View All Lakeview Chicago IL 5-Flats Listings

$700,000
2 Beds ⋅ 2 Baths ⋅ 12616159 MLS ⋅ CLOSED Status
*MULTIPLE OFFERS RECEIVED. Highest & best due by Sunday 4/19/26 at 6pm CT.* Unit has been owner-held and occupied by the same tenants since construction and is currently occupied through 5/30/26. Building is adjacent to the CTA train. Photos are from 2023 when the unit was professionally staged. Showings begin Thursday 4/16/26 and are available during designated windows only. Bright, modern, and thoughtfully designed, this newer construction 2 bed, 2 bath condo offers an open, well-planned layout in an all-masonry building in Lakeview. South and west-facing floor-to-ceiling windows bring in TONS of natural light throughout the day, connecting the living, dining, and kitchen spaces in a way that feels easy and intuitive. The kitchen is centered around an oversized island with seating for eight, and features two-toned flat panel cabinetry, Bosch appliances, and quartz countertops with a full-height backsplash and waterfall edge. Well-executed finishes carry throughout - 9.5' ceilings, wide plank engineered hardwood floors, 8' solid core doors, and a sleek electric fireplace with a custom surround. The primary suite is set apart with a spa-like bath, oversized shower plumbed for steam, and a double vanity, along with generous built-out closet space. Built for comfort, the home includes enhanced soundproofing, energy-efficient European windows to reduce exterior noise, and a covered balcony with gas. Includes one secure garage space with EV capability, plus additional permitted parking nearby. Convenient access to the CTA Brown, Red, and Purple lines.

3035 N Sheffield Avenue Unit #2, Chicago
$1,355,000
9 Beds ⋅ 3 Baths ⋅ 12584580 MLS ⋅ CLOSED Status
Handsome red brick 3 flat building in the heart of Wrigleyville on extra wide 30' lot boasts 3 legal units plus unfinished basement. All three units have 3 bedrooms and one bath, hardwood floors, separate living and dining rooms, updated kitchens and baths, tall ceilings, bay windows, pantries or enclosed porch space. Blaine school district. Parking includes 2 car garage plus exterior space. New tear off roof and tuck pointing in 2016. New windows units 1 and 3 in 2016, unit 2 in 2023. Units 1 and 3 have central air. Newer water heaters (3), New HVAC unit 1 in 2022, unit 3 2016. Annual rental income 86,940. Common utilities approximately 1976 and insurance approximately 3550 annually. Basement ceiling height approximately 6'10. Leases end 5/31/2026, 6/30/2026, 7/31/2026. Please see seller representations in the FAQ in additional information tab.

3732 N Racine Avenue, Chicago
$1,050,000
6 Beds ⋅ 6 Baths ⋅ 12386821 MLS ⋅ CLOSED Status
Meticulously maintained long-time owner-occupied 3-flat in Lakeview. All units with separate utilities. Many updates to include a washer and dryer in each unit. Newer roof and mechanicals throughout the building. Central AC throughout. Large units with a living/ dining open concept. The first and second floors have 2 bedrooms with 1.5 baths. Third floor with vaulted ceilings and 2 bedrooms, 2 baths. Each unit has a good-sized deck to accommodate a table and grill. Charming brick patio in the back, along with a shed perfect for tools, bikes, snowblower, etc. 3 tandem parking spaces to fit 6 cars on the parking pad behind the building. First floor is owner-occupied. 2nd floor leased for $2,500 a month. Third floor leased at $3,145. South-facing building with tons of light in the units! Beautiful original banister in the front stairwell. Location is A+. Walk to Southport Corridor or restaurants on Sheffield. 5 minute walk to the brown line at Wellington or 9 minute walk to the Redline at Belmont. Quiet one-way residential street. MULTIPLE OFFERS received. Highest and Best due Monday 6/16 by noon.

1140 W Barry Avenue, Chicago
$695,000
2 Beds ⋅ 2 Baths ⋅ 12344341 MLS ⋅ CLOSED Status
Offer Deadline Sun 5/4 at 6pm! Quiet top floor retreat nestled among the treetops in West Lakeview 2 blocks from Southport Corridor. Extra-wide 2 bed, 2 bath penthouse in highly sought-after, all-brick, boutique elevator building. Open concept layout & very wide living room has space for home office and huge sectional couch with split bedroom floorplan - one on each side of living room. The two top floor spacious and sun-filled balconies, off each side of living room and each bedroom, provide views of Sears Tower and green treetops. Beautiful chef's kitchen features dark walnut stained 42" flat-panel cabinets, pantry, granite counters, glass subway tile backsplash, stainless steel appliances, and large island with glass pendants above. King-sized primary suite has a huge walk-in customized California closet and spa-like primary bath from a recent total gut renovation with new double vanity, marble counter, porcelain tile on floor and walls, larger frameless glass shower and separate vessel soaking tub. Second bedroom offers space for a queen bed and desk, with an organized closet and 2nd full bath with dark wood vanity, Toto toilet and modern 12x24" porcelain tile on walls and floor. You'll love the gracious foyer that fits entry table and bench & large organized pantry & coat closet, built-in speakers in living, dining, primary bedroom and bathroom. Updates include new living room windows, primary bathroom, hot water heater, dishwasher and washer/dryer. Ride the elevator up to the expansive (1200+ sq ft) common roof deck, furnished with grill and 4 different seating areas with fabulous skyline views. Excellent all brick elevator building with attached heated garage parking, 10-seat theater room, professional management, low assessments, an attentive and responsive HOA and robust reserves with no specials. Great West Lakeview location in top-ranked Blaine Elementary School District. 1 block to Starbucks, 2 blocks to Southport Corridor for shopping and dining, 3 blocks to Brown Line train. Don't miss it!

