Lakeview, Chicago IL · Curated MLS Search

2-Flats in Lakeview, Chicago IL

An editorially curated view of every active 2-flats listing in Lakeview, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings

Lakeview Market — 2-Flats Comparison

Live MLS data — Lakeview vs. 2-Flats

Lakeview
2-Flats
inventory
Active Listings
100
1
Sold (Past 6 Mo.)
571
20
Under Contract
129
1
pricing
Avg. List Price
$919,934
$1,750,000
Cost / Sq. Ft.
$412
—
typical home
Living Area
2,252 ft²
—
Avg. Beds
3.1
10.0
Avg. Baths
2.7
5.0
Days on Market
83
26

2-Flats in Lakeview: Market Data

Data as of (MLS snapshot; listings below update live)

As of October 20, 2026, Chicago Real Estate Source's review of MLS data shows 1 active listing for Lakeview 2-flats. Listings like these do not come up often in Lakeview. These listings made up about 1% of the 100 active listings in Lakeview, across every property type. At the time, 1 more was pending, and 20 sold in the past six months. In a market this small, a listing alert is the most reliable way to hear about the next one.

2-Flats in Lakeview, Chicago IL, October 20, 2026
MeasureValue
Active listings1
All active listings in Lakeview, every property type100
Under contract1
Sold, past six months20

2-Flats in other neighborhoods

Market questions

How many Lakeview 2-flats are for sale?

There was 1 active listing for Lakeview 2-flats as of October 20, 2026, based on Chicago Real Estate Source's review of MLS data.

How do Lakeview 2-flats stack up against other neighborhoods?

As of October 20, 2026, there was 1 active listing for Lakeview 2-flats. In the same search, Chicago had 257 2-flats for sale at a median list price of $479,000, Logan Square had 11 2-flats for sale and Jefferson Park had 10 2-flats for sale.

How many Lakeview 2-flats sold recently?

20 Lakeview 2-flats sold in the six months before October 20, 2026.

How many Lakeview 2-flats are pending?

As of October 20, 2026, 1 listing for Lakeview 2-flats was under contract.

How do Lakeview 2-flats compare with all active listings in Lakeview?

As of October 20, 2026, there was 1 active listing for Lakeview 2-flats, out of 100 active listings in Lakeview across every property type.

Listing data courtesy of Midwest Real Estate Data LLC.

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View All Lakeview Chicago IL 2-Flats Listings

1529 W Nelson Street, Chicago
$1,750,000
10 Beds ⋅ 5 Baths ⋅ 12764264 MLS ⋅ ACTIVE Status
HOT LAKE VIEW 3 FLAT + 3 FLOOR COACH HOUSE | 2 INCOME-PRODUCING PROPERTIES | LIVE-IN & RENT | Envision the possibilities, and bring your best offer! Welcome to an exceptional rare investment opportunity in the heart of Chicago's highly desirable Lake View neighborhood. This Victorian 3 Flat with a rare 3 levels of living space Coach house is offering four income-producing units, these 2 properties present the kind of versatility that sophisticated investors and owner-occupants look for. Whether your vision is to maximize rental income, live in one residence while generating income from the others, or hold a multi-unit asset in a premier Chicago location, this property provides a range of possibilities. Beyond the income potential, the location is a true standout. Enjoy the best of Lake View living with an abundance of restaurants, cafes, shopping, entertainment, parks, neighborhood amenities, and convenient transportation just moments away. It is a location that continues to attract residents who want the energy of the city while enjoying the character and community of a sought-after neighborhood. 4 units total, that includes the 3 flat and a separate Coach house. 2 amazing properties. An outstanding Chicago Lakeview location. Multiple strategies. One exceptional opportunity. Properties offering this combination of income potential, flexibility, and location are not often available. Whether you're an experienced investor or seeking a property with income-producing potential, this unique opportunity is ready for your vision and investment strategy. Come experience the property and explore the possibilities firsthand. Seller intends to review offers following the weekend, with a target of Thursday for highest and best. This is the Lake View opportunity you've been waiting for. Come see it, bring your vision, and make it yours. Serious inquiries only!

