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

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

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

- 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

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

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

Sunny 3-flat in a prime Logan Square location near the Bucktown/Avondale border. Beautifully maintained and updated throughout the years by the same family. First-floor unit has been updated and features soaring 9-foot ceilings, coffered ceilings in the dining room, gorgeous hard wood floors, open concept living & dining room, kitchen has beautiful cabinets & backsplash, French doors open to

Kathy Jewusiak Berkshire Hathaway HomeServices Chicago

Turnkey 4-Unit in Prime Logan Square. Rare opportunity to own a well-maintained 4-unit building on a quiet, tree-lined street in one of Chicago's most sought-after neighborhoods. Each unit has its own PIN, offering potential for future condo conversion. Strong unit mix: (2) 3-bed / 2-bath units and (2) duplex-downs (2 bed / 2 bath and 2 bed / 2.5 bath). All units feature separate utilities,

Travis Wallace Jameson Sotheby's International Realty

This updated and well maintained 2-Flat with garden apartment is situated on an extra-wide lot along a picturesque, tree-lined street in the desirable Arcadia Terrace Neighborhood. The building's wider footprint allows for spacious room sizes throughout. The first-floor kitchen is brand new, featuring high-end finishes and an open layout that connects seamlessly to the dining room, creating a

Michael Hall Baird & Warner

This five-unit property consists of two well-maintained brick buildings on a 40 ft wide corner in the Bell School District. The front greystone offers a updated 3,000 sq. ft. owner's open floorplan of a 4 bedroom plus office duplex with in-unit laundry plus a three-bedroom rental above, also with in-unit laundry. The duplex is move-in ready and ideal for an owner-occupant. The fully rented rear

Kristin Gonnella Coldwell Banker Realty

*Seller has VA loan which may be assumable.* This beautifully maintained, solid brick 2-flat in the highly desirable Lakeview neighborhood is as turn-key as they come-perfect for investors or owner-occupants alike. Nestled on a beautiful tree-lined street within the coveted Hamilton School District, this building combines timeless vintage character with modern updates. Original charm abounds

Sarah Ahmed @properties Christie's International Real Estate

Don't miss this rare opportunity to own a beautifully maintained 3-unit building in the heart of Lakeview, ideally situated on a serene, tree-lined block. Owned and lovingly cared for by the same owner since 1984, this charming Victorian-style property offers timeless character, income potential, and versatile living options. The spacious owner's duplex-up that lives like a single-family home

Jeanine McShea @properties Christie's International Real Estate

Sitting on a quiet, tree-lined block, this jumbo Greystone Multi-Unit Building offers unbelievable space with over 6,900 square feet of living space! The layout consists of a 4BR, 3.5BTH duplex-down apartment, two, 2BR, 2BTH simplex apartments on the 2nd and 3rd floor and another 4BR, 3BTH duplex apartment in the rear of the property as well as a 3-car brick garage. This truly one of a kind

Michael Hall Baird & Warner

Brown Brick 2-flat with un finished basement 3bed rooms each floor. first floor has 1.1 bath. second floor 1 bath. 3 Brick car garage . basement can be finished and become legal after contacting the city for permit. more info with seller attorney. SOLD AS IS CONDITION. MOTIVATED SELLER.

Sam Abushhab American International Realty

Newly Rehabbed Vintage all Blonde Brick Octagon 2 unit. This is in Edgewater ,one of Chicagos Hottest Neighborhoods. New Kitchen and Baths. The first and second floor boasts a large floor plan. Oak Flooring in the Full Living Room and Full Dining room, the bedrooms and the hallways. 3 Bedroom 1.5 bath apartments on the 1st and 2nd Floor. Both units have back porches. Newer bathrooms

John Knuth Landstar Realty Group Inc.