3844 N Ashland Avenue Unit #42, 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
$1,735,000
5 Beds ⋅ 5 Baths ⋅ 12323668 MLS ⋅ CLOSED Status
Discover this stunning FULL GUT RENOVATION of a classic Chicago brick 2-flat, now a luxurious single-family home on one of the best blocks in the vibrant West Lakeview neighborhood. This stunning 5-bedroom, 3.2-bath residence combines modern elegance with a welcoming charm. The spacious layout features an open-concept living and dining area that's perfect for entertaining. The chef's kitchen is truly a highlight, showcasing a sleek 48" Wolf range, Sub-Zero fridge, and a huge island with waterfall quartz counters-ideal for both cooking and gathering with friends. The adjoining family room, complete with a gas fireplace with custom tile surround and walnut mantle, offers a relaxing spot to unwind. The second floor features three bedrooms all on the same level, including a primary suite that feels like a true sanctuary featuring a spa bath with steam shower, dual sink vanity, separate tub and heated floors as well as a sitting room and huge walk-in closet. The second bedroom is large with great closet space, and the third bedroom has some of the most incredible windows with beautiful natural light. The second bathroom is perfection on the second level. Plus, a convenient side-by-side laundry room completes this level. The lower level is perfect for entertaining, featuring a spacious recreation area, a wet bar, powder room. Also on this level are two additional bedrooms connected by a gorgeous jack-and-jill bath. There's ample storage throughout, with the option for a second laundry room if desired. Outside, enjoy a large, lush yard and the rooftop deck over the 2-car garage. Nestled in the heart of West Lakeview, this home is situated in the highly sought-after Hamilton Elementary School district, and just steps from St. Andrew School. This block is super special and hosts multiple block parties during the summer and Halloween! Enjoy easy access to the Addison Brown Line, parks and playgrounds, charming shops and eateries along Southport Corridor and Lincoln Ave, Trader Joe's, and local favorites like Roscoe Village Pub. This home offers a perfect blend of convenience, community, and refined living!

3822 N Paulina Street, 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
$1,145,000
8 Beds ⋅ 4 Baths ⋅ 12222742 MLS ⋅ CLOSED Status
Completely updated two-flat within walking distance to Southport Corridor and in the coveted Blaine School District! Extra wide 31' x 75' lot. 1st floor is a 2,000 sq. ft. 5 bedroom 3 bathroom duplex down currently rented through May 2025. 2nd floor is a 1,300 sq. ft. 3 bedroom, 1 bathroom condo-quality owner's unit flooded with natural light. Occupy one unit while paying down your mortgage with the rental income from the other. An abundance of character and spacious floorplans are complimented by large windows and hardwood flooring throughout. Each unit has central air, heat and in-unit laundry. Enjoy your private backyard oasis, completed in 2024 and perfect for entertaining! Easy street parking with a private 2 car garage leased across the street. Walk to fine dining, boutiques, CTA brown line, gyms, grocers, theaters and everything else the Southport Corridor has to offer!

1604 W Waveland 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
$929,000
12054884 MLS ⋅ CLOSED Status
Ideal for redevelopment! This 25'X125", RS-3.5 zoned parcel is situated in desirable Lakeview right off Southport Corridor, and just .5 mile to Roscoe Village. Steps to Brown Line Stop, Whole Foods, Target, Restaurants, Shops, Low-Line Farmer's Market, Donahue (Margaret) Park. Presently the frame 2-flat on the lot is being used as income producing property. Units #1 & #2 + #3 (an attic apt) are M-T-M and units can be vacated by closing. Renovate existing structure or tear down and build new. No garage on rear of lot. Great possibilities for experienced developers. Please drive by.

1445 W Roscoe Street, Chicago
$700,000
3 Beds ⋅ 3 Baths ⋅ 12050744 MLS ⋅ CLOSED Status
FIRST SHOWINGS 11-1 SATURDAY 5/11, SUNDAY 12-2. Great Southport Corridor/Lakeview location. Dramatic 3 bedroom 3 bathroom duplex up meticulously maintained top 2 floors of brick and limestone 3 flat. Open concept floor plan with cathedral ceilings in living room, gas FP, New white cabinet cook's kitchen with 42" cabinets, abundant granite countertops, island and upgraded stainless steel appliances. This spectacular unit also features 2 primary suites, separate den/office with many built-ins, tons of storage, 2 outdoor decks and 2 car parking. A family-sized condo in Burley School District walkable to shopping, dining, entertainment and various transportation options. Move right in!

