Renovated 2-Flat in Prime Lakeview - High-Performing Airbnb Investment 1442 W Irving Park Road is a rare and exceptional opportunity to own a renovated, turnkey 2-flat currently operating as a high-performing Airbnb investment. This professionally managed property offers 9 bedrooms and 4 full bathrooms across two units: the top floor features 4 bedrooms and 2 bathrooms, and the duplex-down

Barrie Jessome Baird & Warner

Excellent investment in Albany Park! Well-maintained legal 4-unit building with extra-large units. Unit 1/Garden: 3 beds, 2 baths, and tall ceilings throughout. Units 2-4: approximately 1,600 sq ft units with 3-4 beds and 1.5 baths each. Apartments feature spacious kitchens, extra-large living rooms & sunrooms, formal dining rooms in original layouts, plus enclosed porch/dens on each level.

Ledio Samarxhiu Real Broker LLC

Welcome to this well-maintained brick two-flat situated on a quiet residential block in the heart of Portage Park. Ideal for owner-occupants or investors, this versatile property offers exceptional potential either live in one unit and rent the other, or enjoy steady rental income from both. Each unit features spacious rooms, hardwood flooring, and a functional layout with separate living and

Jon Ellingsen xr realty

Exceptional multi-family property in the heart of Skokie, featuring five spacious 2-bedroom units, each thoughtfully designed with a separate living room, kitchen, dining area, & two bedrooms. Units feature kitchens with solid wood cabinetry & contemporary fixtures. Plenty of storage with coat closet, linen closet & pantry in each unit. Copper piping installed throughout building. Common area

John Vodopic Coldwell Banker Realty

Portage Park 2-flat on a quiet tree-lined street with brand new tear-off roof (September 2025). This well-maintained building features two spacious 2 bed/1 bath units, each offering a classic layout with a bright living room, separate dining room, hardwood floors, and central air. The first-floor unit boasts a cozy fireplace, and the second-floor kitchen was updated in 2017, adding modern

Nancy Huetteman Redfin Corporation

WOW! Rare, Custom-Built Jumbo 3-Flat Near O'Hare! Over 8,500 Sq Ft of Living Space! Incredible opportunity to own a one-of-a-kind, oversized building featuring three huge 3-bedroom units plus a finished in-law garden unit. Meticulously maintained by long-time owners. Each unit is updated and includes a refrigerator, oven, dishwasher, and microwave. Perfect for an owner-occupant or investor.

Gregorio Cirone xr realty

WOW! Rare 3-Flat in North Park! Incredible opportunity to own a solid, income-producing property in one of Chicago's most sought-after neighborhoods! This meticulously maintained building features two expansive 3-bedroom units plus a fully finished 2-bedroom garden apartment-perfect for multigenerational living or maximizing rental income. Each unit includes a refrigerator, oven, and

Gregorio Cirone xr realty

Classic brick 2-flat in Irving Park with vintage charm + modern updates! Each unit offers three bedrooms including a private bedroom with half bath, front den, sound-dampening windows, copper plumbing, updated electric w/separate panels, and GFA/central A/C. Kitchens feature maple cabinets, granite counters & SS appliances. Hardwood floors, enclosed porch w/side-by-side washer and dryer.

Jenny Choe Baird & Warner

Modern Luxury Meets Smart Investment at 6129 N Ravenswood Ave - A Fully Renovated Two-Unit Gem in Edgewater. This exceptional property has been completely rehabbed down to the studs, offering two spacious duplex units that blend contemporary design with functional layouts-perfect for an owner-occupant seeking rental income or an investor looking for a turnkey asset. Each unit features

Gerardo Tapia-Quiroz Baird & Warner

Located steps from Dee Rd Metra station, this two flat offers incredible potential for both investors and owner-occupants. The current layout offers flexibility for renovations (see floorplans). With a little vision and some updates, this property could easily be transformed into a cash flowing gem. 1st floor apt (currently vacant) features 2 bedrooms, 1 bath, and an eat in kitchen. 2nd floor is

Anne Camarano @properties Christie?s International Real Estate

BEAUTIFULL 2 FLAT IN NORTH PARK AREA WITH INLAW FINISHED BASEMENT. 2 BED ROOMS EACH WITH BONUS ROOM INTHE BACK. SEPERATE UTILITIES BRAND NEW 3 HOT WATER TANKS.1.5 CAR GARAGE ,NEW BACK PORCH DONE IN 2019, ROOF AND TUCK- POINT ALSO DONE 2019.CLOSE TO NOTHEASTERN AND NORTH PARK UNIV. BASEMENT HAS ONE BED ROOM AND ONE FULL BATH. FIRST FLOOR VACANT FOR EASY SHOWING NEWLY PAINTED , HARDWOO FLOOR

Charlie Barbari Vision Realty Inc.

