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$599,000
5 Beds 3 Baths 12751156 MLS NEW Status
Classic yellow-brick, legal three-flat in Portage Park, situated on an oversized 31' x 125' lot. All three units are currently rented and occupied. The first- and second-floor units feature gorgeous original woodwork and detailing, along with two-bedroom, one-bath layouts, large dining rooms, hardwood floors, spacious kitchens, and generously sized rooms. The garden unit offers one bedroom and one bath. Recent building improvements include new windows, newer roofs on both the building and garage, lintel and masonry work, and updated landscaping. Each unit has its own boiler, and tenants pay their own utilities. The basement offers common-area coin-operated laundry and a bonus room ideal for storage, an art studio, crafts, or other uses. A large, landscaped backyard and detached two-car garage complete the property. Please refer to the showing schedule for prearranged showing times.

5057 W Newport Avenue, Chicago

$549,900
5 Beds 3 Baths 12748829 MLS NEW Status
Your Portage Park investment is ready for you to call home sweet home as you collect the rents or keep as the perfect arm chair investment! Don't miss your opportunity to invest in this well maintained legal 2 unit plus in-law near 6 corners! 1-2 blocks away! Nice size units with tall ceilings. 1st floor unit is spacious and bright with 2 bedrooms + Den ( was used as a 3rd bedroom), hardwood floors, eat in kitchen with an amazing living/dining space with fireplace. Spacious garden unit with hardwood flooring, large living space and recently upgraded bathroom with bathfitter surround. Many updates...HVAC is less than 6 years old, water heaters, windows, siding, roof, leafguard gutters and more. Deck off the main floor unit offers a great place to relax and entertain with view of the fenced in yard. 2.5 car garage with alley access. Laundry room and ample storage space. Current owner was doing some DIY projects inside the building but did not get a chance to finish. Needs some cosmetic work but the bones and exterior is in GREAT shape! Not many in the area I am sure you have looked. See you soon.

4823 W Grace Street, Chicago

$585,000
6 Beds 2 Baths 12738628 MLS NEW Status
Solid brick 2 flat in coveted Avondale/Belmont Garden area on quiet tree lined street. The building offers two spacious units each with living room, separate dining room, kitchen and 3 bedrooms, as well as storage in enclosed porches. Each unit also has large bathroom, separate GFA heat, electric and water heaters. The full basement is semi finished with drywalled ceiling and walls, as well as a roughed in bathroom. Owner has maintained and made recent improvements such as newer furnaces & hallway painting. Both 1st and 2nd floor units are tenant occupied with leases ending at end of 2026. Current rents are below market with room for increase with capital improvements such as kitchen and bath updates. This is a great opportunity for investors or owner occupants in a fast appreciating area.

4140 W Barry Avenue, Chicago

$585,000
4 Beds 3 Baths 12748911 MLS NEW Status
Amazing brick 2-flat opportunity in Portage Park, situated on an oversized 35' x 125' lot. This property offers excellent upside potential by duplexing the first-floor unit into the lower level, which features good ceiling height and an existing bathroom. The front stairwell is configured to allow for a straightforward entryway modification, seamlessly connecting the two levels. Once completed, the duplex-down unit could offer either 3 beds / 2 baths or 4 beds / 2 baths. Both units are currently configured with 2 bedrooms and 1 bathroom. The second-floor unit features an enclosed rear porch that has been incorporated into the living space and works perfectly as an office or den. Additional highlights include basement laundry, a two-car detached garage, and a separate parking pad for a third vehicle. This property is an excellent alternative to a single-family home, with the added benefit of rental income to help balance ownership costs. The first-floor tenant will vacate at the end of September. Please refer to the showing schedule for prearranged showing times.

5051 W Berenice Avenue, Chicago

$609,000
5 Beds 3 Baths 12741864 MLS ACTIVE Status
Incredible opportunity to own a well-maintained legal two-flat with an additional garden unit! Each spacious unit features hardwood flooring, generous living rooms, formal dining areas, large kitchens, ample closet space, and wide enclosed porches. The first-floor unit offers two bedrooms plus a versatile den-perfect for a home office, guest room, or additional living space. Major improvements include a newer roof and water heater (2016), HVAC upgrades completed in 2021, and updated plumbing within the past two years. Situated on a wide lot with a side driveway and one-car garage, this property is conveniently located near restaurants, theaters, shopping, and public transportation. An excellent opportunity for an owner-occupant or investor!

