Real Estate Investment Properties for Sale in South Chesterfield, VA

Looking for investment property in South Chesterfield, VA with high ROI ?

Explore a variety of short-term homes & houses in South Chesterfield, VA. Invest wisely with VRBO & South Chesterfield, VA 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 South Chesterfield, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
21611 Pannill St South Chesterfield, VA 21611 Pannill St, South Chesterfield, VA 23803 \| Single Family Residential	3 beds \| 1 baths \| 996 sq.ft.	$248,500	Airbnb cash on cash: 2.29% Traditional cash on cash: 7.27% Airbnb Rental Income: $1331 Traditional Rental Income: $2090 Airbnb ROI: 2.29% Traditional ROI: 7.27%
5900 River Rd South Chesterfield, VA ""SPACIOUS brick home nicely landscaped located on a corner lot in Matoaca - MUST SEE TO A...	4 beds \| 3 baths \| N/A	$379,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 6.42% Airbnb Rental Income: $1041 Traditional Rental Income: $3035 Airbnb ROI: -0.21% Traditional ROI: 6.42%
21310 Chesterfield Ave South Chesterfield, VA SO, you know all these listings that say âMust Seeâ, and you look and goâ¦.Ehhâ¦.big...	4 beds \| 3 baths \| 1,704 sq.ft.	$319,999	Airbnb cash on cash: 0.7% Traditional cash on cash: 9.18% Airbnb Rental Income: $1041 Traditional Rental Income: $3232 Airbnb ROI: 0.7% Traditional ROI: 9.18%
20413 Loyal Ave South Chesterfield, VA Back on the market at no fault of this MOTIVATED Seller! This one-level, mid-century brick...	4 beds \| 2 baths \| 2,429 sq.ft.	$330,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.71% Airbnb Rental Income: $1041 Traditional Rental Income: $1769 Airbnb ROI: 0.19% Traditional ROI: 3.71%
20117 Laurel Road South Chesterfield, VA Welcome home to this charming three bed, one and a half bath bungalow in Chesterfield. Thi...	3 beds \| 2 baths \| 1,080 sq.ft.	$230,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 5.55% Airbnb Rental Income: $1331 Traditional Rental Income: $1668 Airbnb ROI: 2.12% Traditional ROI: 5.55%
25506 Simmons Ave South Chesterfield, VA Fantastic new construction for sale, offering tons of value for your hard earned money. Ho...	4 beds \| 3 baths \| 2,023 sq.ft.	$395,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 5.08% Airbnb Rental Income: $1041 Traditional Rental Income: $2646 Airbnb ROI: -0.23% Traditional ROI: 5.08%
21210 Chesterfield Avenue South Chesterfield, VA Chesterfield Schools! Great investment / rental property. Brick home, metal roof, wood flo...	2 beds \| 1 baths \| 1,080 sq.ft.	$179,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 6.6% Airbnb Rental Income: $929 Traditional Rental Income: $1532 Airbnb ROI: 1.05% Traditional ROI: 6.6%
20501 Hickory Court South Chesterfield, VA Welcome to 20501 Hickory Court, a move-in ready and beautifully renovated 4-bedroom, 2-bat...	4 beds \| 2 baths \| 1,176 sq.ft.	$319,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 3.57% Airbnb Rental Income: $1041 Traditional Rental Income: $1627 Airbnb ROI: 0.41% Traditional ROI: 3.57%
21204 Orange Hill Ave South Chesterfield, VA 21204 Orange Hill Ave, South Chesterfield, VA 23803 \| Single Family Residential	3 beds \| 1 baths \| 1,700 sq.ft.	$315,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 4.93% Airbnb Rental Income: $1331 Traditional Rental Income: $2090 Airbnb ROI: 0.98% Traditional ROI: 4.93%
9324 Oak River Dr South Chesterfield, VA 9324 Oak River Dr, South Chesterfield, VA 23803 \| Single Family Residential	5 beds \| 3 baths \| 4,117 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.03% Airbnb Rental Income: $null Traditional Rental Income: $2250 Airbnb ROI: N/A Traditional ROI: 2.03%
20001 Chesdin Harbor Dr South Chesterfield, VA 20001 Chesdin Harbor Dr, South Chesterfield, VA 23803 \| Other	N/A beds \| N/A baths \| N/A	$249,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 4.78% Airbnb Rental Income: $1359 Traditional Rental Income: $1653 Airbnb ROI: 1.77% Traditional ROI: 4.78%
21312 Warrior Dr South Chesterfield, VA 21312 Warrior Dr, South Chesterfield, VA 23803 \| Single Family Residential	3 beds \| 2 baths \| 1,104 sq.ft.	$259,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 6.36% Airbnb Rental Income: $1331 Traditional Rental Income: $2090 Airbnb ROI: 1.57% Traditional ROI: 6.36%
3807 Dupuy Road South Chesterfield, VA Great New Construction waiting for you to move in. Great location with easy access to High...	3 beds \| 3 baths \| N/A	$350,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.97% Airbnb Rental Income: $1331 Traditional Rental Income: $2090 Airbnb ROI: 1.41% Traditional ROI: 4.97%