This Gem in Chicago's Portage Park offers three spacious legal units in a distinctive brick building with a pitched roof, set on an oversized lot that's virtually unheard of in the city. Lack of parking would never be an issue with it's extra long side driveway which allows for many tandem spots that leads to a huge backyard-creating a private oasis ideal for outdoor living, expansion, or simply

Keisha Williams Fulton Grace Realty

This lovingly maintained brick 2-flat is ideally located just steps from the scenic river and the Riverbank Neighbors Park walking path on a 30 foot-wide lot in the heart of desirable North Center and within the coveted Waters Elementary School district. This is a rare opportunity to own a classic Chicago property with charm, space, and location. Each unit features 2 large bedrooms and 1 full

Michael McCallum Baird & Warner

Hard to find Legal 3-Flat in the Heart of Albany Park This beautifully updated 3-flat offers spacious, modern living in one of Chicago's most diverse and vibrant neighborhoods. The first and second-floor units feature hardwood floors throughout, updated kitchens and baths, and generous closet space in each bedroom. The finished basement includes 2 bedrooms and 1 bathroom-ideal for in-law

Mohammed Iftikhar Guidance Realty

Investor Opportunity in North Mayfair! Discover this charming 2-flat situated on an oversized lot in the highly desirable North Mayfair neighborhood. Nestled on a quiet, tree-lined street, this property offers a rare combination of space, location, and potential. Just minutes from shopping, dining, public transportation, and expressway access. Each spacious unit features generous living and

Peter Deja Cross County Realty Inc.

Distinctive-looking corner 2-flat with very spacious rooms throughout. The first unit floor features a large living room (18x13), two generously sized bedrooms (15x12 and 16x12), an eat-in area (13x8), and a kitchen (13x9). The second floor unit includes a living room (16x13), kitchen (10x10), and bedroom (12x11), hardwood floor through out the house, central AC. The basement offers an in-law

Angela Pop Core Realty & Investments Inc.

All-brick two flat in a prime Uptown location. Just one block to FFC Health Club, three blocks to the Metra station, and close to restaurants, Trader Joe's, the farmer's market, and more. A great opportunity for an investor or owner-occupant. The second floor features a beautifully remodeled 2-bedroom, 1-bath (updated) unit with a new eat-in kitchen as well as new flooring throughout. The first

Craig Tinder @properties Christie's International Real Estate

Great Location in Portage Park, Long term owner . Well maintained building , One 3 bed 1 bath on top floor, 2 bed one bath on main level , both units have private enclosed rear porchs , Full basement , two car brick garage. Walking distance to 6 corners , great transportation area.

John Fleming Baird & Warner

Massive. Versatile. Rare. This extra-wide 37-foot lot holds an expanded two-flat with an oversized three-car garage and endless possibilities. The owner's duplex-down boasts 5 bedrooms, two full kitchens, hardwood floors, and a sprawling living/dining room perfect for big gatherings. Upstairs, the bright 3 bed unit + den/office/nursery) features huge living and dining rooms, a dishwasher-equipped

Kevin Hinton Keller Williams ONEChicago

Opportunity knocks! This well-maintained 2-flat in a highly desirable Skokie location is now available for the first time in more than 20 years. Perfectly situated within walking distance to downtown Skokie, shopping, dining, and the Yellow Line, this property offers an outstanding investment or owner-occupant opportunity. Unit 1 features a spacious 2BD/1BA layout, while Unit 2 offers a generous

Jose Hernandez Coldwell Banker Realty

Introducing this classic 3 unit brick building...situated on a lovely tree-lined street in the heart of Lincoln Square. Fully occupied and well-maintained, this building offers a tremendous investment opportunity. All 3 units are 2 bedroom / 1 bathroom layouts and are very spacious in size (almost 1400 sqft). Each apartment gets great natural light and has a separate living room, dining room and

Owen Duffy Fulton Grace Realty

- Prime Wrigleyville Location Just One Block from Wrigley Field & Steps to CTA Red Line - Surrounded by Dining, Retail & Entertainment - Unit Mix Consisting of Six (6) Spacious 2 Bed/2 Bath Units and One (1) 1 Bed/1 Bath Garden Unit - Recently Renovated Units Featuring Hardwood Floors, Quartz Countertops, Stainless Steel Appliances, Central HVAC & Exposed Brick Accents

Michael Masterson Essex 312, LLC

Incredible 4-unit building in Skokie featuring four spacious two-bedroom, one-bath units approximately 1,000 sq ft each. Several units have been recently updated with modern kitchens and bathrooms. Hardwood floors throughout the building add to its appeal. Each unit offers an HVAC system, including Ac's for added convenience. Great school districts. Ample parking available in the back for

Harris Ali Sky High Real Estate Inc.

