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.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.17% Airbnb Rental Income: $null Traditional Rental Income: $1632 Airbnb ROI: N/A Traditional ROI: 0.17%
TBD Pawpaw Branch Rd Chester, AR TBD Pawpaw Branch Rd, Chester, AR 72934 \| Other	N/A beds \| N/A baths \| N/A	$75,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $722 Airbnb ROI: N/A Traditional ROI: 6.86%
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: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $722 Airbnb ROI: N/A 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	$240,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.16% Airbnb Rental Income: $null Traditional Rental Income: $722 Airbnb ROI: N/A Traditional ROI: 1.16%
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: N/A Traditional cash on cash: 2.41% Airbnb Rental Income: $null Traditional Rental Income: $832 Airbnb ROI: N/A 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 \| 2 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: -0.71% Traditional cash on cash: 5.77% Airbnb Rental Income: $571 Traditional Rental Income: $1666 Airbnb ROI: -0.71% Traditional ROI: 5.77%
TBD Freedom Rd Chester, AR TBD Freedom Rd, Chester, AR 72934 \| Other	N/A beds \| N/A baths \| N/A	$210,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $845 Airbnb ROI: N/A Traditional ROI: 2.16%
9005 Rackley Mountain Rd Chester, AR Tucked away in the peaceful hills of Chester, Arkansas, 9005 Rackley Mountain Road offers ...	3 beds \| 1 baths \| 1,374 sq.ft.	$215,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 8.43% Airbnb Rental Income: $1380 Traditional Rental Income: $2078 Airbnb ROI: 2.94% Traditional ROI: 8.43%
1716 Dry Hill Rd Chester, AR 1716 Dry Hill Rd, Chester, AR 72934 \| Other	N/A beds \| N/A baths \| N/A	$55,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.79% Airbnb Rental Income: $null Traditional Rental Income: $838 Airbnb ROI: N/A Traditional ROI: 11.79%
24055 Freedom Rd Chester, AR 24055 Freedom Rd, Chester, AR 72934 \| Manufactured Home	N/A beds \| N/A baths \| 1,232 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $1656 Airbnb ROI: N/A Traditional ROI: 3.92%
TBD Dry Hill Rd Chester, AR TBD Dry Hill Rd, Chester, AR 72934 \| Other	N/A beds \| N/A baths \| N/A	$73,280	Airbnb cash on cash: N/A Traditional cash on cash: 9.27% Airbnb Rental Income: $null Traditional Rental Income: $883 Airbnb ROI: N/A Traditional ROI: 9.27%

Real Estate investment in Chester, AR

There are 12 properties for sale in the city of Chester . The median list price in Chester is $194,000 and the average price per square foot is $65. In September 2026, the average monthly cash on cash return in Chester is 6.00%. The average monthly rental income in Chester is $864.

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

There are 12 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 $864.

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.

$1,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.17%

Airbnb Rental Income: $null

Traditional Rental Income: $1632

Airbnb ROI: N/A

Traditional ROI: 0.17%

TBD Pawpaw Branch Rd

Chester, AR

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

$75,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.86%

Airbnb Rental Income: $null

Traditional Rental Income: $722

Airbnb ROI: N/A

Traditional ROI: 6.86%

TBD Dry Hill Loop

Chester, AR

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

$80,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.37%

Airbnb Rental Income: $null

Traditional Rental Income: $722

Airbnb ROI: N/A

Traditional ROI: 6.37%

TBD Big Bear Canyon Trl

Chester, AR

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

$240,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.16%

Airbnb Rental Income: $null

Traditional Rental Income: $722

Airbnb ROI: N/A

Traditional ROI: 1.16%

7238 Chester Cutoff

Chester, AR

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

$193,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.41%

Airbnb Rental Income: $null

Traditional Rental Income: $832

Airbnb ROI: N/A

Traditional ROI: 2.41%

12131 Old 88 RD

Chester, AR

5 beds | 2 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: -0.71%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $571

Traditional Rental Income: $1666

Airbnb ROI: -0.71%

Traditional ROI: 5.77%

TBD Freedom Rd

Chester, AR

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

$210,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.16%

Airbnb Rental Income: $null

Traditional Rental Income: $845

Airbnb ROI: N/A