South Shore, Chicago IL · Curated MLS Search

3-Flats in South Shore, Chicago IL

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

Browse Active Listings

South Shore Market — 3-Flats Comparison

Live MLS data — South Shore vs. 3-Flats

South Shore
3-Flats
inventory
Active Listings
119
6
Sold (Past 6 Mo.)
138
8
Under Contract
55
5
pricing
Avg. List Price
$283,589
$430,000 ↑ 52%
Cost / Sq. Ft.
$124
—
typical home
Living Area
1,297 ft²
—
Avg. Beds
3.3
8.0 ↑ 144%
Avg. Baths
2.2
3.8 ↑ 77%
Days on Market
169
99 ↓ 41%

3-Flats in South Shore: Market Data

Data as of (MLS snapshot; listings below update live)

As of October 20, 2026, Chicago Real Estate Source's review of MLS data shows 6 active listings for South Shore 3-flats. That is about 5% of the 119 active listings in South Shore across every property type. At the time, 5 more were pending, and 8 sold in the past six months.

3-Flats in South Shore, Chicago IL, October 20, 2026
MeasureValue
Active listings6
All active listings in South Shore, every property type119
Under contract5
Sold, past six months8

3-Flats in other neighborhoods

Market questions

How many South Shore 3-flats are on the market?

There were 6 South Shore 3-flats for sale as of October 20, 2026, based on Chicago Real Estate Source's review of MLS data.

How do South Shore 3-flats stack up against other neighborhoods?

As of October 20, 2026, there were 6 South Shore 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 Bronzeville had 5 3-flats for sale.

How many South Shore 3-flats sold in the past six months?

8 South Shore 3-flats sold in the six months before October 20, 2026.

How many South Shore 3-flats are pending?

As of October 20, 2026, 5 South Shore 3-flats were under contract.

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

As of October 20, 2026, there were 6 South Shore 3-flats for sale, out of 119 active listings in South Shore across every property type.

Listing data courtesy of Midwest Real Estate Data LLC.

Next Steps in South Shore, Chicago IL

View All South Shore Chicago IL 3-Flats Listings

7741 S Yates Boulevard, Chicago
$590,000
9 Beds ⋅ 3 Baths ⋅ 12780562 MLS ⋅ ACTIVE Status
Welcome to this exceptional South Shore three-flat offering timeless Chicago architecture, generous living space, and outstanding investment potential. This classic brick building features three spacious units, each thoughtfully designed with large room sizes, abundant natural light, hardwood flooring, separate dining rooms, and versatile den spaces that can easily serve as home offices, sitting rooms, or additional bedrooms. Rich in vintage character, select units showcase beautiful built-in bookcases and original architectural details that blend seamlessly with tasteful updates. The property is currently producing income with two units occupied, while the vacant third-floor unit presents an outstanding opportunity for an owner-occupant or savvy house hacker to move right in while offsetting their mortgage with rental income from the other two units. For investors, the unit is also being actively marketed for lease, offering the flexibility to bring the building to full occupancy and maximize cash flow. The partially finished basement offers additional usable space and is ready for your finishing touches, creating even more potential to add value. A common-area coin-operated laundry provides an additional income stream, while the detached brick 3-car garage offers valuable parking and the opportunity for supplemental rental income. Completing the property are a rear porch and ample storage, enhancing both functionality and tenant appeal. Ideally situated in the heart of South Shore, you'll enjoy convenient access to Lake Michigan, Rainbow Beach, Jackson Park, the South Shore Cultural Center, the future Obama Presidential Center, Metra and CTA transportation, shopping, dining, parks, and major expressways. Whether you're looking to expand your investment portfolio or take advantage of a rare owner-occupied house hacking opportunity, this is your chance to own a well-maintained, income-producing building in one of Chicago's most historic and steadily revitalizing lakefront neighborhoods. Schedule your private showing today!

