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
103 Estate Dr 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.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.71% Airbnb Rental Income: $null Traditional Rental Income: $2652 Airbnb ROI: N/A Traditional ROI: 6.71%
1009 Swanwick St 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%
1924 High St Chester, IL Classic farmhouse with large pole barn garage sits on 5 acres. Updated with new addition w...	4 beds \| 2 baths \| 1,906 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.52% Airbnb Rental Income: $null Traditional Rental Income: $1820 Airbnb ROI: N/A Traditional ROI: 4.52%
718 State St Chester, IL NEW PICTURES AND FLOOR PLAN added! This one is a true Chester gem my friends. Having lived...	5 beds \| 3 baths \| 5,709 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.55% Airbnb Rental Income: $null Traditional Rental Income: $4707 Airbnb ROI: N/A Traditional ROI: 8.55%
620 Opdyke St 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%
328 Van Zant St Chester, IL BACK ON MARKET - No fault of seller. If you are looking for a fully updated 3-bed 1 bath h...	3 beds \| 1 baths \| 1,088 sq.ft.	$188,000	Airbnb cash on cash: N/A Traditional cash on cash: 7% Airbnb Rental Income: $null Traditional Rental Income: $1689 Airbnb ROI: N/A Traditional ROI: 7%
209 Knapp Ave Chester, IL Put this one on your "checks a lot of boxes" and "must see" list! To name just a few of th...	4 beds \| 2 baths \| 2,200 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.79% Airbnb Rental Income: $null Traditional Rental Income: $2900 Airbnb ROI: N/A Traditional ROI: 8.79%
201 Estate Dr Chester, IL This one will take your breath away folks. Fully updated and move-in ready. You'll love th...	3 beds \| 3 baths \| 2,640 sq.ft.	$379,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 4.37%
1027 William St Chester, IL This 1930-built classic awaits a new owner to love it! So much to love here! The arched fr...	3 beds \| 1 baths \| 1,399 sq.ft.	$145,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.37% Airbnb Rental Income: $null Traditional Rental Income: $1690 Airbnb ROI: N/A Traditional ROI: 10.37%
1040 William St Chester, IL COMING SOON-Showings begin June 26! Welcome to 1040 William Street! An adorable 3 bed-2 ba...	3 beds \| 2 baths \| 1,464 sq.ft.	$149,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.03% Airbnb Rental Income: $null Traditional Rental Income: $1924 Airbnb ROI: N/A Traditional ROI: 11.03%
1713 High St Chester, IL 1713 High St, Chester, IL 62233 \| Single Family Residential	6 beds \| N/A baths \| 2,914 sq.ft.	$299,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $1765 Airbnb ROI: N/A Traditional ROI: 2.68%
2432 State St Chester, IL 2432 State St, Chester, IL 62233 \| Single Family Residential	4 beds \| 1 baths \| 1,480 sq.ft.	$130,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.25% Airbnb Rental Income: $null Traditional Rental Income: $1401 Airbnb ROI: N/A Traditional ROI: 7.25%
601 Erskine St Chester, IL 601 Erskine St, Chester, IL 62233 \| Single Family Residential	3 beds \| 2 baths \| 2,514 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.53% Airbnb Rental Income: $null Traditional Rental Income: $1989 Airbnb ROI: N/A Traditional ROI: 2.53%
10631 Wine Hill Rd Chester, IL 10631 Wine Hill Rd, Chester, IL 62233 \| Single Family Residential	4 beds \| 3 baths \| 3,778 sq.ft.	$2,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.52% Airbnb Rental Income: $null Traditional Rental Income: $1806 Airbnb ROI: N/A Traditional ROI: -2.52%
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%
2002 State Chester, IL Welcome to this charming 4 bedroom, 2 bathroom home located in Randolph County, Illinois, ...	4 beds \| 2 baths \| 1,376 sq.ft.	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.23% Airbnb Rental Income: $null Traditional Rental Income: $1866 Airbnb ROI: N/A Traditional ROI: 8.23%

Real Estate investment in Chester, IL

There are 16 properties for sale in the city of Chester . The median list price in Chester is $157,906 and the average price per square foot is $79. In August 2026, the average monthly cash on cash return in Chester is 9.00%. The average monthly rental income in Chester is $1,866.

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

There are 16 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

103 Estate Dr

Chester, IL

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

$299,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.71%

Airbnb Rental Income: $null

Traditional Rental Income: $2652

Airbnb ROI: N/A

Traditional ROI: 6.71%

1009 Swanwick St

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%

1924 High St

Chester, IL

4 beds | 2 baths | 1,906 sq.ft.

$300,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.52%

Airbnb Rental Income: $null

Traditional Rental Income: $1820

Airbnb ROI: N/A

Traditional ROI: 4.52%

718 State St

Chester, IL

5 beds | 3 baths | 5,709 sq.ft.

$450,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.55%

Airbnb Rental Income: $null

Traditional Rental Income: $4707

Airbnb ROI: N/A

Traditional ROI: 8.55%

620 Opdyke St

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%

328 Van Zant St

Chester, IL

3 beds | 1 baths | 1,088 sq.ft.

$188,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7%

Airbnb Rental Income: $null

Traditional Rental Income: $1689

Airbnb ROI: N/A

Traditional ROI: 7%

209 Knapp Ave

Chester, IL

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

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.79%

Airbnb Rental Income: $null

Traditional Rental Income: $2900

Airbnb ROI: N/A

Traditional ROI: 8.79%

201 Estate Dr

Chester, IL

3 beds | 3 baths | 2,640 sq.ft.

$379,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.37%

Airbnb Rental Income: $null

Traditional Rental Income: $2534

Airbnb ROI: N/A