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
5 CURIE DR South Boston, VA Under construction for JAN/FEB 2027. The Carter offers a bright and open layout designed f...	4 beds \| 4 baths \| 1,866 sq.ft.	$489,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 3.35%
302 Dunncroft Ct South Boston, VA This very inviting rustic-style home in Brentwood not only offers 4 bedrooms & 3 full bath...	4 beds \| 3 baths \| 1,971 sq.ft.	$330,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.29% Airbnb Rental Income: $null Traditional Rental Income: $2918 Airbnb ROI: N/A Traditional ROI: 7.29%
1194 Wolf Trap Rd South Boston, VA Seller is offering a $5,000 buyer incentive with an acceptable offer! Use it toward closin...	3 beds \| 2 baths \| 1,860 sq.ft.	$299,999	Airbnb cash on cash: 1.49% Traditional cash on cash: 7.38% Airbnb Rental Income: $1458 Traditional Rental Income: $2690 Airbnb ROI: 1.49% Traditional ROI: 7.38%
617 Greenway Dr 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.	$235,500	Airbnb cash on cash: 2.38% Traditional cash on cash: 9.71% Airbnb Rental Income: $1458 Traditional Rental Income: $2659 Airbnb ROI: 2.38% Traditional ROI: 9.71%
1425 Moore St South Boston, VA Welcome to this beautiful, move-in-ready Cape Cod home, perfect for you and your family! F...	3 beds \| 1 baths \| 1,456 sq.ft.	$265,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 5.75% Airbnb Rental Income: $1458 Traditional Rental Income: $1984 Airbnb ROI: 1.92% Traditional ROI: 5.75%
2929 Halifax Rd South Boston, VA Welcome to a home where timeless architecture meets modern versatility. This stately 4,819...	4 beds \| 4 baths \| 3,086 sq.ft.	$565,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.16% Airbnb Rental Income: $null Traditional Rental Income: $3772 Airbnb ROI: N/A Traditional ROI: 5.16%
513 Forest Dr South Boston, VA Welcome home to this beautiful 3 bedroom, 2.5 bath two-story home located in the desirable...	3 beds \| 2 baths \| 2,146 sq.ft.	$329,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 4.9% Airbnb Rental Income: $1458 Traditional Rental Income: $2174 Airbnb ROI: 1.2% Traditional ROI: 4.9%
1414 Berry Hill Rd South Boston, VA Welcome to this beautifully refreshed 3 bedroom, 2 full bath ranch offering comfortable on...	3 beds \| 2 baths \| 1,484 sq.ft.	$224,900	Airbnb cash on cash: 3.19% Traditional cash on cash: 9.29% Airbnb Rental Income: $1458 Traditional Rental Income: $2324 Airbnb ROI: 3.19% Traditional ROI: 9.29%
306 Forest Dr South Boston, VA Impeccably maintained one-owner home with a virtually maintenance-free exterior! This spac...	4 beds \| 2 baths \| 2,620 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $2843 Airbnb ROI: N/A Traditional ROI: 6.04%
2100 Rivoli St South Boston, VA Stately 2 story brick colonial situated on 3 lots totaling 1.53 acres in the desirable San...	3 beds \| 3 baths \| 2,669 sq.ft.	$449,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 6.76% Airbnb Rental Income: $1458 Traditional Rental Income: $3487 Airbnb ROI: 0.92% Traditional ROI: 6.76%
2700 Halifax Rd South Boston, VA This stunning split-level brick home sits proudly on .96 of an acre (corner lot) right in ...	4 beds \| 3 baths \| 2,055 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.68% Airbnb Rental Income: $null Traditional Rental Income: $3724 Airbnb ROI: N/A Traditional ROI: 10.68%
1247 Sandy Beach Rd South Boston, VA Located on Sandy Beach Road just minutes from the Philpott Road industrial corridor, this ...	3 beds \| 3 baths \| 3,393 sq.ft.	$289,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 4.19% Airbnb Rental Income: $1458 Traditional Rental Income: $1727 Airbnb ROI: 1.62% Traditional ROI: 4.19%
302 Monroe St 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.	$375,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 7.05% Airbnb Rental Income: $1458 Traditional Rental Income: $3040 Airbnb ROI: 1.33% Traditional ROI: 7.05%
3193 Bold Springs Rd South Boston, VA 3193 Bold Springs Rd, South Boston, VA 24592 \| Single Family Residential	4 beds \| 2 baths \| 2,100 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.22% Airbnb Rental Income: $null Traditional Rental Income: $2376 Airbnb ROI: N/A Traditional ROI: 10.22%
3203 N Main St 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.	$339,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 5.33% Airbnb Rental Income: $1458 Traditional Rental Income: $2374 Airbnb ROI: 1.11% Traditional ROI: 5.33%
427 Taylor Ave South Boston, VA Welcome Home! Here is your chance to pick your own colors, counter tops and cabinets. Make...	3 beds \| 2 baths \| 960 sq.ft.	$234,500	Airbnb cash on cash: 2.4% Traditional cash on cash: 8.33% Airbnb Rental Income: $1458 Traditional Rental Income: $2343 Airbnb ROI: 2.4% Traditional ROI: 8.33%
5202 Philpott Rd South Boston, VA 5202 Philpott Rd, South Boston, VA 24592 \| Other	N/A beds \| N/A baths \| N/A	$349,000	Airbnb cash on cash: -2.42% Traditional cash on cash: 0.96% Airbnb Rental Income: $98 Traditional Rental Income: $1001 Airbnb ROI: -2.42% Traditional ROI: 0.96%
00 Philpott Rd South Boston, VA 00 Philpott Rd, South Boston, VA 24592 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: -2.52% Traditional cash on cash: 1.41% Airbnb Rental Income: $98 Traditional Rental Income: $1001 Airbnb ROI: -2.52% Traditional ROI: 1.41%
