Real Estate Investment Properties for Sale in Oak Lawn, IL

Looking for investment property in Oak Lawn, IL with high ROI ?

Explore a variety of short-term homes & houses in Oak Lawn, IL. Invest wisely with VRBO & Oak Lawn, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Oak Lawn, IL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5909 W 99th Street Oak Lawn, IL Adorable Juliet Split Level awaits you! Vaulted ceiling makes a great first impression, gi...	3 beds \| 2 baths \| 1,107 sq.ft.	$256,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 5.12% Airbnb Rental Income: $1921 Traditional Rental Income: $2343 Airbnb ROI: 1.27% Traditional ROI: 5.12%
4108 W 103rd St Oak Lawn, IL Vintage Colonial in the heart of Oak Lawn offering classic charm, generous space, and grea...	4 beds \| 1 baths \| 1,800 sq.ft.	$399,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.83% Airbnb Rental Income: $1710 Traditional Rental Income: $2718 Airbnb ROI: -0.12% Traditional ROI: 3.83%
9440 S 51st Avenue #502 Oak Lawn, IL Top Floor Unit! This is a very spacious unit with an open concept living/dining combo, thi...	1 beds \| 1 baths \| 1,052 sq.ft.	$189,900	Airbnb cash on cash: -0.54% Traditional cash on cash: 5.1% Airbnb Rental Income: $1356 Traditional Rental Income: $1959 Airbnb ROI: -0.54% Traditional ROI: 5.1%
9812 S Karlov Ave #4D Oak Lawn, IL WELCOME HOME TO OAK LAWN! THIS BEAUTIFUL 2 BED, 2 BATH CONDO IN DESIRABLE AREA. ENJOY A SU...	2 beds \| 2 baths \| 1,100 sq.ft.	$219,900	Airbnb cash on cash: 0.84% Traditional cash on cash: 4.21% Airbnb Rental Income: $1529 Traditional Rental Income: $1818 Airbnb ROI: 0.84% Traditional ROI: 4.21%
10048 S Pulaski Rd #3E Oak Lawn, IL STUNNING MOVE IN READY RECENTLY UPGRADED TWO-BEDROOM, TWO-BATH CONDO IN DESIRABLE ELEVATOR...	2 beds \| 2 baths \| 1,080 sq.ft.	$154,900	Airbnb cash on cash: 1.37% Traditional cash on cash: 5.59% Airbnb Rental Income: $1529 Traditional Rental Income: $1730 Airbnb ROI: 1.37% Traditional ROI: 5.59%
5121 Deblin Ln Oak Lawn, IL Come check out this beautiful townhome Located in the desirable Eagle Ridge area of Oak La...	2 beds \| 1 baths \| 1,850 sq.ft.	$258,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 6.04% Airbnb Rental Income: $1529 Traditional Rental Income: $2642 Airbnb ROI: -0.35% Traditional ROI: 6.04%
9725 S Karlov Ave #401 Oak Lawn, IL Large 2 bedroom, 1.5 bath unit on 4th floor. Huge living room/formal dining combo & big m...	2 beds \| 1 baths \| 1,000 sq.ft.	$165,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 7.44% Airbnb Rental Income: $1529 Traditional Rental Income: $2070 Airbnb ROI: 1.19% Traditional ROI: 7.44%
9601 S Karlov Avenue #101 Oak Lawn, IL Beautiful first-floor condo now available in desirable Oak Lawn! This well-maintained 2-be...	2 beds \| 2 baths \| 1,000 sq.ft.	$235,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 6.11% Airbnb Rental Income: $1529 Traditional Rental Income: $1993 Airbnb ROI: 2.03% Traditional ROI: 6.11%
9330 S 51st Avenue Oak Lawn, IL Awesome 2 flat in a great residential area. One tenant 10 + years renting in lower unit. A...	4 beds \| 2 baths \| N/A	$450,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 2.94% Airbnb Rental Income: $1710 Traditional Rental Income: $2537 Airbnb ROI: -0.15% Traditional ROI: 2.94%
