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

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

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!!! WOW!!! OMG!! Amazing, Stunning, Melrose Park legal 2 Flat! The Perfect location! ALL Updated!! Great Opportunity to live in one unit and rent the others or rent the whole building! Great Investment Opportunity! Updated Units! One 2-Bedroom Unit, One 1-Bedroom Units and a partially finished Basement that can be finished into an In-Law Unit or keep for extra storage and common area!

Gregorio Cirone xr realty

HAVE SOMEONE ELSE PAY YOUR MORTGAGE WITH THIS RARE OPPORTUNITY TO LIVE IN A RECENTLY RENOVATED 3BD+FAM RM/3BA SFH COACH HOUSE THAT IS PART OF A UNIQUE LEGAL 4-UNIT PROPERTY ON ONE OF WICKER PARK'S BEST TREE LINED ONE-WAY STREETS PERFECTLY SUITED FOR LIVE/RENT OR PURE INVESTMENT FEATURING AN ALL BRICK 3-UNIT FRONT BUILDING WITH GENEROUS FLOOR PLANS & THOUGHTFUL UPGRADES & THE AFOREMENTIONED COACH

Mario Greco Compass

On a wonderful tree lined street sits this beautifully maintained brick 2-flat that stands as an example of a great home and a solid investment. The units offer spacious 3-bedroom 1-bathroom layout both with gleaming hardwood floors and plush newer carpet that adds warmth and comfort. The updated electrical system ensures modern flexibility and the tuck-pointed exterior, new gutters and fence

Vicki Vranas Berkshire Hathaway HomeServices Chicago

Three-Unit Building for Sale - Avondale, Chicago Incredible investment opportunity in the vibrant Avondale neighborhood! This solid three-unit building offers tons of potential and endless ideas to upgrade, modernize, or customize to your style. Whether you're looking to live in one unit and rent out the others or fully renovate for strong rental income, this property is full of possibilities.

Maria Gutierrez Golden City Realty, Inc.

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

Exquisite Old Town Row Home: Nestled on a charming, tree-lined one-block street, this exceptional end-unit row home at 328 W Concord Pl offers a unique blend of sophisticated city living and astute investment opportunity. Spanning three stories, this property is configured as two separate units, appealing to a wide range of buyers, from the savvy investor to the live-in owner seeking

Victoria Ossorio Compass

An incredible opportunity awaits! Tucked between Portage Park and Jefferson Park, this charming multi-unit property offers flexibility, comfort, and thoughtful updates throughout. The spacious garden apartment features radiant heated floors and a recent renovation, while Unit 1 includes a brand-new stainless steel refrigerator. Enjoy a gated front yard, interior stairwells, and a

Marina Collazo Redfin Corporation

Rare opportunity to own a fully renovated, income-producing 3-unit building in vibrant Humboldt Park, just steps from the popular 606 Trail. This turnkey property was completely redone in 2022 with brand-new plumbing, electrical, mechanicals, windows, kitchens, and baths. Each unit features spacious, light-filled layouts with large bedrooms and stylish, modern finishes throughout. Perfect for

Omar Mohiudin Redfin Corporation

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

Come view this unique Edison Park multi unit property located just behind Olympia Park! Seller purchased this as a single family home and reconstructed it back to its original build as a legal conforming 2 Flat with an RS-3 zoning by the City of Chicago. An extremely rare find in the area, this building boasts an all brick exterior, with areas of aluminum siding, multiple entryways, back deck off

Meghan O'Keefe Baird & Warner

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

Exceptional Investment Opportunity in Hot Humboldt Park! This solid, fully rehabbed legal 3-flat offers strong income potential and modern upgrades throughout. Each spacious unit features 3 full bedrooms and recently updated kitchens with stainless steel appliances including refrigerator, stove, microwave, and dishwasher. Units 1 and 2 are equipped with central air. Independent furnaces and water

German Llanos 24 Hour Real Estate LLC

RARE 2.75 ASSUMABLE MORTGAGE - House Hack or Invest in Prime Logan Square! Seize a once-in-a-generation opportunity to assume a 2.75 mortgage-far below today's rates! Whether you're looking to live nearly rent-free or build your investment portfolio, this updated legal 4-unit brick building on an oversized lot in Logan Square is a true find. Perfect for: Owner-occupants who want minimal housing