1529 W Nelson Street, Chicago
3657 N Hermitage Avenue, Chicago
$1,174,000
5 Beds ⋅ 3 Baths ⋅ 12758512 MLS ⋅ CLOSED Status
Outstanding opportunity to purchase a 2 flat building on a picturesque residential corner with 2 car parking garage and incredible outdoor space 3657 N. Hermitage Avenue. Prime Lakeview Location! This desirable two-flat is located on a quiet, tree-lined residential street in the heart of Chicago's sought-after Lakeview neighborhood. The property offers an excellent combination of classic Chicago character, convenient city living, and strong neighborhood appeal. Enjoy easy access to the Southport Corridor, Wrigleyville, North Center, Roscoe Village and Lincoln Park, with an abundance of restaurants, cafes, shopping, entertainment and everyday conveniences nearby. Southport Avenue, Lincoln Avenue, Belmont Avenue and the Wrigleyville entertainment district are all within easy walking or biking distance. Residents also enjoy convenient access to neighborhood parks, playgrounds and Chicago's lakefront recreational opportunities. Schools: Chicago Public Schools District 299, including Hamilton Elementary School and Lake View High School. With its highly walkable location, nearby public transportation, restaurants, shopping, parks and entertainment, 3657 N. Hermitage Avenue is an excellent opportunity for an owner-occupant or investor seeking a two-flat in one of Chicago's most desirable North Side neighborhoods. This is a well-maintained property with a new garage roof. The property is available for owner occupants and investors; basement can also be converted to a 3rd unit which will be financially benefit a new owner

3657 N Hermitage Avenue, Chicago
3709 N Bosworth Avenue, Chicago
$1,450,000
10 Beds ⋅ 5 Baths ⋅ 12728198 MLS ⋅ CLOSED 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
3431 N Paulina Street, Chicago
$1,425,000
5 Beds ⋅ 4 Baths ⋅ 12716023 MLS ⋅ CLOSED 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
3141 N Oakley 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
3714 N Bosworth 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
1448 W George Street, 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
1341 W Eddy 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
1033 W Wellington Avenue, 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
2317 W Barry 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
1539 W Addison Street, 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
1322 W Barry Avenue, 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
1532 W Oakdale 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
1658 W Nelson Street, 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
3750 N Hermitage Avenue, Chicago
$935,000
4 Beds ⋅ 3 Baths ⋅ 12588842 MLS ⋅ CLOSED Status
Welcome to this classic Lakeview / North Center Greystone 2 flat . Vintage charm abounds as both units boast solid hardwood floors, original woodwork, gorgeous built in hutches, a separate dining room, and bedrooms big enough to fit a queen size bed. The 2nd floor unit also offers a charming gas fireplace to cozy up to, a rear deck perfect for morning coffee, summer nights and enjoying the sunshine; a sizable walk-in closet, and a den/office area with built in cabinetry. This building is an excellent opportunity for an owner occupant with a rental unit downstairs, a conversion to a single family home, or to use strictly as an investment property. The building has central heat and air, separate utilities, newer windows, shared laundry in the basement, a full back yard, and garage. The seven foot basement height gives potential to duplex down. The first floor unit is 2 beds, 1 bath. Second floor unit is 2 beds /1.1 bath with a den/office area. The building is tucked away on a quiet street in an excellent location- a quick commute to the Addison brown line, and a short trip in any direction to the many shopping and dining options in Lakeview and North Center!

3750 N Hermitage Avenue, Chicago
3732 N Racine Avenue, 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
2909 N Hoyne Avenue, Chicago
$650,000
4 Beds ⋅ 2 Baths ⋅ 12585373 MLS ⋅ CLOSED Status
Well-maintained frame 2-flat in a prime location just steps from Hamlin Park. This building features two units, each with a 2bd/1ba layout, many of the appliances have been replaced as well as many of the mechanical systems. Some of the updates include a new AC and furnace for unit 2, new flooring in unit 2, updated kitchen in unit 2, new garage door, front steps, and much more. Investors and owner-occupants will appreciate the efficiency of separate HVAC systems for each unit. The property includes a two-car garage and offers a solid opportunity in a high-demand area. Property is being sold as-is.

2909 N Hoyne Avenue, Chicago
3034 N Greenview 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
1325 W Cornelia Avenue, Chicago
$1,575,000
4 Beds ⋅ 2 Baths ⋅ 12589110 MLS ⋅ CLOSED 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
1330 W Roscoe Street, 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
3020 N Clybourn Avenue, Chicago
$725,000
4 Beds ⋅ 4 Baths ⋅ 12551028 MLS ⋅ CLOSED Status
Great Income on this Updated 2-Flat in Awesome Hamlin Park/Roscoe Village Location. Updated units rent quickly, perfect for Live-In Owner or Investor. Location is walkable to Belmont Street & downtown Roscoe Village. Two Duplexed Units feature updated Kitchens & Baths, New HW floors throughout, laundry in the Bldg and 4-car tandem parking in the back. 2nd Floor Improvements include, New Furnace & A/C (~2024) New Kitchen & Appliances (~2022), New Bathrooms (~2022), HW Flooring (~2022), Updated Electric (~2022), H2O Tank (~2021), Laundry (~2019). 1st Floor improvements include New W/D (~2023), New Appliances (~2021), H2O Tank (~2021), New Furnace & A/C (~2020), Updated Kitchen & Bathrooms (~2018). Other Bldg Improvements include some updates to Electric & Plumbing as the units were renovated, plus New Roof (~2012). Lots of New Construction on the block and in the area, great destination location, perfect for AirBnb or traditional rentals. Steps to Shopping, Dining, Nightlife, CTA, Expy and all the City has to Offer. This location is HOT!!!

