View All Lakeview Chicago IL 3-Flats Listings

10 Beds ⋅ 5 Baths ⋅ 12728198 MLS ⋅ CONTINGENT Status

Situated on a premier, tree-lined street in the highly coveted Blaine School District. Exceptionally rare Lakeview multi-family investment asset presenting an unrivaled turn-key opportunity for either a yield-focused portfolio investor or a live-in owner looking to substantially subsidize their mortgage. Brick 2 flat with a non-conforming basement apartment and a 2-unit coach house in the rear. All kitchens and baths have been updated. All separate gas forced air furnaces. Currently generating $125,580. gross income. With expenses at $38607. that's a net cash flow of $86973. or about a 5.7% cap rate. Rents as follows: Front building 1st floor $1910 6/27, 2nd floor $3000 Vac. Garden $1450. 6/27, Coach house 1st $1705. 6/27, Coach house 2 3 BR 2 bath $2850. 7/27. Multi million dollar homes up and down the block in this highly sought after location.

3709 N Bosworth Avenue, 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

$960,000

5 Beds ⋅ 2 Baths ⋅ 12711898 MLS ⋅ CLOSED Status

Handsome Lakeview Brick Chicago two flat awaiting your rehab and/or single-family home conversion ideas. Current owner has maintained the home and has installed a completely new roof (2026), new water heater (2024), Furnace and CAC (2016). Lot is 25'X125' and has RS-3 Zoning. Full basement is partially finished and is dry with center beam height of 6'4". Windows were done in 2000 and are in good shape. Kitchens and baths are dated. Location, Location, Location. Perfect distance from the train, Wrigley Field, Lake Michigan, and all the restaurants, schools, entertainment and shopping.

3714 N Hermitage Avenue, Chicago

$1,249,900

8 Beds ⋅ 3 Baths ⋅ 12697754 MLS ⋅ CLOSED Status

3141 N Oakley - gut-renovated 3-flat in the heart of Roscoe A rare opportunity to own a fully updated multifamily asset in one of Chicago's most consistently in-demand neighborhoods, just steps from Hamlin Park. This handsome brick 3-flat features two 3BD/1BA units and one 2BD/1BA unit - every unit gut-renovated top to bottom with new kitchens, quartz countertops, modern baths, and central A/C. Nothing to do but collect rent. The full unfinished basement offers clear value-add potential (storage, laundry expansion, or future buildout), and the brick 2-car garage is a premium amenity rarely found in the area. Strong in-place rental income with long-term upside as Roscoe Village continues to appreciate. Turnkey condition, proven rents, and a compelling basis - ideal for investors and house-hackers alike.

3141 N Oakley Avenue, Chicago

$1,340,000

5 Beds ⋅ 4 Baths ⋅ 12674025 MLS ⋅ CLOSED Status

Exceptional opportunity in the heart of the Southport Corridor and highly sought-after Blaine Elementary School District. This well-maintained 2-flat features a spacious owner's duplex-up with 3 bedrooms and 3 baths plus a separate 2 bed, 1 bath rental unit for additional income. The owner's residence offers tall ceilings, hardwood floors, expansive living and dining spaces, and an updated kitchen with white cabinetry, quartz countertops, and stainless steel appliances. The rear of the home opens to a sunny west-facing deck and flexible family room or dining area. A dramatic open staircase leads to the bedroom level featuring newer carpeting, a generous primary suite with attached bath and ample closet space, two additional bedrooms, and a full hallway bath. Central heat and air conditioning throughout. Additional features include a backyard, 2-car garage, unfinished basement with laundry for the rental unit, and an unbeatable location near restaurants, shopping, parks, transportation, and all that Lakeview has to offer.

3714 N Bosworth Avenue, Chicago

$1,346,475

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

$1,575,000

8 Beds ⋅ 3 Baths ⋅ 12659463 MLS ⋅ CLOSED Status

Welcome to 1341 W. Eddy, a stunning all brick 3-flat in the heart of Wrigleyville, ideally located just steps from the Brown Line and all of the shops, restaurants, and nightlife along the vibrant Southport Corridor. This turnkey investment property features three charming and sun-filled units: Unit 1 offers 2 bedrooms and 1 bathroom, while Units 2 and 3 each feature 3 bedrooms and 1 bathroom. All units boast great natural light, spacious layouts, and access to large outdoor decks. Recent improvements include a new roof installed in 2022 with transferable warranties, updated windows, and new copper piping installed on the first floor. Additional features include basement laundry and a 2-car garage that was rebuilt within the last five years. The garage is not currently leased to tenants and provides additional income potential through rentals during Cubs games and concerts. All units are tenant-occupied with leases in place through 2027, making this a true armchair investment in an unbeatable A+ location with consistent rental demand. Explore the property in 3D by clicking the virtual tour button and walk through every detail from the comfort of your home.