Fantastic Opportunity in Evanston! This classic 2-flat offers incredible potential for the right buyer. Each spacious unit features 3 bedrooms and 1 bathroom, with plenty of natural light and a functional layout. The property includes a full unfinished basement, providing additional space for storage or future expansion. With some updates and vision, this property can be transformed into a

David Dominguez Realty of America, LLC

Come check out this legal 3-unit located in prime Lincoln Square! Perfect for an owner-user or investor! Units 2 & 3 are comprised of 3-bedrooms and 1-bathroom with approximately 1,700-square feet each. Garden unit is a 2-bedroom / 1-bath. All units have individual washer and dryers! Unit 3 was renovated in 2020 with new kitchen, Garden unit was renovated in 2022 and Unit 2 was renovated in 2017

Kelsey Zurweller Horvath & Tremblay IL, LLC

First time on market in over 25 yrs.!! This is a fantastic opportunity for a owner occ or investor. This Brick 4 unit has 4 separate gas forced (HVAC) systems, 4 hot water heaters and seporate elect. Possibility for duplexing down basement. Roof is 9 yrs, windows aprox 7 yrs, many other updates have been done over the past couple years. Coin laundry owned by seller, great extra income. Rents

Mark Chereso Gateway Realty LLC

Welcome to Albany Park! This charming 2-flat property is perfect for owner-occupants looking to generate rental income. The top unit features a spacious duplex-up layout with 3 bedrooms & 1.1 bathrooms. Top unit also offers updated kitchen cabinetry. The first-floor unit offers 2 bedrooms and 1 bathroom. Both units boast updated bathrooms, modern light fixtures, and beautifully refinished floors

Loreal Urso Baird & Warner

LOCATION, LOCATION, LOCATION!!! DON'T MISS OUT ON THIS CHARMING CLASSIC JUMBO RED BRICK 2 FLAT WITH GREAT BONES IN THE DESIRABLE LINCOLN SQUARE/BUD LONG NEIGHBORHOOD!!! GREAT OPPORTUNITY FOR OWNER OCCUPIED OR SAVVY INVESTOR TO REMODEL TO YOUR PREFERENCE OR RENT OUT FOR POSITIVE CASH FLOW. LOCATED ON A QUIET RESIDENTIAL STREET NEAR TO RIVER PARK WITH A POOL, RIVER, KAYAK LAUNCH, TENNIS COURT,

Sophath Sath PROSALES REALTY

This classic Chicago brick four-flat sits on an oversized lot in the charming Magnolia Glen pocket of Edgewater. Each of the four apartments offers functional floor plans that present exciting opportunities to reconfigure. An internal staircase down to the basement with high ceilings from unit 1E allows for an incredible duplex down option. Located in the ADU pilot program zone, there is

Randy Nasatir @properties Christie's International Real Estate

Beautiful grey stone three flat on an amazing street in Lakeview just blocks away form Wrigley Field. Family owned since the 1920's. This building will be well suited for a developer or someone who knows how to bring a property back to its original glory.

Thomas Marchetti Baird & Warner

Welcome to 3608 N Tripp Ave, a classic Chicago brick two-flat located on a quiet, tree-lined street in highly sought-after Irving Park. This well-maintained property sits on an extra-wide 5,304 sq ft lot and offers exceptional space, flexibility, and investment potential for both homeowners and savvy investors. With over 2,400 sq ft of above-grade living space and an additional 1,355 sq ft of

Amanda Zick @properties Christie's International Real Estate

Bell School District Alert! Hot new listing of a double brick, Chicago-style, two-flat, with a finished basement, front entry side driveway, and extra wide (35' RS-3) lot with beautiful yard and garden. Lovingly maintained and owned by the same family for over 50 years. Improvements in 2025 include: New roof on garage and reflective-coat on main building, new boiler, cedar outdoor decks,

Joe Wilcox The Wilcox Company

beautifuly updated 2-story building just minutes from downtown Park Ridge! Features includ remodeled kitchens Granite counter top.Remodeled bathroms in both units (2018),fully finshed basement,adds valuable living space ideal for family room,and big bedroom (2020),new windows (2019), private outdoor patio providing perfect spot for relaxing or hosting gatherings. Wether your searching for

Ikhlass Jubrail Century 21 Circle

4241 N. Laramie Avenue is a legal four-unit building in Portage Park with (4) 2-bedroom/1-bath apartments plus a non-conforming garden unit. Units feature hardwood floors, laminate countertops, a mix of white/stainless appliances, and two surface parking spots. All apartments are boiler-heated except Unit 2S, which has individual HVAC. The property is located just north of Irving Park Road and

Ryan Blake Nara Advisors, Inc