Woodlawn, Chicago IL · Curated MLS Search

3-Flats in Woodlawn, Chicago IL

An editorially curated view of every active 3-flats listing in Woodlawn, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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Woodlawn Market — 3-Flats Comparison

Live MLS data — Woodlawn vs. 3-Flats

Woodlawn

3-Flats

inventory

Active Listings

Sold (Past 6 Mo.)

Under Contract

pricing

Avg. List Price

$427,689

$939,633

Cost / Sq. Ft.

$207

—

typical home

Living Area

1,723 ft²

—

Avg. Beds

4.0

8.3

Avg. Baths

3.0

5.7

Days on Market

142

3-Flats in Woodlawn: Market Data

Data as of October 20, 2026 (MLS snapshot; listings below update live)

Chicago Real Estate Source's review of MLS data as of October 20, 2026 shows 3 active listings for Woodlawn 3-flats. Listings like these do not come up often in Woodlawn. That is about 5% of the 58 active listings in Woodlawn across every property type. Over the past six months, 1 listing in this search sold. With so few listings, setting up a listing alert is the easiest way to learn of the next one.

3-Flats in Woodlawn, Chicago IL, October 20, 2026
Measure	Value
Active listings	3
All active listings in Woodlawn, every property type	58
Sold, past six months	1

3-Flats in other neighborhoods

Chicago: 173 active, median $529,900
Logan Square: 8 active
South Shore: 6 active
Bronzeville: 5 active
West Ridge: 5 active

Market questions

How many Woodlawn 3-flats are on the market?

There were 3 Woodlawn 3-flats for sale as of October 20, 2026, based on Chicago Real Estate Source's review of MLS data.

How do Woodlawn 3-flats compare with other neighborhoods?

As of October 20, 2026, there were 3 Woodlawn 3-flats for sale. In the same search, Chicago had 173 3-flats for sale at a median list price of $529,900, Logan Square had 8 3-flats for sale and South Shore had 6 3-flats for sale.

How many Woodlawn 3-flats sold recently?

There was 1 sale of Woodlawn 3-flats in the six months before October 20, 2026.

How do Woodlawn 3-flats compare with all active listings in Woodlawn?

As of October 20, 2026, there were 3 Woodlawn 3-flats for sale, out of 58 active listings in Woodlawn across every property type.

Listing data courtesy of Midwest Real Estate Data LLC.

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View All Woodlawn Chicago IL 3-Flats Listings

$959,900

9 Beds ⋅ 6 Baths ⋅ 12770959 MLS ⋅ ACTIVE Status

Welcome to this exceptional 3-flat multi-unit property with a 3-car detached garage, located in the desirable Woodlawn neighborhood, just minutes from the University of Chicago and the Obama Presidential Center. Solid brick building with high-end finishes throughout, ideal for strong rental income and long-term appreciation. Each unit features 42" cabinetry, quartz countertops, custom backsplash, recessed lighting, and a fireplace. Spacious layouts include primary suites with walk-in closets and spa-style baths with frameless glass showers and double vanities. In-unit laundry in all units. Top-floor unit offers vaulted ceilings and additional storage with a large pantry. Professionally organized closets maximize space and tenant appeal. Perfect for investors or owner-occupants-high-demand location with excellent income potential. Don't miss this opportunity to add a quality asset to your portfolio.

