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$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

$350,000
5 Beds 2 Baths 12738750 MLS ACTIVE Status
Welcome to 1431 S. Christiana Avenue, a classic Chicago Greystone two-flat that offers an exceptional turn-key opportunity for savvy investors or owner-occupants looking for live-in rental income with strong upside. Beautifully presented with timeless stone masonry and a secure fenced perimeter, this property features bright, versatile living spaces highlighted by beautiful hardwood floors, light neutral tones, and classic arched pass-throughs. The main residential layout offers expansive, light-filled living rooms and dedicated dining areas, seamless eat-in kitchens equipped with extensive cabinet storage and gas ranges, functional full baths, and comfortable bedrooms alongside flexible bonus rooms ideal for home offices. Beyond the upper living quarters, the home presents incredible equity potential with a massive unfinished basement ready for duplexing down or future expansion, plus a low-maintenance back yard complete with a private concrete parking pad and easy access to local transit and Downtown Chicago.

1431 S Christiana Avenue, Chicago

$559,999
7 Beds 3 Baths 12739688 MLS ACTIVE Status
Attention - Prime Irving Park Location. Exceptional opportunity for owner-occupants, investors, or developers in a highly desirable Irving Park area. Conveniently situated near CTA, Metra, I-90/94, shopping, restaurants, parks, and coffee shops. This family-owned property of over 40 years offers versatile options - keep it as a two-flat with additional rental income, or transform it into your dream home, surrounded by luxurious single-family residences. First Floor: 2 bedrooms, living room, dining room, kitchen, 1 bathroom. Second Floor (duplexed to attic): Living room, dining room, kitchen, 5 bedrooms, 2 bathrooms. Additional features: ample storage, enclosed porches, 2-car garage, and a fully fenced yard & Separate laundry hookup .New roof will be put on this month , Property is being sold As-Is. Pre-approved buyers only.

4019 N Bernard Street, Chicago

$289,900
11 Beds 7 Baths 12738865 MLS ACTIVE Status
Rarely does an opportunity such as this arise in the sought after South Shore! This building is a jumbo, all brick, three unit building with a full basement and a three car all brick garage in which the renovations have been started but never finished. The units have all of the hard work completed, hardwood floors run through each unit, there are large octagon living rooms in each unit with a wall of windows that allow tons of natural light to shine into the unit. This building is in an ideal location, steps from Lake Michigan, close to train and much more! Buildings like this do not hit the market often and this one will not last long! Sold strictly as-is. No survey. Buyer to take subject to any violations/municipal requirements. Utilities will not be activated.

7726 S Kingston Avenue, Chicago

$599,900
9 Beds 3 Baths 12739580 MLS ACTIVE Status
Incredible investment opportunity in Hermosa! Situated on an extra-wide lot, this legal 3-flat offers exceptional income potential with spacious units, recent renovations, and ample parking. The building features a 2-bedroom, 1-bath first-floor unit, a 3-bedroom, 1-bath second-floor unit, and a 4-bedroom, 1-bath third-floor unit. An additional finished attic with access from Unit 3 provides excellent potential for added living space or future income opportunities. Almost the entire property has been extensively renovated, with all units except the tenant-occupied second-floor unit featuring refinished or new flooring, updated appliances, fresh paint, and renovated bathroom fixtures. Additional improvements include recently updated roofs, adding peace of mind for the next owner. Outside, you'll find a detached one-car garage plus a large parking pad with space for 4-5 additional vehicles, a rare feature in the area. Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the others, this property offers tremendous flexibility and upside. Explore the property in 3D by clicking the 3D Tour button and walk through every detail from the comfort of your home.

2050 N Kenneth Avenue, Chicago

$599,000
5 Beds 3 Baths 12739226 MLS PRICE CHANGE 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

$769,000
9 Beds 6 Baths 12739181 MLS ACTIVE Status
**$20,000 Grant Available Through the Cook County Land Bank!** Introducing this stunning new construction 3-flat in the heart of Humboldt Park, ideally located just off Franklin Boulevard - only 10 minutes from Downtown Chicago and 2 minutes from the Garfield Park Conservatory. This exceptional property offers a rare opportunity for owner-occupancy while generating strong rental income. Each spacious unit features 3 bedrooms and 2 full bathrooms, including a private primary suite with an en-suite bath. Designed with modern living in mind, the kitchens showcase sleek stainless-steel appliances, quartz countertops, custom slow-close cabinetry, and luxury flooring throughout. Foam insulation on exterior walls enhances energy efficiency and year-round comfort. Additional highlights include in-unit washer and dryer, low-maintenance new construction, and a 3-car parking pad in the rear. Conveniently located near shopping, public transportation, and local amenities, this turnkey investment is especially ideal for homeowners looking to gain equity in an up-and-coming neighborhood. *Interior and exterior photos shown are from a similar property located on the 500 block of Lawndale* **Expected delivery: October 2026.**

