View All Lakeview Chicago IL 4-Flats Listings

8 Beds ⋅ 4 Baths ⋅ 12659654 MLS ⋅ CLOSED Status

Classic and beautifully maintained, this income-producing Lakeview 3-flat offers the perfect blend of vintage charm, flexible living space, and strong investment potential. The sun-filled first-floor unit features 2 bedrooms and 1 bath, highlighted by timeless woodwork, generous living space, and a private rear deck. The garden apartment offers an additional 2-bedroom, 1-bath layout, ideal for steady rental income. The standout top-floor duplex-up lives like an owner's home, featuring 4 bedrooms, 2 baths, and a private top-level deck perfect for entertaining or relaxing outdoors. Currently tenant-occupied, it presents an exceptional future owner's unit opportunity. Additional highlights include separate utilities for all units, well-maintained mechanicals, and an unbeatable Lakeview location close to restaurants, shopping, parks, nightlife, and public transportation. A rare opportunity for investors or owner-occupants seeking strong income and long-term value in one of Chicago's most desirable neighborhoods.

1448 W George Street, Chicago

$1,050,000

9 Beds ⋅ 4 Baths ⋅ 12626232 MLS ⋅ CLOSED Status

An exceptional investment opportunity in the highly sought-after Roscoe Village / West Lake View location. Situated on an oversized 38 x 124 lot along tree-lined Barry Avenue, this property offers convenient access to grocery stores, dining, shopping, and public transit. This well-maintained three-flat has undergone significant recent improvements, including a gut renovation and dormer expansion of the top floor, adding a full bathroom and two additional bedrooms. The garden unit, currently in original condition, features 2 bedrooms and 1 bathroom and is leased MTM for $1,350/month to a long-term 10+ yr tenant, with strong upside potential to $2,400+ with updates. The second-floor unit, recently renovated, offers 3 bedrooms and 1 bathroom and is rented at $2,750/month. The top-floor owner's unit is configured as a spacious 4-bedroom + den, 2-bath duplex with an estimated rental potential of $4,000/month. Additional value-add opportunities include the potential to add a kitchenette to create a separate in-law suite on the upper level. A detached three-car garage, currently owner-occupied, presents further income potential of approximately $300-$400 per month, making this a rare opportunity to acquire a high-performing asset with immediate upside in one of Chicago's most desirable neighborhoods.

2317 W Barry Avenue, Chicago

$725,000

4 Beds ⋅ 4 Baths ⋅ 12551028 MLS ⋅ CLOSED Status

Great Income on this Updated 2-Flat in Awesome Hamlin Park/Roscoe Village Location. Updated units rent quickly, perfect for Live-In Owner or Investor. Location is walkable to Belmont Street & downtown Roscoe Village. Two Duplexed Units feature updated Kitchens & Baths, New HW floors throughout, laundry in the Bldg and 4-car tandem parking in the back. 2nd Floor Improvements include, New Furnace & A/C (~2024) New Kitchen & Appliances (~2022), New Bathrooms (~2022), HW Flooring (~2022), Updated Electric (~2022), H2O Tank (~2021), Laundry (~2019). 1st Floor improvements include New W/D (~2023), New Appliances (~2021), H2O Tank (~2021), New Furnace & A/C (~2020), Updated Kitchen & Bathrooms (~2018). Other Bldg Improvements include some updates to Electric & Plumbing as the units were renovated, plus New Roof (~2012). Lots of New Construction on the block and in the area, great destination location, perfect for AirBnb or traditional rentals. Steps to Shopping, Dining, Nightlife, CTA, Expy and all the City has to Offer. This location is HOT!!!

3020 N Clybourn Avenue, Chicago

$1,600,000

7 Beds ⋅ 3 Baths ⋅ 12569466 MLS ⋅ CLOSED Status

Incredible Opportunity to acquire an updated brick Legal 3-Flat Multi-Family investment property on an Oversized Lot in coveted Top Performing CPS Blaine School District!!!! This property is ideal for the Live in Owner and is Zoned RT-4 which also provides for upper bracket multi-family new development. The current apartment configuration is as follows: 2nd Floor Apartment Three Bedroom One Bathroom, 1st Floor Apartment Two Bedroom One Bathroom and Ground Level Apartment 2 Bedroom One Bathroom. Very bright and open apartment floor plans containing hardwood/tiled floors with updated finishes including stainless steel appliances, granite counters, updated cabinetry in excellent condition. Large exterior rear decks overlook an oversized rear backyard ideal for play and comfort. On site common area coin laundry and separate owner's storage shed is located in detached two car garage. Existing rents are well below market and ready for a price reset. This property is situated within walking distance to the Southport entertainment and shopping district as well as Wrigley Field. Recent Improvements include: Windows 2010, New Roof 2010-Silver Coat 2022, Boiler 2010-Updated Thermostat-2025, H2O Tank 2017, Garage Floor and Door-2019, 2nd Floor Updates 2014, 1st Floor Updates, 2016 and Ground Unit updates 2017.

