Real Estate Investment Properties for Sale in Winston Salem, NC

Looking for investment property in Winston Salem, NC with high ROI ?

Explore a variety of short-term homes & houses in Winston Salem, NC. Invest wisely with VRBO & Winston Salem, NC 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 Winston Salem, NC

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
420 Inverness Drive Winston Salem, NC Gorgeous golf course lot! Gracious living in this beautiful brick home offering 4 bedrooms...	4 beds \| 4 baths \| 3,235 sq.ft.	$695,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.09% Airbnb Rental Income: $2110 Traditional Rental Income: $3073 Airbnb ROI: 0.77% Traditional ROI: 3.09%
1001 Madison Avenue Winston Salem, NC Gorgeous Ardmore cottage ready to call home! 1001 Madison is tucked away in the heart of A...	3 beds \| 1 baths \| 1,161 sq.ft.	$315,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 2.33% Airbnb Rental Income: $1330 Traditional Rental Income: $1383 Airbnb ROI: 0.77% Traditional ROI: 2.33%
131 Carter Circle Winston Salem, NC Welcome to this charming bungalow filled with character and ready to be called home! Nestl...	2 beds \| 1 baths \| 993 sq.ft.	$269,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 3.56% Airbnb Rental Income: $1214 Traditional Rental Income: $1396 Airbnb ROI: 1.3% Traditional ROI: 3.56%
1005 Franklin Street Winston Salem, NC This charming bungalow blends timeless character w/thoughtful modern updates & features pl...	3 beds \| 2 baths \| 1,938 sq.ft.	$349,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.56% Airbnb Rental Income: $1330 Traditional Rental Income: $1696 Airbnb ROI: 1.2% Traditional ROI: 3.56%
5754 Stanleyville Drive Winston Salem, NC Rare find in Winston-Salem! 3.88 acres with THREE homes, and tons of privacy! Main home is...	3 beds \| 3 baths \| 2,030 sq.ft.	$650,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 1.61% Airbnb Rental Income: $1330 Traditional Rental Income: $1960 Airbnb ROI: -0.11% Traditional ROI: 1.61%
4164 Shadetree Drive Winston Salem, NC Located on a quiet street, this beautifully maintained 3 bedroom, 2.5 bath home truly stan...	3 beds \| 3 baths \| 2,224 sq.ft.	$359,999	Airbnb cash on cash: 0.76% Traditional cash on cash: 4.64% Airbnb Rental Income: $1330 Traditional Rental Income: $2230 Airbnb ROI: 0.76% Traditional ROI: 4.64%
4818 Summer Hill Way Winston Salem, NC Welcome home to this gorgeous home nestled on a quiet cul-de-sac in the highly sought-afte...	4 beds \| 4 baths \| 3,899 sq.ft.	$1,075,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.53% Airbnb Rental Income: $2110 Traditional Rental Income: $2918 Airbnb ROI: 0.18% Traditional ROI: 1.53%
4971 Stonington Road Winston Salem, NC Updated ranch-style home in a prime, convenient location. Beautiful hardwoods flow through...	4 beds \| 3 baths \| 2,820 sq.ft.	$369,900	Airbnb cash on cash: 2.7% Traditional cash on cash: 5.96% Airbnb Rental Income: $2110 Traditional Rental Income: $2701 Airbnb ROI: 2.7% Traditional ROI: 5.96%
3010 Hope Valley Road Winston Salem, NC Check out 3010 Hope Valley Rd, arranged for everyday practicality, providing a comforting ...	3 beds \| 2 baths \| 1,769 sq.ft.	$353,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.62% Airbnb Rental Income: $1330 Traditional Rental Income: $1885 Airbnb ROI: 0.71% Traditional ROI: 3.62%
4090 Carriage Manor Cove Winston Salem, NC The French Coves is an exquisite and convenient tucked-away GEM - private, gated entrance ...	4 beds \| 3 baths \| 3,359 sq.ft.	$1,168,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 0.63% Airbnb Rental Income: $2110 Traditional Rental Income: $2285 Airbnb ROI: -0.03% Traditional ROI: 0.63%
104 Westhaven Circle Winston Salem, NC SIGNIFICANT PRICE REDUCTION! Immerse yourself in the charm and sophistication of this cust...	4 beds \| 4 baths \| 3,302 sq.ft.	$575,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 2.72% Airbnb Rental Income: $2110 Traditional Rental Income: $2947 Airbnb ROI: 0.15% Traditional ROI: 2.72%
4460 Greenfield Way Drive Winston Salem, NC Step inside to find a bright and spacious living area with plenty of natural light, creati...	3 beds \| 2 baths \| 1,898 sq.ft.	$389,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.56% Airbnb Rental Income: $1330 Traditional Rental Income: $1940 Airbnb ROI: 0.77% Traditional ROI: 3.56%