804 Grove Ave South Boston, VA 804 Grove Ave, South Boston, VA 24592 \| Single Family Residential	3 beds \| 2 baths \| 2,464 sq.ft.	$269,900	Airbnb cash on cash: 1.85% Traditional cash on cash: 7.06% Airbnb Rental Income: $1458 Traditional Rental Income: $2350 Airbnb ROI: 1.85% Traditional ROI: 7.06%
19.6ac Link Puryear Rd South Boston, VA 19.6ac Link Puryear Rd, South Boston, VA 24592 \| Other	N/A beds \| N/A baths \| N/A	$94,000	Airbnb cash on cash: -3.99% Traditional cash on cash: 8.1% Airbnb Rental Income: $98 Traditional Rental Income: $1001 Airbnb ROI: -3.99% Traditional ROI: 8.1%
1009 Waddell Ln South Boston, VA Update! Sellers are prepared for a timely sale and are receptive to strong, well-qualified...	3 beds \| 2 baths \| 1,634 sq.ft.	$280,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 7.46% Airbnb Rental Income: $1458 Traditional Rental Income: $2341 Airbnb ROI: 2.48% Traditional ROI: 7.46%
0 Bill Tuck Hwy South Boston, VA 0 Bill Tuck Hwy, South Boston, VA 24592 \| Other	N/A beds \| N/A baths \| N/A	$400,000	Airbnb cash on cash: -2.35% Traditional cash on cash: 0.57% Airbnb Rental Income: $98 Traditional Rental Income: $988 Airbnb ROI: -2.35% Traditional ROI: 0.57%
210 Merritt St South Boston, VA Turn key home in pristine condition with high quality finishes. Step into this tranquil sp...	3 beds \| 1 baths \| 1,526 sq.ft.	$309,900	Airbnb cash on cash: 1.39% Traditional cash on cash: 4.84% Airbnb Rental Income: $1458 Traditional Rental Income: $2034 Airbnb ROI: 1.39% Traditional ROI: 4.84%
801 Marshall Ave South Boston, VA Vintage means timeless; the real thing never goes out of style. In a world where new const...	3 beds \| 1 baths \| 1,474 sq.ft.	$184,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 9.74% Airbnb Rental Income: $1458 Traditional Rental Income: $2026 Airbnb ROI: 4.06% Traditional ROI: 9.74%
1214 Washington Ave South Boston, VA Step into a piece of history with this stunning 2-story Victorian Italianate-style residen...	3 beds \| 2 baths \| 2,043 sq.ft.	$274,900	Airbnb cash on cash: 2.39% Traditional cash on cash: 8.21% Airbnb Rental Income: $1458 Traditional Rental Income: $2533 Airbnb ROI: 2.39% Traditional ROI: 8.21%
1424 Washington Ave South Boston, VA Freshly updated brick home in the heart of South Boston. This move in ready residence feat...	3 beds \| 1 baths \| 1,044 sq.ft.	$192,500	Airbnb cash on cash: 3.4% Traditional cash on cash: 8.73% Airbnb Rental Income: $1458 Traditional Rental Income: $2000 Airbnb ROI: 3.4% Traditional ROI: 8.73%
102 White Oak Dr South Boston, VA 102 White Oak Dr, South Boston, VA 24592 \| Single Family Residential	4 beds \| 2 baths \| 1,512 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.69% Airbnb Rental Income: $null Traditional Rental Income: $2100 Airbnb ROI: N/A Traditional ROI: 6.69%
1325 Shepherd St South Boston, VA 1325 Shepherd St, South Boston, VA 24592 \| Single Family Residential	6 beds \| 2 baths \| 2,318 sq.ft.	$195,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.92% Airbnb Rental Income: $null Traditional Rental Income: $2450 Airbnb ROI: N/A Traditional ROI: 10.92%
00 Cluster Springs Rd South Boston, VA 00 Cluster Springs Rd, South Boston, VA 24592 \| Other	N/A beds \| N/A baths \| N/A	$164,900	Airbnb cash on cash: -3.09% Traditional cash on cash: 3.89% Airbnb Rental Income: $98 Traditional Rental Income: $991 Airbnb ROI: -3.09% Traditional ROI: 3.89%
223 Lomax Ave South Boston, VA Welcome to 223 Lomax Ave, South Boston, VA - a move-in ready, fully wheelchair accessible ...	2 beds \| 1 baths \| 960 sq.ft.	$168,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 9.75% Airbnb Rental Income: $735 Traditional Rental Income: $1845 Airbnb ROI: 0.87% Traditional ROI: 9.75%
3073 Jones Ferry Rd South Boston, VA Custom Estate home nestled on 23.53 private, mostly wooded acres offering partial ownershi...	3 beds \| 3 baths \| 4,686 sq.ft.	$1,195,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.56% Airbnb Rental Income: $1458 Traditional Rental Income: $3117 Airbnb ROI: -0.32% Traditional ROI: 1.56%
1403 South Ave South Boston, VA Minimal Tudor in South Boston, VA! For the first time since it was built in 1952, this...	4 beds \| 2 baths \| 2,188 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.45% Airbnb Rental Income: $null Traditional Rental Income: $2988 Airbnb ROI: N/A Traditional ROI: 10.45%
8181 Highway 58 South Boston, VA This house gives off the cozy cottage feeling. Lots of recent improvements. Over the past ...	3 beds \| 1 baths \| 1,197 sq.ft.	$185,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 10.08% Airbnb Rental Income: $1458 Traditional Rental Income: $2185 Airbnb ROI: 3.49% Traditional ROI: 10.08%
3183 Dan River Church Rd South Boston, VA Welcome home to 3183 Dan River Church where comfort, convenience, and one-level living com...	5 beds \| 2 baths \| 1,894 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.71% Airbnb Rental Income: $null Traditional Rental Income: $2632 Airbnb ROI: N/A Traditional ROI: 4.71%
320 Wagstaff Ln South Boston, VA 320 Wagstaff Ln, South Boston, VA 24592 \| Other	N/A beds \| N/A baths \| N/A	$85,000	Airbnb cash on cash: -4.21% Traditional cash on cash: 8.98% Airbnb Rental Income: $98 Traditional Rental Income: $992 Airbnb ROI: -4.21% Traditional ROI: 8.98%