1535 W Oakdale Avenue Unit #3, Chicago
$875,000
6 Beds ⋅ 4 Baths ⋅ 12039266 MLS ⋅ CLOSED Status
We're back and improved! ATTENTION live-in owners and investors! Check out this turn-key 2-flat in desirable Lakeview, near SOUTHPORT CORRIDOR's dining and shopping + Brown Line. The DUPLEX-DOWN unit features hardwood floors on main floor, high ceilings, 3-beds, 2-baths and laundry. DUPLEX-UP is spacious and bright with hardwood floors on the main level, plus wood-burning fireplace, 3-beds, 2-baths + laundry. EXTRA WIDE LOT provides great entertainment space with fenced-in private side yard. NEW roof, NEW fence, NEWLY paved patio, 2-car garage. With a solid cap rate of over 6%, this property is a sound investment. Take advantage of the owner-occupied loan program with just 5% down. Now is your chance to own a piece of Lakeview.

1549 W Barry Avenue, Chicago
$720,000
2 Beds ⋅ 2 Baths ⋅ 11950548 MLS ⋅ CLOSED Status
Welcome to 2852 N Racine Ave #3, Chicago, IL. 60657-an extraordinary urban residence seamlessly bridging Lakeview and Lincoln Park. This stunning luxury penthouse offers a remarkable 5 private outdoor spaces, including a meticulously crafted rooftop oasis spanning the entire building, offering a combined total of 2611 sqft of indoor and outdoor spaces. Your low monthly HOA covers Water, Parking, Common Insurance, Exterior Maintenance, Lawn Care, Scavenger, and Snow Removal. This 2-bedroom, 2-bath residence boasts an additional lofted office/flex space on the upper level. Custom millwork, ceilings, wainscoting, and gleaming hardwood floors create an inviting atmosphere, complemented by a gas fireplace and built-in cabinetry in the capacious living room. The chef's kitchen features Viking and Bosch appliances, granite countertops, and custom cabinets-a culinary dream. Luxuriate in spa-like limestone bathrooms with a steam shower, whirlpool, radiant heated floor, and dual vanities. The thoughtful design extends to custom-built closets and modern conveniences like surround sound throughout entire home and a Nest thermostat system. Step onto the expansive main-level front deck for outdoor enjoyment. The primary bedroom boasts its own substantial deck, while another extended main-level private deck offers space for a lush garden or dog run. Yet, the true piece de resistance awaits upstairs-two expansive private roof decks (east and west), lavishly upgraded with a built-in grill, sink, refrigerator, ice maker, see-through gas fireplace, flat-screen TV, and speaker system. Glass wind shields, an extended roof with skylights, and custom lighting ensure year-round entertainment with stunning Chicago skyline views. Even the garage parking offers a remarkable bonus-it's pre-wired for your Tesla! All light fixtures were upgraded in 2018. New garage sensor from 2023. Hot water heater from 2019. Positioned at the crossroads of Lincoln Park and Lakeview, this residence is steps from premier shopping, dining, nightlife, and public transportation in a well-run, self-managed building. The seller might consider the option of leasing back the unit if the buyers currently have an existing lease and do not intend to relocate until later. Don't miss the opportunity to experience this extraordinary home-schedule your showing today.

2852 N Racine Avenue Unit #3, 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
$1,100,000
10 Beds ⋅ 4 Baths ⋅ 11966167 MLS ⋅ CLOSED Status
This is a versatile, turnkey 3-flat investment property located on the best block in South Lake View with $100K+ rental income. Recently renovated unit mix includes a duplex down (5/2), a 3 bed/1 bath simplex, and a 2 bed/1 penthouse. Summer leases, spacious floor plans, separate utilities, strong tenant mix, in-building laundry, beautiful hardwood built-ins, a half block from the brown/purple line, ample outdoor parking, and Lincoln Park High School. Property is a perfect fit for an owner/occupant, value-add investor, or just collect $100K+ in rent. A fantastic investment property on a wonderful block walkable to all that Lake View has to offer.

1029 W Wolfram Street, Chicago
Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

Lakeview, Chicago IL · Curated MLS Search

5-Flats in Lakeview, Chicago IL

An editorially curated view of every active 5-flats listing in Lakeview, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings

Lakeview, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

Next Steps in Lakeview, Chicago IL

Speak with an Agent

Call (312) 788-7079

Local Lakeview, Chicago IL expertise

Data Brief

Full Lakeview, Chicago IL Market Report

Pricing trends & absorption

Browse Everything

All Lakeview, Chicago IL Listings

Every active property

Direct Inquiry

Request a Callback

Reply from Chicago Real Estate Source
← Back to Lakeview, Chicago IL Homes for Sale