Real Estate Investment Properties for Sale in Oakland, IL

Looking for investment property in Oakland, IL with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
22263 133 Highway Oakland, IL Welcome to your private paradise. Home is located well off the main road. 4 Bedroom 2 bath...	4 beds \| 2 baths \| 1,696 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.45% Airbnb Rental Income: $null Traditional Rental Income: $2457 Airbnb ROI: N/A Traditional ROI: 4.45%
Investment Properties for Sale in Other Cities of Illinois
4517 N Whipple Street Chicago , IL Stunning 5 bedroom 3.5 bath luxury farmhouse nestled in between the Ravenswood Manor and E...	4 beds \| 4 baths \| N/A	$999,000	Airbnb cash on cash: 1.25% Traditional cash on cash: -0.24% Airbnb Rental Income: $4331 Traditional Rental Income: $2037 Airbnb ROI: 1.25% Traditional ROI: -0.24%
1155 W 111th Street Chicago , IL 2-bedroom, 1-bath half duplex in Morgan Park. This home has a full basement and detached ...	2 beds \| 1 baths \| 1,264 sq.ft.	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.92% Airbnb Rental Income: $null Traditional Rental Income: $1570 Airbnb ROI: N/A Traditional ROI: 6.92%
5737 N Oriole Avenue Chicago , IL Perfect LOCATION! This lovely updated brick home is ideally situated close to exceptional ...	2 beds \| 2 baths \| 1,875 sq.ft.	$440,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.95% Airbnb Rental Income: $1741 Traditional Rental Income: $2596 Airbnb ROI: 0.71% Traditional ROI: 3.95%
4836 S Dorchester Avenue Chicago , IL Stunning 3-Flat Georgian Style Multi-Family Building in Hyde Park, where historical elegan...	6 beds \| N/A baths \| N/A	$1,150,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 0.32% Airbnb Rental Income: $7292 Traditional Rental Income: $2659 Airbnb ROI: 3.33% Traditional ROI: 0.32%
1122 W Catalpa Avenue #501 Chicago , IL Beautifully appointed move-in ready corner unit concrete loft drenched in natural light st...	2 beds \| 2 baths \| N/A	$299,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 1.51% Airbnb Rental Income: $2832 Traditional Rental Income: $2382 Airbnb ROI: 0.76% Traditional ROI: 1.51%
5455 N Sheridan Road #1415 Chicago , IL Incredible lake, park and city views from this corner unit 1 bed, 1 bath condo at Edgewate...	1 beds \| 1 baths \| 980 sq.ft.	$214,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.44% Airbnb Rental Income: $2248 Traditional Rental Income: $2056 Airbnb ROI: 0.62% Traditional ROI: 2.44%
4848 N Central Ave #301 Chicago , IL 4848 N Central Ave #301, Chicago, IL 60630 \| Condo/Coop	3 beds \| 2 baths \| 1,500 sq.ft.	$395,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 0.83% Airbnb Rental Income: $2437 Traditional Rental Income: $2063 Airbnb ROI: 0.23% Traditional ROI: 0.83%
1711 W Division Street #204 Chicago , IL Impressive, light-filled condo in a boutique elevator building set in the heart of Wicker ...	2 beds \| 2 baths \| 1,750 sq.ft.	$749,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.41% Airbnb Rental Income: $3941 Traditional Rental Income: $2848 Airbnb ROI: 0.77% Traditional ROI: 0.41%
1619 N BELL Avenue Chicago , IL Welcome to your new home that embodies the epitome of luxury, located in the vibrant heart...	5 beds \| 4 baths \| 4,350 sq.ft.	$1,899,000	Airbnb cash on cash: 1.05% Traditional cash on cash: -0.21% Airbnb Rental Income: $7817 Traditional Rental Income: $4093 Airbnb ROI: 1.05% Traditional ROI: -0.21%
840 N Lake Shore Drive #1502 Chicago , IL This stunning two-bedroom, two-and-a-half-bath condo in one of Chicago's premier buildings...	2 beds \| 3 baths \| 2,158 sq.ft.	$1,395,000	Airbnb cash on cash: -1.91% Traditional cash on cash: -2.14% Airbnb Rental Income: $5454 Traditional Rental Income: $4062 Airbnb ROI: -1.91% Traditional ROI: -2.14%
1815 N Harding Avenue Chicago , IL BRICK BUNGALOW LOCATED IN QUIET TREE LINED STREET. 3 LEVEL OF LIVING SPACE. ZIP CODE 60647...	4 beds \| 3 baths \| N/A	$519,000	Airbnb cash on cash: 8.95% Traditional cash on cash: 4.9% Airbnb Rental Income: $6798 Traditional Rental Income: $3509 Airbnb ROI: 8.95% Traditional ROI: 4.9%
8246 S Calumet Avenue Chicago , IL Welcome home to this charming two-story brick home in Chicago. This meticulously maintaine...	3 beds \| 2 baths \| 2,091 sq.ft.	$299,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 7.63% Airbnb Rental Income: $2385 Traditional Rental Income: $2818 Airbnb ROI: 4.01% Traditional ROI: 7.63%

Real Estate investment in Oakland, IL

There are 1 properties for sale in the city of Oakland . The median list price in Oakland is $214,950 and the average price per square foot is $121. In December 2024, the average monthly cash on cash return in Oakland is 14.00%. The average monthly rental income in Oakland is $2,448.

Oakland, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 1 investment properties available for sale in Oakland.

The ROI for Short-Term is higher than the Long-Term in Oakland with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, IL

22263 133 Highway

Oakland, IL

4 beds | 2 baths | 1,696 sq.ft.

$335,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.45%

Airbnb Rental Income: $null

Traditional Rental Income: $2457

Airbnb ROI: N/A

Traditional ROI: 4.45%

Investment Properties for Sale in Other Cities of Illinois

Chicago , IL

4 beds | 4 baths | N/A

$999,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $4331

Traditional Rental Income: $2037

Airbnb ROI: 1.25%

Traditional ROI: -0.24%

Chicago , IL

2 beds | 1 baths | 1,264 sq.ft.

$170,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.92%

Airbnb Rental Income: $null

Traditional Rental Income: $1570

Airbnb ROI: N/A

Traditional ROI: 6.92%

Chicago , IL

2 beds | 2 baths | 1,875 sq.ft.

$440,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1741

Traditional Rental Income: $2596

Airbnb ROI: 0.71%

Traditional ROI: 3.95%

Chicago , IL

6 beds | N/A baths | N/A

$1,150,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 0.32%

Airbnb Rental Income: $7292

Traditional Rental Income: $2659

Airbnb ROI: 3.33%

Traditional ROI: 0.32%

Chicago , IL

2 beds | 2 baths | N/A

$299,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2832

Traditional Rental Income: $2382

Airbnb ROI: 0.76%

Traditional ROI: 1.51%

Chicago , IL

1 beds | 1 baths | 980 sq.ft.

$214,900

Airbnb cash on cash: 0.62%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $2248

Traditional Rental Income: $2056

Airbnb ROI: 0.62%

Traditional ROI: 2.44%

Chicago , IL

3 beds | 2 baths | 1,500 sq.ft.

$395,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $2437

Traditional Rental Income: $2063

Airbnb ROI: 0.23%

Traditional ROI: 0.83%

Chicago , IL

2 beds | 2 baths | 1,750 sq.ft.

$749,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 0.41%