6621 S Drexel Avenue, Chicago

$1,100,000

11 Beds ⋅ 7 Baths ⋅ 12726785 MLS ⋅ PRICE CHANGE 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

$659,000

5 Beds ⋅ 4 Baths ⋅ 12673209 MLS ⋅ ACTIVE Status

Attainable, comfortable, healthy, and cool! Award-winning, Greenline Homes Two Flat in Southeast Woodlawn! Greenline Homes has made Woodlawn the destination for high-performance homes in Chicago. We're thrilled to offer a resale of a groundbreaking two-unit building that showcases cutting-edge construction and high-performance materials and design throughout. Unit 1 is a bright, modern garden unit with two bedrooms. Unit 2 is a spacious and modern 3-bedroom/2.5-bath duplex. Sustainable without compromise. Both units boast beautiful and durable quartz countertops, custom cabinetry, and energy-efficient appliances. Own your energy. The building includes a solar photovoltaic system on the roof, which produces much of the building's energy needs and reduces the building's carbon footprint with clean, free renewable energy. Efficiency by design. Engineer-designed and sized zoned Mitsubishi heating and cooling provide extreme comfort and efficiency to both units. Comfort is built right in. Incredible engineered insulation, triple-pane glass, and an air-sealed building envelope make this building quieter and more comfortable than any standard building on the market. Healthy air is standard. Energy return ventilators and Panasonic whisper-quiet exhaust fans ensure consistent, high-quality indoor air while maintaining peak efficiency. The low-maintenance lifestyle. Well-designed exteriors with high-quality materials like James Hardie siding and commercial-grade roofing reduce maintenance, allowing your home to work harder for you, instead of you working hard for it. Greenline Homes is making sustainable, green homes more accessible, and now you can own a sustainable green home with income! Plus, a 2-car garage is included. The home is currently leased, and access for showing is limited. Located steps to Metra Electric Trains, Jackson Park, and the Obama Presidential Center.

1221 E Marquette Road, Chicago

$410,000

6 Beds ⋅ 2 Baths ⋅ 12663098 MLS ⋅ CLOSED Status

Stunning Greystone two-flat in SIZZLING hot Woodlawn! This is an exceptional opportunity in one of Chicago's fastest-growing neighborhoods. This classic multi-unit property offers two spacious 3-bedroom residences with soaring ceilings, original woodwork, and beautiful vintage details, including decorative fireplaces and charming built-ins that showcase timeless character. The partially finished basement already includes a bathroom and offers incredible potential-create a garden unit, duplex down, or reimagine the entire property as a grand single-family home. The options here are truly endless, so bring your vision, your creativity, and your contractor. Ideal for a 203K loan and surrounded by exciting new development. The location is unbeatable-minutes from the Obama Presidential Library, Griffin Museum of Science and Industry, University of Chicago, beaches, golf courses, parks, top-rated schools, and a vibrant dining scene. Schedule your showing today and explore the possibilities. Property is being sold **AS-IS**.

6418 S Drexel Avenue, Chicago

$680,000

8 Beds ⋅ 3 Baths ⋅ 12493562 MLS ⋅ CLOSED Status

Brick 3 flat on over-sized 171' lot in Woodlawn/Hyde Park. One 2 bedroom 1 bathroom unit and two 3 bedroom 1 bathroom units. All oversized units with newer rehabs. Each unit has separate living and dining rooms with balconies, individual furnaces, fireplaces and hardwood floors. Units also include side by side washer/dryer and exterior parking. Unit 2 is vacant allowing for owner occupant buyer. New roof in 2022.

6239 S Ellis Avenue, Chicago

$955,000

10 Beds ⋅ 7 Baths ⋅ 12178324 MLS ⋅ CLOSED Status

Brand new rehab of a graystone three flat. Turn key investment with nothing to do but collect rent! Perfect for a 1031 exchange. Beautiful stone facade with tons of vintage character. Fresh interiors with on trend design features. Unit 1 is a large, 4 bed/3 bath duplex down with walkout lower-level family room. Unit 2 is a 3 bed/2 bath second floor simplex. Unit 3 is a 3 bed/2 bath top floor simplex. Enclosed yard + large parking area with one space per unit. Conveniently located near the lake, Jackson Park, shopping, dining, transportation, and much more. Rents are estimated.

6520 S Minerva Avenue, Chicago

$962,000

9 Beds ⋅ 6 Baths ⋅ 12050216 MLS ⋅ CLOSED Status

LAST ONE OF TWO REMAINING! Welcome 6340-42 S Drexel Discerning Designed Residences. Set in exceptionally well located Woodlawn on the confluence of Hyde Park walking distance to University of Chicago Campus. Magazine Caliber Simply Stunning, Expansive footprint, set on 25 x 132 deep lot with 3 car garage. New Construction 3 flat all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Custom Back splash, Engineered floors, Fireplace, Curated Gallery of Cohesive Design Offering relief from ordinary, Sequestered Primary Suite with walk in closet, lifestyles primary bathroom offer Opulent over sized Shower w/ Frame less Glass, Double Vanity, Custom Mirrors and Designer Plumbing fixtures. Professional closet organizers throughout, 3 car Garage. Urban Intimacy w/ Hyper Convenience Experience excellence. Veteran developers of 25 + years, 1 year warranty included. Hyper Convenient, AAA Trophy Piece Perfect Turn key, Owner Occupied, Investor or 1031. This is part of a 2 building series. This is an exceptional property and location. Show and sell. Delivery end of April 2024 - Pictures of Similar Building. All showings will start at model location @ 4228 S Langley then Looping Back through Drexel.

