Real Estate Investment Properties for Sale in Oak Park, IL

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

Explore a variety of short-term homes & houses in Oak Park, IL. Invest wisely with VRBO & Oak Park, 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 Park, IL

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
601 South Boulevard #E OAK PARK, IL Beautifully Renovated 3-Bedroom, 3.5-Bathroom Townhome. This stunning 3-story townhome off...	3 beds \| 4 baths \| 1,785 sq.ft.	$484,900	Airbnb cash on cash: -0.84% Traditional cash on cash: 1.95% Airbnb Rental Income: $2366 Traditional Rental Income: $3047 Airbnb ROI: -0.84% Traditional ROI: 1.95%
938 North Boulevard #204 OAK PARK, IL Location, updates, and convenience all in one! Just steps from downtown Oak Park, this bea...	2 beds \| 1 baths \| 880 sq.ft.	$235,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.6% Airbnb Rental Income: $1663 Traditional Rental Income: $1804 Airbnb ROI: 0.87% Traditional ROI: 3.6%
2 Le Moyne Parkway #2N OAK PARK, IL	2 beds \| 1 baths \| 1,000 sq.ft.	$139,999	Airbnb cash on cash: 2.08% Traditional cash on cash: 6.77% Airbnb Rental Income: $1663 Traditional Rental Income: $1827 Airbnb ROI: 2.08% Traditional ROI: 6.77%
845 S Humphrey Avenue #1 OAK PARK, IL Vintage Oak Park charm + the practical stuff you actually want. This spacious high first f...	1 beds \| 1 baths \| N/A	$200,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 2.9% Airbnb Rental Income: $1469 Traditional Rental Income: $1759 Airbnb ROI: -0.91% Traditional ROI: 2.9%
651 South Boulevard #5 OAK PARK, IL Amazingly quiet neighborhood! Walking distance from public transportation, and Downtown Oa...	2 beds \| 1 baths \| 625 sq.ft.	$197,500	Airbnb cash on cash: 1.72% Traditional cash on cash: 3.85% Airbnb Rental Income: $1663 Traditional Rental Income: $1596 Airbnb ROI: 1.72% Traditional ROI: 3.85%
449 N Lombard Avenue #3 OAK PARK, IL Fall in Love with this Oak Park Gem! This charming, sun-filled 2 bedroom, 2 bath condo ble...	2 beds \| 2 baths \| 1,357 sq.ft.	$294,900	Airbnb cash on cash: -1.4% Traditional cash on cash: 1.51% Airbnb Rental Income: $1663 Traditional Rental Income: $2005 Airbnb ROI: -1.4% Traditional ROI: 1.51%
202 Harrison Street OAK PARK, IL Offering approximately 2,400 square feet, this distinctive three-bedroom, 2.5-bath townhom...	3 beds \| 3 baths \| 2,417 sq.ft.	$599,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.3% Airbnb Rental Income: $2366 Traditional Rental Income: $3467 Airbnb ROI: -0.71% Traditional ROI: 2.3%
904 S Elmwood Avenue #3 OAK PARK, IL MOVE-IN READY, FULLY FURNISHED CHARMING CONDO IN A PRIME OAK PARK LOCATION! This inviting ...	1 beds \| 1 baths \| 617 sq.ft.	$180,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 2.61% Airbnb Rental Income: $1469 Traditional Rental Income: $1450 Airbnb ROI: 0.18% Traditional ROI: 2.61%
500 Washington Boulevard #206 OAK PARK, IL Updated 1-Bedroom Condo in Sought-After Oak Park! This inviting condo features a spaci...	1 beds \| 1 baths \| 850 sq.ft.	$180,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 4.76% Airbnb Rental Income: $1469 Traditional Rental Income: $1713 Airbnb ROI: 0.81% Traditional ROI: 4.76%
214 S Oak Park Avenue S #5 OAK PARK, IL Calling all Savvy buyers! Come take a look at this 1 bedroom, 1 bath, 3rd floor condo that...	1 beds \| 1 baths \| 800 sq.ft.	$150,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 7.72% Airbnb Rental Income: $1469 Traditional Rental Income: $1565 Airbnb ROI: 4.03% Traditional ROI: 7.72%
425 S Harvey Avenue #E OAK PARK, IL	3 beds \| 3 baths \| 1,774 sq.ft.	$424,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.15% Airbnb Rental Income: $2366 Traditional Rental Income: $2848 Airbnb ROI: 0.47% Traditional ROI: 3.15%
426 S AUSTIN Boulevard #3S OAK PARK, IL Charming 2 bed, 1 bath Oak Park condo! This 3rd floor unit has large windows which allows ...	2 beds \| 1 baths \| 1,350 sq.ft.	$255,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.01% Airbnb Rental Income: $1663 Traditional Rental Income: $1988 Airbnb ROI: -0.28% Traditional ROI: 3.01%