1341 W Eddy Street, Chicago

$1,610,000

7 Beds ⋅ 3 Baths ⋅ 12627838 MLS ⋅ CLOSED Status

GREAT OPPORTUNITY FOR THE ADD-VALUE INVESTOR, LIVE-IN OWNER, OR SINGLE-FAMILY CONVERSION. RARE EXTRA-WIDE 37.5 x 124 LOT (ZONED R3). CERTIFIED / LEGAL 3-FLAT. This professionally managed building offers strong potential throughout including duplex-up or duplex-down configurations or expansion from the rear to create a larger single-family home making this an exceptional redevelopment opportunity on an oversized lot. Significant value-add potential includes updates to increase rental income and overall property value. Two-car garage with possible room to add a third parking space provides additional flexibility for future use. Central air and heat on the first and second floors along with high ceilings create a bright and comfortable living experience. Buyers should verify local ordinances regarding ADU possibilities and development options. The first floor will be vacant June 1st. Tenant 2 has been in place since 2020 and Tenant 3 since 2023 both long-term occupants. Lincoln Park High School. Prime Lakeview location walk to the Red Line and Illinois Masonic Medical Center and just moments from everything the neighborhood has to offer. Please note this property is being conveyed "as-is."

1033 W Wellington Avenue, 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

$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

$1,200,000

6 Beds ⋅ 4 Baths ⋅ 12612088 MLS ⋅ CLOSED Status

HOT Lakeview 2-flat situated on a 25x125 lot! Both units are duplexes featuring 3 bedrooms, 2 baths, central HVAC, wood-burning fireplaces, and updated kitchens with large islands. Spacious yard and 2-car garage. Numerous upgrades throughout, including in-unit washer/dryers in both units, new furnace, new A/C, and more-making this a strong investment opportunity. Current rents: Unit 1 at $2,875/month and Unit 2 at $4,175/month, with additional potential garage income. Property offers excellent cash flow. Do not disturb tenants. Explore the property in 3D-click the virtual tour link to walk through every detail.

1532 W Oakdale Avenue, Chicago

$1,337,000

8 Beds ⋅ 5 Baths ⋅ 12610788 MLS ⋅ CLOSED Status

Greystone rehabbed 3 flat on oversized corner lot in prime Lakeview location. All units rented. Two units 3 bedroom 2 baths. Hardwood floors throughout, formal dining rooms, eat-in kitchens, fireplaces, GFA heat and central AC, large rear decks and yard. All units have separate entries. tenants pay all utilities. Beautiful units, turn key property, impeccably maintained. Fabulous location. Walk to restaurants, shops, transportation.

1658 W Nelson Street, 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

$1,425,000

4 Beds ⋅ 4 Baths ⋅ 12595235 MLS ⋅ CLOSED Status

Great investment opportunity to own this money making 3-flat on a corner lot in highly desired Lakeview! Gorgeous 1st floor 2 bed/ 2 bath + den, duplex-down has lovely owners finishes with, crown molding, beautiful hardwood floors, stylish exposed brick with tons of natural light throughout, custom chef's kitchen with 42" white shaker cabinets, stainless steel appliances, mother-of-pearl backsplash, under-mount LED lighting and granite countertops with an expansive breakfast bar and nook - perfect for entertaining! The Lower-Level features high ceilings, thoughtfully designed primary suite with tons of natural light, custom windows and updated en-suite bathroom and walk-in closet. Unit 2 (1 bed/ 1 bath + den) and Unit 3 (1 bed/ 1 bath) both have great long-term tenants and updated and show very well. Major exterior renovation 2016 (new cedar siding and stonework, full landscape and hardscape, 2 car garage). Building offers additional storage, and coin laundry in the lower level (whirlpool commercial grade) plus a lovely common landscaped yard. This property is seconds from coffee shops, restaurants, grocery stores, public transit, and Southport Corridor! Unit 1- $4000 including 1 garage space. Unit 2- $2300. Unit 3- $1925. Extra Garage available for $150 per month. Coin Laundry brings in $100 per month. TOTAL RENT ROLL is $8500 per month. Broker Owned.

3034 N Greenview Avenue, Chicago

$1,299,000

4 Beds ⋅ 2 Baths ⋅ 12589110 MLS ⋅ CONTINGENT Status

Well-maintained brick 2-flat with full basement on a 3,750 sq ft lot. The first-floor unit features an updated 3 bed / 1 bath with modern finishes and great natural light. The second-floor unit offers a 2 bed / 1 bath that is older but well maintained. Roof replaced in 2018, with updated electric and plumbing (dates unknown). Full basement with high ceilings, partially finished for storage with potential to expand into additional living space. Excellent opportunity for owner-occupants or investors in a prime Lakeview location.