209 Brooks Landing Drive Winston Salem, NC Enjoy primarily one-level living in this beautiful brick home on a corner lot across from ...	3 beds \| 3 baths \| 3,202 sq.ft.	$519,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 3.18% Airbnb Rental Income: $1330 Traditional Rental Income: $2544 Airbnb ROI: -0.16% Traditional ROI: 3.18%
339 Junia Avenue Winston Salem, NC BACK ON THE MARKET! NO FAULT OF THE SELLER! Welcome to this beautifully updated bungalow-s...	3 beds \| 1 baths \| 1,147 sq.ft.	$185,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 5.52% Airbnb Rental Income: $1330 Traditional Rental Income: $1288 Airbnb ROI: 3.43% Traditional ROI: 5.52%
2390 Autumn Mist Drive Winston Salem, NC	3 beds \| 3 baths \| 2,058 sq.ft.	$290,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 5.62% Airbnb Rental Income: $1330 Traditional Rental Income: $2139 Airbnb ROI: 1.15% Traditional ROI: 5.62%
4871 Westchester Road Winston Salem, NC Updated homes like this don't come along often in this peaceful, established neighborhood ...	3 beds \| 2 baths \| 1,993 sq.ft.	$290,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 5.47% Airbnb Rental Income: $1330 Traditional Rental Income: $2020 Airbnb ROI: 1.44% Traditional ROI: 5.47%
1153 Twin Oak Drive Winston Salem, NC ADDITIONAL PRICE ADJUSTMENT!!! Spacious and home located in the serene neighborhood of Pin...	3 beds \| 2 baths \| 1,800 sq.ft.	$288,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 3.45% Airbnb Rental Income: $1330 Traditional Rental Income: $1448 Airbnb ROI: 1.5% Traditional ROI: 3.45%
238 Bond Street Winston Salem, NC 2 BD / 1 BA property in Washington Park features a functional layout with spacious living ...	2 beds \| 1 baths \| 773 sq.ft.	$140,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 6.74% Airbnb Rental Income: $1214 Traditional Rental Income: $1211 Airbnb ROI: 3.85% Traditional ROI: 6.74%
728 W Banner Avenue Winston Salem, NC Better than new in a wonderful neighborhood. This home has been completely reimagined from...	4 beds \| 2 baths \| 1,680 sq.ft.	$339,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.81% Airbnb Rental Income: $2110 Traditional Rental Income: $1788 Airbnb ROI: 3.12% Traditional ROI: 3.81%
1282 Cedarline Lane Winston Salem, NC Well-appointed 3BR/2BA home tucked away in a quiet neighborhood just off Jonestown Road! A...	3 beds \| 2 baths \| 1,646 sq.ft.	$345,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.52% Airbnb Rental Income: $1330 Traditional Rental Income: $1787 Airbnb ROI: 0.84% Traditional ROI: 3.52%
1686 Stonewood Drive Winston Salem, NC Carefree, Cozy, and Convenient in Stonewood with landscaping included! Wonderful 2 bedroom...	2 beds \| 2 baths \| 1,483 sq.ft.	$224,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 4.54% Airbnb Rental Income: $1214 Traditional Rental Income: $1550 Airbnb ROI: 1.13% Traditional ROI: 4.54%
125 Millers Crossing Court Winston Salem, NC Prime Ardmore property, beautifully updated for modern comfort while maintaining charm and...	3 beds \| 3 baths \| 1,876 sq.ft.	$425,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.99% Airbnb Rental Income: $1330 Traditional Rental Income: $1938 Airbnb ROI: 0.43% Traditional ROI: 2.99%
884 Northwind Drive Winston Salem, NC Don't miss this one-of-a kind custom build French Provincial inspired home perched on a se...	4 beds \| 3 baths \| 3,347 sq.ft.	$559,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 2.66% Airbnb Rental Income: $2110 Traditional Rental Income: $2267 Airbnb ROI: 1.32% Traditional ROI: 2.66%
5005 Mayberry Lane Winston Salem, NC Welcome to this beautifully maintained all-brick home in desirable Winston-Salem offering ...	4 beds \| 4 baths \| 3,309 sq.ft.	$625,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 2.66% Airbnb Rental Income: $2110 Traditional Rental Income: $2619 Airbnb ROI: 0.86% Traditional ROI: 2.66%
3820 Country Club Road #E Winston Salem, NC Enjoy easy, low-maintenance living in this charming 2-bedroom, 1-bath condo conveniently l...	2 beds \| 1 baths \| 880 sq.ft.	$95,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 7.68% Airbnb Rental Income: $1214 Traditional Rental Income: $1185 Airbnb ROI: 3.76% Traditional ROI: 7.68%
1708 Briar Lake Road Winston Salem, NC Beautiful 4-bedroom, 3.5-bath home nestled in the Huntington Woods neighborhood! 1708 Bria...	4 beds \| 4 baths \| 3,493 sq.ft.	$515,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.36% Airbnb Rental Income: $2110 Traditional Rental Income: $2049 Airbnb ROI: 1.36% Traditional ROI: 2.36%
