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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5902 W Madison St #3 OAK PARK, IL 5902 W Madison St #3, OAK PARK, IL 60644 \| Condo/Coop	1 beds \| 1 baths \| 750 sq.ft.	$124,900	Airbnb cash on cash: 4.31% Traditional cash on cash: 6.08% Airbnb Rental Income: $1730 Traditional Rental Income: $1465 Airbnb ROI: 4.31% Traditional ROI: 6.08%
222 N Grove Avenue #2B OAK PARK, IL Oak Park's Premier Location in the Historic Frank Lloyd Wright District! This beautifully ...	2 beds \| 2 baths \| 1,200 sq.ft.	$310,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.37% Airbnb Rental Income: $2018 Traditional Rental Income: $2381 Airbnb ROI: 0.32% Traditional ROI: 3.37%
1122 S Maple Avenue OAK PARK, IL Welcome home to comfort & charm! Step into this beautifully maintained 3-bedroom, 1 and a ...	3 beds \| 2 baths \| 1,768 sq.ft.	$500,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 1.81% Airbnb Rental Income: $1886 Traditional Rental Income: $2608 Airbnb ROI: -0.81% Traditional ROI: 1.81%
344 S MAPLE Avenue #3B OAK PARK, IL MOTIVATED SELLER...Absolutely lovely condo, rehabbed in 2008 including plumbing & electric...	3 beds \| 2 baths \| 1,451 sq.ft.	$335,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 2.81% Airbnb Rental Income: $1886 Traditional Rental Income: $2603 Airbnb ROI: -1.07% Traditional ROI: 2.81%
415 Wesley Avenue #21 OAK PARK, IL Spectacular, pet-friendly condo with elevator access and an open floor plan. Sliding glass...	1 beds \| 1 baths \| 850 sq.ft.	$152,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 4.42% Airbnb Rental Income: $1730 Traditional Rental Income: $1660 Airbnb ROI: 1.62% Traditional ROI: 4.42%
120 Chicago Avenue #A OAK PARK, IL Welcome to this rare, fully detached 3-story townhome that lives like a single-family home...	3 beds \| 3 baths \| 1,556 sq.ft.	$369,999	Airbnb cash on cash: -0.61% Traditional cash on cash: 3.76% Airbnb Rental Income: $1886 Traditional Rental Income: $2898 Airbnb ROI: -0.61% Traditional ROI: 3.76%
246 S Maple Avenue #3W OAK PARK, IL Welcome to 246 S. Maple Unit 3W - Your Perfect Oak Park Retreat! This stunning top-floor, ...	2 beds \| 1 baths \| 951 sq.ft.	$280,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 1.63% Airbnb Rental Income: $2018 Traditional Rental Income: $1714 Airbnb ROI: 0.79% Traditional ROI: 1.63%
508 Madison Street #2S OAK PARK, IL Welcome to 508 Madison Street, Oak Park - where charm meets convenience. This vintage cond...	1 beds \| 1 baths \| 824 sq.ft.	$155,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 5.56% Airbnb Rental Income: $1730 Traditional Rental Income: $1558 Airbnb ROI: 3.5% Traditional ROI: 5.56%
1185 S LOMBARD AVE OAK PARK, IL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	4 beds \| 2 baths \| 1,349 sq.ft.	$401,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 2.47% Airbnb Rental Income: $2181 Traditional Rental Income: $2293 Airbnb ROI: 0.71% Traditional ROI: 2.47%
1022 Alexander Lane OAK PARK, IL This four-bedroom Oak Park townhouse offers modern living with the space, privacy, and fle...	4 beds \| 5 baths \| 2,450 sq.ft.	$549,853	Airbnb cash on cash: -1.36% Traditional cash on cash: 3.27% Airbnb Rental Income: $2181 Traditional Rental Income: $4007 Airbnb ROI: -1.36% Traditional ROI: 3.27%
928 Lyman Avenue OAK PARK, IL Welcome to 928 Lyman Ave., a stunning gut-rehabbed 3-story home on a corner lot in Oak Par...	5 beds \| 4 baths \| 3,746 sq.ft.	$1,150,000	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.77% Airbnb Rental Income: $2178 Traditional Rental Income: $1644 Airbnb ROI: -0.79% Traditional ROI: -0.77%
5934 W Erie St OAK PARK, IL Buy through Auction.com. This foreclosure property is a great opportunity to invest in thi...	5 beds \| 3 baths \| 2,000 sq.ft.	$450,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 4.96% Airbnb Rental Income: $2178 Traditional Rental Income: $2829 Airbnb ROI: 2.11% Traditional ROI: 4.96%
1124 Lake Street #411 OAK PARK, IL LUXURY CONDO IN DOWNTOWN OAK PARK AT THE 1120 CLUB. ELEVATOR BUILDING, WALK TO EVERYTHING,...	2 beds \| 2 baths \| N/A	$445,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 0.89% Airbnb Rental Income: $2018 Traditional Rental Income: $2236 Airbnb ROI: -0.89% Traditional ROI: 0.89%
1115 N Taylor Avenue OAK PARK, IL Welcome to beautiful 1115 N Taylor Ave ~ This home features 5 bedrooms, 2 bathrooms, nicel...	3 beds \| 2 baths \| 1,800 sq.ft.	$620,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 1.97% Airbnb Rental Income: $1886 Traditional Rental Income: $2388 Airbnb ROI: 0.23% Traditional ROI: 1.97%