1325 W Cornelia Avenue, Chicago

$1,425,000

7 Beds ⋅ 4 Baths ⋅ 12583646 MLS ⋅ CLOSED Status

All Brick 2 flat on oversized 30 x 100 lot. Gut rehab in 2005-2006. Plumbing, electrical, sewer, roof, kitchens, baths, flooring, windows, etc. Central heat and AC in each unit with separate meters - tenants pay gas and electric. Washer dryer in each unit. $8200 per month gross rent with very low expense load. Great for investor or potential owner occupant. Both units have a legitimate primary bedroom with en suite bath. Extra width allows for larger than average bedrooms and additional living space. 3 parking spaces in rear on concrete slab.

1330 W Roscoe Street, 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

$1,465,000

8 Beds ⋅ 6 Baths ⋅ 12461474 MLS ⋅ CLOSED Status

Discover an exceptional investment opportunity or the perfect single family conversion in this stately, rehabbed Greystone located in Chicago's sought after Wrigleyville/Lakeview community. Situated on the historic Newport Avenue District, a landmark block renowned for its beautiful, intact stone fronted three flats. This building offers a classic Chicago experience with modern amenities. The building is comprised of three well maintained units. The top floor, duplex up, owner's unit, offers the scale and comfort of a single family home. Spanning the second and third floors, it features an open concept main level with a chef's kitchen, 42" cabinets, stone countertops and hardwood floors a private rear decks and a spacious bedroom and full bath. The upper level features an open style primary bedroom with a walk in closet, a large seating area and fireplace. The primary bath features double vessel sinks, a whirlpool tub and a separate steam shower. This level includes the spacious third bedroom, a full bath and it's own private rear deck. The true highlight is the rare, private 27'x22' rooftop deck, perfect for entertaining with stunning city skyline views. The first floor unit is a bright and spacious 3-bedroom, 2-bath with soaring windows, tall ceilings, and a large open kitchen. This unit has it's own private rear deck and direct access to the expansive 20'x19' deck above the garage. The garden unit, a bright 2-bedroom, 1-bath, offers direct access to the generous brick paved backyard. This property has been cared for by the live in owner for 30 years, with significant updates including plumbing and electrical, tuck-pointing (2016), a new roof (2015), and premium windows (2020). Parking for three cars adds significant value. Currently configured as a high income three flat, the building generates a total annual income of $117,600 with a net operating income of $90,822, representing a consistent 6 percent CAP rate with room for growth. This is a remarkable opportunity for a live in owner to generate a large income stream while building equity, a long term investor seeking a strong return, or a developer looking to convert it into a magnificent single family home. Located in the desirable Nettlehorst Elementary School District, this property is just steps from Wrigley Field, shopping, dining, and a short walk to the "L" train and Lake Michigan. Don't miss this chance to own a piece of classic Chicago in an unbeatable location.

902 W Newport Avenue, Chicago

$1,425,000

7 Beds ⋅ 4 Baths ⋅ 12477908 MLS ⋅ CLOSED Status

Exceptional Lakeview/Southport 3-Flat. Located in the heart of Lakeview's desirable Southport Corridor, this all-brick 3-unit building offers a rare investment opportunity in one of Chicago's most vibrant and walkable neighborhoods. Perfect for investors and potential owner-occupants, the property combines timeless vintage charm with thoughtful modern updates. The building features two spacious 2-bedroom/1 Bath units, and a 3-bedroom, 2-bath duplex-down-each with rear decks, in-unit laundry, and individual HVAC systems (GFA/CA). Vintage details throughout include hardwood floors, crown molding, and original millwork, complemented by ongoing updates over the years. Kitchens have been renovated with granite countertops and newer appliances. All bedrooms are generously sized, and the front dens in the upper units make ideal office or workout spaces. The duplex unit includes a large lower-level family room and third bedroom, full bath, walk-in closet, and side-by-side washer/dryer. Just steps from top-rated Blaine Elementary, boutique shopping, parks, restaurants, and public transit, this property offers unmatched location, flexibility, and long-term value. (Please note pictures are from previous sale.)

3760 N Wayne Avenue, Chicago

$1,360,000

9 Beds ⋅ 3 Baths ⋅ 12422590 MLS ⋅ CLOSED Status

Built in 1893, this property has been in the same family since 1967. This historic, handsome and well-maintained three-unit property is not only a rare find, but also a must see. A classic brick and limestone three-flat that offers a unique blend of vintage charm and updates in one of Chicago's most desirable neighborhoods. Each of the three units features 2-3 bedrooms, one full bath, a light-filled living room, formal dining room, and a sunny kitchen, making them ideal for both tenants and owner-occupants alike. Original architectural details-such as original built-ins, tall ceilings, and hardwood floors add timeless character throughout. The property includes a newer 2.5-car garage, a large rear yard perfect for entertaining or gardening, and is located on a tree-lined, residential street just steps from parks, shopping, dining, and public transportation. With excellent income potential, this is a rare chance to own a solid investment property in an A+ location-perfect for live-in owners, investors, or those looking to expand their portfolio in a high-demand rental market. Don't miss this opportunity to own a piece of Chicago history with upside potential! Property is vacant and being sold as-is.