SELLER SAID BRING OFFER ------Hello investors and owner occupiers---- this Classic Chicago brick 6 + units building in the Ravenswood neighborhood, very well-kept and fully rented to a long-time tenant All large units with 2 bedrooms and 1 bath, hardwood floors throughout. low rents that can be increased with time large Livingroom and Dining room. enclosed porch, beautiful back yard for

Sam Elddine Coldwell Banker Realty

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

2224 W. Eastwood Ave is a 2,472 square foot stabilized 2 flat on a 2,700 square foot lot with 7 bedrooms and 3 bathrooms in the desirable Lincoln Square neighborhood near shopping, restaurants, bars, shops and public transport. Units are in excellent condition and the owner has maintained the property professionally for more than a decade. New roof with a 20 year warranty, low temp electrical

Stephen Fisher Westward360 RM

Location , Location, Location! Stately large brick 2 flat located in a popular Lakeview location! Steps to award winning Bell school and Lane Tech ! Beautiful solid oak woodwork & oak beamed ceiling ! Large eat-in kitchens and a large bonus room off the kitchens which can be a den or office.Convenient walk in pantry in both units and large window box in top floor kitchen. Beautiful oak built-in

Joan Brennock Baird & Warner

Located in the vibrant and highly desirable Lakeview neighborhood of Chicago, this property presents a unique opportunity for both investors and owner-occupiers. It is a 3-flat with a coach house and a fifth unit available-though the legality of the additional unit is not confirmed. Currently, the first-floor space is rented as a one-bedroom, one-bathroom residence, but it has the potential to be

Olga Kocherlk Coldwell Banker Realty

Fully updated and stabilized, this turnkey 5-unit multi-family in the heart of Roscoe Village offers strong in-place income, future upside, and low-maintenance operations. The property includes two buildings: a stately 4-story front building with 3 updated units and an unfinished attic, and a rear 2-story coach house with a 2-bedroom unit on the main floor, an unfinished attic above, and a

Haaris Ishaq Volta Investments LLC

Prime 3-Flat in the highly sought-after AVONDALE neighborhood! This meticulously maintained building is situated on an extra-wide lot, offering exceptional versatility for both homeowners and investors. It is well-suited for an owner-occupant who wishes to reside in one unit while generating rental income from the others, or for investors seeking strong, consistent returns. This property offers a

Regina Rueda Exit Grace Realty

Welcome to Devon Avenue's Little India neighborhood! This unique Legal 4-Unit building on an over-sized lot has been completely renovated and all leased out! Currently generating $100,800/annually giving it an amazing 8-cap rate for your investment! Garden, 1st, and 3rd floor units are all 3BD/1BA units while the 2nd floor unit is a nicely split 2BD/2BA unit. Each unit has been intricately

Feras Abbas Jameson Sotheby's Intl Realty

RARELY AVAILABLE 3 FLAT IN ROSCOE VILLAGE FEATURES DUPLEX UNIT, #1, 4 BEDROOM, 3 BATH DUPLEX DOWN, #2, 3 BEDROOM, 2 BATH #3, 3 BEDROOM 2 BATH! TWO UNITS ARE RENOVATIONS WITH QUARTZ COUNTERS, STAINLESS KITCHEN APPLIANCES, ESPRESSO HARDWOOD FLOORS AND IN-UNIT LAUNDRY. DUPLEX DOWN FEATURES CENTRAL AIR, GFA HEATING, SPACIOUS ISLAND KITCHEN, TALL CEILINGS, HARDWOOD FLOORS, OPEN LIVING/DINING ROOM,

Stephen Fisher Westward360 RM

Exceptional Opportunity in the Heart of Lakeview : Discover this rare chance to own a charming 2-flat perfectly situated in Chicago's vibrant Lakeview neighborhood. Nestled just steps from the bustling Southport Corridor, you'll be surrounded by some of the city's best restaurants, cozy coffee shops, stylish boutiques, grocery stores, and lively nightlife. Wrigley Field is right around the

