View All Woodlawn Chicago IL 4-Flats Listings

$1,200,000
11 Beds 7 Baths 12726785 MLS ACTIVE Status
Turnkey cash flowing Rarely Available 4 Flat Building Located in prime East Woodlawn desirable community just steps from Obama Presidential Library, University of Chicago Campuses including Medical School, Law School, University of Chicago Hospital, Charter School, Museum of Science and Industry, Chicago Theological Seminary, Mount Carmel High School, Lake Michigan, Grocery Stores, Multiple Eatery's including the South Shore Cultural Center. A true gem for investors and or owner occupant alike. The 3 above ground oversized units each feature 3 bed/2 Full baths configurations & 1 lower level features an oversized 2 bed 2bath configuration. Property features new interior upgrades such as Copper Plumbing infrastructure, Electrical infrastructure, HVAC infrastructure and drywall. Open floorplan concept layout within each unit with the top floor unit giving a penthouse vibe. Kitchens positioned in the front of each unit 42' Maple shaker style cabinets, granite & laminate countertops, stainless steel appliances & recessed lighting. Meticulously preserved & refinished woodwork architecture & hardwood flooring in the property was blended with new upgrades to keep the charm & character of this historic property. Exterior upgrades include new vinyl windows, concrete parking pad with rear wrought iron gated fence, front wrought iron gated fence with intercom system, treated wood The lower level was renovated by excavating the floor & creating higher head space & upgrading to a new sump pump rainwater drainage system & concrete slab. The property shares a common area laundry with washer/dryer owned by Landlord. Each unit is individually metered & has separate HVAC & Hot Water Heater tanks.

6638 S Woodlawn Avenue, Chicago

$260,000
6 Beds 5 Baths 11953038 MLS CLOSED Status
PRICED TO SELL!!! DON'T PASS ON THIS OPPORTUNITY. LOOKING FOR EXPERIENCED INVESTOR. EXTREMELY RARE OPPORTUNITY IN EAST WOODLAWN IS NOW AVAILABLE!! INVESTOR HAD AN EMERGENCY AND COULDN'T FINISH THE PROJECT. THIS HAS A LUXURY-DESIGNED LAYOUT WITH THREE MASTER SUITES ON THE 2ND FLOOR DUPLEXED TO THE MAIN LEVEL WITH COMPLETE OPEN CONCEPT FLOOR PLAN!!! GREAT FOR 203K OWNER WITH OPTION TO RENT OR AIRBNB LOWER LEVEL. OVER 2,500SF OF LIVING SPACE WITH 4 BEDROOMS AND 3.5 BATHS DUPLEX WITH SEPARATE LARGE LOWER LEVEL APARTMENT WITH 2 BEDROOMS AND 1 FULL BATH EQUIPPED FOR AIRBNB OR RENTAL THAT WILL NEARLY PAY THE MORTGAGE! LOTS OF WORK HAS ALREADY BEEN COMPLETED WITH FULL ARCHITECTUAL PLANS AND PERMIT ALREADY ACQUIRED. ALL NEW ROUGH FRAMING, SUPPORT BEAMS AND STAIRCASE IS 100% COMPLETED. ALL NEW DUCTWORK COMPLETED 100%. ALL NEW ROUGH ELECTRICAL 100% COMPLETED WITH DUAL 200AMP SERVICE AND PANELS INSTALLED. THE BASEMENT ALREADY HAS UNDERGROUND PLUMBING (PASSED CITY INSPECTION), DRAIN TILE INSTALLED, ALL NEW CEMENT BASEMENT FLOOR POURED WITH OVER 7FT CEILING HEIGHT. NEW ROOF HAS BEEN INSTALLED. GARAGE ROOF, OVERHEAD DOOR AND TUCKPOINTING COMPLETED. ALL NEW FLAT ROOF INSTALLED FOR BUILDING. EVERYTHING HAS BEEN DONE UP TO CITY CODE. JUST ADD ROUGH PLUMBING AND YOU'RE READY FOR ALL CITY INSPECTIONS. THE VALUE POTENTIAL IS ENDLESS AS EAST WOODLAWN IS ONE OF THE MOST PRIME REAL ESTATE IN CHICAGO WITH THE PROXIMITY TO ALL AMENITIES: NEW OBAMA LIBRARY, UNIVERSITY OF CHICAGO, MUSUEM OF SCIENCE AND INDUSTRY, LAKE SHORE BEACHES, JACKSON PARK GOLF COURSE, CTA GREEN LINE, HYDE PARK AND SO MUCH MORE. ARV IN THE 700'S. GREAT FOR 203K OR INVESTOR TO FINISH AND REAP THE BENEFITS! SOLD AS-IS. TAX PRORATION 100%. Listing Agent Interest. 2022 Survey provided. MOTIVATED SELLER! Send all offers!