1415 W George 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

$1,175,000

6 Beds ⋅ 4 Baths ⋅ 12397937 MLS ⋅ CLOSED Status

Exceptional Legal 3-Flat in the Heart of Lakeview. Proudly maintained by long-term local owners for 27 years, this exceptional property offers a rare opportunity to benefit from decades of care and attention. Ideally located within walking distance of Trader Joe's and the Irving Park Brown Line, it's perfectly positioned to meet the lifestyle needs of today's renters. Each unit features real hardwood floors, individual HVAC systems, and separate hot water heaters for added convenience and efficiency. Unit #1, a charming 2-bedroom with an updated bathroom, den/office space, and a spacious living room. Unit #2 (Owner's Unit) offers the potential to expand into a duplex-up, creating additional living space and value. A large unfinished basement provides ample storage and includes a shared laundry area currently used by Units #1 and #2. Between the front building and the coach house, enjoy a beautifully maintained garden, patio, and small deck - perfect for summer evenings.The coach house was fully renovated in 2015. This 2-bedroom, 2-bathroom private residence includes an all-season porch, office nook, private basement storage, and a deck. High-end finishes throughout include: red oak hardwood floors white quartz countertops in the kitchen and bathroom, stylish tile backsplash, kohler bathroom fixtures and a soaking tub and walk-in shower. The coach house also features a new furnance, along with high-end GE and Fisher & Paykel stainless steel appliances. A front-loading, double-stack Frigidaire washer and dryer complete the home.

3818 N Hermitage 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

$1,111,000

6 Beds ⋅ 3 Baths ⋅ 12389603 MLS ⋅ CLOSED Status

Charming brick 3-flat on a quiet, tree-lined street in the heart of Lakeview. This legal multi-unit offers excellent flexibility-two units are tenant-occupied with stable rents, while the top-floor unit is vacant and freshly updated, making it ideal for an owner-occupant or new lease opportunity. All three units share the same spacious 2 bed, 1 bath layout, featuring hardwood floors, separate living / dining rooms, and private rear decks. Unit 3 recent updates include refinished floors, a full repaint, and newly installed central HVAC. Each floor has high ceilings and abundant natural light. Common amenities include shared laundry in the basement, tenant storage, a large backyard, and a 2-car garage. Utilities are separately metered. The sizable unfinished basement offers potential for a garden unit conversion or duplex-down expansion. Located near public transit, Wrigley Field, and a vibrant mix of dining and nightlife, this is a rare opportunity to invest in or live within one of Chicago's most desirable neighborhoods.

3746 N Hermitage Avenue, Chicago

$1,150,000

5 Beds ⋅ 5 Baths ⋅ 12365128 MLS ⋅ CLOSED Status

Set on an extra-wide 37-foot lot in Lakeview's coveted Newport Avenue Historic District, 938 W Newport is a rare and architecturally significant Greystone offering classic Chicago charm, preserved character, and strong rental income with ideal owner-occupant potential. This stately 3-flat features original millwork, pocket doors, large bay windows, and sun-filled upper units with 10-foot ceilings. The garden-level unit is a spacious 1 bed, 1 bath with additional storage in the entry foyer and a separate storage closet. The main-level unit includes 2 bedrooms, 2 full baths, 2 fireplaces a bay-front living room, a large formal dining room, and a bright rear sunroom ideal as an office or flex space. The top-floor unit mirrors the main-level layout and was previously configured as a 3-bedroom. It now functions as a 2 bedroom, 2 bath plus den with a closet, and is vacant and move-in ready with refinished hardwood floors, new carpet, and fresh paint. A three-car garage plus a side parking pad provide four off-street spaces. The exterior pad has been successfully rented during Cubs home games for extra income. Tenants share access to the basement laundry and storage. Just steps from Wrigley Field, the Red Line, Whole Foods, the lakefront, neighborhood dining and shopping, this is a rare opportunity to own a piece of Chicago history with flexible use, timeless curb appeal, and lasting value.