5840 W 104th Street #415 Oak Lawn, IL Rarely available top-floor corner unit offering exceptional privacy, abundant natural ligh...	2 beds \| 2 baths \| 1,200 sq.ft.	$184,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 5.17% Airbnb Rental Income: $1529 Traditional Rental Income: $1971 Airbnb ROI: 0.13% Traditional ROI: 5.17%
10934 S Pulaski Rd Oak Lawn, IL Move right into this beautifully updated brick ranch situated on a spacious, fenced lot! T...	2 beds \| 1 baths \| 908 sq.ft.	$265,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 3.26% Airbnb Rental Income: $1529 Traditional Rental Income: $1840 Airbnb ROI: 0.35% Traditional ROI: 3.26%
9721 S Keeler Avenue #204 Oak Lawn, IL Welcome home to this beautifully refreshed 2 bedroom, 1 bath condo in the heart of Oak Law...	2 beds \| 1 baths \| 1,100 sq.ft.	$154,900	Airbnb cash on cash: 1.8% Traditional cash on cash: 4.67% Airbnb Rental Income: $1529 Traditional Rental Income: $1511 Airbnb ROI: 1.8% Traditional ROI: 4.67%
9821 Natoma Avenue Oak Lawn, IL	4 beds \| 2 baths \| 1,200 sq.ft.	$310,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 5.84% Airbnb Rental Income: $1710 Traditional Rental Income: $2306 Airbnb ROI: 2.17% Traditional ROI: 5.84%
6630 W 95th Street #3D Oak Lawn, IL Welcome to this charming and move-in ready 2-bedroom, 1-bath condo that perfectly blends c...	2 beds \| 1 baths \| 950 sq.ft.	$159,500	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.62% Airbnb Rental Income: $1529 Traditional Rental Income: $1576 Airbnb ROI: 1.4% Traditional ROI: 4.62%
8700 Melvina Ave Oak Lawn, IL Multiple Offers have been received. Highest and Best due 2-12-24 by NOON Excellent oppor...	4 beds \| 2 baths \| 1,390 sq.ft.	$334,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.85% Airbnb Rental Income: $1710 Traditional Rental Income: $2261 Airbnb ROI: 0.64% Traditional ROI: 3.85%
10300 S Pulaski Rd #110A Oak Lawn, IL 2 Bedroom Condo located in the Longwood Place Condominium complex. Open Living/Dining roo...	2 beds \| 1 baths \| N/A	$175,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 5.2% Airbnb Rental Income: $1529 Traditional Rental Income: $1497 Airbnb ROI: 2.73% Traditional ROI: 5.2%
10448 S Pulaski Rd Oak Lawn, IL 10448 S Pulaski Rd, Chicago, IL 60453 \| Other	N/A beds \| N/A baths \| N/A	$1,550,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.33% Airbnb Rental Income: $null Traditional Rental Income: $1517 Airbnb ROI: N/A Traditional ROI: -2.33%
9209 Massasoit Avenue Oak Lawn, IL EXCELLENT HOUSE, SUPER CLEAN AND IN MINT CONDITION TOTAL OF E BEDROOMS IN THE MAIL LEVEL 1...	3 beds \| 4 baths \| 2,680 sq.ft.	$493,500	Airbnb cash on cash: 0.63% Traditional cash on cash: 3.32% Airbnb Rental Income: $1921 Traditional Rental Income: $2653 Airbnb ROI: 0.63% Traditional ROI: 3.32%
9013 S 49th Court Oak Lawn, IL Welcome home to this charming ranch style residence featuring 3 spacious bedrooms- 1 full ...	3 beds \| 1 baths \| 1,100 sq.ft.	$294,900	Airbnb cash on cash: 2.04% Traditional cash on cash: 3.91% Airbnb Rental Income: $1921 Traditional Rental Income: $1932 Airbnb ROI: 2.04% Traditional ROI: 3.91%
6634 W 95th Street #1D Oak Lawn, IL Completely updated 1st floor condo offering modern style and comfortable living! This move...	2 beds \| 1 baths \| 900 sq.ft.	$184,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 4.01% Airbnb Rental Income: $1529 Traditional Rental Income: $1606 Airbnb ROI: 1.04% Traditional ROI: 4.01%
