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

3851 N. Hermitage is a highly upgraded custom single-family home. The meticulous attention to detail is apparent the minute you walk into this gorgeous home. The many details include a natural stone mosaic-tiled entry with a coat closet, hardwood flooring throughout, and beautiful custom millwork with coffered, vaulted, and beamed ceiling accents. The stunning light fixtures are custom from

Bill Danaher Victory Real Estate, LLC

Welcome to your next urban oasis where high quality vintage meets today's luxurious upgrades! Gorgeous, spacious 5 bedroom, 4.5 bath home on a quiet street on an oversized lot (37.5 x 121), thoughtfully renovated & redesigned (2010, 2025) in Coonley School District. Highlights include - main level - a large foyer that leads to a light-filled living room anchored by a fireplace, a formal dining

Lida Downey eXp Realty

Experience elevated urban living in this remarkable newly renovated and expanded 6-bedroom/6.5-bath luxury residence, offering 5,400+ SF of refined, professionally designed interior and ~2,000 SF of exceptional outdoor living across 4 private areas. Situated on a 30' wide lot along picturesque Magnolia Ave, this stunning greystone showcases superb craftsmanship and exudes luxury at every turn.

Lucy Antanovich Berkshire Hathaway HomeServices Chicago

Newly refreshed, staged, and ready for its next owner! This 6,350-square-foot residence sits on a 36-foot-wide lot on one of Southport Corridor's most desirable streets. Built as a custom home to the highest standards, it offers three levels of well-planned living with 5-6 bedrooms, four full baths, and three half baths. Move-in ready, it combines timeless craftsmanship with modern comfort...a

Jennifer Ames Engel & Voelkers Chicago

This is 6 bedroom, 6 full bath and 2 half bath residence is not your average city home-this extra deep lot features four levels of sophisticated luxe living totaling 5,486 Sq Ft. The main living space is meticulously designed for a light & open feel perfect for entertaining and living. It features custom millwork, dramatic soaring and coffered ceilings and stone fireplaces. A gourmet chef's

Melissa Siegal @properties Christie's International Real Estate

Welcome to 1252 W Carmen Avenue, a beautifully renovated Greystone situated on an oversized lot on a quiet, tree-lined street in Andersonville, offering convenient access to the shops, dining, and cultural destinations of Andersonville and Broadway. Sitting on a rare 40' x 150' lot with no alley behind it, the spacious backyard is truly a peaceful oasis in the city providing a unique, private

Kathleen Bradshaw @properties Christie's International Real Estate

Step into this stunning, custom-built Ravenswood home on an extra-wide 50' x 165' lot and prepare to be wowed. At its heart is a dramatic two-story atrium that floods the home with light and opens onto a private stone courtyard with an outdoor fireplace-blending architecture, light, and outdoor living in a way rarely seen in Chicago.A wraparound stone porch and gated front yard create a warm

Jeffrey Lowe Compass

An unbelievable and unmissable opportunity to purchase the 1st resale of this exquisite all brick single family home! Developed by the renowned and respected ' Savane Design & Build ' properties. Located in the sought-after Southport Corridor & Blaine School district on Greenview Ave. This stunning home, approx. 6000 sqft sits on an extra wide 30 x 125 ft lot. This gracious, beautiful and

Michael Kearney Berkshire Hathaway HomeServices Chicago

Luxury Living in the Heart of the City: Only 4 Homes Left at the Wolfram Collection. Located in Chicago's desirable Burley School District, the Wolfram Collection presents an exclusive opportunity to own a stunning, newly built single-family home that masterfully combines modern luxury, functional design, and urban convenience. With only 4 homes remaining, this boutique development is ideal for

Jennifer Liu Baird & Warner

Turn-Key, Fully Leased Multi-Unit Investment in Prime Edgewater | $87,600 Annual Income Exceptional opportunity to own a fully tenant-occupied, cash-flowing property in the highly sought-after Edgewater neighborhood. This unique setup features a classic all-brick 2-flat in the front and a legal, detached coach house in the rear-perfectly suited for both seasoned investors and 1031 exchange

Anthony Maione @properties Christie's International Real Estate

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.

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.