938 W Newport Avenue, Chicago

$950,000

6 Beds ⋅ 4 Baths ⋅ 12356736 MLS ⋅ CLOSED Status

Incredible opportunity for a savvy buyer. This well maintained 3-flat can be a turnkey investment. Or an owner occupant can have most of their monthly expenses covered by tenants. Current monthly income of $6,300/month and a 6% cap rate. The top floor duplex up features three bedrooms, 2 full bathrooms . The large eat-in kitchen leads out to a back deck perfect for grilling and entertaining. The second level has TONS of extra storage and a bonus office/work space. This large unit lives like a single family home. ($2,650/month - Unit 2 improvements: AC 2022, furnace 2023, water heater 2021). First floor unit is a 2 bed,1 bath with a large eat-in kitchen and a back deck. ($2,100/month - Unit 1 improvements: AC 2022, furnace 2018, fridge 2020, bathroom renovated 2019). Garden unit is a 1 bed, 1 bath. ($1,550/month - renovated bathroom 2018). TENANTS PAY ELECTRIC/GAS. The owner only pays for water, trash and insurance. Common laundry in the basement. 2 car garage. Owners have taken excellent care of the property and IMPROVEMENTS INCLUDE new siding 2017, new electric panels 2019, new front windows 2021, new washer/dryer 2022, new water pump 2023, new fence & landscaping 2025. The unit is currently fully rented. Units G & 2 rented through May 2026. Unit 1 will be vacant as of June 1 2025 and could be an owner occupant or easily rented at an INCREASED RATE from its current $2100 month (estimated new rental rate would be $2300-$2400). LOCATION CANNOT BE BEAT. Just steps from Whole Foods, Target, Brown Line L, and all the shops and restaurants of Lakeview.

1535 W Barry Avenue, Chicago

$1,500,000

9 Beds ⋅ 6 Baths ⋅ 12343264 MLS ⋅ CLOSED Status

Beautifully maintained Greystone 3-flat in a prime Lakeview location. The first-floor unit features 3 bedrooms and 2 full bathrooms. Excellent opportunity to duplex down for added space and value. Second and third floor units offer spacious layouts consisting of 3 bedrooms plus a den, 2 full baths, and updated kitchens. The third-floor unit includes in-unit laundry; first and second floors enjoy free shared laundry in the basement. Each unit boasts individual central HVAC, expansive open-concept living and dining areas, and hardwood floors throughout. Three exterior parking spaces located behind the building. A strong income-producing property in a highly desirable rental area-easy to lease and consistently in demand. Currently at a 6.36 CAP Rate! Schedule your viewing today!

822 W Newport Avenue, Chicago

$910,000

4 Beds ⋅ 2 Baths ⋅ 12342736 MLS ⋅ CLOSED Status

Attention Builders, Developers, and Visionaries! An incredible opportunity awaits in the Red-Hot Lakeview neighborhood! 1442 W Fletcher is fresh on the market and zoned RS-3 for both Single-Family and Multi-Family use. Currently a 2-flat, this property offers endless potential for redevelopment, renovation, or conversion. Being sold AS-IS. Don't miss out on this rare chance to invest in one of Chicago's most sought-after communities! Lot size is approx. 24' x 125' - Official Survey can be located in documents. 1st Floor Tenant lease expires April 30th, 2025 - 2nd Floor is Vacant.

1442 W Fletcher 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

$900,000

7 Beds ⋅ 4 Baths ⋅ 12296367 MLS ⋅ CLOSED Status

Looking for a prime investment property in West Lakeview? This 2 Flat is nestled in a fantastic location. Steps to Trader Joe's and less than 1/2 mile to Jewel, Southport Grocer + 3 train stops. Short walk to loads of restaraunts/bars/shops & Southport Corridor. The property features two spacious duplex units: Duplex up + duplex down - 3 bedrooms/2 bathrooms each. Generous living and dining areas, 2-car garage, rear deck for each unit, and garage roof deck. Terrific rental opportunity. Full rental property or live in the duplex up while earning rental income.

3757 N Hermitage Avenue, 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

$1,145,000

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

$985,000

5 Beds ⋅ 2 Baths ⋅ 12218262 MLS ⋅ CLOSED Status

This amazing Greystone 2-flat, located on an EXTRA-WIDE 30 x 125 lot, includes a newer 2-car garage and sits on one of the most sought-after streets in Wrigleyville, in the heart of the Southport Corridor. Zoned R3.5, this meticulously maintained property showcases refinished hardwood floors, charming vintage details, and thoughtful updates throughout. The first-floor unit features a spacious 2-bedroom, 1-bathroom layout with a living room, separate formal dining room, full bath, kitchen with a built-in butler pantry, and an in-unit washer and dryer. The second-floor unit offers a 3-bedroom, 1-bathroom floor plan with a large living room, a formal dining room, a kitchen, and an in-unit washer and dryer. Additional highlights include central HVAC, a rear deck, a backyard, and a 2-car garage. Recent improvements include new washers and dryers in both units, tuck-pointing of the building facade in 2023, and the installation of clean-out access. The unfinished garden unit offers 1 bedroom and is plumbed for a kitchen and bath, providing potential for additional space. This easy-to-rent property is conveniently located near CTA Red, Brown, and Purple Lines, multiple bus routes, Lake Shore Drive, Wrigley Field, Belmont Harbor, Whole Foods, and the incredible shops, restaurants, and recreational activities that Wrigleyville and the Southport Corridor are known for. Don't miss this exceptional opportunity!