Real Estate investment in South-boston, VA

There are 37 properties for sale in the city of South Boston . The median list price in South Boston is $219,868 and the average price per square foot is $112. In July 2026, the average monthly cash on cash return in South Boston is 9.00%. The average monthly rental income in South Boston is $2,111.

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

There are 37 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 $2,111.

Your search for investment property begins and ends here

Investment Property for Sale in South Boston, VA

5 CURIE DR

South Boston, VA

4 beds | 4 baths | 1,866 sq.ft.

$489,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2534

Airbnb ROI: N/A

Traditional ROI: 3.35%

302 Dunncroft Ct

South Boston, VA

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

$330,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2918

Airbnb ROI: N/A

Traditional ROI: 7.29%

1194 Wolf Trap Rd

South Boston, VA

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

$299,999

Airbnb cash on cash: 1.49%

Traditional cash on cash: 7.38%

Airbnb Rental Income: $1458

Traditional Rental Income: $2690

Airbnb ROI: 1.49%

Traditional ROI: 7.38%

617 Greenway Dr

South Boston, VA

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

$235,500

Airbnb cash on cash: 2.38%

Traditional cash on cash: 9.71%

Airbnb Rental Income: $1458

Traditional Rental Income: $2659

Airbnb ROI: 2.38%

Traditional ROI: 9.71%

1425 Moore St

South Boston, VA

3 beds | 1 baths | 1,456 sq.ft.

$265,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 5.75%

Airbnb Rental Income: $1458

Traditional Rental Income: $1984

Airbnb ROI: 1.92%

Traditional ROI: 5.75%

2929 Halifax Rd

South Boston, VA

4 beds | 4 baths | 3,086 sq.ft.

$565,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3772

Airbnb ROI: N/A

Traditional ROI: 5.16%

513 Forest Dr

South Boston, VA

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

$329,900

Airbnb cash on cash: 1.2%

Traditional cash on cash: 4.9%

Airbnb Rental Income: $1458

Traditional Rental Income: $2174

Airbnb ROI: 1.2%

Traditional ROI: 4.9%

1414 Berry Hill Rd

South Boston, VA

3 beds | 2 baths | 1,484 sq.ft.

$224,900

Airbnb cash on cash: 3.19%

Traditional cash on cash: 9.29%

Airbnb Rental Income: $1458

Traditional Rental Income: $2324

Airbnb ROI: 3.19%