3020 N Clybourn Avenue, Chicago
1411 W Byron 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
3021 N Racine Street, Chicago
$800,000
5 Beds ⋅ 4 Baths ⋅ 12516294 MLS ⋅ CLOSED Status
Opportunity for prime Lakeview land. 24x121 R3 in heart of Lakeview. Occupied 2 flat; Unit 1 $2235 11/25 lease end; Unit 2 $3250 m2m. Taxes $15,297. Do not disturb tenant.

3021 N Racine Street, Chicago
1329 W Nelson 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
902 W Newport Avenue, 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
3760 N Wayne 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
3621 N Ravenswood Avenue, Chicago
$825,000
5 Beds ⋅ 3 Baths ⋅ 12479496 MLS ⋅ CLOSED Status
*Seller has VA loan which may be assumable.* This beautifully maintained, solid brick 2-flat in the highly desirable Lakeview neighborhood is as turn-key as they come-perfect for investors or owner-occupants alike. Nestled on a beautiful tree-lined street within the coveted Hamilton School District, this building combines timeless vintage character with modern updates. Original charm abounds with preserved woodwork, detailed moldings, built-in hutches, hardwood floors, and high ceilings. Both units are 2beds/1bath and feature updated kitchens and baths, plus separate utilities, updated electrical, and central air/heat. Thoughtful maintenance includes tuckpointing (2020), newer windows, freshly repaired and painted front steps, and a recently maintained and painted steel rear staircase/balconies. The fully finished basement offers a non-conforming 1bed/1bath unit-ideal for an in-law suite, duplex-down, or potential ADU. Shared laundry, a 2-car garage, and a spacious backyard add even more value. This property has endless possibilities, whether you're seeking rental income, a future single-family home conversion, or a blend of both. All in an unbeatable location-steps to the Brown Line, Trader Joe's, Wrigley Field, Southport Corridor, parks, restaurants, and shops.

3621 N Ravenswood Avenue, Chicago
1415 W George Street, 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
3854 N Janssen Avenue, 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
3818 N Hermitage 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
1328 W Nelson Street, Chicago
$1,030,600
7 Beds ⋅ 4 Baths ⋅ 12392961 MLS ⋅ CLOSED Status
Located in the heart of Lakeview, this lovingly maintained 2-flat with extraordinary Coach House offers a plethora of options for a live-in owner, investor, or single family conversion. Main building units are both 2 bedroom, 1 bathroom, with gleaming hardwood flooring and generous, light filled, room sizes. The adorable Coach House features three second level bedrooms with 1.1 bathrooms and outstanding curb appeal. Full unfinished basement with plenty of storage options. Incredible location near Southport shopping, transportation, parks, and schools.

1328 W Nelson Street, Chicago
1140 W Barry 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
3746 N Hermitage 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
938 W Newport 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
1535 W Barry 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
822 W Newport 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
1442 W Fletcher Street, 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
1048 W Dakin Street, 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
851 W Oakdale Avenue, 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
1046 W Dakin 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
3710 N Paulina Street, Chicago
$1,700,000
6 Beds ⋅ 6 Baths ⋅ 12304166 MLS ⋅ CLOSED Status
Gorgeous completely renovated 2 flat on gorgeous tree lined Paulina street. Two spectacular duplexes for the discriminating buyer located in the highly acclaimed Hamilton school district. Duplex down with incredible finishes and detail. Duplex down first floor offers a dream kitchen with larger island, SS appliances and custom cabinetry plus large pantry. Neutral countertops ,backsplash and gorgeous lighting enhance this functional kitchen. Unique bookcase under the stairs utilizes the open space.Open family room with fireplace, built in custom bookcases, exceptional lighting and plenty of room for a large dining table. Plus there is a built in planning desk. Front office/bedroom with French doors and closet provide optional space .Hardwood flooring throughout both duplexes. Lower level offers Master suite with numerous closets and custom bath with walk in shower. 2 large additional bedrooms with windows for extra light and plenty of storage. Additional full bath on the lower level.Radiant heated floors throughout the lower level. Duplex up has similar finishes with hardwood flooring throughout. Gorgeous family room with fireplace and custom bookshelves. Additional skylights and vaulted ceiling in kitchen provide natural light throughout the space. Spectacular kitchen with large island, cabinets with lighting, SS appliances and neutral countertops and backsplash. Upgraded lighting throughout the home. Plenty of storage throughout the 2nd floor. 2nd floor master bedroom with beautifully finished bathroom and walk in closets. Gorgeous staircase to the third level. Additional bedroom PLUS family room/game room.on the third floor. Full bath PLUS a unique office/bedroom with ceiling trim and vaulted ceilings complete the third floor. Even the back staircase has been redone with a gorgeous landing with windows and updated carpeting. Back staircase leads to the beautiful landscaped backyard complete with a patio with awning PLUS a newer 2 car garage and garage deck for entertaining. This home has been equipped with drain tiles, sump pump and state of the art mechanicals.Everything in the 2 flat (mechanicals, appliances, roof and exterior were new in 2020.) So many architectural detail's throughout the two duplexes. Perfect for in laws or an additional family. Investor friendly with potential rent producing duplex. Separate entrances to both duplexes. Please see the list of updates! Walk to St. Andrews school and highly rated Hamlin school. Merryman park is 1 block away. CTA stop is right down Paulina. Wrigley Field is within walking distance. This is a gem that you don't want to miss! Location on quiet Paulina but walking distance to Lakeview, Roscoe Village and Southport. Possibilities are endless with this property!