5005 W Eddy Street, Chicago

$580,000
5 Beds 3 Baths 12741656 MLS ACTIVE Status
Seize the day with this Updated, Versatile two-flat in Portage Park offering Cash Flow and Value-add upside. The property features one duplex-down unit with 3 bedrooms and 2 baths, plus a 2nd floor Simplex apartment with 2-bedroom/1-bath. Separate utilities and private laundry for each unit add convenience and investor appeal. Fully fenced yard, plus a 2-car garage with potential for additional income. Ideally located near historic 38-acre Portage Park, with access to nature walks, Olympic-size pool with aquatics, team & individual sports, gymnasium facilities, and fieldhouses. Walk to neighborhood favorites including Binny's, Target, PetSmart, Jewel-Osco, Ross, restaurants, shopping, and everyday conveniences. Enjoy easy access to I-90/94, CTA, Metra, O'Hare Airport, and Downtown Chicago. Make your appointment today!

4817 W Dakin Street, Chicago

$575,000
6 Beds 3 Baths 12693206 MLS ACTIVE Status
Tucked into Portage Park, this rare legal three-flat has been generating steady income for years and comes fully tenant-occupied from closing. Built in 1922 on a generous 31x126 lot, it offers three two-bedroom units, a two-car garage, and a fenced backyard, giving an investor solid fundamentals to build on or a house-hacker room to move into one unit while the others help carry the mortgage. This property offers the new owner has real flexibility, whether that means adjusting rents to market or eventually settling into one of the units. The location does a lot of the work here too, maximizing rentability, just steps from the Montrose Blue Line, the #152 bus, Metra's Mayfair stop, and the shops around Six Corners, with Chopin Park close by. Interior photos are being held back out of respect for current residents, but are available on request through the listing agent, who's happy to arrange a private tour. Please allow a minimum 48 hrs' notice for showings. Property is being conveyed as-is.

5357 W Waveland Avenue, Chicago

$624,000
5 Beds 3 Baths 12739226 MLS ACTIVE Status
Excellent Investment or Owner-Occupant Opportunity in Chicago! This Well-Maintained Two-flat offers Two Spacious Residences plus a versatile In-law Garden Unit. The Main-Level Unit features a Large Living Room, Separate Dining Room, Eat-in Kitchen, Primary Bedroom, Secondary Bedroom with Adjoining Sitting Room / Office, One Full Bathroom and an Entry Area with Stairs that lead to the One Bedroom, One Bathroom In-Law Garden Unit with Family Room, Office, and Kitchen. The Upper-Level Unit features a Large Living Room, Separate Dining Room, Eat-in Kitchen, Primary Bedroom, Secondary Bedroom with Adjoining Sitting Room / Office, and One Full Bathroom. With Flexible Accommodations across Three Levels, this Property offers Outstanding Potential for Multigenerational Living and/or Rental Income with a Fantastic Opportunity to live in one unit while generating income from the others! There is a Fenced Backyard and a Two Car Garage! The Prime Location is Moments to: CTA Bus Stops, Wrigley Field, Montrose Beach, Local Parks, Tons of Dining Options, Shopping and Nightlife. This is an Estate Sale and Property is sold As-Is and Hold Harmless. Sellers does not provide survey or disclosures - please verify all details on your own.

5105 W School Street, Chicago

$629,900
4 Beds 3 Baths 12728185 MLS ACTIVE Status
Location, location, and location. Just across from Irving Park Blueline and Metra stations. Great investment opportunity. Rare model duplex townhouse in Old Irving Park near expressway I-90/94. This beautiful townhouse consists of two legal units with individual HVAC systems, two offstreet parking spots, common courtyard patio, storage area in the basement. The rental income of one unit covers the monthly expenses of the townhouse or live in one unit and use another one as an in-law unit. Monthly HOA fee of $150 covers common area maintenance including but not limited to parking lot, sidewalk, snow removal, garbage pickup, reserve for repairs of sewer and water service lines in the common area, and insurance. Unit #1: Aprox. 683 sq ft - One bedroom one bath garden unit with open concept, 10x12 bedroom, full size kitchen and dining, one full bath, newer HVAC system with central air, washer and dryer in the basement. Unit was freshly painted in July, 2026. Unit #2: Aprox. 1365 sq ft- Three bedrooms one and a half baths in second and third level. 11x17 master bedroom, spacious living room(13x18), updated eat-in kitchen with 42" maple cabinets, quartz countertops, and stainless steel appliances, in-unit washer and dryer, newer HVAC system with central air. Unit was freshly painted in June, 2026. Sold "As-Is".