6627 S Maryland Avenue, Chicago

$867,500
11 Beds 7 Baths 11882076 MLS CLOSED Status
Located in prime Woodlawn location, rarely available Legal 4 Flat was renovated in 2016 by a reputable rehabber. Purchase as an investment or to live in. The 3 above ground oversized units each feature 3 bed/2 bath configurations & 1 lower level features an oversized 2 bed/bath configuration. Property renovations were completed in 2016 and feature new interior upgrades such as Copper Plumbing infrastructure, Electrical infrastructure, HVAV infrastructure and drywall. The floorplan layout was reworked to have open concept Kitchens in the front area of the units with 42' Maple shaker style cabinets, granite & laminate countertops, stainless steel appliances & recessed lighting. Meticulously preserved & refinished woodwork architecture & hardwood flooring in the property was blended with new upgrades to keep the charm & character of this historic property. Exterior upgrades include new vinyl windows, concrete parking pad with rear wrought iron gated fence, front wrought iron gated fence with intercom system, treated wood rear staircase & maintenance fee vinyl siding wrapped porch. The lower level was renovated by excavating the floor & creating higher head space & upgrading to a new sump pump rainwater drainage system & concrete slab. The property shares a common area laundry with washer/dryer owned by Landlord. Each unit is individually metered & has separate HVAC & Hot Water Heater tanks. This property is located walking distance to University of Chicago Hospital & University of Chicago, University of Chicago Law School, University of Chicago Charter School, Toyota Technological Institute of Chicago, Chicago Theological Seminary, Mount Carmel High School, Lake Michigan, Parks, multiple grocery & eating locations.

6638 S Woodlawn Avenue, Chicago

$131,900
7 Beds 2 Baths 11858076 MLS CLOSED Status
East Woodlawn is one of the fastest appreciating neighborhoods in the entire nation! This 2-unit is available for an absolute steal! There is so much upside for an investor looking to make a large profit or a homeowner looking to plant their feet in an area that will continue to aggressively appreciate for years to come! This solid 2-flat includes two residential units, a full walkout basement and a private enclosed back yard! Unit #1 has 3-bedrooms, and 1 full bathroom and Unit #2 has 4-bedrooms and 1 full bathroom. Updated 4-bedroom apartments can rent for $2,000+ per month and updated 3-bedroom apartments can rent for $1,700+ per month in this neighborhood! The strategy that will yield the maximum equity or profit margin will be achieved by converting this 2-unit into a legal 3-unit by digging down the large unfinished basement 3-5 inches and cooperating with the city of Chicago to improve the zoning from a 2 to 3-unit residential property. This strategy was effective at 6235 S. Eberhart which was sold in December of 2022 for $585,000. The after-repair-value for non-new construction 3-units or 2-units with legal garden apartments is $570,000, based on comparable sales within the past 6 months! With the right construction strategy there is an approximate $170,000 - $200,000 profit margin available! In 2020 the city of Chicago passed the Additional Dwelling Unit Ordinance which provides owners of multi-units with up to $35,000 in funds in the form of a forgivable loan to create additional living space in the basement or attic! For more ambitious investors, there is also potential to dormer the attic to create additional living space or build a coach house in the back yard which the ADU ordinance also supports in the effort to achieve an even higher valuation ($600,000+). For the traditional retail buyer that wants to convert this multi-unit into a single-family home, the approximate after-repair-value for this strategy is $700,000+ based on comparable SFH sales! The retail buyer has the equity available to significantly invest in the conversion project and enjoy a great home with $100,000+ in equity upon completion or an investor can enjoy an approximate $75,000 - $150,000 profit with the right construction strategy implemented. There are a plethora of new construction projects on Maryland Ave with many multi-units that have recently sold for a little under 1-million dollars each! A+ location! Walking distance from Washington Park, Minutes from the Lakefront, proximity to The University of Chicago, the Obama Presidential Library, Dan Ryan, Red Line and Jackson Park! Priced to sell so please act swiftly! ***This property is already hard money approved with our lender that requires 7% down and will finance 100% of the renovation***

6605 S Maryland Avenue, Chicago

Start Your Search



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.

Woodlawn, Chicago IL · Curated MLS Search

4-Flats in Woodlawn, Chicago IL

An editorially curated view of every active 4-flats listing in Woodlawn, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings