking to add a solid 2-unit property to their portfolio. Being sold strictly AS IS

3858 N Sawyer Avenue, Chicago
$635,000
6 Beds ⋅ 4 Baths ⋅ 12739841 MLS ⋅ CONTINGENT Status
Endless possibilities await at this classic two-unit property in the highly desirable location. Featuring a spacious duplex-up and duplex-down configuration, this building offers an outstanding opportunity for investors, rehabbers, or owner-occupants looking to build equity in one of Chicago's most sought-after neighborhoods. Both units offer generous living space and the convenience of in-unit laundry, providing an excellent foundation for a renovation or value-add project. With strong bones and an ideal layout, this property is ready for your vision. Renovate and maximize rental income, create stunning owner-occupied living with additional rental revenue, or update both units for long-term investment potential. Located in an unbeatable location, you'll enjoy easy access to restaurants, coffee shops, grocery stores, parks, entertainment, public transportation, and major expressways. Just minutes from Roscoe Village, Lakeview, Bucktown, and the Southport Corridor, the neighborhood continues to attract homeowners and renters alike, making this an exceptional investment opportunity.

3008 N Clybourn Avenue, Chicago
$575,000
6 Beds ⋅ 3 Baths ⋅ 12693206 MLS ⋅ ACTIVE Status
Tucked into Portage Park, this rare legal three-flat has been generating steady income for years and comes fully tenant-occupied from closing. Built in 1922 on a generous 31x126 lot, it offers three two-bedroom units, a two-car garage, and a fenced backyard, giving an investor solid fundamentals to build on or a house-hacker room to move into one unit while the others help carry the mortgage. This property offers the new owner has real flexibility, whether that means adjusting rents to market or eventually settling into one of the units. The location does a lot of the work here too, maximizing rentability, just steps from the Montrose Blue Line, the #152 bus, Metra's Mayfair stop, and the shops around Six Corners, with Chopin Park close by. Interior photos are being held back out of respect for current residents, but are available on request through the listing agent, who's happy to arrange a private tour. Please allow a minimum 48 hrs' notice for showings. Property is being conveyed as-is.

5357 W Waveland Avenue, Chicago
$350,000
5 Beds ⋅ 2 Baths ⋅ 12738750 MLS ⋅ ACTIVE Status
Welcome to 1431 S. Christiana Avenue, a classic Chicago Greystone two-flat that offers an exceptional turn-key opportunity for savvy investors or owner-occupants looking for live-in rental income with strong upside. Beautifully presented with timeless stone masonry and a secure fenced perimeter, this property features bright, versatile living spaces highlighted by beautiful hardwood floors, light neutral tones, and classic arched pass-throughs. The main residential layout offers expansive, light-filled living rooms and dedicated dining areas, seamless eat-in kitchens equipped with extensive cabinet storage and gas ranges, functional full baths, and comfortable bedrooms alongside flexible bonus rooms ideal for home offices. Beyond the upper living quarters, the home presents incredible equity potential with a massive unfinished basement ready for duplexing down or future expansion, plus a low-maintenance back yard complete with a private concrete parking pad and easy access to local transit and Downtown Chicago.

1431 S Christiana Avenue, Chicago
$400,000
10 Beds ⋅ 4 Baths ⋅ 12738449 MLS ⋅ CONTINGENT Status
GREAT DEAL - SOLD AS - IS- AWESOME 4 UNIT IN NICE WEST SIDE LOCATION - ONE TENANT SUBSIDIZED -TWO 2 BED 1 BATH AND TWO 3 BED 1 BATH. SPACIOUS UNITS IN VERY GOOD CONDITION - 1 UNIT VACANT WAS GETTING 1350 - EXCELLENT INCOME AND PRICED TO SELL - REHABBED AND - SOLD AS IS

525 W 118Th Street, Chicago
$559,999
7 Beds ⋅ 3 Baths ⋅ 12739688 MLS ⋅ ACTIVE Status
Attention - Prime Irving Park Location. Exceptional opportunity for owner-occupants, investors, or developers in a highly desirable Irving Park area. Conveniently situated near CTA, Metra, I-90/94, shopping, restaurants, parks, and coffee shops. This family-owned property of over 40 years offers versatile options - keep it as a two-flat with additional rental income, or transform it into your dream home, surrounded by luxurious single-family residences. First Floor: 2 bedrooms, living room, dining room, kitchen, 1 bathroom. Second Floor (duplexed to attic): Living room, dining room, kitchen, 5 bedrooms, 2 bathrooms. Additional features: ample storage, enclosed porches, 2-car garage, and a fully fenced yard & Separate laundry hookup .New roof will be put on this month , Property is being sold As-Is. Pre-approved buyers only.

4019 N Bernard Street, Chicago
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