1243 W Newport 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

$1,205,000

9 Beds ⋅ 6 Baths ⋅ 12148117 MLS ⋅ CLOSED Status

First time on the market! Fantastic opportunity to own a well-cared-for 3-flat w/3 car garage in the center of Wrigleyville! This prime property sits on a serene tree-lined one-way street near transportation, shopping, grocery store, Lake Michigan, and Wrigley. The top floor unit was rehabbed in 2018 and features central air, front-loading in-unit washer & dryer, and more. The first and second floors were updated in approximately 2008-09 and still run on radiator heat, no central air, common laundry in the basement, and a newer boiler. Storage lockers in the basement, and a gated shared backyard.

3653 N Magnolia 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

$735,000

7 Beds ⋅ 3 Baths ⋅ 12099978 MLS ⋅ CLOSED Status

Welcome to this exceptional legal 3-flat nestled in the heart of Roscoe Village, presenting a prime investment opportunity for savvy buyers. Boasting a sought-after location, this property is an ideal addition to any portfolio. The garden unit offers comfortable living with 2 bedrooms and 1 bathroom, complemented by the convenience of central air conditioning. This cozy space provides an inviting atmosphere for residents to relax and unwind. Step into the first-floor unit, meticulously renovated in 2024 to offer contemporary elegance. Featuring 2 bedrooms and 1 bathroom, this unit showcases modern finishes and amenities, including central air conditioning, providing a stylish and comfortable living environment. Ascend to the second floor to discover a spacious unit offering 3 bedrooms and 1 bathroom. With ample natural light and generous living spaces, this unit presents an ideal setting for families or professionals seeking room to grow. Outside, a private back patio beckons for outdoor gatherings and al fresco dining, providing a serene escape from city life. A coveted amenity, the 2-car garage ensures convenient parking for residents, adding to the property's allure. Don't miss out on this rare opportunity to own a legal 3-flat in Roscoe Village, offering a blend of comfort, convenience, and investment potential.

2253 W Belmont Avenue, Chicago

$885,000

5 Beds ⋅ 3 Baths ⋅ 12051370 MLS ⋅ CLOSED Status

Southport Corridor- This classic Chicago 2-flat sits on an extra-wide lot and features a 3BR, 2BTH duplex down apartment as well as a 2nd floor 2BR, 1BTH apartment. Sitting in a prime Lakeview location close to absolutely everything, including world class shopping, restaurants and bars, the Brown Line Southport Corridor "L" Stop and a short walk to Wrigley Field, the location couldn't be better. This building has so much charm, very high ceilings and tons of custom built-ins, with gorgeous original dining room hutch on 2nd floor and fireplaces in both apartments. Recent building improvements include: New AC condenser, new dishwasher, fridge and coin-op washer as well as new backyard deck. Property has 3-car parking pad and is zoned RT-3.5. All this in an A+ Location!

3419 N Greenview Avenue, Chicago

$1,605,000

6 Beds ⋅ 4 Baths ⋅ 11998113 MLS ⋅ CLOSED Status

Nestled just steps away from the vibrant Southport Corridor, 1317 W School presents an exceptional opportunity as a legal 3-flat investment property, with a unique duplex-up owner's unit. Recently completed in early 2024, this residence is a testament to modern luxury and thoughtful design. The top floor duplex unit stands out with its expansive floorplan, providing ample space for comfortable living. This unit ideal an owner-occupant seeking a blend of sophistication and practicality. With hardwood floors, spa bathrooms, 42-inch kitchen cabinets, quartz countertops, and stainless-steel appliances in the whole building, it will be easy to find quality tenants. Located in the sought-after Burley school district, this property is also an attractive option for families seeking excellent educational opportunities. Multiple transportation options in close proximity make commuting a breeze, and spacious units allow for comfort if you work from home. Invest in the future with 1317 W School-a fully rehabbed 3-flat property that marries modern amenities with a prime location. Whether you are an investor or an owner-occupant, this residence beckons with its contemporary design, top-notch features, and proximity to the best of Southport Corridor living.

