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$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
$579,000
4 Beds ⋅ 3 Baths ⋅ 12739570 MLS ⋅ ACTIVE Status
Beautiful, Legal 2 Flat with in-law arrangement in the heart of Jefferson Park. Excellent building includes top floor unit 2 Bed 1 Bath. First floor unit 2 Bed 1 Bath and in-law down for an additional Bed and Bath. Bright open units each equipped with private rear porches. Pictures only reflect second floor unit but first floor is even bigger and more updated. Long time owner, solid and well maintained building. Excellent locations, located on a quiet street close to restaurants, shopping, parks, schools, train and highway! This home has it all! Don't miss out! HURRY!!

4923 N Mason Avenue, 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
$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
$699,000
7 Beds ⋅ 3 Baths ⋅ 12734497 MLS ⋅ ACTIVE Status
Solid Legal Three Unit in this highly sought-after Logan Square neighborhood. Where an incredible investment opportunity awaits. The property can use a little TLC or max its full potential and transform into a modern masterpiece. Prime location is across the street from YMCA and yards away from the 606 trail. Don't miss this exceptional opportunity to invest in Logan Square's dynamic real estate market.

1809 N Lawndale Avenue, Chicago
$549,000
5 Beds ⋅ 2 Baths ⋅ 12738174 MLS ⋅ ACTIVE Status

3556 W Dickens Avenue, Chicago
$69,990
7 Beds ⋅ 3 Baths ⋅ 12738401 MLS ⋅ ACTIVE Status
GREYSTONE TWO UNIT ready for rehab. Two bedroom apartment previously in the basement. First floor 2 bedroom and second floor 3 bedroom. Property in need a lot of work, but will be a good investment/flip. Sold as is. No survey provided.

7137 S Carpenter Street, Chicago
$435,900
5 Beds ⋅ 3 Baths ⋅ 12738280 MLS ⋅ ACTIVE Status
Excellent opportunity to own a well-maintained two-unit property with a versatile third-floor in-law arrangement featuring its own full bathroom. Extensive improvements were completed approximately three years ago, including updates to the electrical systems, HVAC, flooring, kitchens, appliances, fencing, and landscaping. Both units offer comfortable living spaces, while the basement provides a spacious laundry area and additional storage. Enjoy a fully fenced yard with plenty of room for outdoor gatherings, plus a two-car garage. Currently tenant-occupied, this property is an attractive option for investors seeking immediate rental income or owner-occupants planning for future occupancy.

5746 S Paulina Street, Chicago
$599,900
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
$499,900
6 Beds ⋅ 3 Baths ⋅ 12738231 MLS ⋅ PRICE CHANGE Status
CLASSIC CHICAGO BRICK 2-FLAT WITH GARDEN UNIT - EXCELLENT INVESTMENT OR OWNER-OCCUPANT OPPORTUNITY! This well-maintained brick building in desirable West Humboldt Park features 3 spacious 2-bedroom, 1-bath apartments with large formal dining rooms, generous-sized bedrooms, beautiful hardwood floors, and separate utilities. The finished garden unit offers 2 bedrooms, 1 bathroom, (legality of the garden unit is not warranted), making it ideal for extended family or additional rental income. The property has been carefully maintained with three gas meters, and three separate electrical panels. Conveniently located near CTA transportation, shopping, schools, and neighborhood amenities. The building could benefit from some TLC, but it offers tremendous value, solid cash-flow potential, and long-term appreciation. Taxes do not reflect any exemptions. Don't miss this outstanding investment opportunity!

1543 N Avers Avenue, Chicago
$415,000
6 Beds ⋅ 3 Baths ⋅ 12737523 MLS ⋅ ACTIVE Status
Stunning, fully renovated brick 2-flat offering the perfect blend of timeless Chicago character and modern luxury! Whether you're an owner-occupant looking to help out your mortgage or an investor seeking a turnkey income-producing property, this beautifully updated building checks every box. Each spacious unit has been thoughtfully renovated with gleaming hardwood floors, recessed lighting, and an open, light-filled layout. The modern kitchens feature espresso shaker cabinetry, granite countertops, stainless steel appliances, subway tile backsplashes, and abundant cabinet space, creating an ideal setting for everyday living and entertaining. The expansive living rooms showcase beautiful bay windows that flood the space with natural light, while the generously sized bedrooms and updated bathrooms provide both comfort and style. Major improvements throughout offer peace of mind, making this a truly move-in-ready investment. Situated on a quiet, tree-lined street, the property offers easy access to public transportation, major expressways, parks, schools, shopping, and dining. Conveniently located near the University of Chicago, the future Obama Presidential Center, and several ongoing neighborhood revitalization projects, this is an exceptional opportunity to own in one of Chicago's rapidly appreciating South Side communities.

8019 S Eberhart Avenue, Chicago
$310,000
4 Beds ⋅ 2 Baths ⋅ 12735558 MLS ⋅ ACTIVE Status

4903 W Rice Street, Chicago
$200,000
8 Beds ⋅ 3 Baths ⋅ 12737026 MLS ⋅ ACTIVE Status
This property is located in a prime area, close to the Newly opened Obama Center and is already totally gutted. It is ready for Your personal taste and flare to make it your own.