Jason Wagner Greystone Realty

Rare and Incredible Bucktown Opportunity! Located on a quiet, tree-lined street just steps from Holstein Park, this property offers four legal units in an unbeatable location. The all-brick main building features three fully renovated 2-bedroom, 1-bath units-each with private entrances, private outdoor space, large kitchens, hardwood floors, high ceilings, updated finishes, central HVAC,

Tyler Weekes Star Realty & Management

Attention House Hackers and Investors! Invest in this classic Chicago multi-unit and start collecting cash flow on day one! Legal 2 flat with an additional 2 bedroom 1 bath garden unit. These units are easy to rent and maintain. Recent updates include: Hot Water Heaters (2025), Kitchen Cabinets & Countertops (2025) Tear Off Roof (2018), New Fence (2023), Concrete walkway (2021). Newer appliances

Amir Abed Kale Realty

Discover this well-maintained 2-flat building perfect for owner-occupants or savvy investors! Each unit offers spacious layouts with 2-3 bedrooms, bright living rooms, kitchens, and separate utilities. The property also features a full finished basement, perfect for storage or potential expansion and a backyard ideal for outdoor enjoyment. Located in a desirable neighborhood close to public

Chayanta Spaniol Chayanta Spaniol

Investor's opportunity in Ravenswood - rare 7BR/4BA 2-flat with proven Airbnb success. Fully functional short-term rental setup with smart updates for a seamless, automated guest experience. Top unit offers 4BR/2BA; lower unit features 3BR/2BA. Renovated kitchens and baths with granite countertops, stainless steel appliances, and modern finishes. Major updates: tear-off roof/new parapet (2018),

Barrie Jessome Baird & Warner

An exceptional investment opportunity in the heart of Lincoln Park-this fully renovated 4-unit building checks all the boxes for a hands-off, armchair investor. Each oversized unit offers four bedrooms and two full baths with no vacancies. Originally gut-renovated in 2018, this landmarked property blends historic charm with modern upgrades, including condo-quality finishes, individual HVAC

Jim Buczynski Compass

Portage Park Two-Unit property with tons of potential. First floor offers a large living room, dining room, two bedrooms and one bath. The rear porch is ideal for extra storage. The second floor unit features a spacious living room, one bedroom, one bath and ready for your finishing ideas. Two car garage plus a side driveway for extra parking. Convenient location near parks, shopping and

Patricia Santiago Nelly Corp Realty

Meticulously upgraded and maintained three-unit red brick building in Andersonville, ideal for both live-in owners and investors. The top-floor owner's unit has been remodeled into a spacious two-bedroom, one-bathroom residence, featuring a bright, eat-in kitchen with 42" cabinets, upgraded stainless steel appliances, white quartz countertops, a chevron tile backsplash, under-cabinet lighting,

Jacqueline Lafferty Baird & Warner

Portgage Park Solid Brick 2 Flat in desirable location. Has a full basement with access and regress 3 rooms and 1 bedroom. Brick 2 car garage. Ready for a new owner. Bring your ideas.

Harry Rivera Coldwell Banker Realty

North Mayfair- Meticulously maintained and upgraded through out- Spacious 3 bedroom apartments with today's kitchens and bath- Quality white kitchen cabinets, granite and quartz countertops with stainless steel appliances- 1st flr 2024- 2nd flr 2015- Remodeled baths (2006-2008)- Vintage charm with original artificial fireplaces and bookcases- Natural woodwork and hardwood floors- Good size

Irene Yungerman Baird & Warner

Beautifully rehabbed, 2 unit building. This property is perfect for rentals or live in one and rent the other, or use it as an in-law quarters. Rehabbed in 2025 with all new appliances, new granite countertops, new closet doors, new laminate flooring, new trim work, new tile in kitchen and baths, freshly painted, new bathroom fixtures, 2 new furnaces, new epoxy garage floor, all new matching

DAVID MANUEL Core Realty & Investments, Inc

Exceptional brick 3-flat on a RARE 30x160 extra-long & wide lot in coveted Lincoln Square-just 3 blocks to Western & Rockwell Brown Lines! Approx. 1,300 sqft. units include 2 beds+den/office, 1 bath, spacious kitchens featuring abundant cabinetry, expansive granite countertops, and generous walk-in pantries, dining rooms with 4 windows, bright living rooms with an 8-window bay front and charming