4035 N Keystone Avenue, Chicago

$569,000
3 Beds 2 Baths 12735726 MLS ACTIVE Status
WOW! amazing Well-maintained legal 2-flat in desirable Portage Park! Come see the classic charm of this 2 unit that has stained glass, built-ins original woodwork with crown molding. Also features forced heating and Central air for both units which is rare for this type of buildings The main floor has all beautiful hardwood floors, a spacious Spacious living room, formal dining room, also has additional sunroom that was finished and insulated which can be used for Den or Office! 1st floor has eat in kitchen with back porch that can be used for extra storage. The bright second-floor unit features large kitchen formal living and dining rooms all hardwood floors. Bathroom features beautiful bath tub and standup shower! Each unit has a separate forced air furnace and AC unit along with its own hot water heater! Outside, you'll find a good-sized yard with plenty of green space along with garage with o the yard-perfect for outdoor entertaining and gatherings. Building has all newer windows copper plumbing mechanicals are in good shape as well. This corner 2 unit is on a great block Conveniently located near shopping, public transportation, restaurants, parks, and more.

5258 W Dakin Avenue, Chicago

$650,000
4 Beds 2 Baths 12729742 MLS ACTIVE Status
Beautiful Brick 2-Flat with Full Walkout Basement! Great Northeast Belmont Cragin location. Well-maintained brick 2-flat offering spacious layouts and classic Chicago charm. Each unit features 2 bedrooms, 1 full bath, a generous living room, and a separate formal dining room. Both units also feature original hardwood floors, beautiful original wood trim and molding, and decorative fireplaces that add character and warmth. The property includes enclosed porch space and a full walkout basement offering additional storage. Outside, enjoy a nicely landscaped yard, a 2-car detached garage with an additional carport, and plenty of outdoor space. Conveniently located near schools, shopping, and public transportation. The CTA bus stop is right at the corner, providing easy access to the Cicero and Belmont bus routes and making commuting a breeze. A great opportunity for an investor and a convenient location for tenants.

4818 W Fletcher Street, Chicago

$575,000
4 Beds 3 Baths 12536937 MLS ACTIVE Status
Live in one, rent the other! This well-maintained brick two-flat in the heart of Portage Park is perfect for an owner-occupant looking to build wealth while enjoying the benefits of homeownership. The second floor unit is vacant and move-in ready, offering a blank slate to make it your own from day one while the first floor unit provides immediate rental income. Each unit features spacious rooms, hardwood flooring, and a functional layout with separate living and dining areas, plus an enclosed back porch ideal for added storage, a home office, or extra living space. The finished basement adds even more flexibility, whether you envision an in-law suite, a rec room, or a future duplex-down to maximize rental income potential. Add a detached 2-car garage, a fenced yard, and an oversized Chicago lot to round out the package. All of this on a quiet residential block that still puts you close to everything...steps from Chopin Park, the Blue Line, Metra, and CTA buses, with the Six Corners shopping and dining district just around the corner. Quick access to I-90/94 makes commuting a breeze. Whether you're a first-time buyer ready to stop renting, or a seasoned investor adding to your portfolio, this Portage Park two-flat is a smart, long-term move in one of Chicago's most sought-after neighborhoods.

5121 W Henderson Avenue, Chicago

$579,999
6 Beds 3 Baths 12712329 MLS ACTIVE Status
Welcome to this legal 3 unit property located in the heart of the highly desirable Portage Park neighborhood. Enjoy the perfect blend of vintage charm and modern updates in this bright, spacious building on tree-lined Byron Street. Perfectly suited for an investor looking for strong rental yields or an owner-occupant looking to house-hack and have their tenants pay the mortgage! New siding (2026), Roof (2025), and all kitchens have been redone in the last 5 years! Unit 2 is vacant for an owner occupied buyer and Unit 1 and Unit G are leased through May 2027. Outdoors, you'll find a fully fenced-in backyard-ideal for summer gatherings or pets-and a secure, detached 2-car garage. An absolute walker's paradise! Enjoy an unbeatable location just a short stroll away from the historic Six Corners shopping, dining, and entertainment district. Commuting is a breeze with easy access to I-90/94, multiple Blue Line stations, and the Grayland Metra station just minutes away. Best of all, you are blocks from the expansive 40-acre Portage Park, featuring magnificent green space, playgrounds, athletic fields, and its famous Olympic-size pool. Don't miss out on adding this turnkey gem to your portfolio! Owner is a licensed real estate broker.

4824 W Byron Street, Chicago



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