6321 S Rhodes Avenue, Chicago
$495,000
4 Beds ⋅ 2 Baths ⋅ 12737296 MLS ⋅ ACTIVE Status
Great investment opportunity in this rapidly appreciating area. Fully leased Logan Square two-flat featuring 2 bed/1 bath units is ready for its next owner. Each unit offers a good-sized kitchen, 2016 appliances, and a large front porch. The unit is set back on the lot with a large front yard and no buildings on either side. Keep as an income-producing property or redevelop.

3512 W Belden Avenue, Chicago
$847,000
9 Beds ⋅ 6 Baths ⋅ 12736649 MLS ⋅ ACTIVE Status
Discover timeless Chicago architecture in this stately three-unit greystone located in the heart of Bronzeville. Showcasing the distinctive Romanesque style-one of Chicago's most recognized architectural traditions-this classic building blends historic character with modern convenience. Each spacious residence features 3 bedrooms, 2 full bathrooms, and a separate formal dining room offering generous living space ideal for both everyday living and entertaining. The thoughtfully designed interiors include hardwood floors, soaring ceilings, in-unit laundry, and abundant natural light. Spacious kitchens are appointed with granite countertops, ample cabinetry, and room for a breakfast table or casual dining. Each unit is separately metered and equipped with its own furnace and water heater, providing convenience, efficiency, and simplified property management. The first and second-floor units are occupied by long-term tenants, providing immediate, stable rental income. The third-floor unit is currently vacant, presenting an ideal opportunity for an owner-occupant to move right in while benefiting from rental income, or for an investor to lease the unit and maximize the property's income potential. Step outside to enjoy brand-new rear porches, providing each unit with a private outdoor deck. The property also features gated parking with one dedicated parking space for each unit, offering added convenience for residents. The full basement provides additional value with the potential to create an additional dwelling unit or expand the property's existing living space. Situated on a picturesque tree-lined street, this exceptional investment or owner-occupant opportunity is just minutes from public transportation, neighborhood parks and green spaces, and the vibrant dining, shopping, and cultural attractions of nearby Hyde Park and South Loop. Whether you're looking to expand your investment portfolio or own a piece of Chicago's architectural heritage, this exceptional Bronzeville greystone offers the perfect blend of historic character and modern amenities. Enjoy stable rental income or sell later as individual condos. An outstanding opportunity for both investors and owner-occupants.

4408 S Michigan Avenue, Chicago
$415,000
9 Beds ⋅ 3 Baths ⋅ 12737093 MLS ⋅ ACTIVE Status
2 flat with a finished basement apartment featuring 10 bedrooms 3 bathrooms total through out the building , off street parking ,newer roof! tear off 2 years ago with a new chimney built in , the rear porch is a 2019 .no central air-conditioning , theres space for laundry hookups in basement common area. units 1&2 have been renovated with new cabinets and bathrooms have been updated on both floors, pictures online does not reflect that and will be updated. basement features 3 beds 1 bathroom full kitchen and living room area rented out at $1,450 as extra income.

5744 S Green Street, Chicago
$619,998
4 Beds ⋅ 2 Baths ⋅ 12720299 MLS ⋅ ACTIVE Status
An incredible opportunity to add a multi-unit in an outstanding location to your portfolio! This well maintained East Avondale blond brick building can be immediately rented or could also be updated to increase the rental rate. Basement has both an ingress and egress to potentially create a garden unit. Walking distance to the heart of East Avondale/the six corner at Belmont/Elston/California. Close to Logan Square and Roscoe Village. Close to the Metra Station at Clybourn and Ashland. Close to 90/94.Quiet stretch of Elston.

2959 N Elston Avenue, Chicago
$415,000
8 Beds ⋅ 3 Baths ⋅ 12736954 MLS ⋅ ACTIVE Status

830 E 90Th Street, Chicago
$849,900
9 Beds ⋅ 4 Baths ⋅ 12736859 MLS ⋅ ACTIVE Status
Welcome to this beautifully maintained classic 2-unit brick building. Located in the vibrant Tri-Taylor neighborhood, just steps away from the Medical District and UIC campus. This prime location offers easy access to a variety of restaurants, shops, and public transportation options, making it perfect for investors and owner-occupants. All units have tenants on a month to month arrangement. Private parking in the back of building with alley access.

2312 W Taylor Street, Chicago
$390,000
4 Beds ⋅ 2 Baths ⋅ 12735732 MLS ⋅ ACTIVE Status
Great opportunity to own a 2-flat in the heart of Brighton Park, offering excellent options for both owner-occupants and investors. Each unit features 2 bedrooms, 1 bathroom, a spacious living room, and a kitchen with separate utilities. The semi-finished attic already includes insulation, heating, and electricity, offering great potential for additional living space or extra storage with your finishing touches. The property also features forced air heating in both units and a 2-car detached garage. Conveniently located near schools, parks, shopping, public transportation, and the Orange Line.