Didem Greco DCG Realty

Roscoe Village Turnkey 2-Flat - Ideal for investors with a solid rental history! Enjoy numerous updates throughout, from electrical to central air, plus a 2.5-car garage (with heater!) and more. First Floor Unit: Includes the basement and offers 4 bedrooms, 1.5 baths, living room, dining room, kitchen, back porch, and eat-in kitchen area. Second Floor Unit: Features 2 bedrooms, 1 bath, living

Jennifer Fay RE/MAX PREMIER

Yellow Brick 2flat with 3 bedroom each floor o. Full unfinished basement .can be converted to a 2 br unit with city permit. . . Convenience location/ big cars Dealer of Toyota and Honda around. Chase Bank / Walgreen / groceries store just one block walking. . SALE AS IS. Owners nor broker guaranty legality of basement or improvements. 2 car garage plus one additional parking space.

Sam Abushhab American International Realty

SUPER BRICK 2 FLAT WITH FINISHED BASEMENT, 1ST AND 2ND FLOOR UNITS 3 BEDROOMS 1 BATH WITH FINISHED 1 BED 1 BATH IN THE BASEMENT, feature large open layouts, WITH LIVING ROOM & DINING ROOM COMBO, natural light, hardwood floors, closet/storage space beautiful condition. separate utilities, SEPARATE CENTRAL HEAT AND A/C, large backyard, CAR BRICK GARAGE AND SIDE DRIVE GREAT LOCATION, CLOSE TO CTA.

Sam Gorail Coldwell Banker Realty

GREAT OPPORTUNITY! 2 UNITS BUILDING WITH FULL FINISHED BASEMENT, 2 CARS GARAGE WITH 1 PARKING SPACE, TWO AND THREE BEDROOMS UNIT, PLUS 2 BEDROOM AND 1 BATH IN BASEMENT. CORP OWNED, PROPERTY CONVEY IN AS IS WHERE IS CONDITION, BUYER RESPONSIBLE FOR ANY AND ALL VIOLATION WITH THE CITY OF CHICAGO. PROOF OF FUND MUST ACCOMPANY WITH ALL OFFER.THE SELLER DOES NOT MAKE ANY REPRESENTATION AS TO THE

Lam Tran VNT Realty

Exceptional 3-Unit Investment Opportunity in the Heart of Logan Square! Located just one block from the iconic Logan Boulevard, this well-maintained property offers the perfect blend of investment potential and owner-occupant comfort on a quite tree lined street. The spacious owner's duplex-up features tons of natural light, hardwood floors, 3 bedrooms, 1.5 baths, in-unit laundry, master suite, a

Anna Huls @properties Christie's International Real Estate

Check out this beautiful brick two-flat plus finished garden nestled in the heart of Andersonville, one of Chicago's most vibrant neighborhoods. This charming property is a perfect blend of classic character and modern convenience, just one block away from the bustling shops and restaurants of Clark Street. Enjoy hardwood floors on the 1st and 2nd floors, updated kitchens and baths, stainless

Kieran Conlon Compass

Beautifully updated Belmont Cragin 2-unit brick building with a full finished basement, just blocks from major stores, groceries, and public transit. Each unit has its own HVAC system, the roof was coated 2 years ago, and windows have been updated.The first floor offers 2 bedrooms, 1 bathroom, hardwood floors, formal dining and living rooms, and spacious bedrooms. The second floor features 2

Luz Gutierrez Garcia RE/MAX LOYALTY

Welcome to this multi-unit property in Rogers Park, which consists of a 2 unit building AND a COACH HOUSE! Both properties are very well maintained but are ready for a modern touch and remodeling to bring them to their maximum potential. The 2 units in the front building are both 2 bedroom and 1 bathroom, the building also has a finished attic and an unfinished basement ready for your ideas! The

Gamaliel Marin Smart Home Realty

Unbelievable opportunity to live in sought-after Jefferson Park or expand your rental/investment portfolio with this impeccably maintained all-brick 2-flat featuring additional income-generating living space in the basement. Over $100K in recent improvements include a complete electrical service and distribution replacement ($37K, 2022) by ABC Electric with City of Chicago permits, new GFCIs,

Marc Fried Root Realty, Inc.