21609 Pannill Street South Chesterfield, VA This 1,256-square-foot traditional ranch features 3 bedrooms, 1 full bath, and lvp/vinyl f...	3 beds \| 1 baths \| 1,256 sq.ft.	$224,950	Airbnb cash on cash: 2.27% Traditional cash on cash: 7.77% Airbnb Rental Income: $1331 Traditional Rental Income: $2090 Airbnb ROI: 2.27% Traditional ROI: 7.77%
4221 River Rd South Chesterfield, VA 4221 River Rd, South Chesterfield, VA 23803 \| Single Family Residential	3 beds \| 2 baths \| 2,156 sq.ft.	$240,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 6.99% Airbnb Rental Income: $1331 Traditional Rental Income: $2090 Airbnb ROI: 1.83% Traditional ROI: 6.99%
21622 Beverley Street South Chesterfield, VA *Price Improvement*Situated on a .56 acre lot in the well established community of Riv...	3 beds \| 1 baths \| 960 sq.ft.	$270,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 4.24% Airbnb Rental Income: $1331 Traditional Rental Income: $1575 Airbnb ROI: 1.67% Traditional ROI: 4.24%
20104 Starr Court South Chesterfield, VA Beautifully Updated Tri-Level with Garage, Outdoor Living, and Flexible Space Welcome home...	4 beds \| 2 baths \| 1,855 sq.ft.	$375,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 7.28% Airbnb Rental Income: $1041 Traditional Rental Income: $3232 Airbnb ROI: 0.03% Traditional ROI: 7.28%
3008 Plumtree Street South Chesterfield, VA This smartly designed home offers spacious living on a starter home level. You will be liv...	3 beds \| 2 baths \| 1,152 sq.ft.	$299,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 4.47% Airbnb Rental Income: $1331 Traditional Rental Income: $1921 Airbnb ROI: 0.91% Traditional ROI: 4.47%
2812 Amherst Ridge Way South Chesterfield, VA 2812 Amherst Ridge Way, South Chesterfield, VA 23834 \| Single Family Residential	4 beds \| N/A baths \| 2,026 sq.ft.	$411,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 6.33% Airbnb Rental Income: $1041 Traditional Rental Income: $3232 Airbnb ROI: -0.29% Traditional ROI: 6.33%
200 Swift Creek Ln South Chesterfield, VA 200 Swift Creek Ln, South Chesterfield, VA 23834 \| Other	N/A beds \| N/A baths \| N/A	$175,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 7.54% Airbnb Rental Income: $1359 Traditional Rental Income: $1653 Airbnb ROI: 3.29% Traditional ROI: 7.54%
17330 Branders Bridge Rd South Chesterfield, VA	3 beds \| 2 baths \| 2,380 sq.ft.	$485,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 2.59% Airbnb Rental Income: $1331 Traditional Rental Income: $2090 Airbnb ROI: 0.01% Traditional ROI: 2.59%
19515 Julep Circle South Chesterfield, VA Welcome home to this thoughtfully renovated home. Featuring a brand new primary and second...	3 beds \| 2 baths \| 1,200 sq.ft.	$297,500	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.47% Airbnb Rental Income: $1331 Traditional Rental Income: $2090 Airbnb ROI: 1.3% Traditional ROI: 5.47%
1213 Walthall Creek Drive South Chesterfield, VA Five-bedroom, four-bath transitional home located in Chesterfield, Virginia. Built in 2005...	5 beds \| 4 baths \| 3,588 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $3717 Airbnb ROI: N/A Traditional ROI: 4.78%
2901 Tipton Street South Chesterfield, VA This custom-built, traditional-style, one level home is everything but traditional. When t...	4 beds \| 2 baths \| 2,352 sq.ft.	$380,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 4.52% Airbnb Rental Income: $1041 Traditional Rental Income: $2409 Airbnb ROI: -0.33% Traditional ROI: 4.52%
15531 Saddlebrook Road South Chesterfield, VA Welcome to 15531 Saddlebrook Rd - beautifully renovated, truly turnkey living on nearly ha...	3 beds \| 2 baths \| 1,056 sq.ft.	$305,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 4.25% Airbnb Rental Income: $1331 Traditional Rental Income: $1789 Airbnb ROI: 1.22% Traditional ROI: 4.25%
1731 River Vista Road South Chesterfield, VA MOVE-IN READY! Welcome to Chappell Creek in Prince George, VA! This established community ...	4 beds \| 2 baths \| 1,698 sq.ft.	$389,990	Airbnb cash on cash: -0.21% Traditional cash on cash: 3.87% Airbnb Rental Income: $1041 Traditional Rental Income: $2170 Airbnb ROI: -0.21% Traditional ROI: 3.87%
1775 River Vista Road South Chesterfield, VA MOVE-IN READY! Welcome to Chappell Creek in Prince George, VA! This established community ...	3 beds \| 3 baths \| 1,657 sq.ft.	$405,990	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.79% Airbnb Rental Income: $1331 Traditional Rental Income: $2224 Airbnb ROI: 0.36% Traditional ROI: 3.79%