6340 S Drexel Avenue, Chicago

$949,000

9 Beds ⋅ 6 Baths ⋅ 12022430 MLS ⋅ CLOSED Status

Welcome 6340-42 S Drexel Discerning Designed Residences. Set in exceptionally well located Woodlawn on the confluence of Hyde Park walking distance to University of Chicago Campus. Magazine Caliber Simply Stunning, Expansive footprint, set on 25 x 132 deep lot with 3 car garage. New Construction 3 flat all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Custom Back splash, Engineered floors, Fireplace, Curated Gallery of Cohesive Design Offering relief from ordinary, Sequestered Primary Suite with walk in closet, lifestyles primary bathroom offer Opulent over sized Shower w/ Frame less Glass, Double Vanity, Custom Mirrors and Designer Plumbing fixtures. Professional closet organizers throughout, 3 car Garage. Urban Intimacy w/ Hyper Convenience Experience excellence. Veteran developers of 25 + years, 1 year warranty included. Hyper Convenient, AAA Trophy Piece Perfect Turn key, Owner Occupied, Investor or 1031. This is part of a 2 building series. This is an exceptional property and location. Show and sell. Delivery end of April 2024 - Pictures of Similar Building. All showings will start at model location @ 4228 S Langley then Looping Back through Drexel.

6342 S Drexel Avenue, Chicago

$385,900

8 Beds ⋅ 3 Baths ⋅ 11908620 MLS ⋅ CLOSED Status

Introducing this exceptional 2 flat Graystone with Garden unit, composed of a 4 bed/1 bath on 2nd floor, 3 bed/1 bath on main floor and a 1 bed/1 bath garden. Each unit features a private entrance to the residence and a beautiful fully fenced in backyard perfect for relaxing & enjoying the outdoors or ample entertaining space. With updated and extremely spacious units, every level can enjoy hardwood floors, high ceilings, abundance of natural light, and potential to have a home office, fitness room, guest room, art studio, game room, craft room...the possibilities are endless! This property presents an incredible investment opportunity (projected rent of $1,000+ for the 1st and 2nd floor units and $875+ for the Garden unit) while tenants can enjoy everything Woodlawn and Hyde Park have to offer. Or seamlessly blend owner occupant convenience, income generating potential, and equity building for the future! Perfectly located along the developing 63rd Street corridor, walking distance to The University of Chicago and The Obama Presidential Library, nearby gorgeous Lake Michigan & beaches including Jackson Park Harbor, Downtown Chicago, CTA and Metra stations, expressways, shopping, restaurants, entertainment, and museums! Detached 2 car garage and permitted street parking are available.

6147 S Drexel Avenue, Chicago

$587,500

11 Beds ⋅ 6 Baths ⋅ 11899197 MLS ⋅ CLOSED Status

East Woodlawn 3 Flat; 0ne-3 bedroom unit & two-4 bedroom units. New plumbing and electrical, updated baths and kitchens, hardwood floors, in-unit washer & dryers. Individual heat and central air. Small backyard with parking pad for two cars.

6625 S Minerva Avenue, Chicago

$210,000

6 Beds ⋅ 5 Baths ⋅ 11884641 MLS ⋅ CLOSED Status

Nice 2-flat building in HOT Woodlawn that needs work but could be a gem! Each unit has 3 bedrooms 1.1 bathrooms in each unit, a formal living room and dining room in each unit, eat-in kitchen, a 1/2 bathroom in the primary bedroom on the second floor, an updated bathroom on the second floor and a sun room in the second floor unit. There is a 2-car brick garage, an enclosed porch and a partially finished basement with a 1/2 bathroom and family room with a dry bar. Can be used as a total investment property or live in one unit and have a tenant in the other unit to help pay your mortgage! Tenants pay their electric and cooking gas. There a number of possibilities! Being sold "as is".

6617 S Minerva 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

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