4530 W 93rd Street #2B Oak Lawn, IL Beautiful freshly painted 2nd Floor Condo with 2 bedrooms, 2 full bathrooms (both remodele...	2 beds \| 2 baths \| 1,200 sq.ft.	$244,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 5.1% Airbnb Rental Income: $1529 Traditional Rental Income: $2335 Airbnb ROI: -0.3% Traditional ROI: 5.1%
4042 Trafalgar Ln #4042 Oak Lawn, IL Move right into this spacious 3-bedroom, 2.5-bath townhome offering 1,780 sq. ft. of comfo...	3 beds \| 2 baths \| 1,780 sq.ft.	$255,900	Airbnb cash on cash: -0.19% Traditional cash on cash: 2.28% Airbnb Rental Income: $1921 Traditional Rental Income: $2030 Airbnb ROI: -0.19% Traditional ROI: 2.28%
9208 S Monitor Avenue Oak Lawn, IL The listing price is the value from the appraisal from the bank, this is the minimum purch...	4 beds \| 2 baths \| 2,478 sq.ft.	$275,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 6.43% Airbnb Rental Income: $1710 Traditional Rental Income: $2745 Airbnb ROI: 0.61% Traditional ROI: 6.43%
5721 CIRCLE Drive #304 Oak Lawn, IL	2 beds \| 2 baths \| 1,100 sq.ft.	$140,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 8.66% Airbnb Rental Income: $1529 Traditional Rental Income: $2102 Airbnb ROI: 1.09% Traditional ROI: 8.66%
9418 Tulley Avenue Oak Lawn, IL Welcome to this stunning, move-in-ready, 5 bed/4 bath home in the heart of Oak Lawn. This ...	4 beds \| 4 baths \| 2,750 sq.ft.	$469,900	Airbnb cash on cash: -0.46% Traditional cash on cash: 4.83% Airbnb Rental Income: $1710 Traditional Rental Income: $3564 Airbnb ROI: -0.46% Traditional ROI: 4.83%
4037 Trafalgar Ln Oak Lawn, IL 4037 Trafalgar Ln, Chicago, IL 60453 \| Townhouse	2 beds \| 1 baths \| 988 sq.ft.	$205,500	Airbnb cash on cash: 0.25% Traditional cash on cash: 1.85% Airbnb Rental Income: $1529 Traditional Rental Income: $1407 Airbnb ROI: 0.25% Traditional ROI: 1.85%
4024 W 106th St Oak Lawn, IL Big Backyard. Beautiful Updates. Prime Location! Welcome home to this beautifully updated ...	3 beds \| 2 baths \| 1,700 sq.ft.	$369,999	Airbnb cash on cash: 0.88% Traditional cash on cash: 2.2% Airbnb Rental Income: $1921 Traditional Rental Income: $1864 Airbnb ROI: 0.88% Traditional ROI: 2.2%
10002 S Pulaski Rd #207 Oak Lawn, IL MULTIPLE OFFERS RECEIVED: SUBMIT HIGHEST & BEST OFFER by WEDNESDAY 9/24/25 @ 12:00 pm... W...	2 beds \| 1 baths \| 960 sq.ft.	$175,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3% Airbnb Rental Income: $1529 Traditional Rental Income: $1402 Airbnb ROI: 1.1% Traditional ROI: 3%
10036 Kedvale Avenue Oak Lawn, IL Discover this stunning raised ranch in a prime Oak Lawn location! This gorgeous brick home...	3 beds \| 3 baths \| 1,735 sq.ft.	$457,700	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.33% Airbnb Rental Income: $1921 Traditional Rental Income: $2722 Airbnb ROI: 0.27% Traditional ROI: 3.33%
4232 W 109th Street Oak Lawn, IL Welcome to 4232 W. 109th Street, a completely renovated home offering the perfect blend of...	3 beds \| 3 baths \| 2,400 sq.ft.	$426,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 1.93% Airbnb Rental Income: $1921 Traditional Rental Income: $1868 Airbnb ROI: 0.79% Traditional ROI: 1.93%
8758 Central Avenue Oak Lawn, IL THIS 2500 SQ FT PROPERTY IN THE HEART OF OAK LAWN OFFERS A RARE, VERSATILE OPPORTUNITY FOR...	2 beds \| 1 baths \| 2,500 sq.ft.	$319,900	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.96% Airbnb Rental Income: $1529 Traditional Rental Income: $2561 Airbnb ROI: 0.06% Traditional ROI: 4.96%