821 N Harlem Avenue OAK PARK, IL UNMATCHED SPACE & VALUE \| 1,900+ SF OAK PARK TOWNHOME - Sun-drenched, 3-story fee-simple t...	2 beds \| 3 baths \| 1,909 sq.ft.	$399,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 3.01% Airbnb Rental Income: $1663 Traditional Rental Income: $2715 Airbnb ROI: -1.04% Traditional ROI: 3.01%
504 S AUSTIN Boulevard #1 OAK PARK, IL Discover a rare opportunity to own a spacious 3-bedroom, 2-bath first-floor condo in a bea...	3 beds \| 2 baths \| 1,600 sq.ft.	$310,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.2% Airbnb Rental Income: $2366 Traditional Rental Income: $2646 Airbnb ROI: 1.24% Traditional ROI: 4.2%
425 WESLEY Avenue #101 OAK PARK, IL Welcome to Unit 101 at 425 Wesley Avenue, a spacious and bright first-floor corner condomi...	1 beds \| 1 baths \| 820 sq.ft.	$164,900	Airbnb cash on cash: 2.77% Traditional cash on cash: 7.32% Airbnb Rental Income: $1469 Traditional Rental Income: $1751 Airbnb ROI: 2.77% Traditional ROI: 7.32%
221 N Oak Park Avenue #2E OAK PARK, IL Discover this charming 1-bedroom, 1-bathroom condo in the heart of Oak Park, IL, ideally l...	1 beds \| 1 baths \| N/A	$192,500	Airbnb cash on cash: 1.73% Traditional cash on cash: 4.42% Airbnb Rental Income: $1469 Traditional Rental Income: $1527 Airbnb ROI: 1.73% Traditional ROI: 4.42%
934 Fair Oaks Avenue OAK PARK, IL NORTH OAK PARK. CLASSIC CHARACTER. INCREDIBLE POTENTIAL. (The After Repair Value ( ARV) of...	4 beds \| 3 baths \| 2,240 sq.ft.	$879,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 0.69% Airbnb Rental Income: $3406 Traditional Rental Income: $3393 Airbnb ROI: -0.22% Traditional ROI: 0.69%
938 NORTH Boulevard #402 OAK PARK, IL Welcome to your dream condo in the heart of downtown Oak Park! This spacious, light-filled...	2 beds \| 1 baths \| 880 sq.ft.	$244,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 4.09% Airbnb Rental Income: $1663 Traditional Rental Income: $1747 Airbnb ROI: 1.72% Traditional ROI: 4.09%
1041 Susan Collins Lane #501 OAK PARK, IL Price improved! Classy top-floor 1-bedroom condo in a prime Oak Park location! Well-mainta...	1 beds \| 1 baths \| 800 sq.ft.	$175,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 6.66% Airbnb Rental Income: $1469 Traditional Rental Income: $1813 Airbnb ROI: 1.99% Traditional ROI: 6.66%
170 N Marion Street #14 OAK PARK, IL Gorgeous 2BD/2.5BA penthouse duplex in prime Oak Park location with private attached 2car ...	2 beds \| 3 baths \| 1,738 sq.ft.	$457,800	Airbnb cash on cash: -0.98% Traditional cash on cash: 3.11% Airbnb Rental Income: $1663 Traditional Rental Income: $2946 Airbnb ROI: -0.98% Traditional ROI: 3.11%
314-316 N Maple Avenue OAK PARK, IL Excellent investment opportunity in Oak Park! This well-maintained 7-unit multifamily buil...	17 beds \| 7 baths \| N/A	$1,490,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.9% Airbnb Rental Income: $4343 Traditional Rental Income: $5963 Airbnb ROI: -0.93% Traditional ROI: 0.9%
420 S HOME Avenue #109N OAK PARK, IL Welcome home to this beautifully remodeled 1-bedroom, 1-bath condo in the heart of Oak Par...	1 beds \| 1 baths \| N/A	$189,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 6.14% Airbnb Rental Income: $1469 Traditional Rental Income: $1674 Airbnb ROI: 2.58% Traditional ROI: 6.14%
403 S Harvey Avenue #2B OAK PARK, IL Welcome home to this bright vintage condo in Oak Park's Ridgeland Historic District! the o...	1 beds \| 1 baths \| N/A	$175,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 5.42% Airbnb Rental Income: $1469 Traditional Rental Income: $1482 Airbnb ROI: 2.74% Traditional ROI: 5.42%
909 Wenonah Avenue OAK PARK, IL Realize the potential of this historic home, hitting the market for the first time in gene...	2 beds \| 1 baths \| N/A	$295,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 1.58% Airbnb Rental Income: $1663 Traditional Rental Income: $1882 Airbnb ROI: -0.89% Traditional ROI: 1.58%

