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
106 Allan Street Chester, IL Welcome home to this beautifully maintained brick ranch situated on a spacious corner lot!...	4 beds \| 3 baths \| 2,930 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.23% Airbnb Rental Income: $null Traditional Rental Income: $2682 Airbnb ROI: N/A Traditional ROI: 7.23%
4427 Chester Rd. Chester, IL Welcome to this nicely updated 2 bd 1.5 bath home located on a spacious 2.34 acre lot. In...	2 beds \| 2 baths \| 1,120 sq.ft.	$150,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.61% Airbnb Rental Income: $null Traditional Rental Income: $1573 Airbnb ROI: N/A Traditional ROI: 8.61%
5 Prairie Lane Chester, IL Words just aren't enough to describe this beautiful home. Sitting on 1.1 acres in a beauti...	3 beds \| 4 baths \| 4,276 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.64% Airbnb Rental Income: $null Traditional Rental Income: $3216 Airbnb ROI: N/A Traditional ROI: 6.64%
624 Palestine Road Chester, IL Desirable location! Country type living close to town! This big house has been well loved ...	4 beds \| 1 baths \| 2,369 sq.ft.	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.37% Airbnb Rental Income: $null Traditional Rental Income: $1791 Airbnb ROI: N/A Traditional ROI: 9.37%
103 PAULETTE Street Chester, IL Ready to move in house featuring a handicapped ramp in the front and a handicapped bath ro...	3 beds \| 2 baths \| 1,056 sq.ft.	$144,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.2% Airbnb Rental Income: $null Traditional Rental Income: $1747 Airbnb ROI: N/A Traditional ROI: 10.2%
626 Solomon Street Chester, IL Just what you were looking for to check all the boxes - A beautiful multi-level 3-bed, 2.5...	3 beds \| 4 baths \| 2,200 sq.ft.	$255,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.96% Airbnb Rental Income: $null Traditional Rental Income: $2638 Airbnb ROI: N/A Traditional ROI: 8.96%
153 Chester Street Chester, IL Historic Charm Meets Modern Comfort in Chester! Donât miss this rare opportunity to own ...	4 beds \| 2 baths \| 2,130 sq.ft.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.69% Airbnb Rental Income: $null Traditional Rental Income: $2259 Airbnb ROI: N/A Traditional ROI: 8.69%
2412 State Street Chester, IL Beautiful classic brick home features circular asphalt driveway, detached garage, workshop...	3 beds \| 2 baths \| 1,320 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.88% Airbnb Rental Income: $null Traditional Rental Income: $1916 Airbnb ROI: N/A Traditional ROI: 7.88%
3061 State Route 150 Chester, IL A beautiful fully updated home just outside city limits but so close to everything! Everyt...	3 beds \| 2 baths \| 1,708 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.11% Airbnb Rental Income: $null Traditional Rental Income: $2121 Airbnb ROI: N/A Traditional ROI: 6.11%

Real Estate investment in Chester, IL

There are 11 properties for sale in the city of Chester . The median list price in Chester is $165,000 and the average price per square foot is $88. In October 2025, the average monthly cash on cash return in Chester is 9.00%. The average monthly rental income in Chester is $2,018.

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

There are 11 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

106 Allan Street

Chester, IL

4 beds | 3 baths | 2,930 sq.ft.

$295,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.23%

Airbnb Rental Income: $null

Traditional Rental Income: $2682

Airbnb ROI: N/A

Traditional ROI: 7.23%

4427 Chester Rd.

Chester, IL

2 beds | 2 baths | 1,120 sq.ft.

$150,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.61%

Airbnb Rental Income: $null

Traditional Rental Income: $1573

Airbnb ROI: N/A

Traditional ROI: 8.61%

5 Prairie Lane

Chester, IL

3 beds | 4 baths | 4,276 sq.ft.

$359,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.64%

Airbnb Rental Income: $null

Traditional Rental Income: $3216

Airbnb ROI: N/A

Traditional ROI: 6.64%

624 Palestine Road

Chester, IL

4 beds | 1 baths | 2,369 sq.ft.

$149,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.37%

Airbnb Rental Income: $null

Traditional Rental Income: $1791

Airbnb ROI: N/A

Traditional ROI: 9.37%

103 PAULETTE Street

Chester, IL

3 beds | 2 baths | 1,056 sq.ft.

$144,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.2%

Airbnb Rental Income: $null

Traditional Rental Income: $1747

Airbnb ROI: N/A

Traditional ROI: 10.2%

626 Solomon Street

Chester, IL

3 beds | 4 baths | 2,200 sq.ft.

$255,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2638

Airbnb ROI: N/A

Traditional ROI: 8.96%

153 Chester Street

Chester, IL

4 beds | 2 baths | 2,130 sq.ft.

$205,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.69%

Airbnb Rental Income: $null

Traditional Rental Income: $2259

Airbnb ROI: N/A

Traditional ROI: 8.69%

2412 State Street

Chester, IL

3 beds | 2 baths | 1,320 sq.ft.

$189,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.88%

Airbnb Rental Income: $null

Traditional Rental Income: $1916

Airbnb ROI: N/A