Real Estate investment in Oak-lawn, IL

There are 148 properties for sale in the city of Oak Lawn . The median list price in Oak Lawn is $309,815 and the average price per square foot is $204. In August 2026, the average monthly cash on cash return in Oak Lawn is 5.00%. The average monthly rental income in Oak Lawn is $2,276.

Oak-lawn, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 148 investment properties available for sale in Oak-lawn.

In 2026, the best neighborhood to buy investment property is Oak Lawn.

The ROI for Long-Term is higher than the Short-Term in Oak-lawn with average rental income of $2,276.

Your search for investment property begins and ends here

Investment Property for Sale in Oak Lawn, IL

5909 W 99th Street

Oak Lawn, IL

3 beds | 2 baths | 1,107 sq.ft.

$256,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1921

Traditional Rental Income: $2343

Airbnb ROI: 1.27%

Traditional ROI: 5.12%

4108 W 103rd St

Oak Lawn, IL

4 beds | 1 baths | 1,800 sq.ft.

$399,900

Airbnb cash on cash: -0.12%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $1710

Traditional Rental Income: $2718

Airbnb ROI: -0.12%

Traditional ROI: 3.83%

9440 S 51st Avenue #502

Oak Lawn, IL

1 beds | 1 baths | 1,052 sq.ft.

$189,900

Airbnb cash on cash: -0.54%

Traditional cash on cash: 5.1%

Airbnb Rental Income: $1356

Traditional Rental Income: $1959

Airbnb ROI: -0.54%

Traditional ROI: 5.1%

9812 S Karlov Ave #4D

Oak Lawn, IL

2 beds | 2 baths | 1,100 sq.ft.

$219,900

Airbnb cash on cash: 0.84%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $1529

Traditional Rental Income: $1818

Airbnb ROI: 0.84%

Traditional ROI: 4.21%

10048 S Pulaski Rd #3E

Oak Lawn, IL

2 beds | 2 baths | 1,080 sq.ft.

$154,900

Airbnb cash on cash: 1.37%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $1529

Traditional Rental Income: $1730

Airbnb ROI: 1.37%

Traditional ROI: 5.59%

5121 Deblin Ln

Oak Lawn, IL

2 beds | 1 baths | 1,850 sq.ft.

$258,000

Airbnb cash on cash: -0.35%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $1529

Traditional Rental Income: $2642

Airbnb ROI: -0.35%

Traditional ROI: 6.04%

9725 S Karlov Ave #401

Oak Lawn, IL

2 beds | 1 baths | 1,000 sq.ft.

$165,000

Airbnb cash on cash: 1.19%

Traditional cash on cash: 7.44%

Airbnb Rental Income: $1529

Traditional Rental Income: $2070

Airbnb ROI: 1.19%

Traditional ROI: 7.44%

9601 S Karlov Avenue #101

Oak Lawn, IL

2 beds | 2 baths | 1,000 sq.ft.

$235,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 6.11%

Airbnb Rental Income: $1529

Traditional Rental Income: $1993

Airbnb ROI: 2.03%