1411 W Byron Street, Chicago

$1,060,000

3 Beds ⋅ 2 Baths ⋅ 12378254 MLS ⋅ CLOSED Status

This 2 flat frame is located in hot south Lakeview. Southport corridor is walking distance, having access to restaurants, shopping, grocery stores, public transportation 4 blocks away. Building currently has a 2 bedroom 1 bath rental on 1st floor. Second floor is home owner duplex unit used as 3 bedroom 2 bath. Could be downsized to single family or new construction. Back yard garden is spectacular with pear tree, flowers, small pond. 1 car garage. Best and final offers by Sunday October 19, 2025, 3 pm

1329 W Nelson Street, Chicago

$1,500,000

8 Beds ⋅ 4 Baths ⋅ 12322152 MLS ⋅ CLOSED Status

Welcome to this meticulously maintained full-brick legal 3-flat, which is just one block from top-rated Blaine Elementary and in the heart of Southport Coordidor! Steps from some of the city's best restaurants, shops, and nightlife. This architecturally significant three-story building features a beautiful brick facade, making it a standout in the Southport corridor neighborhood. A prime investment opportunity, this fully leased property has had zero vacancies under current ownership, offering immediate income potential. The top two floors each feature 2 bedrooms and 1 bathroom, while the first-floor duplex-down offers 4 bedrooms and 2 bathrooms with separate front and rear entrances on both levels, ideal for an in-law suite, nanny quarters, or additional rental income. Recent updates include new stainless steel appliances throughout, fresh paint in the first- and second-floor units (2023), new windows on both floors (2023), tuckpointing (2021), and a resealed and repainted roof (2022). Additional highlights include a built out deck perfect for entertaining, three parking spaces with potential for six tandem spots, separate utilities for each unit, and newer mechanicals for easy maintenance. Whether you're looking to live in one unit while generating rental income, lease all units long-term, or explore short-term rental opportunities like Airbnb, this is a rare chance to own a stunning income-generating property in one of Chicago's most desirable locations. With the Brown Line nearby, commuting downtown is effortless, while Wrigley Field is just a short stroll away for game days and concerts. So much more to see for yourself, get your private tour today!

3854 N Janssen Avenue, Chicago

$1,425,000

9 Beds ⋅ 5 Baths ⋅ 12340414 MLS ⋅ CLOSED Status

Wrigleyville 2-flat greystone. Unit 1 is a 5 bedroom, 2.5 bathroom duplex down. Unit 2 is a 4 bedroom, 2 bathroom simplex.

1048 W Dakin Street, Chicago

$1,017,500

5 Beds ⋅ 2 Baths ⋅ 12322542 MLS ⋅ CLOSED Status

Available for the first time in over 50 years, we are excited to present a large legal brick 2-flat in the heart of Lakeview. This property is just half a block from the vibrant Halsted Corridor and within walking distance to Wrigley Field, theaters, parks, shopping, and restaurants. Each of the apartments has 2 bedrooms and 3 bedrooms specifically on the 1st and 2nd floor. They both feature 1 full bath, separate dining room, living room, sunroom, enclosed porch, and a spacious kitchen. Both units boast high ceilings and large windows throughout. The basement is clean and unfinished, with approximately 7-foot 6-inch ceilings, front and back entrances as well above grade windows. A two-car brick garage offers the potential for a rooftop garden or deck. This home is in the sought-after Oakdale Historic District, making it an excellent opportunity for investors or owner-occupants to own a character-filled property in one of Chicago's most desirable neighborhoods. The structure cannot be torn down, but with R4 zoning, you can easily add value to this investment by expanding unit 1 into the basement and adding a partial level to unit 2 or convert it into a spacious 4 story single-family home by adding a partial 3rd floor

