Real Estate Investment Properties for Sale in Chester, AR

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
411 E Front Ave Chester, AR Introducing...The Beard & Lady Inn - A Historic 1887 Bed & Breakfast with Modern Luxury of...	N/A beds \| N/A baths \| 9,600 sq.ft.	$1,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.09% Airbnb Rental Income: $null Traditional Rental Income: $1632 Airbnb ROI: N/A Traditional ROI: 0.09%
TBD Pawpaw Branch Rd Chester, AR TBD Pawpaw Branch Rd, Chester, AR 72934 \| Other	N/A beds \| N/A baths \| N/A	$85,000	Airbnb cash on cash: 7.45% Traditional cash on cash: 5.92% Airbnb Rental Income: $1246 Traditional Rental Income: $722 Airbnb ROI: 7.45% Traditional ROI: 5.92%
TBD Dry Hill Loop Chester, AR TBD Dry Hill Loop, Chester, AR 72934 \| Other	N/A beds \| N/A baths \| N/A	$80,000	Airbnb cash on cash: 7.99% Traditional cash on cash: 6.37% Airbnb Rental Income: $1246 Traditional Rental Income: $722 Airbnb ROI: 7.99% Traditional ROI: 6.37%
TBD Big Bear Canyon Trl Chester, AR TBD Big Bear Canyon Trl, Chester, AR 72934 \| Other	N/A beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.3% Airbnb Rental Income: $1246 Traditional Rental Income: $722 Airbnb ROI: 0.68% Traditional ROI: 0.3%
7738 Rackley Mountain Rd Chester, AR Stunning 40-Acre Retreat with Mountain Views & Waterfalls. This breathtaking 40-acre prope...	3 beds \| 2 baths \| 1,972 sq.ft.	$545,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.19% Airbnb Rental Income: $1110 Traditional Rental Income: $2449 Airbnb ROI: -0.18% Traditional ROI: 3.19%
7238 Chester Cutoff Chester, AR 7238 Chester Cutoff, Chester, AR 72934 \| Other	N/A beds \| N/A baths \| N/A	$193,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 2.41% Airbnb Rental Income: $1246 Traditional Rental Income: $832 Airbnb ROI: 2.51% Traditional ROI: 2.41%
12131 Old 88 Rd Chester, AR Spacious 20-acre property featuring a 5-bedroom, 2-bath home along with a 3-bedroom, 2-bat...	5 beds \| 1 baths \| 3,036 sq.ft.	$340,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.77% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 7.77%
25543 Freedom Rd Chester, AR Escape to the peace and privacy of the countryside with this charming 1-bedroom, 1-bath ho...	1 beds \| 1 baths \| 960 sq.ft.	$225,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 1.57% Airbnb Rental Income: $781 Traditional Rental Income: $772 Airbnb ROI: 0.12% Traditional ROI: 1.57%

Real Estate investment in Chester, AR

There are 8 properties for sale in the city of Chester . The median list price in Chester is $345,000 and the average price per square foot is $99. In May 2026, the average monthly cash on cash return in Chester is 3.00%. The average monthly rental income in Chester is $802.

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

There are 8 investment properties available for sale in Chester.

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

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $802.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, AR

411 E Front Ave

Chester, AR

N/A beds | N/A baths | 9,600 sq.ft.

$1,350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.09%

Airbnb Rental Income: $null

Traditional Rental Income: $1632

Airbnb ROI: N/A

Traditional ROI: 0.09%

TBD Pawpaw Branch Rd

Chester, AR

N/A beds | N/A baths | N/A

$85,000

Airbnb cash on cash: 7.45%

Traditional cash on cash: 5.92%

Airbnb Rental Income: $1246

Traditional Rental Income: $722

Airbnb ROI: 7.45%

Traditional ROI: 5.92%

TBD Dry Hill Loop

Chester, AR

N/A beds | N/A baths | N/A

$80,000

Airbnb cash on cash: 7.99%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $1246

Traditional Rental Income: $722

Airbnb ROI: 7.99%

Traditional ROI: 6.37%

TBD Big Bear Canyon Trl

Chester, AR

N/A beds | N/A baths | N/A

$350,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $1246

Traditional Rental Income: $722

Airbnb ROI: 0.68%

Traditional ROI: 0.3%

7738 Rackley Mountain Rd

Chester, AR

3 beds | 2 baths | 1,972 sq.ft.

$545,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1110

Traditional Rental Income: $2449

Airbnb ROI: -0.18%

Traditional ROI: 3.19%

7238 Chester Cutoff

Chester, AR

N/A beds | N/A baths | N/A

$193,000

Airbnb cash on cash: 2.51%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $1246

Traditional Rental Income: $832

Airbnb ROI: 2.51%

Traditional ROI: 2.41%

12131 Old 88 Rd

Chester, AR

5 beds | 1 baths | 3,036 sq.ft.

$340,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.77%

Airbnb Rental Income: $null

Traditional Rental Income: $2915

Airbnb ROI: N/A

Traditional ROI: 7.77%

25543 Freedom Rd

Chester, AR

1 beds | 1 baths | 960 sq.ft.

$225,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 1.57%

Airbnb Rental Income: $781

Traditional Rental Income: $772

Airbnb ROI: 0.12%