7741 S Yates Boulevard, Chicago

7414 S Chappel Avenue, Chicago
$550,000
9 Beds ⋅ 6 Baths ⋅ 12740010 MLS ⋅ ACTIVE Status
BACK ON THE MARKET THROUGH NO FAULT OF THE PROPERTY! PRIOR FHA APPRAISAL: $575,000-$25,000 ABOVE THE $550,000 ASKING PRICE, WITH NO APPRAISER-REQUIRED REPAIRS! The previous FHA buyer reached the week of closing but could not proceed due to an unexpected family medical emergency, completely unrelated to the property, inspection, or appraisal. Here's a second chance to purchase an exceptional South Shore brick 3-flat offering income from day one, potential built-in equity, and significant room to grow! This well-maintained building features THREE JUMBO approximately 1,700 SF apartments, each with 3 bedrooms and 2 full bathrooms-9 bedrooms and 6 baths total. Enjoy spacious living rooms, formal dining rooms, hardwood floors, generous bedrooms, and layouts rarely found at this price. Fully occupied by established, long-term residents with a consistent payment history; ALL TENANTS PAID OCTOBER 2026 RENT ON TIME! Scheduled income is $3,912/month or $46,944/year, and all three tenancies are month-to-month, providing future flexibility subject to applicable tenant rights and notice requirements. INVESTORS: THE RENTAL UPSIDE IS SUBSTANTIAL! A rental comparable analysis identified an approximately $2,037/month average for similar 3-bedroom apartments within one mile. If all three units eventually reached that benchmark, gross scheduled rent could total $6,111/month or $73,332/year-an increase of $2,199/month or $26,388/year (about 56%). Unit 2 currently rents for $1,287/month; a CHA increase to $2,000/month has been requested and is pending approval, potentially adding $713/month or $8,556/year if approved. OWNER-OCCUPANTS: HOUSE HACK! When legally available, occupy one spacious 3-bedroom/2-bath unit and collect rent from the other two to help offset ownership costs. Tenants pay their own gas, heat, and electricity; each apartment has separate forced-air heating and individual controls. The full basement offers tenant and landlord storage, natural-gas basement heat, and coin-laundry facilities as reported in the prior listing. Its size, ceiling height, layout, and access may present an opportunity to investigate additional living space, a garden unit, or ADU, subject to zoning, permits, City approval, and buyer due diligence. An OWNED DETACHED 3-CAR GARAGE adds value! The prior listing reported a newer tear-off main-building roof with transferable warranty and a 2020 tear-off garage roof; buyers should verify. LET'S TALK EQUITY: The previous $575,000 FHA appraisal is $25,000 above today's $550,000 asking price, offering potential immediate equity (not guaranteed). Comparable-market analysis also identified renovated multifamily properties with finished garden space selling in the $700,000+ range-suggesting a potential $150,000+ gross valuation spread versus asking through thoughtful improvements, rent growth, and maximizing existing space. Comparable properties differ and future value is not guaranteed. Located in established South Shore near the lakefront, beaches, schools, shopping, and neighborhood amenities. Whether you're an investor seeking a performing asset or an owner-occupant seeking rental assistance with your mortgage, don't miss this opportunity! NEW SHOWING DATES WILL BE ANNOUNCED as management coordinates with residents to welcome prospective buyers back into the property.

7414 S Chappel Avenue, Chicago

7544 S Essex Avenue, Chicago
$399,999
9 Beds ⋅ 3 Baths ⋅ 12724446 MLS ⋅ ACTIVE Status
OWNER-OCCUPANT & INVESTOR VALUE-ADD OPPORTUNITY IN SOUTH SHORE! Not turnkey. Not overdone. Full of potential. This solid all-brick 3-flat offers approximately 3,200 sq ft, 9 bedrooms, 3 baths, separate utilities and a full basement-with an opportunity to create value through cosmetic renovation. Owner-occupants: Live in one unit while renting the other two, with anticipated rental potential of approximately $4,600/month from the two rented units, subject to market conditions and tenant demand. Investors: Three units create multiple income streams with anticipated rents of approximately $2,300 per unit, or $6,900/month when fully rented. The strategy is simple: BUY RENOVATE RENT BUILD EQUITY Financing options may include FHA 203(k), Conventional Rehab, Cash, or Hard Money, subject to lender/investor approval, property eligibility, borrower qualifications and applicable loan terms. Located in South Shore amid significant public and private investment, including INVEST South/West, the Obama Presidential Center, THRIVE Exchange and 71st Street corridor investment. Future impact is not guaranteed, but the level of investment makes this an opportunity worth a closer look. This is where the opportunity begins: bring your vision, improve the property and create the value. Short sale. Sold AS-IS. Subject to lender approval. If you're looking for a property where the upside comes from what YOU do with it, don't let this one pass without running the numbers. Anticipated rents are estimates for illustrative purposes only. Actual rents, expenses, renovation costs and values may vary. Financing is subject to lender approval, borrower qualification, property eligibility and applicable terms. Buyer to independently verify all information and projections.