Updated 5-bedroom, 4.1-bath single-family home offering four levels of flexible living space in the highly rated Coonley School District. Features include a sun-filled open main level with hardwood floors, a chef's kitchen with quartz countertops, oversized island, and a spacious mudroom/laundry room ideally situated just off the kitchen. The second level boasts a large primary suite with

Anthony Klementzos Carr Real Estate Investments

Classic Chicago brick 2-flat in the heart of Avondale/Irving Park! This traditional building combines timeless character with modern updates, making it a smart choice for investors or owner-occupants alike. The first-floor unit offers 2 bedrooms, 1 bath, and spacious living and dining rooms with a brand-new heating system installed in 2023. The second-floor unit features 3 bedrooms and 1 bath,

Tanya Orndorff Equity Partners Real Estate, LLC

Amazing 3-flat with an additional garden apartment in a desirable location. Stunning 3 apartments with 3 bedrooms/ 2 bathrooms and a garden apartment with 3 bedrooms/2 bathrooms offering spacious and open-concept floor plans designed for comfort and luxury. Step inside to discover a spacious living and dining area, a bright and airy space, and a modern open kitchen featuring a large peninsula,

Alina Pop American International Realty

ATTENTION INVESTORS! EXCEPTIONAL OPPORTUNITY TO OWN A THREE-UNIT APARTMENT BUILDING FEATURING THREE SPACIOUS APARTMENTS - EACH WITH A SEPARATE LIVING ROOM, SEPARATE DINING ROOM, 3 BEDROOMS AND 2 FULL BATHROOMS. BASEMENT WITH 9-FOOT CEILINGS AND AN IN-LAW APARTMENT. PROJECTED RENT PRO FORMA: $2,800 PER UNIT / PER MONTH. MOTIVATED SELLER + PROPERTY NEEDS TLC. SELLER WILL CONSIDER ALL OFFERS.

Patti Limperis Century 21 Universal

Welcome to 2602-2604 W Winona St, a rare and exceptional investment opportunity nestled in the heart of Lincoln Square. Situated on an oversized 50x150 ft lot, this beautifully maintained property features a classic center-entrance brick 4 UNIT BUILDING AND a spacious COACH HOUSE in the BACK - offering both timeless charm and remarkable versatility. Each unit in the main building includes 2

Beata Rogowski Coldwell Banker Realty

North Park diamond waiting for your ideas. Home has a total of 8 bedrooms & 4 baths, plenty of living space situated close to North Park University, Northeastern University, North Side & Von Steuben High School's. Public transportation at your door step, nearby shopping as well. Please note, home is being sold as-is.

Aldrin Mayen Charles Rutenberg Realty of IL

Discover 5614 N Campbell, a meticulously updated 2-flat with a non-conforming garden unit, offering unmatched style and opportunity in Chicago's thriving multi-family market. Ideal for investors or owner-occupants, this multi-unit gem blends modern upgrades with timeless charm. The two above-grade units boast 2 spacious bedrooms and 1 pristine bathroom each, featuring refinished hardwood

Ben Lalez Compass

BEAUTIFUL THREE UNIT BUILDING IN ALBANY PARK. ALL THREE BEDROOM UNITS, TWO BATHS IN UPPER UNITS, ONE BATH IN BASEMNET UNIT. ALL STAINLESS STEEL APPLAINCES IN ALL UNITS WITH GRANITE COUNTERTOPS IN KITHCENS. IN UNIT LAUDRY IN ALL UNITS. TOP FLOOR HAS GAS FIREPLACE, AND SKYLIGHTS. NEW DECK IN 2011, CONCRETE IN 2013. REFRIGATOR IN TOP UNIT REPLACED IN 2022. CENTRAL AIR THOUGHOUT. TWO CAR GARAGE, WITH

Dante Zorzi @properties Christie's International Real Estate

Incredible opportunity to own a hard-to-find solid brick 2-flat in highly sought-after Lincolnwood. Features spacious units in 1st and 2nd levels each with 3-bedrooms, 1.1-bath including generous living and dining size, hardwood floors, and abundant natural light. Finished basement featuring 2- bathrooms, 1-bath unit with window been above the grade level., and a common laundry area. An

Mark Ahmad Century 21 Circle

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

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

Located in the heart of North Center and the sought-after Bell School District, this nearly new, fully gut-renovated home offers four levels of living just steps from Revere Park and walking distance to St. Ben's. With 5 bedrooms and 4.1 bathrooms, the layout is designed for both daily function and effortless entertaining. The main level features a spacious living and dining area that opens into

Juliana Yeager @properties Christie's International Real Estate

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

Well taken care of 8 bedroom 3 bath 2 flat on a beautiful tree lined street. Both of the main units have 3 bedrooms with the primary bed having an adjoining office space. Recent tuck-point and roof maintenance along with a new installed flood control system makes this a worry free opportunity. The basement can easily be turned into an inlaw suite with roughed in plumbing for a kitchen and a full