538 N Trumbull Avenue, Chicago

$474,900
6 Beds 3 Baths 12739169 MLS CONTINGENT Status
Discover this promising legal 3-unit building located in the vibrant Humboldt Park neighborhood. Each of the three units features two bedrooms and one bathroom, with the first and second-floor residences offering separate living rooms, dining rooms, and kitchens. Tenants enjoy individual control over their own boilers and water heaters, and the second-floor boiler was recently replaced in 2025. The property includes a shared common area with free laundry facilities, a large backyard, and a 1.5-car garage. While the roof is estimated to be 15-20 years old and most appliances are original, the first-floor stove and range were updated in 2025. Currently, all tenants are on month-to-month leases, providing flexibility for new ownership. Situated in the northwest corner of Humboldt Park, residents are just a short drive from the park's extensive amenities, including tennis courts, the beach and lagoon, the National Museum of Puerto Rican Arts & Culture, and various sports fields, while also benefiting from proximity to local grocery options, public transportation, and popular dining spots. Seller offers assumable mortgage with the 2.75% interest rate.

1539 N Kolin Avenue, Chicago

$499,900
12 Beds 5 Baths 12739000 MLS ACTIVE Status
Invesment Opportunity For a Savvy Investor! This Value Add Opportunity has major upside potential. The current offering consists of a Center Entrance 4 Flat with the potential to legalize the 2 garden apartments for a 6 Count! The floor plans are huge with 3 bedrooms, 1 bath apartments, tall ceilings, and 1200 sq ft per unit. There are two independent basement areas with 7 ft ceilings in place, separate gas meters, electrical meters, as well as a front and rear dedicated entrances. Acquisition and Construction on 4 units with a 6 Unit ARV and rent roll if done properly. Floor Plate: 3 bedroom 1 bath apartments with 9 ft ceilings, original hardwood flooring, independent forced air heating systems--NO AC currently-- separately metered gas, and electrical. This is a value add opportunity and is being sold as is. There are 3 out of the 4 units currently leased, and so the offering is subject to existing tenancy which are all M_T_M. currently. There is a massive garage structure in place at the rear, and the lot size is 50 x 125. Images are of the one vacant unit, other units need more work but have exact same layout. Make this your next investment and create massive cash flow for yourself.

4035-37 W Harrison Street, Chicago

$149,900
5 Beds 3 Baths 12738976 MLS ACTIVE Status
Welcome to 8533 S. Manistee Ave., a spacious 5-bedroom, 3-bathroom Chicago property offering an exciting opportunity for investors, house hackers, or buyers ready to create something special. This classic fixer-upper is offered AS-IS and provides a flexible layout with plenty of room to renovate and add value. The home features generously sized bedrooms, two bedrooms on the lower level, three bedrooms on the main floor, additional attic space, and a detached 2-car garage. With thoughtful updates, this property has the potential to become a beautiful income-producing investment or distinctive Chicago home. Conveniently located by the CTA bus service which is just 1-3 minutes away, Metra Electric is approximately 10-15 minutes on foot, and neighborhood dining, including pizza and Mexican cuisine, is within approximately 4-7 minutes. Do not miss out!

8533 S Manistee Avenue, Chicago

$769,000
6 Beds 3 Baths 12736664 MLS ACTIVE Status
**Rare Jefferson Park Multi-Unit Opportunity!** Owned and cared for by the same family for more than 30 years, this well-maintained property offers an incredible combination of space, income potential, and location just down the block from Dunham Park. Situated on an oversized approximately **50' x 190' lot**, this **legal 2-unit with garden-level living space** is currently being enjoyed by the seller as one expansive single-family residence-showcasing just how much living space this property provides. Featuring approximately **6 bedrooms and 3 bathrooms throughout the building**, the layout includes 2 bedrooms on the second floor, 3 bedrooms on the first floor, and 1 bedroom at the garden level. The property offers **central heat and air**, new driveway, 3 year old roof, generous living areas, and has been lovingly maintained throughout its longtime family ownership. Outside, the property continues to impress with a **long driveway, garage, and additional land beyond the garage**, a combination rarely found in this part of the city. **Longtime ownership. Oversized lot. Multiple income possibilities. Prime Jefferson Park location near Dunham Park.** A unique opportunity for investors, owner-occupants, and multi-generational families alike.

