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
830 N Austin Blvd OAK PARK, IL SOME KEY THINGS TO CONSIDER WHEN PURCHASING A HOME IS LOCATION, EQUITY POTENTIAL AND GOOD ...	5 beds \| 2 baths \| 1,380 sq.ft.	$425,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.47% Airbnb Rental Income: $2036 Traditional Rental Income: $2048 Airbnb ROI: 0.11% Traditional ROI: 1.47%
222 N Grove Avenue unit: 2B #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.	$299,999	Airbnb cash on cash: -1.52% Traditional cash on cash: 3.51% Airbnb Rental Income: $1380 Traditional Rental Income: $2381 Airbnb ROI: -1.52% Traditional ROI: 3.51%
1103 Holley Court unit: 207 #207 OAK PARK, IL Treetop Views in the Heart of Downtown Oak Park! Move right into this sun-drenched vintage...	1 beds \| 1 baths \| N/A	$157,500	Airbnb cash on cash: -0.01% Traditional cash on cash: 4.77% Airbnb Rental Income: $1245 Traditional Rental Income: $1567 Airbnb ROI: -0.01% Traditional ROI: 4.77%
908 Clinton Avenue OAK PARK, IL Unbeatable Oak Park location featuring a spacious tri-level floor plan with a fully finish...	3 beds \| 2 baths \| 1,631 sq.ft.	$409,900	Airbnb cash on cash: -1.38% Traditional cash on cash: 2.58% Airbnb Rental Income: $1503 Traditional Rental Income: $2585 Airbnb ROI: -1.38% Traditional ROI: 2.58%
19 Augusta St OAK PARK, IL Great House! Great Location! Short distance to local shops, restaurants and schools. Nicel...	3 beds \| 2 baths \| 1,426 sq.ft.	$549,000	Airbnb cash on cash: -2.46% Traditional cash on cash: 3.01% Airbnb Rental Income: $1503 Traditional Rental Income: $3870 Airbnb ROI: -2.46% Traditional ROI: 3.01%
825 Highland Avenue OAK PARK, IL Recent updates in this 4 bedroom 2.5 bath with bonus basement bedroom / office. 1st floor ...	4 beds \| 3 baths \| 2,400 sq.ft.	$730,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 2.75% Airbnb Rental Income: $2022 Traditional Rental Income: $3960 Airbnb ROI: -0.87% Traditional ROI: 2.75%
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: 0.35% Traditional cash on cash: 2.47% Airbnb Rental Income: $2022 Traditional Rental Income: $2293 Airbnb ROI: 0.35% Traditional ROI: 2.47%
914 N Austin Blvd #A5 OAK PARK, IL Located in the heart of North Oak Park, this is an amazing oppertunity to get into Oak Par...	3 beds \| 2 baths \| 1,300 sq.ft.	$265,700	Airbnb cash on cash: -1.18% Traditional cash on cash: 3.13% Airbnb Rental Income: $1503 Traditional Rental Income: $2146 Airbnb ROI: -1.18% Traditional ROI: 3.13%
330 N Ridgeland Avenue OAK PARK, IL North Oak Park home on an extra large corner lot with lots of light inside home on a tree ...	4 beds \| 2 baths \| 1,628 sq.ft.	$499,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 2.37% Airbnb Rental Income: $2022 Traditional Rental Income: $3045 Airbnb ROI: -0.95% Traditional ROI: 2.37%
810 S Austin Ave OAK PARK, IL 810 S Austin Ave, Chicago, IL 60302 \| Multi Family	4 beds \| 2 baths \| N/A	$349,900	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.71% Airbnb Rental Income: $2022 Traditional Rental Income: $2050 Airbnb ROI: 1.03% Traditional ROI: 2.71%
514 S Humphrey Ave OAK PARK, IL 514 S Humphrey Ave, OAK PARK, IL 60304 \| Single Family Residential	5 beds \| 2 baths \| 2,915 sq.ft.	$650,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.71% Airbnb Rental Income: $2036 Traditional Rental Income: $2496 Airbnb ROI: -0.92% Traditional ROI: 0.71%
316 N Austin Blvd OAK PARK, IL 316 N Austin Blvd, OAK PARK, IL 60302 \| Other	N/A beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: -2.24% Traditional cash on cash: -1.82% Airbnb Rental Income: $1073 Traditional Rental Income: $962 Airbnb ROI: -2.24% Traditional ROI: -1.82%
