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.

Investment Property for Sale in South Boston, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
703 Traver Avenue South Boston, VA Check out this three bedroom home for sale in town. The kitchen has stainless appliances a...	3 beds \| 2 baths \| 2,062 sq.ft.	$195,000	Airbnb cash on cash: 8.46% Traditional cash on cash: 11.49% Airbnb Rental Income: $2621 Traditional Rental Income: $2556 Airbnb ROI: 8.46% Traditional ROI: 11.49%
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.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.78% Airbnb Rental Income: $null Traditional Rental Income: $2918 Airbnb ROI: N/A Traditional ROI: 6.78%
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%
2700 Halifax Road South Boston, VA Check out this completely renovated home in South Boston on a large corner lot that goes t...	4 beds \| 4 baths \| 2,597 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.85% Airbnb Rental Income: $null Traditional Rental Income: $3724 Airbnb ROI: N/A Traditional ROI: 9.85%
305 Ellyson Avenue South Boston, VA Don't miss out ? Rare opportunity to own 4 apt renting in the town of South Boston. All t...	N/A beds \| N/A baths \| 3,248 sq.ft.	$130,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 11.28% Airbnb Rental Income: $1245 Traditional Rental Income: $1667 Airbnb ROI: 4.73% Traditional ROI: 11.28%
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%
725 Magnolia Drive South Boston, VA Looking for that home that is move in ready? Take a look at this one! Living room, large...	3 beds \| 1 baths \| N/A	$182,500	Airbnb cash on cash: 9.14% Traditional cash on cash: 8.73% Airbnb Rental Income: $2621 Traditional Rental Income: $1923 Airbnb ROI: 9.14% Traditional ROI: 8.73%
3100 Philpott Road South Boston, VA New construction-Just completed! Don't miss this fantastic opportunity to own a stunning n...	3 beds \| 2 baths \| 1,358 sq.ft.	$289,900	Airbnb cash on cash: 5.15% Traditional cash on cash: 5.94% Airbnb Rental Income: $2621 Traditional Rental Income: $2211 Airbnb ROI: 5.15% Traditional ROI: 5.94%
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	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.62% Airbnb Rental Income: $null Traditional Rental Income: $3867 Airbnb ROI: N/A Traditional ROI: 9.62%
5055 Old Cluster Springs Road South Boston, VA Homestead ready! This charming cottage features a covered front porch to welcome you home....	2 beds \| 1 baths \| 1,216 sq.ft.	$225,000	Airbnb cash on cash: 7.72% Traditional cash on cash: 7.07% Airbnb Rental Income: $2616 Traditional Rental Income: $1851 Airbnb ROI: 7.72% Traditional ROI: 7.07%
1103 N Main Street South Boston, VA Stately 1927 home has large 16'x17' rooms just waiting for you to personalize the space. ...	5 beds \| 2 baths \| 3,048 sq.ft.	$285,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.02% Airbnb Rental Income: $null Traditional Rental Income: $2868 Airbnb ROI: N/A Traditional ROI: 9.02%
1421 N Main Street South Boston, VA Step into Southern elegance with this 1912 beauty, which seamlessly blends timeless charm ...	3 beds \| 4 baths \| 4,314 sq.ft.	$425,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 7.61% Airbnb Rental Income: $2621 Traditional Rental Income: $3647 Airbnb ROI: 3.46% Traditional ROI: 7.61%
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.	$396,500	Airbnb cash on cash: 3.77% Traditional cash on cash: 5.3% Airbnb Rental Income: $2621 Traditional Rental Income: $2566 Airbnb ROI: 3.77% Traditional ROI: 5.3%
2154 Huell Matthews Highway South Boston, VA Charming 4-bedroom, 1-bath brick home offering 1,247 square feet of comfortable living spa...	4 beds \| 1 baths \| 1,247 sq.ft.	$164,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.54% Airbnb Rental Income: $null Traditional Rental Income: $2109 Airbnb ROI: N/A Traditional ROI: 11.54%

Real Estate investment in South-boston, VA

There are 18 properties for sale in the city of South Boston . The median list price in South Boston is $210,000 and the average price per square foot is $99. In September 2025, the average monthly cash on cash return in South Boston is 10.00%. The average monthly rental income in South Boston is $2,524.

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

There are 18 investment properties available for sale in South-boston.

In 2025, the best neighborhood to buy investment property is South Boston.

The ROI for Short-Term is higher than the Long-Term in South-boston with average rental income of $2,621.

Your search for investment property begins and ends here

Investment Property for Sale in South Boston, VA

703 Traver Avenue

South Boston, VA

3 beds | 2 baths | 2,062 sq.ft.

$195,000

Airbnb cash on cash: 8.46%

Traditional cash on cash: 11.49%

Airbnb Rental Income: $2621

Traditional Rental Income: $2556

Airbnb ROI: 8.46%

Traditional ROI: 11.49%

302 Dunncroft Court

South Boston, VA

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

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.78%

Airbnb Rental Income: $null

Traditional Rental Income: $2918

Airbnb ROI: N/A

Traditional ROI: 6.78%

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%

2700 Halifax Road

South Boston, VA

4 beds | 4 baths | 2,597 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.85%

Airbnb Rental Income: $null

Traditional Rental Income: $3724

Airbnb ROI: N/A

Traditional ROI: 9.85%

305 Ellyson Avenue

South Boston, VA

N/A beds | N/A baths | 3,248 sq.ft.

$130,000

Airbnb cash on cash: 4.73%

Traditional cash on cash: 11.28%

Airbnb Rental Income: $1245

Traditional Rental Income: $1667

Airbnb ROI: 4.73%

Traditional ROI: 11.28%

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