3710 N Paulina Street, Chicago
3757 N Hermitage 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
3623 N Janssen 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
1604 W Waveland 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
1243 W Newport 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
1447 W Roscoe Street, Chicago
$940,000
5 Beds ⋅ 2 Baths ⋅ 12198790 MLS ⋅ CLOSED Status
Charming and well-maintained Legal 2-flat in the heart of Roscoe Village/Lake View, just half a block from the vibrant Southport Corridor and walking distance to Wrigley Field, theaters, parks, shopping, and restaurants. Unit 1 offers 2BD plus additional office/bedroom space, 1 full bath, original oak woodwork and doors, a double closet in the main bedroom, a laundry chute, and glass shelves in the dining room. The main bedroom has brand new carpet. Unit 2 features 3BD/1BA, showcasing original oak woodwork, doors, and a built-in dining room hutch. There are high ceilings and large windows throughout. The basement is clean and unfinished with approximately 7ft ceilings. This property features a 7-year-old roof, a shared washer/dryer in the basement, back porches and stairs replaced in 2005, and a garage resided in 2018 with new windows and gutters. Tuck-pointing was completed in 2020 and 2022. This home is located in the sought-after Hamilton School District. It is an excellent opportunity for investors or owner-occupants to own a character-filled property in one of Chicago's most desirable neighborhoods.

1447 W Roscoe Street, Chicago
3412 N Greenview Avenue, Chicago
$750,000
5 Beds ⋅ 3 Baths ⋅ 12133321 MLS ⋅ CLOSED Status
Great opportunity to own a well-maintained 2 flat in Lakeview / Southport Corridor! Large units w/ potential to increase income by renting the parking pad that owner currently uses. Units are over 1400 sq ft and have been recently updated. All of the bedrooms in the building are on the opposite side of the train. Tenants pay all utilities other than water - each unit has its own HVAC. Easy to find tenants and room to increase rents. Walk to everything - bars, restaurants, shopping, CTA, and more! Neither seller nor agent represents the legality of the garden unit.

3412 N Greenview Avenue, Chicago
814 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
3709 N Janssen 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
1616 W Roscoe Street, Chicago
$699,000
4 Beds ⋅ 3 Baths ⋅ 12182265 MLS ⋅ CLOSED Status
This Spacious Brick, Two Flat with Non-Conforming Garden Unit is Located on a Quiet, One-Way, Tree-Lined Street with Sidewalks on both Sides. Beautifully Maintained, Unit 1 on the Main Level offers 1 Bedroom plus an Office / Den and a Full Bathroom. In addition, there are Separate Living and Dining Rooms, Hardwood Floors, Custom Window Treatments and the Kitchen boasts Granite Countertops and Stainless Steel Appliances. Unit 2, on the Upper Level, offers 2 Bedrooms and a Full Bathroom, Hardwood Floors throughout, Separate Living and Dining Rooms, both filled with Great Natural Light and a Spacious Kitchen. The Non-Conforming Garden Unit offers an Open Floor Plan with a Living Room that overlooks the Kitchen, 1 Bedroom, and a Full Bathroom. There is Convenient On-Site Storage, Common Area Laundry Room and a Detached 2 Car Garage. This Prime Location is Moments to: Brown Line, Whole Foods, Trader Joe's, Wrigley Field, Belmont Harbor / Belmont Harbor Dog Beach, Sydney Marovitz Golf Course, Dining, Shopping, Nightlife and More.

1616 W Roscoe Street, Chicago
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