1317 W School Street, Chicago

$1,080,000

7 Beds ⋅ 3 Baths ⋅ 12086231 MLS ⋅ CLOSED Status

BROKER OWNED PROPERTY. Assumable 3.5% fixed rate mortgage available for buyer with 30% down payment. Beautifully renovated Roscoe Village 2-Flat in Jahn school district has a terrific duplex up and wonderful 1st floor simplex. The 2nd unit is a beautifully renovated duplex up with four bedrooms (fourth bedroom is tandem) and two full baths, with white quartz counter tops in the kitchen, stainless steel appliances, expansive soft close cabinetry, eat-in center quartz counter island, and a farm sink. There is a separate dining room and a large living room, complete with a wood burning fireplace and front balcony, perfect for morning coffee. Two bedrooms along with a full bathroom with white subway tile and mud room complete the main/1st level of unit 2. Unit 2's second level has a massive primary suite with skylights and a luxurious ensuite bathroom complete with dual vanity and an oversized rain shower with seamless glass. The fourth bedroom is tandem through the primary bedroom and is perfect as an office or nursery. Laundry is conveniently located in its own closet in the primary bedroom. Unit 2 and unit 1 both have hardwood floors throughout. Unit 1 features 3 bedrooms, 1 bath, and in-unit laundry. It has a very large kitchen with stainless steel appliances and a dining room separated from the living room with original pocket French doors. All three levels of this building have their own private back deck overlooking the fully fenced yard and two car garage. The front patio has brick pavers and is perfect for a firepit. Mechanicals and roof are over 10 years old functioning without issue. Unit 2 is currently rented for $4200 per month. Unit 1 is currently rented for $2750 per month. The basement is unfinished and less than 6 feet tall, but presents opportunity to dig down and expand Unit 1 or create a 3rd garden unit. Separate utilities for each unit. Landlord just pays common electric, about $330 per year. Trash/scavenger expense is included in city water bill, which is about $789 per year.

2119 W Fletcher Street, Chicago

$925,000

5 Beds ⋅ 2 Baths ⋅ 12027102 MLS ⋅ CLOSED Status

Rarely available 2 flat frame in Lakeview near Southport Corridor. lst floor rental is bright, has renovated bathroom & eat in kitchen, with new SS appliance pkg, full dining room and 2 bedrooms. 2nd floor gut rehabbed 2004, granite kitchen, custom maple cabinets with pull out shelves, oak floors, vinyl/wood windows, full dining room & 3 bedrooms. Exterior has newer decks on both levels and new trex front porch stairs, balusters & handrailing. Terrific neighborhood, within a half mile to el, good schools, restaurants, etc. Great tenant has lease til Sept. 30, 2024.

1337 W Nelson Street, Chicago

$950,000

6 Beds ⋅ 4 Baths ⋅ 12041621 MLS ⋅ CLOSED Status

Large Lakeview 3-flat in ideal Southport Corridor location. Unit 2 is a 3 bed/2 bath duplex-up with a sunny living room and dining area with newer oak hardwood floors as well as an eat in kitchen, a sunroom and a large private deck. This unit also features a large bay window, clerestory windows in the kitchen and skylights in the top floor bedrooms/bathroom. Unit 1 offers 2 beds/1 bath with a large eat-in kitchen, sunny living room with dining area, sunroom and private deck. The garden unit features 1 bed/1 bath with a private entrance, newer luxury vinyl tile wood-look floor, a large kitchen and comfortable living room. All units enjoy dishwashers, central air, a shared laundry room in the basement with 2 washers/2 dryers, common storage area, a fenced and gated front yard and a large and sunny back yard. A 2-car garage offers convenience and extra income opportunity. Very desirable location within walking distance to the many restaurants, nightlife and entertainment in the Southport corridor as well as Whole Foods, Target, gyms, theaters, the Red, Brown and Purple Line at the Belmont "L" stop and so much more!

3043 N Southport Avenue, 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

$1,340,000

9 Beds ⋅ 8 Baths ⋅ 12030454 MLS ⋅ CLOSED Status

**Exceptional Investment Opportunity in Lakeview, Chicago** Fully Rented 3-Flat Graystone Near Wrigley Field** Immerse yourself in the energy of Chicago's Lakeview neighborhood with this exceptional three-flat graystone building. An ideal investment for both savvy investors and potential owner-occupants, this property is superbly located near the iconic Wrigley Field, serene lakefront, and an eclectic mix of dining, entertainment, bars, and shopping, including Whole Foods Market and Jewel Osco. Prime Urban Location: Situated in Lakeview, this property offers an urban lifestyle experience just steps away from Wrigley Field and the city's vibrant heart. Each unit boasts 2 bathrooms, in-unit laundry, central heat/AC, and hardwood floors, ensuring high demand and tenant satisfaction. The property includes a charming 1 bedroom, 1.5 bathroom garden unit with radiant floor heating, adding a unique touch. The property has been enhanced with a commercial-grade roof installed in 2016, ensuring durability and low maintenance. It features six tandem outdoor parking spaces. A large backyard offers residents a peaceful retreat for relaxation or social gatherings. This fully rented property ensures a steady income, making it a prime investment choice. It's perfect for those who desire to live in the dynamic Lakeview area while benefiting from rental income. Seize the opportunity to own a part of one of Chicago's most desirable neighborhoods. This is a unique chance to invest in a community rich in culture, convenience, and an engaging lifestyle.