62 Chicago Ave OAK PARK, IL	N/A beds \| N/A baths \| N/A	$750,000	Airbnb cash on cash: -2.38% Traditional cash on cash: -2.01% Airbnb Rental Income: $1073 Traditional Rental Income: $965 Airbnb ROI: -2.38% Traditional ROI: -2.01%
1165 S Humphrey Ave OAK PARK, IL 1165 S Humphrey Ave, Chicago, IL 60304 \| Multi Family	4 beds \| 3 baths \| N/A	$345,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 5.05% Airbnb Rental Income: $1073 Traditional Rental Income: $2781 Airbnb ROI: -1.36% Traditional ROI: 5.05%
426 S Lombard Avenue unit: 205 #205 OAK PARK, IL What a spacious 2 bed 2 bath condo. This layout features large bedrooms, hardwood flooring...	2 beds \| 2 baths \| 1,000 sq.ft.	$200,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 4.98% Airbnb Rental Income: $1380 Traditional Rental Income: $2161 Airbnb ROI: -1.34% Traditional ROI: 4.98%
1041 Susan Collins Lane unit: 203 #203 OAK PARK, IL Walkable to both Downtown Oak Park and Downtown Forest Park, this well-maintained 2-bedroo...	2 beds \| 2 baths \| 999 sq.ft.	$215,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 6.48% Airbnb Rental Income: $1380 Traditional Rental Income: $2390 Airbnb ROI: -0.53% Traditional ROI: 6.48%
212 N Oak Park Avenue unit: 2Ee #2Ee OAK PARK, IL This beautifully maintained second-floor condo blends vintage charm with modern comfort. R...	1 beds \| 1 baths \| N/A	$176,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 2.32% Airbnb Rental Income: $1245 Traditional Rental Income: $1492 Airbnb ROI: -1.52% Traditional ROI: 2.32%
1101 S OAK PARK Avenue OAK PARK, IL Discover this beautifully updated three-unit building in the heart of Oak Park, offering a...	8 beds \| 4 baths \| N/A	$1,375,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 0.53% Airbnb Rental Income: $2036 Traditional Rental Income: $4070 Airbnb ROI: -1.47% Traditional ROI: 0.53%
222 Le Moyne Pkwy OAK PARK, IL 222 Le Moyne Pkwy, Chicago, IL 60302 \| Single Family Residential	4 beds \| 3 baths \| N/A	$399,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 4.48% Airbnb Rental Income: $2022 Traditional Rental Income: $2984 Airbnb ROI: 0.5% Traditional ROI: 4.48%
1037 Belleforte Avenue OAK PARK, IL Impeccably built home on an impressive 100' X 175' lot in the desirable and vibrant Oak Pa...	5 beds \| 6 baths \| 5,735 sq.ft.	$1,950,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 1.69% Airbnb Rental Income: $2036 Traditional Rental Income: $6882 Airbnb ROI: -1.28% Traditional ROI: 1.69%
237 Washington Boulevard unit: G #G OAK PARK, IL This high garden corner unit offers the perfect blend of vintage charm and modern updates....	1 beds \| 1 baths \| 950 sq.ft.	$155,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 5.04% Airbnb Rental Income: $1245 Traditional Rental Income: $1780 Airbnb ROI: -1.24% Traditional ROI: 5.04%
847 S Humphrey Ave #1 OAK PARK, IL 847 S Humphrey Ave #1, Chicago, IL 60304 \| Condo/Coop	2 beds \| 1 baths \| 1,012 sq.ft.	$230,000	Airbnb cash on cash: -1.73% Traditional cash on cash: 1.49% Airbnb Rental Income: $1380 Traditional Rental Income: $1662 Airbnb ROI: -1.73% Traditional ROI: 1.49%
224 N Kenilworth Avenue unit: 4D #4D OAK PARK, IL Welcome to an exceptional opportunity to own a spacious 3-bedroom, 3-full-bath penthouse l...	3 beds \| 3 baths \| 2,325 sq.ft.	$399,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 5.14% Airbnb Rental Income: $1503 Traditional Rental Income: $3151 Airbnb ROI: -0.43% Traditional ROI: 5.14%
841 S Taylor Avenue OAK PARK, IL They say timing is everything... and this home just got a glow-up in the form of a new, im...	3 beds \| 2 baths \| 1,463 sq.ft.	$324,900	Airbnb cash on cash: -2.16% Traditional cash on cash: 3.15% Airbnb Rental Income: $1503 Traditional Rental Income: $2685 Airbnb ROI: -2.16% Traditional ROI: 3.15%
