Real Estate Investment Properties for Sale in Chesterfield, SC

Looking for investment property in Chesterfield, SC with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
306 W Main St Chesterfield, SC Colonial Revival architecture at its finest, this 5 BR/3.5 BA, approx. 5000 sq. ft., home...	5 beds \| 3 baths \| 4,552 sq.ft.	$797,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.15% Airbnb Rental Income: $null Traditional Rental Income: $3594 Airbnb ROI: N/A Traditional ROI: 3.15%
107 S Craig St Chesterfield, SC This charming, Victorian home offers over 2000 sq. ft. of living space, wonderful , welcom...	4 beds \| 2 baths \| 2,146 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.98% Airbnb Rental Income: $null Traditional Rental Income: $2905 Airbnb ROI: N/A Traditional ROI: 7.98%
1935 Oakland Church Rd Chesterfield, SC Looking for a total package?!? Hereâs your opportunity! HOME, LAND, POND, POOL, HUGE SHO...	3 beds \| 2 baths \| 2,952 sq.ft.	$849,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.54% Airbnb Rental Income: $null Traditional Rental Income: $3034 Airbnb ROI: N/A Traditional ROI: 2.54%
2082 Mary D Rd #1 Chesterfield, SC 2082 Mary D Rd #1, Chesterfield, SC 29709 \| Single Family Residential	3 beds \| 2 baths \| 1,418 sq.ft.	$269,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $1345 Airbnb ROI: N/A Traditional ROI: 3.35%
102 Dolly Moore Ln Chesterfield, SC 102 Dolly Moore Ln, Chesterfield, SC 29709 \| Single Family Residential	4 beds \| 2 baths \| 2,016 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $1483 Airbnb ROI: N/A Traditional ROI: 2.79%
2734 Center Point Rd Chesterfield, SC 2734 Center Point Rd, Chesterfield, SC 29709 \| Single Family Residential	2 beds \| 2 baths \| 1,152 sq.ft.	$238,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 2.61% Airbnb Rental Income: $1073 Traditional Rental Income: $1034 Airbnb ROI: 1.15% Traditional ROI: 2.61%
332 Watson Hill Rd Chesterfield, SC	3 beds \| 2 baths \| 1,598 sq.ft.	$279,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.56% Airbnb Rental Income: $null Traditional Rental Income: $1973 Airbnb ROI: N/A Traditional ROI: 5.56%
1272 Huntley Shop Rd Chesterfield, SC 1272 Huntley Shop Rd, Chesterfield, SC 29709 \| Single Family Residential	1 beds \| 1 baths \| 1,528 sq.ft.	$325,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 1.54% Airbnb Rental Income: $673 Traditional Rental Income: $1043 Airbnb ROI: -0.65% Traditional ROI: 1.54%
665 Hwy 145 Hwy S Chesterfield, SC 665 Hwy 145 Hwy S, Chesterfield, SC 29709 \| Other	N/A beds \| N/A baths \| N/A	$107,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.59% Airbnb Rental Income: $null Traditional Rental Income: $839 Airbnb ROI: N/A Traditional ROI: 5.59%
1424 Boatwright Rd Chesterfield, SC 1424 Boatwright Rd, Chesterfield, SC 29709 \| Other	N/A beds \| N/A baths \| N/A	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.31% Airbnb Rental Income: $null Traditional Rental Income: $839 Airbnb ROI: N/A Traditional ROI: 0.31%
13691 Highway 9 Chesterfield, SC 13691 Highway 9, Chesterfield, SC 29709 \| Other	N/A beds \| N/A baths \| N/A	$49,995	Airbnb cash on cash: N/A Traditional cash on cash: 11.94% Airbnb Rental Income: $null Traditional Rental Income: $782 Airbnb ROI: N/A Traditional ROI: 11.94%
0000 Jackson Rd W Chesterfield, SC 0000 Jackson Rd W, Chesterfield, SC 29709 \| Other	N/A beds \| N/A baths \| N/A	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.36% Airbnb Rental Income: $null Traditional Rental Income: $839 Airbnb ROI: N/A Traditional ROI: 2.36%
7917 Highway 9 Chesterfield, SC 7917 Highway 9, Chesterfield, SC 29709 \| Other	N/A beds \| N/A baths \| N/A	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $839 Airbnb ROI: N/A Traditional ROI: 3.03%
Hwy 9 Angelus Rd Chesterfield, SC	N/A beds \| N/A baths \| N/A	$159,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.95% Airbnb Rental Income: $null Traditional Rental Income: $782 Airbnb ROI: N/A Traditional ROI: 2.95%
612&614 East Blvd Chesterfield, SC 612&614 East Blvd, Chesterfield, SC 29709 \| Other	N/A beds \| N/A baths \| N/A	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.87% Airbnb Rental Income: $null Traditional Rental Income: $782 Airbnb ROI: N/A Traditional ROI: 0.87%
1636 Shiloh Acres Rd Chesterfield, SC 1636 Shiloh Acres Rd, Chesterfield, SC 29709 \| Single Family Residential	4 beds \| 3 baths \| 2,748 sq.ft.	$499,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.41% Airbnb Rental Income: $null Traditional Rental Income: $1483 Airbnb ROI: N/A Traditional ROI: 1.41%