851 W Oakdale Avenue, Chicago

$1,312,500

9 Beds ⋅ 4 Baths ⋅ 12315571 MLS ⋅ CLOSED Status

Completely updated all brick south facing two-flat within walking distance to Wrigley Field, tucked away on a quiet street. Extra-wide building on an oversized 31' x 123' lot. RM-5 Zoning. Unit 1 is a 2,875 sq. ft. 5 bedroom 2 bathroom duplex down currently rented through May 2026 for 5,250. Unit 2 is a 1,400 sq. ft. 4 bedroom, 2 bathroom condo-quality unit available for an owner to occupy starting May 1st or for new tenants to move in for 4,350 per month. A savvy new owner could occupy one unit while paying down the mortgage with the income from the other. Building was completely updated / rehabbed in 2017. All bedrooms are massive and generous in size because the building is situated on an extra-wide lot. Thoughtful floorplans are complimented by large windows and hardwood flooring throughout. Each unit has central air, heat and in-unit laundry. Enjoy a large private backyard perfect for entertaining! Property has a 2 car garage with a 3rd parking space on an adjacent pad. Walk to restaurants, boutiques, CTA Red line, gyms, grocers, theaters and everything else that Lakeview has to offer!

1046 W Dakin Street, Chicago

$1,275,000

8 Beds ⋅ 5 Baths ⋅ 12290937 MLS ⋅ CLOSED Status

Southport Corridor newly rehabbed Three-Flat with a 4 bed 3 bath duplex-UP owner's unit on a tree-lined quiet one-way street in A+ location in the highly sought after Blaine School District. Walkscore 97 ("Walker's Paradise")! Close to everything: parks, grocery stores, pharmacies, shopping, restaurants, Brown Line and more. Penthouse owner's unit boasts new kitchen and in-unit laundry. English garden unit was also recently rehabbed in 2020. All three units have central HVAC. Large private decks and lovely back yard. 2-car garage. Building also has common coin laundry room. Building upgrades in 2020 include new exterior paint for front porch and rear decks and all new tear-off roof! Plus potential to add unit as property is located in the ADU zone!

3623 N Janssen Avenue, Chicago

$1,500,000

9 Beds ⋅ 6 Baths ⋅ 12188936 MLS ⋅ CLOSED Status

Stunning Rehabbed Greystone 3-flat + tall basement on a quiet 1-way street steps from Wrigley Field & Halsted! Great investment or perfect for a live-in owner. Exceptional income and 2 of the 3 units have been tastefully rehabbed including 2 newer kitchens with modern, flat-panel & shaker-style cabinets, granite countertops & stainless-steel appliances, and newer baths. ALL 3 UNITS HAVE 3 BEDROOMS, IN-UNIT LAUNDRY, GFA w/ CENTRAL-AIR CONDITIONING & 2 BATHROOMS, Large formal living room & dining rooms with Hardwood Floors throughout. All New Windows in 2011, newer Mechanicals (newer plumbing supply, some new electric, etc) & more! VERY Tall Basement and GENEROUS RM-5 ZONING (FAR = FLOOR AREA RATION OF 2.0) will allow for further income by expanding up (for a large duplex-up apartment) and/or down into the tall basement for a 4th, legal apartment OR combine with the first-floor unit to create a very large duplex-down unit! A unique side & back alley allows for 4 full exterior parking spots (with room to expand for a 5th parking spot) all 4 are currently rented through Spot-Hero with an outstanding annual income of $23K! (each spot averages $479 per month per spot). Excellent location with a short walk to Wrigley Field and steps from all the Wrigleyville & Lakeview amenities on Halsted & Clark including great area restaurants, coffeehouses, shopping, nightlife, parks, lakefront, EL stop, schools & more! - Top Floor/UNIT #3; 3-bed/1.5-bath (can easily add a shower for 2nd full bath) - lease exp 7/31/25 @ $2,990 per month...UNIT #2; 2-bed/2-bath and was just rented @ $3,200 per month ...UNIT #1; 3-bed/2-bath (lease exp 7/31/25 @ $2,670 per month). 4 gas meters and 4 electric panels. ***EXCELLENT TOTAL ANNUAL INCOME of $129,320 minus - $31,354 in total expenses = $97,966 (NOI) TOTAL ANNUAL NET OPERATING INCOME for a Solid 6.1% CAP rate.***Also, investing an additional $120K in creating a legal 4th garden unit which is allowed under the current R5 zoning (existing ceiling height is very tall @ 7'-8") & 5th parking spot brings the CAP rate up to 8%!!