403 N Humphrey Ave OAK PARK, IL 403 N Humphrey Ave, OAK PARK, IL 60302 \| Multi Family	6 beds \| 3 baths \| N/A	$490,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 3.01% Airbnb Rental Income: $2181 Traditional Rental Income: $2961 Airbnb ROI: 0.1% Traditional ROI: 3.01%
824 N AUSTIN Boulevard #3E OAK PARK, IL ## Investor Opportunity in Oak Park! Welcome to this 3-bedroom, 2-bath condo in vibrant...	3 beds \| 2 baths \| 1,420 sq.ft.	$190,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 5.97% Airbnb Rental Income: $1886 Traditional Rental Income: $2327 Airbnb ROI: 0.74% Traditional ROI: 5.97%
921 N Humphrey Avenue OAK PARK, IL Welcome to 921 N Humphrey Avenue in Oak Park - A Move-In Ready Renovated Two-Story Home wi...	3 beds \| 2 baths \| 1,730 sq.ft.	$599,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.02% Airbnb Rental Income: $1886 Traditional Rental Income: $2252 Airbnb ROI: -0.53% Traditional ROI: 1.02%
1221 Edmer Avenue OAK PARK, IL Classic Oak Park Colonial - 3 Bed \| 3.5 Bath Where vintage soul meets fresh, modern livin...	3 beds \| 4 baths \| 2,547 sq.ft.	$774,028	Airbnb cash on cash: -1.13% Traditional cash on cash: -0.46% Airbnb Rental Income: $1886 Traditional Rental Income: $1867 Airbnb ROI: -1.13% Traditional ROI: -0.46%
426 Wisconsin Avenue #3S OAK PARK, IL Check out this bright, top floor, 3 bedroom, 2 bath unit with cool vintage details like ar...	3 beds \| 2 baths \| N/A	$275,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 3.21% Airbnb Rental Income: $1886 Traditional Rental Income: $2516 Airbnb ROI: -1.16% Traditional ROI: 3.21%
719 ERIE Street #3A OAK PARK, IL Seller will credit the buyer 3% of the purchase price to buy down their interest rate!!! ...	2 beds \| 1 baths \| 1,016 sq.ft.	$255,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 2.21% Airbnb Rental Income: $2018 Traditional Rental Income: $1927 Airbnb ROI: 0.41% Traditional ROI: 2.21%
915 S Oak Park Avenue #1B OAK PARK, IL Step outside your living room through a sliding glass door onto an impressive 24' x 19' pr...	2 beds \| 2 baths \| 1,195 sq.ft.	$339,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.65% Airbnb Rental Income: $2018 Traditional Rental Income: $2597 Airbnb ROI: 0.19% Traditional ROI: 3.65%
1140 S Harvey Avenue OAK PARK, IL Updated and full of possibilities, this legal non-conforming brick 2-flat in Oak Park offe...	3 beds \| N/A baths \| N/A	$439,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.52% Airbnb Rental Income: $1886 Traditional Rental Income: $2149 Airbnb ROI: -0.34% Traditional ROI: 1.52%
420 Home Avenue #202 OAK PARK, IL	2 beds \| 2 baths \| 1,000 sq.ft.	$259,900	Airbnb cash on cash: 1.08% Traditional cash on cash: 5.3% Airbnb Rental Income: $2018 Traditional Rental Income: $2526 Airbnb ROI: 1.08% Traditional ROI: 5.3%
425 Wisconsin Avenue #2W OAK PARK, IL Welcome to 425 Wisconsin Ave, a charming and well-maintained vintage building nestled in t...	1 beds \| 1 baths \| N/A	$110,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 5.56% Airbnb Rental Income: $1730 Traditional Rental Income: $1452 Airbnb ROI: 3.69% Traditional ROI: 5.56%
936 N Ridgeland Avenue OAK PARK, IL Enjoy Oak Park's exceptional blend of historic charm and modern conveniences in this beaut...	3 beds \| 3 baths \| 1,800 sq.ft.	$455,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 2.54% Airbnb Rental Income: $1886 Traditional Rental Income: $2884 Airbnb ROI: -0.99% Traditional ROI: 2.54%
1104 Fair Oaks Avenue OAK PARK, IL Beautiful brick and stone exterior and an open front porch welcome you to this handsome Co...	5 beds \| 6 baths \| 4,007 sq.ft.	$1,199,000	Airbnb cash on cash: -1.65% Traditional cash on cash: 3.47% Airbnb Rental Income: $2178 Traditional Rental Income: $7336 Airbnb ROI: -1.65% Traditional ROI: 3.47%
339 Home Avenue #3B OAK PARK, IL In the heart of Oak Park's Ridgeland Historic District, this front-facing 2-bedroom, 2-bat...	2 beds \| 2 baths \| 1,200 sq.ft.	$315,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 2.87% Airbnb Rental Income: $2018 Traditional Rental Income: $2354 Airbnb ROI: -0.04% Traditional ROI: 2.87%
426 S Lombard Avenue #205 OAK PARK, IL What a spacious 2 bed 2 bath condo. This layout features large bedrooms, hardwood floorin...	2 beds \| 2 baths \| 1,000 sq.ft.	$225,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 4.33% Airbnb Rental Income: $2018 Traditional Rental Income: $2161 Airbnb ROI: 1.19% Traditional ROI: 4.33%