Dave Johnson City and Field Real Estate

Great 2 Flat Opportunity in West Ridge just steps to Warren Park & Northtown Library! First time on the market in over 50 years! You'll fall in love with the wonderful neighborhood & beautiful original details of the home and the 2-car garage! Each apartment has the same floor plan, hard wood floors throughout and an oversized coat closet in the foyer. The Sunny 18'x13' Living Room features six

Ellen Baren @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

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

BUDLONG WOODS - ACROSS FROM RIVER PARK- BLOCK FROM SWEDISH CONV HOSPITAL TO THE EAST. CTA AND NORTH PARK COLLEGE TO THE WEST. FANTASTIC LOCATION FOR RENTING. BRICK LEGAL 4 UNITS BUIDING WITH 2 BEDRM UNITS( LR=17X13 KIT= 12X11 BR1=12X11 BR2=11X10) WITH 2 EXTRA FINISH BSMT APARTMENT WITH 1 BEDRM EACH - FRONT AND REAR DOORS. 6 SEPARATE GAS FORCE AIR HEATING (NO CENTRAL ) , 6 HOT WATER TANKS. 6

James Miller DIRECT BROKER LLC

Rarely available! Fabulous vintage 5 bed 3 1/2 home on a very deep double lot on a beautiful residential block near CTA public transportation and Metra station. Three levels of living space plus a full unfinished basement. Lots of vintage details with many modern and recent updates. Main floor has living room, dining room, library/office, large updated eat-in kitchen and 1/2 bath. Second floor

Nick Powers Baird & Warner

Lakeview!! Lakeshore Drive Huge duplex co-op with incredible lake views. Huge two story co-op that feels like single-family home. This exceptional corner residence offers a rare blend of timeless elegance, modern luxury, and a single-family home feel-all set in a beautiful vintage co-op on iconic Lake Shore Drive. Boasting sweeping, unobstructed views of Lake Michigan and the lakefront parks,

Grace Sergio @properties Christie's International Real Estate

Live Large in Budlong Woods! Step into this elegant urban oasis where spacious design meets timeless charm. Nestled on a generous 60x133 lot, this 5-bedroom, 4.1-bath stunner delivers everything today's discerning buyer dreams of-space, style, and serenity. On the main floor, a dramatic two-story foyer welcomes you to a layout crafted for effortless entertaining. Picture cozy evenings by the

Liliana Lohan Lohan Realty, Inc.

Welcome to this stunning vintage condo in the heart of Edgewater, offering five spacious bedrooms and three beautifully appointed bathrooms within an expansive 3,800 square feet of living space. Nestled just one block from the serene lakefront, this second-floor walk-up combines classic charm with modern comforts. The unit boasts meticulously restored woodwork throughout, adding warmth and

Sarah Dermody Compass

Owner occupants or investors! Excellent opportunity to own this brick 3-flat (add 4th ADU unit in basement) in the heart of West Ridge. Unbeatable location backing up to Warren Park/Robert Black Golf course and just steps from shopping, restaurants, entertainment, transportation & more! Spacious apartments feature sun-filled living & dining rooms, hardwood floors, & decorative fireplaces.

Mark Kurgan 33 Realty

This is the one Experience the timeless elegance with stunning modern design.!Move in condition ! Meticolously done Spacious,Elegant, quality crftmanship! 5 bedroom & 3 Full baths,Finished basement with a modern bath and nice size bedroom also basement entrance.The suprises are waiting for the future owner is incredible. A total turn key opportunity for next occupant. A great satisfaction and

Mohammed Chowdhury Equity Market Realty Inc.

Welcome to lakeside living in the heart of Chicago's Lakeview East neighborhood, a unique find that eagerly awaits your creative touch. Not only does this residence greet you with a promise of luxury, but also serves as a canvas for your imagination. A pre-war, co-op building, standing tall along the picturesque Lake Shore Drive, exudes the utmost charm with tons of character. With a sprawling

Victoria Rezin Coldwell Banker Realty

Introducing 1535 West Estes Avenue, located in the heart of East Rogers Park! This 2025 beautiful, enormous, completely renovated to the studs 4 unit multi-family building features top-notch design and craftsmanship throughout. The property sits on a huge 30x180 foot lot located on a quiet street and showcases exquisite gorgeous limestone as well as new tuckpointing, a complete tear off roof, all

Peter Fotopoulos Baird & Warner