1150 Red Sage Road Winston Salem, NC Welcome home to this beautifully updated 3-bedroom, 2-bath ranch in an established neighbo...	3 beds \| 2 baths \| 1,021 sq.ft.	$249,900	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.89% Airbnb Rental Income: $1330 Traditional Rental Income: $1616 Airbnb ROI: 1.94% Traditional ROI: 4.89%
134 Rivertree Lane Winston Salem, NC This move-in-ready low maintenance condo checks all the boxes. Conveniently located near s...	2 beds \| 2 baths \| 1,054 sq.ft.	$165,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 6.59% Airbnb Rental Income: $1214 Traditional Rental Income: $1542 Airbnb ROI: 2.02% Traditional ROI: 6.59%
2301 Griffith Road Winston Salem, NC Rare opportunity! This spacious brick rancher sits on over 5 beautiful acres in a highly s...	3 beds \| 4 baths \| 2,707 sq.ft.	$600,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.71% Airbnb Rental Income: $1330 Traditional Rental Income: $2499 Airbnb ROI: -0.11% Traditional ROI: 2.71%
565 Knob View Drive Winston Salem, NC Welcome to 565 Knob View Dr- Tucked away on a secluded lot with over 2 acres, this stunnin...	4 beds \| 4 baths \| 4,476 sq.ft.	$795,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.73% Airbnb Rental Income: $2110 Traditional Rental Income: $4249 Airbnb ROI: 0.11% Traditional ROI: 3.73%
101 Maple Hill Court Winston Salem, NC Motivated Sellers! REDUCED PRICE! SCHEDULE TODAY! Priced well below recent comparable sale...	3 beds \| 2 baths \| 1,672 sq.ft.	$269,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 4.2% Airbnb Rental Income: $1330 Traditional Rental Income: $1866 Airbnb ROI: 0.47% Traditional ROI: 4.2%
391 Act Drive Winston Salem, NC Magazine-worthy custom home on 1.48 acres in Davidson County with no city taxes. Offering ...	3 beds \| 4 baths \| 4,824 sq.ft.	$985,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 1.3% Airbnb Rental Income: $1330 Traditional Rental Income: $2485 Airbnb ROI: -0.41% Traditional ROI: 1.3%
2921 Bittersweet Road Winston Salem, NC Welcome to 2921 Bittersweet Road in Winston-Salem, offering space, flexibility, and outdoo...	4 beds \| 2 baths \| 1,719 sq.ft.	$299,900	Airbnb cash on cash: 3.8% Traditional cash on cash: 4.27% Airbnb Rental Income: $2110 Traditional Rental Income: $1704 Airbnb ROI: 3.8% Traditional ROI: 4.27%
1008 Madison Avenue Winston Salem, NC Quaint renovated cottage convenient to parks and shopping. This home features an abundant ...	2 beds \| 1 baths \| 904 sq.ft.	$252,500	Airbnb cash on cash: 1.53% Traditional cash on cash: 4.03% Airbnb Rental Income: $1214 Traditional Rental Income: $1420 Airbnb ROI: 1.53% Traditional ROI: 4.03%
612 Rittenhouse Court Winston Salem, NC Beautifully maintained 3 BDR, 2.5 BTH brick home in sought-after New Sherwood under $500K!...	3 beds \| 3 baths \| 2,547 sq.ft.	$449,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 3.28% Airbnb Rental Income: $1330 Traditional Rental Income: $2321 Airbnb ROI: -0.05% Traditional ROI: 3.28%
901 Kinloch Drive Winston Salem, NC Commuters Dream! Between Greensboro, High Point, Winston, and Kernersville. PRICE ADJUSTME...	3 beds \| 2 baths \| 1,834 sq.ft.	$449,900	Airbnb cash on cash: -0.06% Traditional cash on cash: 2.65% Airbnb Rental Income: $1330 Traditional Rental Income: $2063 Airbnb ROI: -0.06% Traditional ROI: 2.65%
3771 Holmes Creek Place #201 Winston Salem, NC Come see this 2 bedroom 2 full bath condo located on the second level. Spacious rooms and ...	2 beds \| 2 baths \| 1,216 sq.ft.	$175,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 6.98% Airbnb Rental Income: $1214 Traditional Rental Income: $1683 Airbnb ROI: 1.82% Traditional ROI: 6.98%
4711 Evie Court Winston Salem, NC Just outside the city limits (read no city taxes) sits Rierson Farms, a small development ...	3 beds \| 3 baths \| 2,024 sq.ft.	$365,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 4.43% Airbnb Rental Income: $1330 Traditional Rental Income: $2085 Airbnb ROI: 1.03% Traditional ROI: 4.43%
2480 Hartfield Circle Winston Salem, NC Spacious and inviting 2-story townhome offering comfort, convenience, and a layout designe...	2 beds \| 3 baths \| 1,470 sq.ft.	$218,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 6.24% Airbnb Rental Income: $1214 Traditional Rental Income: $1833 Airbnb ROI: 1.35% Traditional ROI: 6.24%
1526 Cloverdale Avenue Winston Salem, NC Welcome to this beautifully maintained home in the charming West Highlands neighborhood! T...	4 beds \| 3 baths \| 2,366 sq.ft.	$525,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 3.53% Airbnb Rental Income: $2110 Traditional Rental Income: $2651 Airbnb ROI: 1.33% Traditional ROI: 3.53%

