View All Lakeview Chicago IL 2-Flats Listings

$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

$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

$1,465,000
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

$1,500,000
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

$1,150,000
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

$1,700,000
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

$985,000
5 Beds 2 Baths 12218262 MLS CLOSED Status
This amazing Greystone 2-flat, located on an EXTRA-WIDE 30 x 125 lot, includes a newer 2-car garage and sits on one of the most sought-after streets in Wrigleyville, in the heart of the Southport Corridor. Zoned R3.5, this meticulously maintained property showcases refinished hardwood floors, charming vintage details, and thoughtful updates throughout. The first-floor unit features a spacious 2-bedroom, 1-bathroom layout with a living room, separate formal dining room, full bath, kitchen with a built-in butler pantry, and an in-unit washer and dryer. The second-floor unit offers a 3-bedroom, 1-bathroom floor plan with a large living room, a formal dining room, a kitchen, and an in-unit washer and dryer. Additional highlights include central HVAC, a rear deck, a backyard, and a 2-car garage. Recent improvements include new washers and dryers in both units, tuck-pointing of the building facade in 2023, and the installation of clean-out access. The unfinished garden unit offers 1 bedroom and is plumbed for a kitchen and bath, providing potential for additional space. This easy-to-rent property is conveniently located near CTA Red, Brown, and Purple Lines, multiple bus routes, Lake Shore Drive, Wrigley Field, Belmont Harbor, Whole Foods, and the incredible shops, restaurants, and recreational activities that Wrigleyville and the Southport Corridor are known for. Don't miss this exceptional opportunity!

1243 W Newport Avenue, Chicago

$1,500,000
9 Beds 6 Baths 12188936 MLS CLOSED Status
Stunning Rehabbed Greystone 3-flat + tall basement on a quiet 1-way street steps from Wrigley Field & Halsted! Great investment or perfect for a live-in owner. Exceptional income and 2 of the 3 units have been tastefully rehabbed including 2 newer kitchens with modern, flat-panel & shaker-style cabinets, granite countertops & stainless-steel appliances, and newer baths. ALL 3 UNITS HAVE 3 BEDROOMS, IN-UNIT LAUNDRY, GFA w/ CENTRAL-AIR CONDITIONING & 2 BATHROOMS, Large formal living room & dining rooms with Hardwood Floors throughout. All New Windows in 2011, newer Mechanicals (newer plumbing supply, some new electric, etc) & more! VERY Tall Basement and GENEROUS RM-5 ZONING (FAR = FLOOR AREA RATION OF 2.0) will allow for further income by expanding up (for a large duplex-up apartment) and/or down into the tall basement for a 4th, legal apartment OR combine with the first-floor unit to create a very large duplex-down unit! A unique side & back alley allows for 4 full exterior parking spots (with room to expand for a 5th parking spot) all 4 are currently rented through Spot-Hero with an outstanding annual income of $23K! (each spot averages $479 per month per spot). Excellent location with a short walk to Wrigley Field and steps from all the Wrigleyville & Lakeview amenities on Halsted & Clark including great area restaurants, coffeehouses, shopping, nightlife, parks, lakefront, EL stop, schools & more! - Top Floor/UNIT #3; 3-bed/1.5-bath (can easily add a shower for 2nd full bath) - lease exp 7/31/25 @ $2,990 per month...UNIT #2; 2-bed/2-bath and was just rented @ $3,200 per month ...UNIT #1; 3-bed/2-bath (lease exp 7/31/25 @ $2,670 per month). 4 gas meters and 4 electric panels. ***EXCELLENT TOTAL ANNUAL INCOME of $129,320 minus - $31,354 in total expenses = $97,966 (NOI) TOTAL ANNUAL NET OPERATING INCOME for a Solid 6.1% CAP rate.***Also, investing an additional $120K in creating a legal 4th garden unit which is allowed under the current R5 zoning (existing ceiling height is very tall @ 7'-8") & 5th parking spot brings the CAP rate up to 8%!!

814 W Newport Avenue, Chicago

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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.

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