7544 S Essex Avenue, Chicago

6835 S Clyde Avenue, Chicago
$749,900
9 Beds ⋅ 6 Baths ⋅ 12664985 MLS ⋅ PENDING Status
This is the one you've been waiting for! Welcome to 6835 S. Clyde Avenue, a stunning all-brick 3-flat in the heart of South Shore, just moments from Jackson Park, the lakefront, beaches, marinas, golf courses, Hyde Park, the University of Chicago, and the transformative Obama Presidential Center. Fully gutted and meticulously renovated from top to bottom, this exceptional property showcases high-end finishes, quality craftsmanship, and thoughtful design throughout, with no expense spared. Each of the three expansive units features a highly desirable 3-bedroom, 2-bathroom layout, offering outstanding flexibility for owner-occupants, house hackers, or those seeking high rental income. One unit is currently operating as a successful short-term rental, demonstrating the property's exceptional income-producing potential. The building also features a full basement with additional possibilities, a solid brick 2-car garage, and outdoor space perfect for entertaining and enjoying Chicago summers. Situated in a rapidly growing lakefront community benefiting from significant public and private investment, this turnkey multifamily property offers the rare combination of luxury finishes, prime location, and exceptional income potential. Whether you're looking to owner-occupy one unit while generating rental income from the other, or add a high-performing asset to your investment portfolio, this is a rare opportunity that doesn't come around often. Properties with this combination of location, flexibility, and income potential are seldom available on the market.

6835 S Clyde Avenue, Chicago

7223 S Coles Avenue, Chicago
$350,000
7 Beds ⋅ 3 Baths ⋅ 12605581 MLS ⋅ CLOSED Status
This classic Chicago brick income-producing two-flat offers a rare opportunity for investors or owner-occupants seeking strong upside potential. Tucked away on an oversized lot in a quiet, character-filled pocket near the lakefront, this property blends space, charm, and location. Inside, you'll find hardwood floors, decorative fireplaces, and spacious layouts throughout. The first-floor duplex features 3 bedrooms, 2 bathrooms, and expanded living space, while the second-floor 3 bed / 1 bath unit is tenant-occupied on a month-to-month basis, providing immediate income potential. Each unit is equipped with its own separate washer and dryer, adding convenience and independence for both owner and tenant living. Major improvements include a new roof (2024), HVAC and furnace systems for both units under 10 years old, and water heaters replaced in 2019 and 2022. Separate utilities and central air for both units add long-term convenience and efficiency. Outside, the large fenced backyard with gazebo offers rare outdoor entertaining space, complete with a sliding rear gate for easy access and added functionality. Ideally positioned near South Shore Golf Course, Lake Shore Drive, Jackson Park, South Shore Cultural Center, the Obama Center, 71st Street Beach, Rainbow Beach, Quantum Shore, Hyde Park, and easy access to Downtown Chicago, this property offers an exceptional combination of accessibility, lifestyle, and hidden-character appeal. Estate sale - sold AS-IS.

7223 S Coles Avenue, Chicago

7824 S Euclid Avenue, Chicago
$580,000
9 Beds ⋅ 3 Baths ⋅ 12520725 MLS ⋅ CLOSED Status
Welcome to 7824 S. Euclid Ave, a beautifully updated jumbo three-flat located in Chicago's thriving South Shore neighborhood. This turn-key property offers exceptionally large, generous bedrooms and living spaces, creating an ideal home for owners and tenants seeking comfort, style, and modern convenience. Each unit features: 3 spacious bedrooms and 1 well-designed bathroom with a smart, efficient layout that keeps each home open, functional, and easy to maintain. Ultra-modern finishes including floor-to-ceiling tile in the bathrooms for a sleek, high-end look. Fully updated plumbing, electrical, and HVAC systems, with central heat and air in every unit. Contemporary kitchens with modern cabinetry, quartz countertops, and stainless steel appliances, In-unit laundry hookups, offering added convenience and increased rental appeal. Additional improvements include a fully renovated rear enclosed porch with brand-new siding, giving each unit a clean and updated rear entryway. This property is completely turn-key and move-in ready, making it an incredible opportunity for both owner-occupants and investors looking for a no-hassle addition to their portfolio. Located close to the lakefront, public transit, parks, and schools, this jumbo building stands out with its size, style, and thoughtful renovations. Don't miss out on this beautifully finished building in one of Chicago's fastest-growing areas! Detached garage present, improvements underway and to be completed.

