View All Lakeview Chicago IL Multi-Family Homes Listings

$1,499,000
6 Beds 4 Baths 12739752 MLS ACTIVE Status
Prime Wrigleyville/East Lakeview Investment Opportunity! This meticulously maintained and updated 3-unit building offers an exceptional opportunity for investors or owner-occupants looking to capitalize on strong rental demand in one of Chicago's most desirable neighborhoods. Situated on an oversized 35' x 125' lot and zoned RM-5, the property offers excellent current income with additional potential for future development-buyers are encouraged to explore the possibilities offered by the zoning. Each unit has been well cared for, with numerous updates throughout. The spacious garden unit has living, dining room, kitchen with newer appliances, renovated bathroom, one bedroom and a den. The first-floor unit has 2 bedrooms, separate living and dining room, kitchen with new stainless steel appliances(2024), unit painted (2024), hardwood floors throughout (refinished 2024), bathroom remodel(2021), and new A/C (2025). The 2nd floor owner's unit is a 3 bed, 2 bath, duplex up with hardwood floors throughout. The main level features a large living room and dining room with cathedral ceiling and sliding glass doors leading to front deck, an updated kitchen with a large island and stainless steel appliances along with one bedroom. The upper level provides a spacious primary bedroom with balcony and walk in closet, family room, third bedroom, updated bathroom with double sink, separate shower, jacuzzi tub and in unit laundry. Second floor unit has a new furnace (2025). The property boasts a large backyard and expansive side yard, providing a rare amount of outdoor space. Back deck on each level. Additional income from two-car brick garage and additional parking slab. Great location, walk to Wrigley field, Wrigleyville restaurants, bars, entertainment and Red Line, Brown Line and Purple Line trains.

3405 N Seminary Avenue, Chicago

$1,600,000
9 Beds 4 Baths 12723283 MLS CLOSED Status
Beautifully maintained and thoughtfully updated, this classic Chicago three-flat is located in the heart of Lakeview. Ideal for investors or owner-occupants, the property offers a great "house hacking" setup-live in the spacious owner's duplex-down while generating rental income from the two generously sized upper units. Throughout the building, vintage character is paired with modern improvements. Each unit features tall ceilings, oversized windows, hardwood floors, original woodwork, decorative fireplaces, and separate living and dining areas. Updated kitchens include stainless steel appliances, dishwashers, ample cabinetry, and modern finishes. Each residence also has its own HVAC system and in-unit washer and dryer, providing the conveniences today's renters expect. Spanning two levels, the owner's duplex-down offers generous living space and plenty of flexibility. The expansive kitchen features warm wood cabinetry, stone countertops, upgraded appliances, a large island, and abundant storage. Updated bathrooms, flexible office or workout space, multiple living areas, and direct access to the rear outdoor space make it an ideal owner's residence. A brand-new roof, private rear decks, a patio and courtyard area, and three off-street parking spaces add to the property's appeal. Impeccably cared for and updated throughout, this is a turnkey multifamily property near dining, shopping, nightlife, public transportation, and everything Lakeview has to offer. Move in, rent out, or add a strong asset to your investment portfolio.

2838 N Sheffield Street, Chicago

$1,425,000
5 Beds 4 Baths 12716023 MLS PENDING Status
Hot West Lakeview/ Roscoe Village neighborhoods this large 2 flat on a tree lined street perfect for investment / or live in one unit and get rental income from other unit. The top duplex up unit has 3 bedroom/2 bath with many updates - newly renovated chef's kitchen with new SS appliances and built-in breakfast banquette. Large cathedral ceilings with skylights and built-ins in the living room. Wood floors throughout. Loft space ideal for home office or entertainment. Large primary ensuite bathroom with freestanding soaking tub and separate dual shower heads remodeled in the last two years. Unit 1 has two bedrooms/ 1.5 baths and has been renovated in 2023 with an updated kitchen, bathroom with plenty of storage. Separate dining area, bonus room off kitchen great for home office. Great closet space and one bedroom with a connecting powder room. The basement is perfect for storage, common fitness, laundry or future duplex down option with tall ceilings. Fenced in yard with turf in rear with detached, 2 car garage Each unit has its own deck completely rebuilt in 2023. Great location! Steps to Paulina Brown line- walk to Restaurants, grocery, coffee, shops, night life and more. Walking distance to a Cubs game and Southport corridor with Hamilton Elementary school up the block. Don't miss this great investment opportunity in a wonderful area. Unit 1 first floor is currently Rented $3100 until 9/30/27.Proposed basement floorplan in additional information. Offers due Sunday 8/2 by 5pm.