814 W Newport Avenue, Chicago

$1,075,000

6 Beds ⋅ 6 Baths ⋅ 12172071 MLS ⋅ CLOSED Status

Southport Corridor- Brick two-flat with coach house offering 4 apartments in an A+ location in highly sought after Blaine School District. Front building features a 2BR, 2BTH duplex down with large bedroom suite and a 2nd floor 1BR, 1BTH apartment, both with private back decks. Coach House features an updated duplex-up unit with beautiful kitchen, open layout, 2 full baths, a huge ensuite primary bedroom, in-unit laundry and a 1st floor 1BR, 1BTH apartment. This property would make an excellent owner-occupied home with significant rental income to toward your mortgage or a great investment property alone. Just one block from Southport Corridor with all its wonderful restaurants, bars, shopping and the Music Box Theater, 5 blocks from the Brown Line "L" and walking distance to Wrigley Field, the location simply can't be beat. Rents are below market value and could be increased significantly with cosmetic improvements. Front building has back decks and there is a lovely patio and garden in between the buildings that provides a wonderful refuge from busy city life. Property has RT-3.5 Zoning. Stated rental amount for the 1st floor duplex apartment in front building is a projection of market value. This unit is currently vacant.

3709 N Janssen Avenue, Chicago

$1,400,000

8 Beds ⋅ 4 Baths ⋅ 12125084 MLS ⋅ CLOSED Status

Stunning three-flat located in the heart of Wrigleyville neighborhood, sitting on an extra-wide lot. Nestled on a quiet, tree-lined street, this early century greystone has been updated, offering a seamless turnkey investment opportunity. Unit 1 features a spacious 4-bedroom, 2-bathroom layout spread across two levels, while Units 2 and 3 offer comfortable 2-bedroom, 1-bathroom accommodations. All units have high, 10ft ceilings, each featuring a bright and airy living room with a wood-burning fireplace, separate dining room, and large bedrooms sizes due to the extra-wide lot. Each unit has its own back deck and a larger, communal deck, providing ample outdoor living and entertainment possibilities. Whether you aspire to reside in one of the units while tenants contribute to your mortgage or expand your investment portfolio with 1045 W Dakin, this property consistently maintains full occupancy and promises a reliable source of income for the years ahead.

1045 W Dakin Street, Chicago

$1,600,000

11 Beds ⋅ 7 Baths ⋅ 12009538 MLS ⋅ CLOSED Status

This jumbo Greystone sits on an extra-large lot on one of Lakeview's prettiest tree lined streets. The building is comprised of 4 extra-large units including two 3 bed/2 baths, one 4 bed/2 bath and one 1 bed/1 bath garden apartment. The apartments feature hardwood floors, original trim and some with decorative fireplaces, stainless steel appliances, granite counters, subway tile backsplash, tiled bathrooms, separate HVAC, laundry in-unit and rear enclosed porches. The building is ideally situated on the north side of Oakdale Avenue just west of Seminary Avenue, and it is conveniently less than 4 blocks to the Wellington, Belmont & Diversey L Stations, making this an excellent location within the Lakeview neighborhood. Quick access to the CTA Brown, Purple & Red Line Stations, along with several bus stops, offers tenants many excellent public transportation options. Less than three blocks away is Southport Corridor, a popular street full of local charm featuring a wide variety of boutiques, salons & spas, and trendy restaurants & bars. 1104 West Oakdale is a rare opportunity to own a stately Greystone 4-flat in a prime Lakeview location with an endless choice of dining and entertainment options just steps away.

