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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1194 Wolf Trap Road South Boston, VA Experience the perfect combination of comfort and style in this thoughtfully updated 3-bed...	3 beds \| 2 baths \| 1,860 sq.ft.	$359,900	Airbnb cash on cash: 2.12% Traditional cash on cash: 5.87% Airbnb Rental Income: $1933 Traditional Rental Income: $2690 Airbnb ROI: 2.12% Traditional ROI: 5.87%
617 Greenway Drive South Boston, VA SPACIOUS and MOVE-IN READY 3-BEDROOM, 2-FULL BATH home offering APPROX. 2,256 FINISHED SQ ...	3 beds \| 2 baths \| 2,256 sq.ft.	$250,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 9.05% Airbnb Rental Income: $1933 Traditional Rental Income: $2659 Airbnb ROI: 3.81% Traditional ROI: 9.05%
1728 Vaughan Street South Boston, VA Charming 3-bedroom, 1-bath brick home conveniently located in South Boston, just a short w...	3 beds \| 1 baths \| 1,313 sq.ft.	$189,900	Airbnb cash on cash: 6.16% Traditional cash on cash: 9.25% Airbnb Rental Income: $1933 Traditional Rental Income: $1979 Airbnb ROI: 6.16% Traditional ROI: 9.25%
2504 Halifax Road South Boston, VA Classic colonial-style home located along Halifax Road in South Boston, situated on 1.05 a...	4 beds \| 3 baths \| 2,508 sq.ft.	$264,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.47% Airbnb Rental Income: $null Traditional Rental Income: $3271 Airbnb ROI: N/A Traditional ROI: 11.47%
2929 Halifax Road South Boston, VA Welcome to a home where timeless architecture meets modern versatility. This stately 4,819...	4 beds \| 4 baths \| 4,819 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.49% Airbnb Rental Income: $null Traditional Rental Income: $3772 Airbnb ROI: N/A Traditional ROI: 4.49%
2100 Westmoreland Street South Boston, VA Charming two-story home featuring 3 spacious bedrooms located on the second floor. Enjoy t...	3 beds \| 2 baths \| 2,903 sq.ft.	$390,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 4.83% Airbnb Rental Income: $1933 Traditional Rental Income: $2522 Airbnb ROI: 1.82% Traditional ROI: 4.83%
2105 Willow Street South Boston, VA Beautiful home! Home offers hardwood & tile floors, large living room, family room w/ wood...	3 beds \| 2 baths \| 1,416 sq.ft.	$185,900	Airbnb cash on cash: 6.37% Traditional cash on cash: 5.35% Airbnb Rental Income: $1933 Traditional Rental Income: $1242 Airbnb ROI: 6.37% Traditional ROI: 5.35%
1898 Jeffress Blvd South Boston, VA This property is NOT for rent!! Welcome to your three-bedroom, two-bath home in the heart ...	3 beds \| 2 baths \| 1,404 sq.ft.	$159,900	Airbnb cash on cash: 6.89% Traditional cash on cash: 8.64% Airbnb Rental Income: $1933 Traditional Rental Income: $1689 Airbnb ROI: 6.89% Traditional ROI: 8.64%
1905 Wilborn Avenue South Boston, VA PRIME LOCATION! This updated ranch-style home is conveniently located in the heart of Sout...	3 beds \| 2 baths \| 1,728 sq.ft.	$334,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 5.62% Airbnb Rental Income: $1933 Traditional Rental Income: $2432 Airbnb ROI: 2.41% Traditional ROI: 5.62%
306 Forest Drive South Boston, VA Impeccably maintained one-owner home with a virtually maintenance-free exterior! This spac...	4 beds \| 2 baths \| 2,620 sq.ft.	$405,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.95% Airbnb Rental Income: $null Traditional Rental Income: $2843 Airbnb ROI: N/A Traditional ROI: 5.95%
420 Valley Drive South Boston, VA Welcome home to this lovingly maintained 3-bedroom, 1.5-bath brick rancher nestled on a sp...	3 beds \| 1 baths \| 1,445 sq.ft.	$219,900	Airbnb cash on cash: 4.57% Traditional cash on cash: 5.58% Airbnb Rental Income: $1933 Traditional Rental Income: $1632 Airbnb ROI: 4.57% Traditional ROI: 5.58%
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.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.73% Airbnb Rental Income: $null Traditional Rental Income: $2831 Airbnb ROI: N/A Traditional ROI: 9.73%
2100 Rivoli Street South Boston, VA Stately 2 story brick colonial situated on 3 lots totaling 1.53 acres in the desirable San...	3 beds \| 3 baths \| 3,669 sq.ft.	$465,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 6.51% Airbnb Rental Income: $1933 Traditional Rental Income: $3487 Airbnb ROI: 1.76% Traditional ROI: 6.51%