Real Estate investment in Oak-park, IL

There are 45 properties for sale in the city of Oak Park . The median list price in Oak Park is $522,751 and the average price per square foot is $366. In November 2026, the average monthly cash on cash return in Oak Park is 1.00%. The average monthly rental income in Oak Park is $1,875.

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

There are 45 investment properties available for sale in Oak-park.

In 2026, the best neighborhood to buy investment property is OAK PARK.

The ROI for Short-Term is higher than the Long-Term in Oak-park with average rental income of $1,887.

Your search for investment property begins and ends here

Investment Property for Sale in Oak Park, IL

601 South Boulevard #E

OAK PARK, IL

3 beds | 4 baths | 1,785 sq.ft.

$484,900

Airbnb cash on cash: -0.84%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $2366

Traditional Rental Income: $3047

Airbnb ROI: -0.84%

Traditional ROI: 1.95%

938 North Boulevard #204

OAK PARK, IL

2 beds | 1 baths | 880 sq.ft.

$235,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $1663

Traditional Rental Income: $1804

Airbnb ROI: 0.87%

Traditional ROI: 3.6%

2 Le Moyne Parkway #2N

OAK PARK, IL

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

$139,999

Airbnb cash on cash: 2.08%

Traditional cash on cash: 6.77%

Airbnb Rental Income: $1663

Traditional Rental Income: $1827

Airbnb ROI: 2.08%

Traditional ROI: 6.77%

845 S Humphrey Avenue #1

OAK PARK, IL

1 beds | 1 baths | N/A

$200,000

Airbnb cash on cash: -0.91%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $1469

Traditional Rental Income: $1759

Airbnb ROI: -0.91%

Traditional ROI: 2.9%

651 South Boulevard #5

OAK PARK, IL

2 beds | 1 baths | 625 sq.ft.

$197,500

Airbnb cash on cash: 1.72%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1663

Traditional Rental Income: $1596

Airbnb ROI: 1.72%

Traditional ROI: 3.85%

449 N Lombard Avenue #3

OAK PARK, IL

2 beds | 2 baths | 1,357 sq.ft.

$294,900

Airbnb cash on cash: -1.4%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $1663

Traditional Rental Income: $2005

Airbnb ROI: -1.4%

Traditional ROI: 1.51%

202 Harrison Street

OAK PARK, IL

3 beds | 3 baths | 2,417 sq.ft.

$599,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $2366

Traditional Rental Income: $3467

Airbnb ROI: -0.71%

Traditional ROI: 2.3%

904 S Elmwood Avenue #3

OAK PARK, IL

1 beds | 1 baths | 617 sq.ft.

$180,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $1469

Traditional Rental Income: $1450

Airbnb ROI: 0.18%