Real Estate investment in Chesterfield, SC

There are 16 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $509,990 and the average price per square foot is $197. In January 2026, the average monthly cash on cash return in Chesterfield is 10.00%. The average monthly rental income in Chesterfield is $839.

Chesterfield, SC Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 16 investment properties available for sale in Chesterfield.

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

The ROI for Short-Term is higher than the Long-Term in Chesterfield with average rental income of $1,073.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, SC

306 W Main St

Chesterfield, SC

5 beds | 3 baths | 4,552 sq.ft.

$797,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.15%

Airbnb Rental Income: $null

Traditional Rental Income: $3594

Airbnb ROI: N/A

Traditional ROI: 3.15%

107 S Craig St

Chesterfield, SC

4 beds | 2 baths | 2,146 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.98%

Airbnb Rental Income: $null

Traditional Rental Income: $2905

Airbnb ROI: N/A

Traditional ROI: 7.98%

1935 Oakland Church Rd

Chesterfield, SC

3 beds | 2 baths | 2,952 sq.ft.

$849,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.54%

Airbnb Rental Income: $null

Traditional Rental Income: $3034

Airbnb ROI: N/A

Traditional ROI: 2.54%

2082 Mary D Rd #1

Chesterfield, SC

3 beds | 2 baths | 1,418 sq.ft.

$269,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.35%

Airbnb Rental Income: $null

Traditional Rental Income: $1345

Airbnb ROI: N/A

Traditional ROI: 3.35%

102 Dolly Moore Ln

Chesterfield, SC

4 beds | 2 baths | 2,016 sq.ft.

$339,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.79%

Airbnb Rental Income: $null

Traditional Rental Income: $1483

Airbnb ROI: N/A

Traditional ROI: 2.79%

2734 Center Point Rd

Chesterfield, SC

2 beds | 2 baths | 1,152 sq.ft.

$238,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $1073

Traditional Rental Income: $1034

Airbnb ROI: 1.15%

Traditional ROI: 2.61%

332 Watson Hill Rd

Chesterfield, SC

3 beds | 2 baths | 1,598 sq.ft.

$279,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.56%

Airbnb Rental Income: $null

Traditional Rental Income: $1973

Airbnb ROI: N/A

Traditional ROI: 5.56%

1272 Huntley Shop Rd

Chesterfield, SC

1 beds | 1 baths | 1,528 sq.ft.

$325,000

Airbnb cash on cash: -0.65%

Traditional cash on cash: 1.54%

Airbnb Rental Income: $673

Traditional Rental Income: $1043

Airbnb ROI: -0.65%