Refine Search
Sort by
$625,000
8 Beds 2 Baths 12740513 MLS CONTINGENT Status
Brookline Real Estate is pleased to present 823 S. Carpenter Street, a fully leased two-unit investment property in Chicago's Little Italy/University Village neighborhood. The property contains two four-bedroom, one-bath apartments and totals approximately 2,656 square feet. Located within the UIC campus and near the Illinois Medical District, Taylor Street, public transportation and downtown Chicago. The property offers immediate income in a highly desirable, supply-constrained rental market. Additional financial and property information is available in the sales brochure. Proof of funds and pre-approval required. Showing to start Friday afternoon at 12 PM. There may be overlap in showings.

823 S Carpenter Street, Chicago

$464,500
6 Beds 4 Baths 12731701 MLS CONTINGENT Status
Experience a rare opportunity to own an **oversized** two-flat in the highly sought-after Pill Hill community, offering remarkable space, versatility, and comfort. Each unit boasts more than 1900 sq feet of living area, designed with an open-concept layout that's perfect for modern living and entertaining. Step into expansive living and dining rooms that flow seamlessly together, complemented by a generous family room in each unit for added relaxation and gathering space. Both residences feature 3 well-appointed bedrooms and 2 full bathrooms, providing ideal accommodations for owner-occupants, extended families, or savvy investors seeking strong rental potential. The property also includes an attached 2-car garage, a desirable convenience rarely found in the area. A finished basement with a large recreation room and private entry adds even more flexibility-perfect for a home gym, media room, workspace, or additional entertaining zone. Situated in the established Pill Hill neighborhood, this unique oversized two-flat blends space, function, and location-an exceptional opportunity that doesn't come to market often.

1630 E 92Nd Place, Chicago

$649,900
5 Beds 3 Baths 12738930 MLS PENDING Status
Classic brick Chicago two-flat offering two spacious 2-bedroom, 1-bath residences plus a finished non-conforming lower level that adds exceptional flexibility and potential. An excellent opportunity for an owner-occupant or investor, the property provides the ability to live in one unit while generating rental income from the other, with the lower level offering additional potential for supplemental income or extended living arrangements, subject to applicable zoning and legal-use requirements. Both conforming units feature generous living and dining spaces, hardwood flooring, abundant natural light, private kitchens, and well-proportioned bedrooms. The upper residence offers a comfortable, open flow with a spacious kitchen, expansive living and dining areas, and additional enclosed porch space. The main-level residence provides equally flexible living space with its own kitchen and private accommodations. The finished basement includes one bedroom, one full bathroom, a full kitchen, and both interior and exterior access. Additional features throughout the property include multiple enclosed porch and bonus spaces, laundry, storage, and plenty of opportunity to update or personalize over time. Outside, the solid brick exterior is complemented by a fenced front yard, mature landscaping, rear patio and green space, creating additional room to enjoy the property beyond the interior. Conveniently located near neighborhood favorites along Kedzie, Irving Park, and Montrose, with easy access to Independence Park, Horner Park, the Brown and Blue Lines, and notable area schools including Lane Tech College Prep, Northside College Prep, and DePaul College Prep. Whether you're looking to house-hack, expand your investment portfolio, or create a flexible multi-generational living arrangement, this two-flat offers space, versatility, and compelling income potential in a well-connected Chicago neighborhood.

4252 N Whipple Street, Chicago

$649,000
4 Beds 2 Baths 12733369 MLS ACTIVE Status
This rare 1 story style duplex has been completely renovated from top to bottom, inside and out! The exterior features an all new torch-down roof, windows, doors, siding, gutters, vents, mailboxes, light fixtures, and all of the brick has been properly tuck-pointed. Inside, both units have undergone a total transformation into truly turnkey condition, ready for immediate occupancy. All new engineered hardwood flooring, oversized 7" baseboards, doors/hardware, blinds, closet shelving, and wooden railings with metal balusters throughout. Both bathrooms are tastefully remodeled including professionally installed tile work. Both kitchens boast gorgeous white shaker cabinets, quartz countertops, and stainless steel appliances. The basement provides ample storage space and houses the two new high efficiency furnaces along with two new air conditioners outside. The home's zero-front setback allows for a nice large back yard. This location in desirable Norwood Park is only .5 miles from the Metra station and 1 mile from both the CTA Blue Line station and I-90 tollway for easy commuting. See the 3D virtual tour!

7120 W Highland Avenue, Chicago

$420,000
4 Beds 2 Baths 12740079 MLS PENDING Status
Great opportunity to own a classic brick 2-flat in Chicago! Each unit offers 2 bedrooms, 1 full bath, a separate sitting room and approximately 1,000 square feet of living space. The property underwent extensive renovations in 2020, including updates to the kitchens, bathrooms, roof and interior finishes. Both units feature open kitchen and dining areas, quartz countertops, glass tile backsplashes, stainless steel appliances and hardwood flooring. The sitting room in each unit provides flexible additional living space and is ideal for a home office, den or reading room. The full unfinished basement provides plenty of additional storage, and separate utilities add convenience for both owner-occupants and investors. Exterior features include a fenced yard and detached 2.5-car brick garage. An excellent opportunity to live in one unit while generating income from the other or add a solid 2-flat to your investment portfolio. Conveniently located near shopping, dining, transportation and neighborhood amenities. Schedule your showing today!