Real Estate investment in Oak-park, IL

There are 60 properties for sale in the city of Oak Park . The median list price in Oak Park is $337,450 and the average price per square foot is $195. In October 2025, the average monthly cash on cash return in Oak Park is 3.00%. The average monthly rental income in Oak Park is $2,385.

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

There are 60 investment properties available for sale in Oak-park.

In 2025, 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 $2,018.

Your search for investment property begins and ends here

Investment Property for Sale in Oak Park, IL

5902 W Madison St #3

OAK PARK, IL

1 beds | 1 baths | 750 sq.ft.

$124,900

Airbnb cash on cash: 4.31%

Traditional cash on cash: 6.08%

Airbnb Rental Income: $1730

Traditional Rental Income: $1465

Airbnb ROI: 4.31%

Traditional ROI: 6.08%

222 N Grove Avenue #2B

OAK PARK, IL

2 beds | 2 baths | 1,200 sq.ft.

$310,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $2018

Traditional Rental Income: $2381

Airbnb ROI: 0.32%

Traditional ROI: 3.37%

1122 S Maple Avenue

OAK PARK, IL

3 beds | 2 baths | 1,768 sq.ft.

$500,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $1886

Traditional Rental Income: $2608

Airbnb ROI: -0.81%

Traditional ROI: 1.81%

344 S MAPLE Avenue #3B

OAK PARK, IL

3 beds | 2 baths | 1,451 sq.ft.

$335,000

Airbnb cash on cash: -1.07%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $1886

Traditional Rental Income: $2603

Airbnb ROI: -1.07%

Traditional ROI: 2.81%

415 Wesley Avenue #21

OAK PARK, IL

1 beds | 1 baths | 850 sq.ft.

$152,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 4.42%

Airbnb Rental Income: $1730

Traditional Rental Income: $1660

Airbnb ROI: 1.62%

Traditional ROI: 4.42%

120 Chicago Avenue #A

OAK PARK, IL

3 beds | 3 baths | 1,556 sq.ft.

$369,999

Airbnb cash on cash: -0.61%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $1886

Traditional Rental Income: $2898

Airbnb ROI: -0.61%

Traditional ROI: 3.76%

246 S Maple Avenue #3W

OAK PARK, IL

2 beds | 1 baths | 951 sq.ft.

$280,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 1.63%

Airbnb Rental Income: $2018

Traditional Rental Income: $1714

Airbnb ROI: 0.79%

Traditional ROI: 1.63%

508 Madison Street #2S

OAK PARK, IL

1 beds | 1 baths | 824 sq.ft.

$155,000

Airbnb cash on cash: 3.5%

Traditional cash on cash: 5.56%

Airbnb Rental Income: $1730

Traditional Rental Income: $1558

Airbnb ROI: 3.5%