3431 N Paulina Street, Chicago

$1,265,000
7 Beds 5 Baths 12705120 MLS CLOSED Status
Incredible Lakeview investment opportunity with RT-3.5 zoning, allowing for two-flats, townhouses, low-density apartment buildings, and single-family homes. Currently generating below market value $7,000/month in rental income with substantial upside through aesthetic renovations and rental increases, this property is being offered as a portfolio of three individual condo PINs, with the potential to convert to a single tax PIN. Constructed in 1994, the 4-story BRICK & BLOCK building features three units totaling 7 bedrooms and 4 bathrooms. Unit #3 is a spacious 3 bed/2 bath duplex-up with vaulted ceilings and streaming natural light - 1,862sqft, Unit #2 is a 2 bed/1 bath - 919sqft, and Unit #1 is a 2 bed/1 bath garden-level unit - 907sqft. ALL units feature private rear balconies and are individually metered and include in-unit washer and dryer, central HVAC, and individual water heaters. The property also offers a private fenced backyard and three rear parking spaces on a parking pad. Good long-term tenants who pay on time: Unit #3 rents for $3,300/month through 5/31/27, Unit #2 rents for $1,900/month through 4/30/27, and Unit #1 rents for $1,800/month through 8/31/26. Walk to Jewel Osco, Diversey Train and Buses. Rarely does a cash-flowing, value-add asset with flexible zoning, multiple exit strategies, and long-term redevelopment potential become available in one of Chicago's most sought-after neighborhoods!

1507 W George Street, Chicago

$1,212,235
5 Beds 4 Baths 12688705 MLS CLOSED Status
This 3-story multi-unit building features a fantastic 2BR, 2BTH Duplex Up apartment with a modern open floor plan, living room fireplace, skylights, spacious dining area, large kitchen with ample counter space, granite counters, new stainless appliances and new flooring both in 2025, in-unit laundry room and two private outdoor spaces! Perfect for the live-in owner or as a high-end rental. The remainder of the building is comprised of a 2BR, 1BTH apartment with updated bathroom, in-unit laundry, private back deck on the first floor and a garden level 1BR plus den apartment (den could easily be converted into a 2nd bedroom) with newer flooring, recently remodeled kitchen and bath and its own front and back entrances. This building has been incredibly well cared for by its long-term, live-in owner with a long list of improvements including: a new 2-car garage (2024), a new roof (2022), new garden apartment furnace (2023), Hardee Board siding on the front of building (2020) and new windows in 2020. Each apartment has their own HVAC systems with individual controls. This property represents a tremendous opportunity with so much potential for high rental income, all in an unbeatable and very easy-to-rent Lakeview location close to restaurants, coffee houses, grocery stores, shopping, nightlife and public transportation, including the Brown Line Wellington "L" Stop which is just a 7-minute walk away. Zoning Certificate for this property has been ordered but isn't back yet. It should be assumed that this is a legal 2-unit building with a non-confirming garden apartment unless the certification shows differently.

3013 N Racine Avenue, Chicago

$1,685,000
9 Beds 6 Baths 12632607 MLS CLOSED Status
Situated on a premier, tree-lined street in the highly coveted Blaine School District, this exceptionally rare Lakeview multi-family investment asset underwent a comprehensive, high-end rehabilitation in 2025, generating a powerhouse monthly rental income of $11,200 ($134,400 gross annually) anchored by a secure duplex lease extending into March 2028. Presenting an unrivaled turn-key opportunity for either a yield-focused portfolio investor or a live-in owner looking to substantially subsidize their mortgage, the impressive 4,264-square-foot footprint features three renovated two-bedroom residences and an owner-caliber three-bedroom, two-and-a-half-bath penthouse duplex up. The stunning, sun-drenched penthouse showcases soaring cathedral and beamed ceilings illuminated by bright skylights, a gracious living room with architectural bay windows and a gas fireplace, and a professional-grade gourmet kitchen boasting rich granite countertops, a massive prep island, and a premier Viking refrigerator alongside high-end stainless steel appliances. This crown jewel unit is completed by an expansive private roof deck perfect for entertaining, second-floor in-unit laundry, and a tranquil primary suite featuring a spa-like master bathroom with a double-bowl vanity, separate soaking tub, and a custom shower. Complementing the duplex are the three turn-key two-bedroom residences showing high-value finishes such as updated kitchens with stainless steel appliances, new individual thermostats, and pristine hardwood flooring, with the rear unit featuring a large, versatile three-season sunroom. Mechanical and structural integrity is built directly into this passive income producer, highlighted by comprehensively updated electrical wiring, an optimized heating system with freshly insulated lines, and fully flushed radiators for effortless seasonal climate control. Finished with a dry, spacious basement providing dedicated resident storage lockers, new common laundry, and a detached two-car garage with a newly replaced door, this magnificent building sits just steps from the boutique shopping and dining of the Southport Corridor, public transit, and the vibrant local energy of Wrigleyville.