3442 N Halsted Street, Chicago

$1,050,000

3 Beds ⋅ 4 Baths ⋅ 12019476 MLS ⋅ CLOSED Status

YOUR SEARCH IS OVER! COME VIEW THIS BEAUTIFUL RARELY AVAILABLE PROPERTY THAT HAS ALWAYS BEEN KEPT IN IMMACULATE CONDITION. LOCATED IN THE DESIRABLE HISTORIC LAKE VIEW AREA. YOU WILL MOST DEFINITELY BE HIGHLY IMPRESSED BY EVERYTHING THIS PROPERTY HAS TOO OFFER. THE MAIN LEVEL INVITES YOU INTO AN ALLURING FORMAL LIVING ROOM AND DINING ROOM W/ STAIN GLASS WINDOWS/SHUTTERS AND A BEAUTIFUL CUSTOM GAS FIREPLACE. SPACIOUS BEDROOM, FULL CERAMIC TILED BATH AND WELL SIZED KITCHEN AWAITS YOU WITH MODERN PRETTY WHITE CABINETS, LARGE HANEX C-TOP ISLAND W/ BREAKFAST BAR ADJACENT TO A RELAXING FLORIDA SUN ROOM WHICH HAS BEEN CUSTOM MADE W/ WOOD PLANKED CEILINGS AND CUSTOM LARGE ARCH SHAPED WINDOW, THAT BRINGS IN PLENTY OF SUNLIGHT. FROM THE FLORIDA ROOM, THE SLIDING DOORS LEAD TO A REFRESHING CUSTOM PERGOLA. THE MAIN LEVEL DUPLEXES UP WITH A STUNNING WOOD STAIRCASE THAT LEADS TO A BREATHTAKING MASTER SUITE THAT INCLUDES A LARGE BEDROOM WALK-IN CLOSET AND SMALL KITCHENETTE, OFFICE AND FULL CERAMIC TILED BATH WITH DOUBLE VANITY ALSO INCLUDED AND A LARGE PEACEFUL LIBRARY WITH BEAUTIFUL WALL TO WALL CUSTOM BUILT-IN SHELVING AND GAS FIREPLACE. NO EXPENSE WAS SPARED ON THIS SECOND LEVEL CONVERSION. THE 3RD FLOOR FLAT HAS A COZY FEEL TO IT AND INCLUDES A LIVING ROOM, SPACIOUS BEDROOM AND SUN FILLED EAT IN KITCHEN. ALL 3 LEVELS BOASTS WITH ITS OWN PRIVATE DECK FOR SUMMER ENJOYMENT. THE BASEMENT IS TASTEFULLY FINISHED WITH ITS FASHIONABLE CIRCULAR STAIRCASE, CUSTOM CERAMIC TILED REC ROOM AND EXTRA LARGE FULL BATH WITH DOUBLE VANITY AND LARGE DEEP SOAKING JACUZZI WHIRLPOOL. THERE IS TONS OF CLOSETS AND STORAGE SPACE TRU-OUT THE PROPERTY. THIS ONE-OF-A-KIND PROPERTY SITS ON A 37 X 125 LOT THAT TURNS INTO A BACKYARD PARADISE IN THE SUMMER WITH ITS NUMEROUS EVERGREENS AND PEAR AND APPLE TREES. SOUGHT AFTER BLAINE ELEMENTARY AND LAKE VIEW H.S ARE JUST A COUPLE BLOCKS AWAY. BROWN LINE AND CTA SERVICES ARE ALSO NEARBY. WRIGLEY FIELD AND THE LAKEFRONT ARE 1.5 MILES AWAY. DO NOT LET THIS ONE SLIP AWAY MAKE YOUR APPOINTMENT TODAY!

3928 N Paulina 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

$1,116,000

6 Beds ⋅ 4 Baths ⋅ 11978726 MLS ⋅ CLOSED Status

Presenting a rare chance to own a classic brick 3-flat nestled in the vibrant heart of Southport Corridor/Wrigleyville. This cherished property, making its debut on the market after 37 years, boasts meticulously maintained units, offering a blend of modern updates and historic charm. Located on the picturesque tree-lined Bosworth Avenue, this property features three distinct units, each with its own unique appeal. The duplex-up unit boasts three bedrooms plus an office, two bathrooms, separate living and dining rooms, and gleaming hardwood floors. On the first floor, a cozy two-bedroom, one-bathroom unit awaits, while the English garden unit offers one bedroom and one bathroom. The property's basement houses two new boiler pumps and additional storage for added convenience. Each unit has separate laundry and enclosed rear porches. Generating supplementary income, the two-car garage adds further value to this investment opportunity. Benefiting from RT-3.5 zoning, this property is positioned in an ultra-prime location with exceptional rental potential. With Wrigley Field just steps away, the Southport Corridor a mere three blocks distant, and Blaine Elementary School within a short stroll. Tenants enjoy unparalleled access to an array of renowned restaurants, bars, and shops, this property epitomizes the allure of city living. Don't miss this extraordinary chance to own a piece of Wrigleyville/Southport history while embracing a lucrative investment opportunity. Act swiftly to secure this gem before it's gone.

3729 N Bosworth 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

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

3-Flats in Lakeview, Chicago IL

An editorially curated view of every active 3-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

← Back to Lakeview, Chicago IL Homes for Sale