Real Estate Investment Properties for Sale in Chester, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
925 Lehmen Drive Chester, IL BACK ON MARKET-No fault of seller. What a show stopper folks! This one will take your brea...	3 beds \| 2 baths \| 2,332 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.26% Airbnb Rental Income: $null Traditional Rental Income: $2350 Airbnb ROI: N/A Traditional ROI: 7.26%
103 Estate Drive Chester, IL Put this one on your must-see list! A whopping 2,787 square feet with a total of 3 bedroom...	3 beds \| 3 baths \| 2,787 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $2652 Airbnb ROI: N/A Traditional ROI: 6.02%
1009 Swanwick Street Chester, IL A brick antique house that has much remodeling done. It is located near the heart of Chest...	5 beds \| 2 baths \| 3,639 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.28% Airbnb Rental Income: $null Traditional Rental Income: $2088 Airbnb ROI: N/A Traditional ROI: 9.28%
718 State Street Chester, IL NEW PICTURES AND FLOOR PLAN added! This one is a true Chester gem my friends. Having lived...	5 beds \| 5 baths \| 5,709 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.17% Airbnb Rental Income: $null Traditional Rental Income: $4707 Airbnb ROI: N/A Traditional ROI: 5.17%
620 Opdyke Street Chester, IL What a beautiful home! This one has been updated and remodeled by the owner and what a tra...	3 beds \| 2 baths \| 1,696 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.24% Airbnb Rental Income: $null Traditional Rental Income: $2076 Airbnb ROI: N/A Traditional ROI: 7.24%
732 Roosevelt Street Chester, IL Welcome to secluded Roosevelt street! If you are looking for a really big yard, a big deta...	3 beds \| 2 baths \| 1,352 sq.ft.	$155,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.97% Airbnb Rental Income: $null Traditional Rental Income: $1816 Airbnb ROI: N/A Traditional ROI: 9.97%
5108 Palestine Road Chester, IL This incredible property has 2 acres with fully updated open floor plan home with 3 beds, ...	3 beds \| 2 baths \| 1,305 sq.ft.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.57% Airbnb Rental Income: $null Traditional Rental Income: $2234 Airbnb ROI: N/A Traditional ROI: 8.57%

Real Estate investment in Chester, IL

There are 9 properties for sale in the city of Chester . The median list price in Chester is $259,000 and the average price per square foot is $127. In May 2026, the average monthly cash on cash return in Chester is 9.00%. The average monthly rental income in Chester is $2,161.

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

There are 9 investment properties available for sale in Chester.

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

Your search for investment property begins and ends here

Investment Property for Sale in Chester, IL

925 Lehmen Drive

Chester, IL

3 beds | 2 baths | 2,332 sq.ft.

$259,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2350

Airbnb ROI: N/A

Traditional ROI: 7.26%

103 Estate Drive

Chester, IL

3 beds | 3 baths | 2,787 sq.ft.

$329,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.02%

Airbnb Rental Income: $null

Traditional Rental Income: $2652

Airbnb ROI: N/A

Traditional ROI: 6.02%

1009 Swanwick Street

Chester, IL

5 beds | 2 baths | 3,639 sq.ft.

$185,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.28%

Airbnb Rental Income: $null

Traditional Rental Income: $2088

Airbnb ROI: N/A

Traditional ROI: 9.28%

718 State Street

Chester, IL

5 beds | 5 baths | 5,709 sq.ft.

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.17%

Airbnb Rental Income: $null

Traditional Rental Income: $4707

Airbnb ROI: N/A

Traditional ROI: 5.17%

620 Opdyke Street

Chester, IL

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

$239,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2076

Airbnb ROI: N/A

Traditional ROI: 7.24%

732 Roosevelt Street

Chester, IL

3 beds | 2 baths | 1,352 sq.ft.

$155,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.97%

Airbnb Rental Income: $null

Traditional Rental Income: $1816

Airbnb ROI: N/A

Traditional ROI: 9.97%

5108 Palestine Road

Chester, IL

3 beds | 2 baths | 1,305 sq.ft.

$205,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.57%

Airbnb Rental Income: $null

Traditional Rental Income: $2234

Airbnb ROI: N/A

Traditional ROI: 8.57%

Real Estate investment in Chester, IL

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

How many investment properties are available for sale in Chester?

Long-Term vs. Short-Term Rentals in Chester, Illinois: Which will earn the best returns?

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