Refine Search
Map
Sort by
$2,295,000
6 Beds ⋅ 7 Baths ⋅ 12740818 MLS ⋅ CONTINGENT Status
Opportunities of this scale are rarely available in the heart of East Lakeview. Spanning an extraordinary 5,400 square feet, this expansive penthouse offers soaring ceilings, incredible volume, and natural light at every turn, all just steps from Broadway's best shopping and dining and the lakefront at Belmont Harbor. Designed for grand-scale living and entertaining, the residence features four bedrooms, four full bathrooms, three powder rooms, and an exceptionally spacious open floor plan. The oversized kitchen offers tremendous proportions and the opportunity to create a truly spectacular culinary centerpiece. Multiple balconies and a sun-filled solarium provide exceptional indoor-outdoor living, while the rooftop offers an incredible, soon-to-be completed private deck with sweeping views. The primary suite is a dream unto itself, offering remarkable space, an attached private office, an enormous walk-in closet, and a sprawling ensuite bath with the scale to create a true spa-like retreat. Set within a well-maintained elevator building, the home offers an exceptional canvas for a complete transformation, with the space, ceiling heights, light, and outdoor areas to create something truly extraordinary. Two parking spaces complete this rare offering. For those seeking grand proportions and the opportunity to create a one-of-a-kind residence in one of East Lakeview's most desirable locations, this penthouse is unlike anything else on the market.

545 W Aldine Avenue Unit #6E, 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
$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
$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
$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
$3,998,000
6 Beds ⋅ 7 Baths ⋅ 12740854 MLS ⋅ ACTIVE Status
Situated on an extra-wide corner lot in coveted Lincoln Park, this exceptional 6-bedroom, 5.2-bath residence offers approximately 6,400 square feet of beautifully designed living space, creating a truly expansive and open feel throughout the home. Thoughtfully designed for both everyday living and entertaining, the home seamlessly blends scale, luxury, and functionality. The chef's kitchen features top-tier finishes and appliances, abundant cabinetry, and a generous layout perfect for gathering, complemented by a spacious breakfast area and a well-appointed butler's pantry for additional prep and storage. The second level is anchored by a spacious primary suite, complete with a beautifully designed spa-inspired bath and ample closet space. Three additional bedrooms and two well-designed bathrooms complete this level, providing an ideal layout for family living. The top floor offers exceptional flexibility with an additional bedroom and full bathroom, along with a beautiful private office and access to two incredible outdoor spaces. Designed for entertaining, the rooftop level features a bar area, hot tub, and dining space, creating a perfect setting for gatherings while enjoying city views. The lower level boasts an enormous family room, ideal for movie nights, recreation, or entertaining. This level also includes an additional bedroom and bathroom, along with a dedicated wine cellar. A rare highlight for city living, the home features an attached 2.5 car garage with a convenient mudroom entry, offering everyday practicality and storage. This home also includes generous outdoor space, including a large rooftop garage deck with pergola, and ample yard space that could easily accommodate a sports court or additional outdoor recreation space. With incredible scale, abundant storage, multiple outdoor entertaining areas, and an unbeatable Lincoln Park location, this is a truly exceptional home that offers the best of Chicago city living.

2658 N Mildred Avenue, 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
$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
$347,900
6 Beds ⋅ 4 Baths ⋅ 12740190 MLS ⋅ ACTIVE Status

3311 W Monroe Street, 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
$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
6 Beds ⋅ 2 Baths ⋅ 12738329 MLS ⋅ CONTINGENT Status

4950 N Kilpatrick Avenue, Chicago



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.