Real Estate investment in Winston-salem, NC

There are 711 properties for sale in the city of Winston Salem . The median list price in Winston Salem is $299,990 and the average price per square foot is $152. In July 2026, the average monthly cash on cash return in Winston Salem is 4.00%. The average monthly rental income in Winston Salem is $1,886.

Winston-salem, NC Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 711 investment properties available for sale in Winston-salem.

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

The ROI for Long-Term is higher than the Short-Term in Winston-salem with average rental income of $1,886.

Your search for investment property begins and ends here

Investment Property for Sale in Winston Salem, NC

420 Inverness Drive

Winston Salem, NC

4 beds | 4 baths | 3,235 sq.ft.

$695,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $2110

Traditional Rental Income: $3073

Airbnb ROI: 0.77%

Traditional ROI: 3.09%

1001 Madison Avenue

Winston Salem, NC

3 beds | 1 baths | 1,161 sq.ft.

$315,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 2.33%

Airbnb Rental Income: $1330

Traditional Rental Income: $1383

Airbnb ROI: 0.77%

Traditional ROI: 2.33%

131 Carter Circle

Winston Salem, NC

2 beds | 1 baths | 993 sq.ft.

$269,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $1214

Traditional Rental Income: $1396

Airbnb ROI: 1.3%

Traditional ROI: 3.56%

1005 Franklin Street

Winston Salem, NC

3 beds | 2 baths | 1,938 sq.ft.

$349,900

Airbnb cash on cash: 1.2%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $1330

Traditional Rental Income: $1696

Airbnb ROI: 1.2%

Traditional ROI: 3.56%

5754 Stanleyville Drive

Winston Salem, NC

3 beds | 3 baths | 2,030 sq.ft.

$650,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 1.61%

Airbnb Rental Income: $1330

Traditional Rental Income: $1960

Airbnb ROI: -0.11%

Traditional ROI: 1.61%

4164 Shadetree Drive

Winston Salem, NC

3 beds | 3 baths | 2,224 sq.ft.

$359,999

Airbnb cash on cash: 0.76%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $1330

Traditional Rental Income: $2230

Airbnb ROI: 0.76%

Traditional ROI: 4.64%

4818 Summer Hill Way

Winston Salem, NC

4 beds | 4 baths | 3,899 sq.ft.

$1,075,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 1.53%

Airbnb Rental Income: $2110

Traditional Rental Income: $2918

Airbnb ROI: 0.18%

Traditional ROI: 1.53%

4971 Stonington Road

Winston Salem, NC

4 beds | 3 baths | 2,820 sq.ft.

$369,900

Airbnb cash on cash: 2.7%

Traditional cash on cash: 5.96%

Airbnb Rental Income: $2110

Traditional Rental Income: $2701

Airbnb ROI: 2.7%