Airbnb Properties for Sale in Winchester, VA

Looking for a vacation rental investment in Winchester, VA with high ROI ?

Explore a range of newly added short-term rental homes in Winchester, VA. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb Single Family Residential For Sale in Winchester, VA

Search for Single Family Residential for Sale in Winchester, 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 4 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
719 Smithfield Avenue Winchester, VA Bringing all the bungalow love! This 2 bed/1 bath home is move-in ready after a 2025 Refre...	2 beds \| 1 baths \| 720 sq.ft.	$275,000	Airbnb cash on cash: 6.38% Traditional cash on cash: 3.74% Airbnb Rental Income: $2689 Traditional Rental Income: $1368 Airbnb ROI: 6.38% Traditional ROI: 3.74%
108 MARTIN Drive Winchester, VA Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-...	2 beds \| 1 baths \| 997 sq.ft.	$285,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 4.38% Airbnb Rental Income: $2689 Traditional Rental Income: $1631 Airbnb ROI: 5.94% Traditional ROI: 4.38%
116 PINTO Winchester, VA The Perfect Starter Home Awaits! 3-26-26 almost done. Granite and septic going in and fina...	2 beds \| 1 baths \| 1,140 sq.ft.	$349,900	Airbnb cash on cash: 4.15% Traditional cash on cash: 3.53% Airbnb Rental Income: $2689 Traditional Rental Income: $1850 Airbnb ROI: 4.15% Traditional ROI: 3.53%
Other Airbnb Properties for Sale in Winchester
1851 MELVOR Lane Winchester , VA Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottag...	2 beds \| 2 baths \| 1,405 sq.ft.	$399,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 1.74% Airbnb Rental Income: $2689 Traditional Rental Income: $1548 Airbnb ROI: 3.08% Traditional ROI: 1.74%
610 PUMA Trail Winchester , VA Tucked away at the end of the neighborhood and surrounded by serene woods, 610 Puma Trl of...	2 beds \| 1 baths \| 560 sq.ft.	$224,990	Airbnb cash on cash: 7.7% Traditional cash on cash: 4.09% Airbnb Rental Income: $2689 Traditional Rental Income: $1284 Airbnb ROI: 7.7% Traditional ROI: 4.09%
177 DICKS HOLLOW Road Winchester , VA Newly remodeled turn-key starter home with modern updates. 2-bedroom 1-bathroom rancher ju...	2 beds \| 1 baths \| 650 sq.ft.	$245,000	Airbnb cash on cash: 7.21% Traditional cash on cash: 3.96% Airbnb Rental Income: $2689 Traditional Rental Income: $1301 Airbnb ROI: 7.21% Traditional ROI: 3.96%
105 AMBERFIELD Court Winchester , VA Move in Ready!!! Nestled in the serene enclave of Abram's Chase and located within minutes...	2 beds \| 2 baths \| 1,800 sq.ft.	$529,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 2.01% Airbnb Rental Income: $2689 Traditional Rental Income: $1949 Airbnb ROI: 2.22% Traditional ROI: 2.01%
1125 CONWAY Street Winchester , VA Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Pai...	2 beds \| 1 baths \| 870 sq.ft.	$269,900	Airbnb cash on cash: 6.34% Traditional cash on cash: 4.22% Airbnb Rental Income: $2689 Traditional Rental Income: $1512 Airbnb ROI: 6.34% Traditional ROI: 4.22%
111 GENESEE Trail Winchester , VA Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painte...	2 beds \| 1 baths \| 924 sq.ft.	$279,900	Airbnb cash on cash: 6.14% Traditional cash on cash: 3.96% Airbnb Rental Income: $2689 Traditional Rental Income: $1478 Airbnb ROI: 6.14% Traditional ROI: 3.96%
303 FOX Winchester , VA Major Price Reduction! Welcome to this beautifully renovated 2-bedroom, 1-bath ranch-style...	2 beds \| 1 baths \| 960 sq.ft.	$240,000	Airbnb cash on cash: 7.34% Traditional cash on cash: 5.11% Airbnb Rental Income: $2689 Traditional Rental Income: $1548 Airbnb ROI: 7.34% Traditional ROI: 5.11%
523 MONTICELLO Street Winchester , VA Sold "As-IS" Nice investment or starter property. Needs a little updating. Hardwoods throu...	2 beds \| 2 baths \| 1,064 sq.ft.	$250,000	Airbnb cash on cash: 6.63% Traditional cash on cash: 6.08% Airbnb Rental Income: $2689 Traditional Rental Income: $1923 Airbnb ROI: 6.63% Traditional ROI: 6.08%
2640 LIMESTONE Court Winchester , VA Discover this charming Colonial-style townhouse nestled in the desirable Limestone Court c...	2 beds \| 2 baths \| 1,024 sq.ft.	$270,000	Airbnb cash on cash: 5.95% Traditional cash on cash: 5.24% Airbnb Rental Income: $2689 Traditional Rental Income: $1872 Airbnb ROI: 5.95% Traditional ROI: 5.24%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winchester, VA

719 Smithfield Avenue

Winchester, VA

2 beds | 1 baths | 720 sq.ft.

$275,000

Airbnb cash on cash: 6.38%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $2689

Traditional Rental Income: $1368

Airbnb ROI: 6.38%

Traditional ROI: 3.74%

108 MARTIN Drive

Winchester, VA

2 beds | 1 baths | 997 sq.ft.

$285,000

Airbnb cash on cash: 5.94%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $2689

Traditional Rental Income: $1631

Airbnb ROI: 5.94%

Traditional ROI: 4.38%

116 PINTO

Winchester, VA

2 beds | 1 baths | 1,140 sq.ft.

$349,900

Airbnb cash on cash: 4.15%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2689

Traditional Rental Income: $1850

Airbnb ROI: 4.15%

Traditional ROI: 3.53%

Other Airbnb Properties for Sale in Winchester

Winchester , VA

2 beds | 2 baths | 1,405 sq.ft.

$399,900

Airbnb cash on cash: 3.08%

Traditional cash on cash: 1.74%

Airbnb Rental Income: $2689

Traditional Rental Income: $1548

Airbnb ROI: 3.08%

Traditional ROI: 1.74%

Winchester , VA

2 beds | 1 baths | 560 sq.ft.

$224,990

Airbnb cash on cash: 7.7%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $2689

Traditional Rental Income: $1284

Airbnb ROI: 7.7%

Traditional ROI: 4.09%

Winchester , VA

2 beds | 1 baths | 650 sq.ft.

$245,000

Airbnb cash on cash: 7.21%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $2689

Traditional Rental Income: $1301

Airbnb ROI: 7.21%

Traditional ROI: 3.96%

Winchester , VA

2 beds | 2 baths | 1,800 sq.ft.

$529,900

Airbnb cash on cash: 2.22%

Traditional cash on cash: 2.01%

Airbnb Rental Income: $2689

Traditional Rental Income: $1949

Airbnb ROI: 2.22%

Traditional ROI: 2.01%

Winchester , VA

2 beds | 1 baths | 870 sq.ft.

$269,900

Airbnb cash on cash: 6.34%

Traditional cash on cash: 4.22%

Airbnb Rental Income: $2689

Traditional Rental Income: $1512

Airbnb ROI: 6.34%

Traditional ROI: 4.22%

Winchester , VA

2 beds | 1 baths | 924 sq.ft.

$279,900