915 S Oak Park Avenue unit: 1B #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.	$299,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 5.24% Airbnb Rental Income: $1380 Traditional Rental Income: $2360 Airbnb ROI: 0.28% Traditional ROI: 5.24%
816 S Maple Avenue unit: 3S #3S OAK PARK, IL This third-floor condo lives like a house and features fresh neutral decor and gleaming ha...	2 beds \| 1 baths \| 1,050 sq.ft.	$200,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 4.68% Airbnb Rental Income: $1380 Traditional Rental Income: $1645 Airbnb ROI: 1.07% Traditional ROI: 4.68%
208 S Austin Blvd OAK PARK, IL Beautiful brick 2 flat plus 1 bedroom garden apartment. The spacious 1st floor and 2nd flo...	7 beds \| 3 baths \| N/A	$700,000	Airbnb cash on cash: -1.91% Traditional cash on cash: 0.57% Airbnb Rental Income: $1380 Traditional Rental Income: $2585 Airbnb ROI: -1.91% Traditional ROI: 0.57%
1185 Clarence Avenue OAK PARK, IL Cottage-style 4BR/2.5BA home in South Oak Park location-walking distance to shops, restaur...	4 beds \| 3 baths \| 1,320 sq.ft.	$278,800	Airbnb cash on cash: 0.42% Traditional cash on cash: 5.51% Airbnb Rental Income: $2022 Traditional Rental Income: $2832 Airbnb ROI: 0.42% Traditional ROI: 5.51%
1039 Randolph Street unit: 1W #1W OAK PARK, IL Exceptionally updated 2-bedroom 1-bath corner condo offering a spacious, light-filled floo...	2 beds \| 1 baths \| 904 sq.ft.	$199,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 4.81% Airbnb Rental Income: $1380 Traditional Rental Income: $1601 Airbnb ROI: 1.44% Traditional ROI: 4.81%
1192 CLARENCE Avenue unit: 1 #1 OAK PARK, IL Completely upgraded, better than new Townhome! The Bathrooms and Kitchen are absolutely ex...	2 beds \| 4 baths \| 2,294 sq.ft.	$625,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 2.23% Airbnb Rental Income: $1380 Traditional Rental Income: $2957 Airbnb ROI: -1.19% Traditional ROI: 2.23%
810 S Euclid Avenue OAK PARK, IL Welcome to 810 S Euclid, a 5-bed, 4 full-bath home that lives large, meeting all the needs...	4 beds \| 4 baths \| 2,102 sq.ft.	$725,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 2.05% Airbnb Rental Income: $2022 Traditional Rental Income: $3655 Airbnb ROI: -1.15% Traditional ROI: 2.05%
1121 Home Avenue OAK PARK, IL OPPORTUNITY ALERT!!! REBUILD/REHAB!!!! GUNDERSON HISTORIC DISTRICT! COMPLETE REHAB INCLUDE...	4 beds \| 2 baths \| 1,850 sq.ft.	$950,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 1.85% Airbnb Rental Income: $2022 Traditional Rental Income: $2709 Airbnb ROI: 0.48% Traditional ROI: 1.85%
515 Highland Avenue OAK PARK, IL Welcome to 515 Highland Avenue, a picture-perfect blend of timeless Oak Park charm and mod...	5 beds \| 4 baths \| N/A	$1,149,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 1.06% Airbnb Rental Income: $2036 Traditional Rental Income: $3335 Airbnb ROI: -0.65% Traditional ROI: 1.06%
1151 Home Avenue OAK PARK, IL Beautifully updated home in the sought-after Lincoln Elementary School District offers mod...	4 beds \| 4 baths \| 3,386 sq.ft.	$1,000,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 1.21% Airbnb Rental Income: $2022 Traditional Rental Income: $4132 Airbnb ROI: -1.62% Traditional ROI: 1.21%
333 S EAST Avenue unit: 405 #405 OAK PARK, IL Rare gem in the heart of Oak Park's cherished Hemingway District, showcasing bright, top-f...	3 beds \| 2 baths \| 1,200 sq.ft.	$279,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 5.58% Airbnb Rental Income: $1503 Traditional Rental Income: $2502 Airbnb ROI: 0.13% Traditional ROI: 5.58%