4505 S Fairfield Avenue, Chicago
$250,000
8 Beds ⋅ 3 Baths ⋅ 12735976 MLS ⋅ ACTIVE Status
**Multiple offers received. H/B due by 4:00PM on 8/20/2026.** Attention developers and investors: SHORT SALE opportunity in North Lawndale. Unlock the potential of this legal 3-flat with tons of upside. Each unit features 3 bedrooms and 1 full bath, 9' ceilings and hardwood floors. A full, unfinished basement offers future expansion potential. This building is situated on an oversized lot, with plenty of space for a garden, a playset a storage shed or just some extra elbow room. With the right vision, an experienced rehabber can create an oasis in the heart of the city. Easy access to public transit at Roosevelt and Pulaski. Close to I-290. Renovated three bedroom apartments are fetching $1800-$2000/month. ARV $515,000 based on recent sales within half a mile of this property. Seize this chance to own an all-brick, legal 3-unit on a huge lot before it's gone!

3943 W 14Th Street, Chicago
$325,900
5 Beds ⋅ 2 Baths ⋅ 12735806 MLS ⋅ ACTIVE Status
This two-unit brick building presents a lucrative investment opportunity. The building is currently occupied, providing a steady stream of cash flow. The basement is ready for your finishing touches, with framing, electrical, and plumbing work already completed. Additionally, there's a washer/dryer hookup in the basement. Both units feature spacious living and dining rooms, generously sized bedrooms, high ceilings, and elegant hardwood floors. The property is securely fenced in both the front and back, and there's a convenient parking pad.

6515 S Marshfield Avenue, Chicago
$294,000
6 Beds ⋅ 2 Baths ⋅ 12735459 MLS ⋅ PRICE CHANGE Status
Excellent Investment Opportunity! Fully occupied 2-flat brick building generating immediate rental income. Each spacious unit features 3 bedrooms and 1 full bathroom, offering comfortable living spaces for tenants. Additional amenities include a shared basement with washer and dryer, providing added convenience and value. Whether you're looking to expand your investment portfolio or start building wealth through real estate, this well-maintained income-producing property is a fantastic opportunity. Strong rental potential, stable occupancy, and room for long-term appreciation make this a must-see investment property! Schedule your showing today.

5719 S Loomis Boulevard, Chicago
$414,000
5 Beds ⋅ 3 Baths ⋅ 12735595 MLS ⋅ ACTIVE Status

5256 S Carpenter Street, Chicago
$345,000
8 Beds ⋅ 2 Baths ⋅ 12693034 MLS ⋅ ACTIVE Status
Fantastic opportunity to own this spacious brick and vinyl 2-flat featuring two oversized 4-bedroom, 1-bath units in a convenient South Side location. Unit 1 has been thoughtfully updated with a new kitchen, vinyl flooring, fresh paint, ceiling fans, dishwasher, new HVAC and water heater, plus washer and dryer, making it an ideal owner's unit. Both units feature separate utilities, allowing tenants to pay their own gas and electric. The property offers solid rental income with additional upside, an unfinished full basement with storage potential, and low property taxes. Enjoy easy access to I-90/94, CTA, parks, and downtown Chicago, all within minutes. Whether you're looking to house hack or add a strong cash-flowing asset to your portfolio, this well-maintained 2-flat is an excellent opportunity.

4448 S Princeton Avenue, Chicago
$400,000
10 Beds ⋅ 2 Baths ⋅ 12734228 MLS ⋅ ACTIVE Status

1431 N Austin Boulevard, Chicago
$419,000
6 Beds ⋅ 2 Baths ⋅ 12732153 MLS ⋅ ACTIVE Status
BUY ALERT! A Washington Heights two flat with the possibility of a third unit (ADU). One option is to buy and house hack. Another is to make it a family building. Ownership comes with myriad of options. This is located near grocery, multiple public transportation options and highways. Book your appointment and see if 9010 Justine fits your dreams of ownership.

9010 S Justine Street, Chicago
$849,900
2 Beds ⋅ 2 Baths ⋅ 12734110 MLS ⋅ ACTIVE Status
Located in the sought-after neighborhood of West Town and on a prime stretch of Grand Ave, this well-positioned 2-unit offers an excellent investment opportunity. The property combines timeless all brick construction with a desirable location and strong rental income potential. This property provides the opportunity for attractive cash flow, making it an ideal addition to an investor's portfolio or a great option for an owner occupant looking to help with their living expenses. The 1st flr. consists of a Living Rm, Kitchen, 2 Bedrooms and one full Bathroom and the 2nd flr unit has an oversized and updated Kitchen with a walk-in pantry (used to be a bedroom), 3 Bedrooms, a Living room and a new, full Bathroom. Both units have a separate furnace, water heater and electric box with 100 amp circuit breakers. The rear has an enclosed/covered deck, an open deck area, a patio and a carport/covered parking with a gated yard. Its prime location, solid construction & income producing potential make this property a must see!

1811 W Grand Avenue, Chicago



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