3722 N Bosworth Avenue, Chicago

$1,400,000
9 Beds 4 Baths 12627345 MLS CLOSED Status
Stunning Three-Unit Investment Opportunity in the Heart of Roscoe Village. Experience the perfect blend of vintage character and modern reliability with this solidly built, professionally managed three-unit building. Situated in the highly sought-after Roscoe Village neighborhood, this property offers a rare "turn-key" opportunity for savvy investors or owner-occupants looking for a high-yield primary residence. The building features two spacious simplex units and one expansive top-floor duplex-up. Each floor is defined by a sense of scale and craftsmanship. Architectural Grandeur: Impressive very high ceilings create an airy, loft-like atmosphere throughout the building. Premium Finishes: Gleaming hardwood flooring runs through the living spaces, complementing the sturdy, traditional construction. Modern Conveniences: Every unit is equipped with NEW in-unit laundry, and most of the kitchen appliances and HVAC systems are new. Recent Capital Improvements! Rest easy knowing the heavy lifting has been done. Recent updates include brand new roof (2022) for long-term peace of mind. Complete rebuild of rear decks, featuring new wood-constructed outdoor decks and integrated fire escapes. Two-car garage parking providing essential storage and convenience. Investment & Owner-Occupant Potential. Currently generating 9,000/month in total rent, this building is a proven performer. With leases expiring in May 2026, July 2026, and March 2027, you have the flexibility to: House Hack - Move into one of the stunning units as an owner-occupant while the other two units cover a portion of your mortgage. Or, Passive Income: Maintain the current professional management and enjoy a stable, high-performing asset. Don't miss out on this impeccably maintained piece of Chicago real estate!

3115 N Oakley Avenue, Chicago

$955,000
6 Beds 2 Baths 12617239 MLS CLOSED Status
Exceptional two-flat in Southport Corridor that exudes pride of ownership. This Chicago classic sits on an oversized lot and features two large 3 bedroom / 1 bath units with central air and 2 car garage parking. Located within walking distance of the best of Southport Corridor and Roscoe Village, these two units offer the ability to hold the property as a rental or owner-occupy. You'll enter this all-brick building through a side entrance with a vestibule bedecked with a classic mosaic tiling floor. The first floor unit offers beautiful original built-ins surrounding a wood fireplace, wood flooring throughout and a front sun porch. This unit also features 3 large bedrooms, one offering flexibility as a den / bedroom / office, complete with ample closet space and a bath. A very large dining room is capped off by a thoughtful kitchen with a large walk in pantry and built in eating area. The top floor offers a similar floor plan with the same built-ins and wood flooring throughout. However, this former owner's unit comes with in-unit laundry, 2 closets in the primary, an air tub in the bath as well as a heated towel rack. Additionally, the top floor unit's kitchen has been opened up to create a bright, light-filled kitchen and dining space. A walk in pantry off the kitchen is where the in-unit stackable laundry resides. An unfinished basement with laundry for the first floor unit offers extensive storage and the opportunity to duplex down the first floor unit in the future. Capping off this home is a large backyard space with grass and garden beds. Both units also come with garage parking in the detached garage off of the backyard. Ideally located in the Southport Corridor, this home offers easy access to public transit, the bars and restaurants in the area as well as the best of city living.

1539 W Addison Street, Chicago

$1,230,000
8 Beds 3 Baths 12595065 MLS CLOSED Status
*MULTIPLE OFFERS RECEIVED *A RARE chance to own a timeless piece of Chicago history in one of the city's most sought-after neighborhoods. This striking 1897 greystone 3-flat is perfectly positioned on a quiet, tree-lined block just a few minutes from the buzz of the SOUTHPORT CORRIDOR and all the dining, nightlife, and energy along Belmont & Clark. ***Fully leased and meticulously cared for by the same owner for the past 30 YEARS, this building presents FLEXIBLE OPPORTUNITIES for a variety of buyers. Owner-occupants can live in one unit while offsetting their mortgage with rental income from the others. End-users and rehabbers can bring their design vision to update units and maximize rents. Developers will appreciate the solid 1897 construction and potential for condo conversion or a single-family home transformation. Or, turn this timeless beauty into a multi-generational home for decades to come. ***The classic greystone charm is complemented by TIMELESS architectural DETAILS, generous 10ft ceiling height and original built-ins, along with modern peace of mind including a BRAND NEW ROOF (2025), well-maintained exterior, and refreshed entry & common hallways. ***The property also features a 2-car GARAGE (each leased for $175/month), back yard, basement laundry room and additional common storage space. ***This A+ location offers easy access to public transportation, grocery stores, Southport shops, walk to Wrigley, plus an endless array of bars and restaurants, along with convenient access to the lakefront. With immediate rental income and STRONG UPSIDE potential, this VINTAGE GEM delivers the perfect combination of history, location, and flexibility. Truly a rare opportunity in one of Chicago's most beloved neighborhoods. (Please see additional documents tab for lease info, apartment/parking rent roll & operating expenses. Note the property is being sold AS-IS)

1322 W Barry Avenue, 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

Multi-Family Homes in Lakeview, Chicago IL

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

Browse Active Listings