1749 N Meade Avenue, Chicago

$550,000
9 Beds 6 Baths 12740010 MLS CONTINGENT Status
**Exceptional South Shore 3-flat offering immediate rental income, long-term equity potential, and an outstanding opportunity for an investor OR an owner-occupant looking to HOUSE HACK!** Offered at **$550,000**, this well-maintained brick building features **three jumbo approximately 1,700 SF apartments, each with 3 bedrooms and 2 full bathrooms-9 bedrooms and 6 full baths total.** Each unit offers large living rooms and bedrooms, formal dining rooms, beautiful hardwood floors and generous layouts that are increasingly difficult to find. The building is fully occupied by established, long-term residents who have demonstrated consistent payment history, currently carry **$0 tenant balances**, and take pride in caring for their homes. Current scheduled rent is **$3,912 per month/$46,944 per year**, giving a buyer income from day one, while **all three tenancies are currently month-to-month**, providing valuable future flexibility subject to applicable tenant rights and notice requirements. For a **first-time buyer or owner-occupant**, this is a compelling house-hacking opportunity: live in one of the three large 3-bedroom/2-bath units when legally available while collecting rent from the other two to help offset the cost of ownership. For an investor, the rental-growth potential is substantial. Current rents remain well below the approximately **$2,037/month average identified by the property's rental comparable analysis for similar 3-bedroom apartments within one mile**; at that benchmark, three units would generate approximately **$6,111/month or $73,332/year**, representing approximately **$2,199/month/$26,388 per year of potential additional gross rental income-about 56% above today's scheduled rent roll-if all three units ultimately achieved that benchmark.** Unit 2 currently rents for **$1,287/month**, and a **CHA rent increase to $2,000/month has already been submitted and is pending approval**, which alone would add **$713/month or $8,556/year** if approved. The building was designed with income-property ownership in mind: **tenants pay their own gas, heat and electricity**, each unit has **separate forced-air heating and individual controls**, and the property includes a **full basement with tenant storage, landlord storage, natural-gas basement heat and coin-laundry facilities as reported in the prior listing.** The full basement's size, ceiling height, layout and access may also offer an exciting opportunity to investigate future additional living/income-producing space or a garden/ADU configuration, **subject to City of Chicago approval, zoning, permits and buyer due diligence.** Outside, the property includes a valuable **owned detached 3-car garage**; the prior listing also reported a newer tear-off roof on the main building with a transferable warranty and a **2020 tear-off garage roof**, which buyers should independently verify. The equity story is equally exciting: comparable-market analysis reviewed during the listing process included renovated multifamily product with finished garden space selling in the **$700,000+ range**. Against the **$550,000 asking price**, that illustrates a **$150,000+ gross valuation spread** and the potential opportunity to build substantial equity through thoughtful improvements, increasing below-market rents and maximizing the property's existing space; comparable properties differ and future value is not guaranteed. Located in **South Shore**, one of Chicago's established lakefront communities, the property offers convenient access to the lakefront, beaches, schools, shopping and the recreational and cultural amenities surrounding the neighborhood. Whether you're a seasoned investor seeking a stabilized building with significant room to increase income, or a **first-time owner-occupant who wants to live in a spacious unit while tenants help pay the mortgage**, this property offers something increasingly difficult to find: **a clean and proven rent roll, $46,944 in current annual

7414 S Chappel Avenue, Chicago

$250,000
4 Beds 2 Baths 12738692 MLS CLOSED Status
Welcome to this legal 2-unit property in the Chicago Lawn area, offering two 2-bedroom, 1-bathroom units. The first-floor unit features a formal dining room, while both units offer separate electric and gas services, forced-air heating, and thermal-pane windows. The full basement has approximately 6-foot ceilings and offers additional potential for storage or future living space. The basement also includes two washers and two dryers, which will remain with the property. The second-floor unit is currently vacant, offering flexibility for an owner occupant or future tenant. Conveniently located near Western Avenue and CTA bus service. Property is being sold with two units and offers a great opportunity to add value over time. Please do not take photographs or videos inside the units.

6217 S Claremont Avenue, Chicago

$635,000
6 Beds 4 Baths 12739841 MLS CONTINGENT Status
Endless possibilities await at this classic two-unit property in the highly desirable location. Featuring a spacious duplex-up and duplex-down configuration, this building offers an outstanding opportunity for investors, rehabbers, or owner-occupants looking to build equity in one of Chicago's most sought-after neighborhoods. Both units offer generous living space and the convenience of in-unit laundry, providing an excellent foundation for a renovation or value-add project. With strong bones and an ideal layout, this property is ready for your vision. Renovate and maximize rental income, create stunning owner-occupied living with additional rental revenue, or update both units for long-term investment potential. Located in an unbeatable location, you'll enjoy easy access to restaurants, coffee shops, grocery stores, parks, entertainment, public transportation, and major expressways. Just minutes from Roscoe Village, Lakeview, Bucktown, and the Southport Corridor, the neighborhood continues to attract homeowners and renters alike, making this an exceptional investment opportunity.

3008 N Clybourn Avenue, 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

$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 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

$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



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.