1104 W Oakdale Avenue, Chicago

$2,150,000

7 Beds ⋅ 4 Baths ⋅ 11997193 MLS ⋅ CLOSED Status

Definitely unique and incredibly well-maintained large property on a 50' X 176' lot in the heart of highly desirable Wrigleyville area of Lakeview. Land alone is valued over 2 million dollars and there is a large majestic red brick 4 flat plus a lovely 2 story coach house included! All large apartments have been updated within the last 5-8 years with the exception of first floor. Tenant has been there for 20 years and even that unit shows very well. All units (nearly condo quality) have updated cabinet kitchens, tiled baths, beautiful hardwood floors, classic hardwood trim, built-in China hutches and more. Each unit has its own separate HVAC system. Electric mains in basement and each of the units have the circuit panel within the apartment. Newer windows too. Large 50 X 176 lot offers a fantastic private yard for the building and the lovely 2 story coach house. This residence has a spacious living room with functional fireplace, dining area very nice kitchen and half bath on first floor. Upstairs are 3 good size bedrooms with a larger master a full bath and a big open sitting area. The house has its own laundry and an attached 1 car garage. Rents are as follows: Garden $1295. 1st $1795. 2nd $2475. 3rd $2200. and coach house $3400. Total $11,165 a month plus laundry is $134,750 a year with definitely room for increases. Simply put this is a gorgeous one-of-a-kind property waiting for the new owner or possible development opportunity. City zoning certificate states 4 units - recognizes the coach house as one of the units but even though garden apartment fits all criteria and is rented, seller makes no representation as a legal apartment. Any questions, concerns or offers text or call Norbert Mika Offer accepted pending paperwork .

3925 N Janssen Avenue, Chicago

$835,000

7 Beds ⋅ 4 Baths ⋅ 11964216 MLS ⋅ CLOSED Status

Fantastic investment opportunity in one of Chicago's best areas! Nestled in the coveted Blaine school district, this is a fantastic opportunity for either a great investment opportunity or to get the space that you and your family need without breaking the bank. This 3-story 2- flat on a quiet, tree-lined street is comprised of two huge units, a 4 bed/3 bath duplex up and a 3 bed/1 bath, that are fully move-in ready and a breeze to rent! The duplex up has a massive open floor plan that provides as much square footage as many single-family homes. The main floor is perfect for entertaining, with its large expansive spaces and soaring 10-foot ceilings The current owners capitalized on the unfinished attic space by adding an additional 3 bedrooms, 2 baths, and side by side washer and dryer to the top floor. The bathrooms are finished out to a condo quality level, and all of the closets have custom California Closet organizing systems. They also did substantial updates to the first-floor unit, adding in-unit w/d, all new lighting, new door hardware, and refinishing the floors in a lovely espresso tone to give it a more modern feel. It wasn't all about the aesthetics, though. The entire building just received all new siding and window capping, there were structural reinforcements done during the expansion into the attic, and the front porch received an overhaul too. All of this, and you're just moments away from multiple train lines, some of Chicago's best new restaurants, and conveniently located near anything you may need!

3723 N Marshfield Avenue, Chicago

$929,000

8 Beds ⋅ 4 Baths ⋅ 11963546 MLS ⋅ CLOSED Status

Classic Chicago multi unit, with huge 4 Bed/2 Bath Owners duplex unit on top with huge deck. Supremely located 3/4 block of hot Southport Avenue, 3 blocks to L, and easy walking distance to Wrigley Field. Laid out with 3 separate units (4/2, 2/1, 1/1), but being sold as a zoned 2 Flat. 2 sets of HVAC (one for B and 1, one for 2 and 3), 2 laundry, 2 HWH, updated electric. Perfect investment property with pro-forma rents of $3,600, $2,000 and $1,200 or make the top your home in Lakeview and collect rents downstairs. Zoned RT 3.5. Sophisticated flood control system means a dry basement, large yard, 2 car garage.

1450 W School Street, Chicago

$985,000

8 Beds ⋅ 4 Baths ⋅ 11866550 MLS ⋅ CLOSED Status

Amazing well taken care of and completely leased LEGAL 4 flat in the heart of Wrigleyville!! Building has additional off alley parking for 2 cars- for extra tenant leased revenue or rentable for Cubs games. Great fenced green space in back for tenants' use. All units have been updated thru the years and have their own central air, hot water heaters, furnaces, electrical panels, back decks, dishwashers, in unit washers & dryers (except *garden has 2 window ac units, and a separate dedicated laundry room just outside of unit's back door*) 10+ foot ceilings (except garden) The porch has been rebuilt to code and freshly stained!! Building has several recent upgrades throughout the units including several new HVAC units, stainless appliances, & Washing machines. Building is the perfect location for anyone utilizing public transportation with Red and Brown EL lines within blocks and all that is Wrigleyville /Lakeview - Shops, Restaurants, Social/Nightlife, Groceries, and 3 blocks to Wrigley Field Ball Park for Cubs games and concerts. WOW!!!

3351 N Kenmore Avenue, Chicago

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