6134 W Leland Avenue, Chicago

$1,199,999
9 Beds 6 Baths 12738856 MLS ACTIVE Status
Location, Livability, Design, and a little bit of Architectural Drama! The question is not only why is it different, rather, come and find out what exactly makes this opportunity unique? This Newly built 3 -story full masonry building is ready for delivery whether you are looking for a spacious home to live in, or for an effortless investment opportunity. 1 The site location is strategic--the property is located just 2 blocks from the elevated train line and not on top of it which makes it close enough, and yet far enough away( Access without the noise) 2. The Architectural design was thought out and improved on to ensure each bedroom, kitchen, living area and bathroom was maximized for functionality and the highest form of livability. 3. The site lines from the extra tall vaulted ceilings with massive front elevation windows, wide open spaces and natural light directed from all sides. 4. The finishes have been thoughtfully curated and intentionally designed to make for a timeless and exceptional living experience rather than conforming to what is trending. 5 Living space matters and so each unit offers a generous 1400 Sq ft floor plan. 6. The outdoor space is proprietary to each floor and spans wide and runs deep coming in at about 14 x 10 for each balcony. 7. There is a 3 car masonry garage to take the guess work out of where to park, and no car needs to settle for an outdoor space come winter! The garage was constructed with a higher load capacity truss system for your potential ideas to do so much more. The property lends itself to the owner/ user with an opportunity to capture $6,000 per month in income from the other two unit, or serves as an ideal investment for an arm chair investor with about $9000.00 per month in income potential. The property is brand new and so there is literally nothing to do but manage it. You can have it all, location, spacious living areas, outdoor space, full masonry structure, 3 car masonry garage and the peace and quiet you want and deserve!

4217 S Indiana Avenue, Chicago

$599,900
6 Beds 4 Baths 12736543 MLS CONTINGENT Status
MULTIPLE OFFERS. Located in Chicago's Portage Park neighborhood just south of Lawrence Avenue, this brick two-flat offers a solid investment or owner-occupant opportunity. Unit #1 spans the main level with 3 bedrooms and 1.5 baths, while Unit #2 occupies the second floor with 3 bedrooms and 1.5 baths of its own. A full, partially finished basement adds valuable extra space for storage and a detached 2-car garage round out the practical features. The brick exterior offers durability and classic two-flat character. Just steps from the Jefferson Park Transit Center - with CTA Blue Line, Metra, and bus access - and close to the neighborhood's shops, restaurants, and everyday conveniences along Lawrence Avenue, this property offers strong appeal for tenants and owners alike.

4552 N Lockwood Avenue, Chicago

$650,000
10 Beds 4 Baths 12734913 MLS CONTINGENT Status
Excellent investment opportunity in West Humboldt Park! This well-maintained and updated in 2024 three-flat INCLUDES AN ADDITIONAL GARDEN UNIT, OFFERING FOUR SPACIOUS LIVING SPACES with strong income-producing potential. Each unit features generous room sizes, abundant natural light, and newer stainless-steel appliances. New roof 2022,New Copper Plumbing lines replaced 2024 in all units. The flexible layouts provide comfortable living areas and plenty of space for tenants to feel at home. Whether you are an experienced investor or an owner-occupant, this property offers exceptional possibilities. Conveniently located near the CTA Green Line, several bus routes, Garfield Park Conservatory, shopping, dining, and major roadways. Don't miss your opportunity to own a versatile multi-unit property in West Humboldt Park!