Carrie McCormick @properties Christie's International Real Estate

TOTAL GUT REHAB. 2Bedrooms/1Bathroom/kitchen/Living Room on all 3 Floors Basement is unfinished and can be its own unit. The basement height is 6 ft appx. at it's highest point. The property also comes with a detached 2-car garage and fenced-in yard. Great uptown location on small 2 block run of Magnolia - close to the train, lake and shopping districts. Great rent potential and an area that is

Ruqia Naqi Baird & Warner

Welcome to this well-maintained and stylishly updated 2-flat with additional non-conforming basement unit, perfectly positioned on a full 25x125 lot in the heart of West Lakeview-less than a block from Hamlin Park! This high-demand location is surrounded by million-dollar homes and offers unbeatable access to outdoor and urban amenities! Inside, this turnkey investment features a total of 6

Leigh Marcus @properties Christie's International Real Estate

Prime Investment Opportunity! Nestled in the heart of Lakeview/Wrigleyville, this high-income, multi-unit property offers an unbeatable location just steps from Wrigley Field. Whether you're an investor looking for a lucrative rental property or a homeowner eager to live in one of Chicago's most vibrant neighborhoods, this classic Chicago apartment building is a rare find. This legal 3-flat has

Cory Jones eXp Realty - St. Charles

Prime Investment Opportunity in West Lincoln Park! Well-maintained 3-flat in one of Chicago's most desirable neighborhoods. This solid building features a new boiler and updated electrical systems, ensuring peace of mind for investors and future tenants. Includes a 2-car garage and a beautifully landscaped backyard - perfect for relaxing or entertaining. Ideally located near top-tier amenities:

Elva Chavez Illinois Real Estate Partners Inc

37.5'x148' Lot, Zoned B3-3, TOD, There are 2 Commercial spaces, 4 Studio apartments recently renovated and ready to rent and 4 more units(2- studios and 2- 1bedrooms) that are being gutted and converted to 2- 2bedroom apartments. Bldg Survey and Drawings available for the 2 bedroom renovations under "Additional Info" tab. The entire property is vacant.There is also an additional structure on the

John Moumouris Buckingham Property Management INC

Two unit building in Lincoln Park. Sunny well designed second floor duplex with vaulted ceilings, spacious layout and a working fireplace. Second floor unit has its own washer dryer installed. Easy to rent. First floor unit is large and attractive. Both units have Private Decks with sliding glass doors. Both units have fireplaces. Both units were recently remodeled and have their own HVAC units.

Tamara Verdin Prello Realty

Generational Opportunity to Purchase a South Andersonville Brick and Stone Multi-Family Residential Property with a Move-In Ready Owner's Three Bedroom 2 Bath Triplex Unit with Four Additional Income Producing Rental Apartments located in the City of Chicago ADU Pilot Program for additional permitted rental unit!!!! Oversized Lot with 2 Car Garage and Additional Carport for easy come and

Nicholas Jakubco Jakubco Development, Inc

Attention Developers/ rehabbers!! Oversized lot prime for rezone, build 4 condos at 1900Sq feet each. Building has good bones but needs lot of work. Could be a good single family conversion. 1 Bath in Partially finished basement. This property is being sold "AS IS" currently winterized. Only serious offer will be considered. No low ballers.

Daniel Nierman 4 Sale Realty Advantage

Heart of Roscoe Village, 3 blocks from Brown Line, 1 block from Roscoe Street, restaurants, boutiques, & shopping. Great opportunity with 2 buildings on 1 corner lot with 5 apartments divided as follows: main building has 3 units and coach house has 2 units. The coach house was gut-rehabbed in 2021 with brand-new plumbing, electrical, HVAC, siding, walls, windows, designer kitchens, baths, and

Luminita Ispas Century 21 S.G.R., Inc.

This historic Chicago 3-flat blends classic architectural charm with modern convenience. Situated on a corner lot line with no setbacks, the over 8,000-square-foot building features expansive units and a detached two-car garage accessible via a curb cut on Nelson Street. Enjoy outdoor living with a bluestone patio and two large decks. Formerly a storefront, Unit #1 offers more than 2,000 square

Jennifer Ames Engel & Voelkers Chicago