Real Estate Investment Properties for Sale in South Boston, VA

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

Explore a variety of short-term homes & houses in South Boston, VA. Invest wisely with VRBO & South Boston, VA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in South Boston, VA

Search for Single Family Residential for Sale in South Boston, Virginia. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 13 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1308 Friend Avenue South Boston, VA Welcome to this beautifully maintained 4-bedroom, 3-bathroom home in the heart of South Bo...	4 beds \| 3 baths \| 2,856 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.2% Airbnb Rental Income: $null Traditional Rental Income: $3471 Airbnb ROI: N/A Traditional ROI: 7.2%
302 Dunncroft Court South Boston, VA Welcome to this spacious 4 bedroom, 3 bath home designed for comfort and flexibility! Offe...	4 beds \| 3 baths \| 1,971 sq.ft.	$344,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.92% Airbnb Rental Income: $null Traditional Rental Income: $2918 Airbnb ROI: N/A Traditional ROI: 6.92%
1340 Jeffress Street South Boston, VA CUSTOM BUILT HOME IN THE HEART OF SOUTH BOSTON IS WAITING FOR YOU! THE PROPERTY HAS OVER 2...	4 beds \| 2 baths \| 2,856 sq.ft.	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.97% Airbnb Rental Income: $null Traditional Rental Income: $2831 Airbnb ROI: N/A Traditional ROI: 8.97%
2100 Rivoli Street South Boston, VA Located within the town limits of South Boston, VA, this stunning two-story colonial home ...	3 beds \| 4 baths \| 3,366 sq.ft.	$465,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 6.51% Airbnb Rental Income: $2621 Traditional Rental Income: $3487 Airbnb ROI: 3.08% Traditional ROI: 6.51%
20 FOWLER ST South Boston, VA PRESALE 2025 DELIVERY. Located in a vibrant area where every corner tells a story, Dunlora...	3 beds \| 3 baths \| 1,996 sq.ft.	$861,530	Airbnb cash on cash: 0.4% Traditional cash on cash: 1.19% Airbnb Rental Income: $2621 Traditional Rental Income: $2628 Airbnb ROI: 0.4% Traditional ROI: 1.19%
20 STEEP ROCK PL South Boston, VA PRESALE 2026 delivery. The MULBERRY showcases an open concept design with three bedrooms e...	4 beds \| 4 baths \| 2,652 sq.ft.	$859,390	Airbnb cash on cash: N/A Traditional cash on cash: 2.03% Airbnb Rental Income: $null Traditional Rental Income: $3357 Airbnb ROI: N/A Traditional ROI: 2.03%
1312 Willingham Avenue South Boston, VA Welcome to this lovingly maintained single-level home, which seamlessly blends comfort, ch...	4 beds \| 4 baths \| N/A	$344,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.38% Airbnb Rental Income: $null Traditional Rental Income: $3867 Airbnb ROI: N/A Traditional ROI: 10.38%
509 Bellwood Lane South Boston, VA Welcome to Brentwoodâone of South Boston's most sought-after neighborhoods! This classic...	4 beds \| 3 baths \| 1,798 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.36% Airbnb Rental Income: $null Traditional Rental Income: $2802 Airbnb ROI: N/A Traditional ROI: 6.36%
4507 Brentwood Drive South Boston, VA The home features an open floor plan with 3 bedrooms 2 baths, great room with fireplace an...	3 beds \| 2 baths \| 2,063 sq.ft.	$386,500	Airbnb cash on cash: 3.89% Traditional cash on cash: 5.46% Airbnb Rental Income: $2621 Traditional Rental Income: $2566 Airbnb ROI: 3.89% Traditional ROI: 5.46%
207 Yates Street South Boston, VA Professional pictures are coming! Charming 3-bedroom, 2-bath brick home in one of the area...	3 beds \| 2 baths \| N/A	$319,900	Airbnb cash on cash: 4.51% Traditional cash on cash: 5.71% Airbnb Rental Income: $2621 Traditional Rental Income: $2357 Airbnb ROI: 4.51% Traditional ROI: 5.71%
103 Woods Court South Boston, VA Step into modern elegance at 103 Woods Ct, nestled in the sought-after Waddell Woods subdi...	4 beds \| 4 baths \| 2,880 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.42% Airbnb Rental Income: $null Traditional Rental Income: $3468 Airbnb ROI: N/A Traditional ROI: 5.42%
1014 Washington Avenue South Boston, VA Travel back to the age of elegance in this Victorian Italianate masterpiece, known locally...	5 beds \| 5 baths \| 4,608 sq.ft.	$398,500	Airbnb cash on cash: N/A Traditional cash on cash: 11.26% Airbnb Rental Income: $null Traditional Rental Income: $4979 Airbnb ROI: N/A Traditional ROI: 11.26%

Your search for investment property begins and ends here

Single Family Homes for Sale in South Boston, VA

1308 Friend Avenue

South Boston, VA

4 beds | 3 baths | 2,856 sq.ft.

$399,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.2%

Airbnb Rental Income: $null

Traditional Rental Income: $3471

Airbnb ROI: N/A

Traditional ROI: 7.2%

302 Dunncroft Court

South Boston, VA

4 beds | 3 baths | 1,971 sq.ft.

$344,500

Airbnb cash on cash: N/A

Traditional cash on cash: 6.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2918

Airbnb ROI: N/A

Traditional ROI: 6.92%

1340 Jeffress Street

South Boston, VA

4 beds | 2 baths | 2,856 sq.ft.

$280,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.97%

Airbnb Rental Income: $null

Traditional Rental Income: $2831

Airbnb ROI: N/A

Traditional ROI: 8.97%

2100 Rivoli Street

South Boston, VA

3 beds | 4 baths | 3,366 sq.ft.

$465,000

Airbnb cash on cash: 3.08%

Traditional cash on cash: 6.51%

Airbnb Rental Income: $2621

Traditional Rental Income: $3487

Airbnb ROI: 3.08%

Traditional ROI: 6.51%

20 FOWLER ST

South Boston, VA

3 beds | 3 baths | 1,996 sq.ft.

$861,530

Airbnb cash on cash: 0.4%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $2621

Traditional Rental Income: $2628

Airbnb ROI: 0.4%

Traditional ROI: 1.19%

20 STEEP ROCK PL

South Boston, VA

4 beds | 4 baths | 2,652 sq.ft.

$859,390

Airbnb cash on cash: N/A

Traditional cash on cash: 2.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3357

Airbnb ROI: N/A

Traditional ROI: 2.03%

1312 Willingham Avenue

South Boston, VA

4 beds | 4 baths | N/A

$344,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.38%

Airbnb Rental Income: $null

Traditional Rental Income: $3867

Airbnb ROI: N/A

Traditional ROI: 10.38%

509 Bellwood Lane

South Boston, VA

4 beds | 3 baths | 1,798 sq.ft.

$379,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.36%

Airbnb Rental Income: $null

Traditional Rental Income: $2802

Airbnb ROI: N/A