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$1,500,000
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



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