Real Estate investment in South-chesterfield, VA

There are 28 properties for sale in the city of South Chesterfield . The median list price in South Chesterfield is $302,000 and the average price per square foot is $182. In March 2026, the average monthly cash on cash return in South Chesterfield is 5.00%. The average monthly rental income in South Chesterfield is $2,090.

South-chesterfield, VA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 28 investment properties available for sale in South-chesterfield.

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

The ROI for Long-Term is higher than the Short-Term in South-chesterfield with average rental income of $2,090.

Your search for investment property begins and ends here

Investment Property for Sale in South Chesterfield, VA

21611 Pannill St

South Chesterfield, VA

3 beds | 1 baths | 996 sq.ft.

$248,500

Airbnb cash on cash: 2.29%

Traditional cash on cash: 7.27%

Airbnb Rental Income: $1331

Traditional Rental Income: $2090

Airbnb ROI: 2.29%

Traditional ROI: 7.27%

5900 River Rd

South Chesterfield, VA

4 beds | 3 baths | N/A

$379,000

Airbnb cash on cash: -0.21%

Traditional cash on cash: 6.42%

Airbnb Rental Income: $1041

Traditional Rental Income: $3035

Airbnb ROI: -0.21%

Traditional ROI: 6.42%

21310 Chesterfield Ave

South Chesterfield, VA

4 beds | 3 baths | 1,704 sq.ft.

$319,999

Airbnb cash on cash: 0.7%

Traditional cash on cash: 9.18%

Airbnb Rental Income: $1041

Traditional Rental Income: $3232

Airbnb ROI: 0.7%

Traditional ROI: 9.18%

20413 Loyal Ave

South Chesterfield, VA

4 beds | 2 baths | 2,429 sq.ft.

$330,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $1041

Traditional Rental Income: $1769

Airbnb ROI: 0.19%

Traditional ROI: 3.71%

20117 Laurel Road

South Chesterfield, VA

3 beds | 2 baths | 1,080 sq.ft.

$230,000

Airbnb cash on cash: 2.12%

Traditional cash on cash: 5.55%

Airbnb Rental Income: $1331

Traditional Rental Income: $1668

Airbnb ROI: 2.12%

Traditional ROI: 5.55%

25506 Simmons Ave

South Chesterfield, VA

4 beds | 3 baths | 2,023 sq.ft.

$395,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $1041

Traditional Rental Income: $2646

Airbnb ROI: -0.23%

Traditional ROI: 5.08%

21210 Chesterfield Avenue

South Chesterfield, VA

2 beds | 1 baths | 1,080 sq.ft.

$179,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 6.6%

Airbnb Rental Income: $929

Traditional Rental Income: $1532

Airbnb ROI: 1.05%

Traditional ROI: 6.6%

20501 Hickory Court

South Chesterfield, VA

4 beds | 2 baths | 1,176 sq.ft.

$319,000

Airbnb cash on cash: 0.41%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $1041

Traditional Rental Income: $1627

Airbnb ROI: 0.41%