2700 Halifax Road South Boston, VA This stunning split-level brick home sits proudly on .96 of an acre (corner lot) right in ...	4 beds \| 3 baths \| 3,512 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.17% Airbnb Rental Income: $null Traditional Rental Income: $3724 Airbnb ROI: N/A Traditional ROI: 10.17%
1247 Sandy Beach Road South Boston, VA Historic home with ties to Irvine's Ferry on Dan River offered with 5+Acres. This property...	N/A beds \| N/A baths \| 3,393 sq.ft.	$289,000	Airbnb cash on cash: -2.06% Traditional cash on cash: 4.19% Airbnb Rental Income: $257 Traditional Rental Income: $1727 Airbnb ROI: -2.06% Traditional ROI: 4.19%
350 Powell Road South Boston, VA Great Investment Opportunity! Greens Folly Apartments consists of 9 low-maintenance brick ...	112 beds \| N/A baths \| 45,402 sq.ft.	$3,790,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.41% Airbnb Rental Income: $null Traditional Rental Income: $2261 Airbnb ROI: N/A Traditional ROI: -0.41%
400 Tanglewylde Drive South Boston, VA Introducing an exceptional investment opportunity in the heart of South Boston, VA. Tangle...	60 beds \| N/A baths \| 24,174 sq.ft.	$1,830,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.18% Airbnb Rental Income: $null Traditional Rental Income: $2170 Airbnb ROI: N/A Traditional ROI: 0.18%
302 Monroe Street South Boston, VA Charming 2 story colonial in an established neighborhood-with a private pool! Welcome home...	3 beds \| 3 baths \| 2,776 sq.ft.	$395,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 6.65% Airbnb Rental Income: $1933 Traditional Rental Income: $3040 Airbnb ROI: 2.28% Traditional ROI: 6.65%
3203 N Main Street South Boston, VA Welcome home to this inviting family friendly residence featuring a bright, open floor pla...	3 beds \| 2 baths \| 1,762 sq.ft.	$349,900	Airbnb cash on cash: 2.23% Traditional cash on cash: 5.13% Airbnb Rental Income: $1933 Traditional Rental Income: $2374 Airbnb ROI: 2.23% Traditional ROI: 5.13%
427 Taylor South Boston, VA Welcome Home! Here is your chance to pick your own colors, counter tops and cabinets. Make...	3 beds \| 2 baths \| N/A	$234,500	Airbnb cash on cash: 4.18% Traditional cash on cash: 8.33% Airbnb Rental Income: $1933 Traditional Rental Income: $2343 Airbnb ROI: 4.18% Traditional ROI: 8.33%
1404 N Main Street South Boston, VA Welcome home, where character, grace, & space come together beautifully, minutes from down...	4 beds \| 3 baths \| 3,448 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.32% Airbnb Rental Income: $null Traditional Rental Income: $3332 Airbnb ROI: N/A Traditional ROI: 6.32%
2205 Parker Avenue South Boston, VA Welcome to 2205 Parker Avenue in South Boston! This beautifully refreshed 1 bedroom, 1 bat...	1 beds \| 1 baths \| 730 sq.ft.	$125,000	Airbnb cash on cash: -2.81% Traditional cash on cash: 8.63% Airbnb Rental Income: $193 Traditional Rental Income: $1350 Airbnb ROI: -2.81% Traditional ROI: 8.63%
1526 Berry Hill Road South Boston, VA Step into this meticulously crafted home located within town limits yet offering a peacefu...	3 beds \| 3 baths \| 2,771 sq.ft.	$445,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.94% Airbnb Rental Income: $1933 Traditional Rental Income: $1242 Airbnb ROI: 1.38% Traditional ROI: 0.94%
1207 Alphonse Dairy Road South Boston, VA This 3 bedroom, 2 bath home brings more to the table than your typical layout. With both a...	3 beds \| 2 baths \| 1,640 sq.ft.	$239,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 7.95% Airbnb Rental Income: $1933 Traditional Rental Income: $2298 Airbnb ROI: 4.07% Traditional ROI: 7.95%
109 Sycamore Road South Boston, VA New flooring, paint and half bathroom added to this this beautiful brick home in the heart...	3 beds \| 2 baths \| 1,419 sq.ft.	$195,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 7.65% Airbnb Rental Income: $1933 Traditional Rental Income: $1928 Airbnb ROI: 4.91% Traditional ROI: 7.65%
4505 Brentwood Drive South Boston, VA 4 bedroom, 2.5 bath, 2 story home in the Brentwood subdivision. Features include 2 new hea...	4 beds \| 3 baths \| 2,250 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2351 Airbnb ROI: N/A Traditional ROI: 5.22%