3814 W Ohio Street, Chicago

$374,900
6 Beds 3 Baths 12515780 MLS CONTINGENT Status
Recently renovated duplexed-down all-brick 2-unit building offering 6 bedrooms and 2.1 bathrooms in the vibrant Auburn Gresham neighborhood. Situated on a well-maintained block just minutes from downtown Chicago, this turnkey investment presents an excellent opportunity for both owner-occupants and investors. The main-level unit features a spacious eat-in kitchen with ample cabinets, granite countertops, stainless steel appliances, custom tile backsplash, and hardwood flooring. The spacious living room showcases original built-ins with custom glasswork and a decorative fireplace, blending timeless character with modern updates. Two bedrooms and a tastefully renovated full bath complete the main level, while the finished lower level offers a large family room, two additional bedrooms, an updated powder room, laundry area, and ample storage. The upper unit has also been thoughtfully remodeled with an eat-in kitchen featuring new cabinetry, updated countertops, stainless steel appliances, a breakfast peninsula, and new LVP flooring. Featuring another generous living room with original built-ins and a decorative fireplace, two bedrooms and a renovated full bathroom. 2 car garage for convenience and added storage. All improvements were completed with approved plans and permits including new HVAC systems, electrical, plumbing, appliances, vanities, flooring, lighting, paint, and a new rear staircase. Each unit is equipped with separate forced-air heating and central air conditioning, providing added efficiency and individual tenant control. Conveniently located near parks, schools, shopping, dining, and public transportation, this move-in-ready property is well-positioned to attract strong, long-term tenant demand.

7824 S Morgan Street, Chicago

$580,000
5 Beds 3 Baths 12738475 MLS CONTINGENT Status
Discover the opportunity in Archer Heights with this well-maintained two-unit property, ideal for an owner-occupant or investor looking to expand their portfolio. Each unit offers 2 spacious bedrooms, a bright living room, a full bathroom, and an updated kitchen featuring appliances, modern cabinetry, and stylish countertops. The first-floor unit and basement are currently vacant, offering immediate flexibility for an owner-occupant, rental opportunity, or additional living space. The partially finished basement includes an additional bedroom and bathroom, with the potential to duplex with the first-floor unit. The second-floor unit provides additional rental income potential, while the spacious unfinished attic offers excellent possibilities for future expansion and the potential to duplex with the second-floor unit. Outside, enjoy a generously sized backyard, perfect for entertaining, gardening, or relaxing, along with a detached 2-car garage for added convenience. With flexible living arrangements, expansion potential, and a desirable Archer Heights location, this property offers a great combination of space and opportunity. Schedule your private showing today!

4730 S Komensky Avenue, Chicago

$300,000
6 Beds 4 Baths 12738426 MLS CONTINGENT Status
Endless possibilities await at this unique Chicago property featuring a classic brick 2-unit with a detached coach house, offering exceptional flexibility for investors, owner-occupants, or multi-generational living. The front building features a new roof (2026), two spacious 2-bedroom, 1-bath residences filled with natural light and vintage charm, while the separate coach house provides a private 1-bedroom, 1-bath living space with its own entrance. Set on a generously sized lot, the property also offers a 2-car garage, private patio, and a fenced yard, creating rare outdoor space that's hard to find in the city. Whether you're looking to generate multiple income streams, live in one unit while renting the others, or add value over time, this property delivers incredible potential. Conveniently located near schools, parks, shopping, restaurants, public transportation, and expressways, it offers easy access to everything the city has to offer.

2639 S Trumbull Avenue, Chicago

$74,900
3 Beds 3 Baths 12736520 MLS CONTINGENT Status
Investor special in the highly sought-after Woodlawn area! This property at 6405 S. Everhart presents a full gut rehab opportunity-perfect for seasoned investors or developers looking to bring their vision to life. The building requires a complete renovation, offering a blank slate to design modern, income-producing units from top to bottom. Ideal for a fix-and-flip or long-term rental portfolio addition. Lender-owned, bring all OFFERS! The seller would consider seller financing, including repairs, as part of the loan. Property is being sold as-is. Buyer reserves the right to an inspection contingency. However, the Seller will not renegotiate the price after the offer has been accepted.Setup for a non-conforming 3rd garden unit

6405 S Eberhart Avenue, Chicago

$574,900
5 Beds 3 Baths 12736554 MLS CONTINGENT Status
Location, Location, Location! Beautiful legal 2 flat in exceptional area. Situated on a prime corner lot in the highly desirable Jefferson Park/Forest Glen neighborhood, this meticulously maintained 2 flat features a first floor that offers a beautifully updated kitchen with granite countertops, stainless steel appliances, hardwood floors, and recessed lighting throughout the living room, dining room and sunroom, two spacious bedrooms, generous closet space, and full ceramic-tiled bath complete the first floor. The well cared for second floor features a living room, dining room, kitchen, two bedrooms and a full bath. The finished basement features a one bedroom suite complete with its own kitchen, full bath, and combined living and dining area, providing even more flexibility for multigenerational living. Conveniently located just minutes from the Metra, CTA blue line, Kennedy and Edens Expressways, and only one block from Mariano's and the secretary of State office. Broker or seller do not represent the legality of the basement in law suite.

5364 N Latrobe Avenue, Chicago



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