Real Estate investment in Oak-park, IL

There are 35 properties for sale in the city of Oak Park . The median list price in Oak Park is $399,900 and the average price per square foot is $248. In February 2026, the average monthly cash on cash return in Oak Park is 1.00%. The average monthly rental income in Oak Park is $2,315.

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

There are 35 investment properties available for sale in Oak-park.

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

The ROI for Long-Term is higher than the Short-Term in Oak-park with average rental income of $2,315.

Your search for investment property begins and ends here

Investment Property for Sale in Oak Park, IL

830 N Austin Blvd

OAK PARK, IL

5 beds | 2 baths | 1,380 sq.ft.

$425,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $2036

Traditional Rental Income: $2048

Airbnb ROI: 0.11%

Traditional ROI: 1.47%

222 N Grove Avenue unit: 2B #2B

OAK PARK, IL

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

$299,999

Airbnb cash on cash: -1.52%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $1380

Traditional Rental Income: $2381

Airbnb ROI: -1.52%

Traditional ROI: 3.51%

1103 Holley Court unit: 207 #207

OAK PARK, IL

1 beds | 1 baths | N/A

$157,500

Airbnb cash on cash: -0.01%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1245

Traditional Rental Income: $1567

Airbnb ROI: -0.01%

Traditional ROI: 4.77%

908 Clinton Avenue

OAK PARK, IL

3 beds | 2 baths | 1,631 sq.ft.

$409,900

Airbnb cash on cash: -1.38%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $1503

Traditional Rental Income: $2585

Airbnb ROI: -1.38%

Traditional ROI: 2.58%

19 Augusta St

OAK PARK, IL

3 beds | 2 baths | 1,426 sq.ft.

$549,000

Airbnb cash on cash: -2.46%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $1503

Traditional Rental Income: $3870

Airbnb ROI: -2.46%

Traditional ROI: 3.01%

825 Highland Avenue

OAK PARK, IL

4 beds | 3 baths | 2,400 sq.ft.

$730,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $2022

Traditional Rental Income: $3960

Airbnb ROI: -0.87%

Traditional ROI: 2.75%

1185 S LOMBARD AVE

OAK PARK, IL

4 beds | 2 baths | 1,349 sq.ft.

$401,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $2022

Traditional Rental Income: $2293

Airbnb ROI: 0.35%

Traditional ROI: 2.47%

914 N Austin Blvd #A5

OAK PARK, IL

3 beds | 2 baths | 1,300 sq.ft.

$265,700

Airbnb cash on cash: -1.18%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $1503

Traditional Rental Income: $2146

Airbnb ROI: -1.18%