Real Estate investment in South-boston, VA

There are 33 properties for sale in the city of South Boston . The median list price in South Boston is $334,900 and the average price per square foot is $93. In April 2026, the average monthly cash on cash return in South Boston is 7.00%. The average monthly rental income in South Boston is $2,321.

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

There are 33 investment properties available for sale in South-boston.

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

The ROI for Long-Term is higher than the Short-Term in South-boston with average rental income of $2,321.

Your search for investment property begins and ends here

Investment Property for Sale in South Boston, VA

1194 Wolf Trap Road

South Boston, VA

3 beds | 2 baths | 1,860 sq.ft.

$359,900

Airbnb cash on cash: 2.12%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $1933

Traditional Rental Income: $2690

Airbnb ROI: 2.12%

Traditional ROI: 5.87%

617 Greenway Drive

South Boston, VA

3 beds | 2 baths | 2,256 sq.ft.

$250,000

Airbnb cash on cash: 3.81%

Traditional cash on cash: 9.05%

Airbnb Rental Income: $1933

Traditional Rental Income: $2659

Airbnb ROI: 3.81%

Traditional ROI: 9.05%

1728 Vaughan Street

South Boston, VA

3 beds | 1 baths | 1,313 sq.ft.

$189,900

Airbnb cash on cash: 6.16%

Traditional cash on cash: 9.25%

Airbnb Rental Income: $1933

Traditional Rental Income: $1979

Airbnb ROI: 6.16%

Traditional ROI: 9.25%

2504 Halifax Road

South Boston, VA

4 beds | 3 baths | 2,508 sq.ft.

$264,900

Airbnb cash on cash: N/A

Traditional cash on cash: 11.47%

Airbnb Rental Income: $null

Traditional Rental Income: $3271

Airbnb ROI: N/A

Traditional ROI: 11.47%

2929 Halifax Road

South Boston, VA

4 beds | 4 baths | 4,819 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.49%

Airbnb Rental Income: $null

Traditional Rental Income: $3772

Airbnb ROI: N/A

Traditional ROI: 4.49%

2100 Westmoreland Street

South Boston, VA

3 beds | 2 baths | 2,903 sq.ft.

$390,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $1933

Traditional Rental Income: $2522

Airbnb ROI: 1.82%

Traditional ROI: 4.83%

2105 Willow Street

South Boston, VA

3 beds | 2 baths | 1,416 sq.ft.

$185,900

Airbnb cash on cash: 6.37%

Traditional cash on cash: 5.35%

Airbnb Rental Income: $1933

Traditional Rental Income: $1242

Airbnb ROI: 6.37%

Traditional ROI: 5.35%

1898 Jeffress Blvd

South Boston, VA

3 beds | 2 baths | 1,404 sq.ft.

$159,900

Airbnb cash on cash: 6.89%

Traditional cash on cash: 8.64%

Airbnb Rental Income: $1933

Traditional Rental Income: $1689

Airbnb ROI: 6.89%