7824 S Euclid Avenue, Chicago

7419 S Coles Avenue, Chicago
$395,000
4 Beds ⋅ 2 Baths ⋅ 12292831 MLS ⋅ CLOSED Status
Phenomenal South Shore Multi-Family Gem - A Rare Find with Lake Views! An incredible opportunity awaits in South Shore with this well-maintained, expansive 2-flat, perfect for an owner-occupant looking to build long-term equity or an investor seeking strong cash flow in one of Chicago's most sought-after neighborhoods. Each legal unit features formal living and dining areas, a cozy sitting area, spacious bedrooms with high ceilings and striking coffered ceilings in the primary bedrooms, large kitchens with space for an eat-in area, and full-size bathrooms. The partially finished basement with 7+ ft ceiling height and front and rear entry access offers tremendous potential-convert it into a third unit, duplex down the first floor, or utilize it for storage and coin laundry to generate passive income. Recent upgrades include a brand-new back porch (2024) with second-level lake views, a newer fully fenced backyard, a newer garage with a freshly poured concrete parking slab, a roof replaced in 2017, and a brand-new boiler (2018) with a new hot water tank. Investment potential is massive, with fully renovated 2-unit comps appraising at $431,333+ and values reaching $661,750+ with a basement conversion, while 2-bed units rent for $1,900+/mo, and 3-bed layouts can generate $2,300+. Conveniently located steps from the lake, parks, shopping, dining, public transit, and major expressways, this property is also near the soon-to-be-completed Obama Presidential Library and South Shore developments, making it primed for future appreciation. Property sold as-is-schedule your showing today and secure your piece of South Shore's future!

7419 S Coles Avenue, Chicago

7148 S Cornell Avenue, Chicago
$410,000
6 Beds ⋅ 5 Baths ⋅ 12223351 MLS ⋅ CLOSED Status
***SELLER SAYS SELL!!! TWO COMPLETELY SEPARATE UNITS*** Welcome to one of the most UNIQUE PROPERTIES in all of the highly sought SOUTH SHORE area. Whether you have a LARGE FAMILY or are the smart INVESTOR looking for that PERFECT portfolio ASSET, this is the place for you. This property possesses 2 completely REMODELED homes on one lot: The FRONT HOME has 3 bedrooms and 2.5 baths, REAR HOME has 3 bedrooms and 2 baths AND IS RENTED FOR MARKET RATE. Both feature NEW KITCHENS boasting CUSTOM CABINETS with QUARTZ COUNTERS and brand new STAINLESS APPLIANCES. All baths are rehabbed with ornate tile inlays. There are UPDATED electric, plumbing and HVAC systems as well as LAUNDRY IN EACH UNIT. The front home features a NEW ROOF. The rear home has a LARGE WOODEN DECK in front great for getting some outdoor time. This property is the PERFECT IN-LAW LIVING/EXTENDED FAMILY situation or INVESTMENT RENTALS that could garner ALMOST 2000 a month each leased(REAR HOME IS LEASED). Its location and set-up cater to an IDEAL AirBNB opportunity. METRA to HYDE PARK, McCormick Place, Museum Campus and downtown is a HALF BLOCK AWAY. The amazing Chicago LAKEFRONT, two golf courses and the new OBAMA LIBRARY are less than 2 miles. This can live like a single family with the "PERKS" of a two-flat. This IS what you've been looking for so set up your viewing today. VERY MOTIVATED SELLER SO BRING AN OFFER( Sold as/is)

7148 S Cornell Avenue, Chicago

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