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 For Sale in Winchester, VA

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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%
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: 5.33% Airbnb Rental Income: $2689 Traditional Rental Income: $1548 Airbnb ROI: 7.7% Traditional ROI: 5.33%
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%
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%
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%
151 MCCORMICK CIRCLE unit: 105 Winchester, VA Welcome to refined 55+ living in the highly sought-after Winchester Landing Commons. This ...	2 beds \| 2 baths \| 1,154 sq.ft.	$314,900	Airbnb cash on cash: 4.17% Traditional cash on cash: 2.47% Airbnb Rental Income: $2689 Traditional Rental Income: $1548 Airbnb ROI: 4.17% Traditional ROI: 2.47%
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: 3.97% Airbnb Rental Income: $2689 Traditional Rental Income: $1548 Airbnb ROI: 5.95% Traditional ROI: 3.97%

Vacation Rentals in Winchester

There are 18 vacation rental properties available for sale in the city of Winchester . The median list price of Airbnb properties available for sale in Winchester is $414,999 and the average price per square foot is $197. The cash on cash return on vacation rentals in Winchester is 1.00%. The average monthly short term rental income in Winchester is $1,337.

Winchester, VA Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 18 Airbnb properties available for sale in Winchester.

In 2026, the best neighborhood to buy short term rental property is Winchester.

In April 2026, the average Airbnb occupancy rate in Winchester is 60%.

Airbnb data on vacation rentals in Winchester, VA is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winchester, VA market insights, guest information and booking details, seasonality trends and historical Winchester, VA Airbnb performance data.

Your search for investment property begins and ends here

Airbnb 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%

1851 MELVOR Lane

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%

610 PUMA Trail

Winchester, VA

2 beds | 1 baths | 560 sq.ft.

$224,990

Airbnb cash on cash: 7.7%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $2689

Traditional Rental Income: $1548

Airbnb ROI: 7.7%

Traditional ROI: 5.33%

177 DICKS HOLLOW Road

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%

105 AMBERFIELD Court

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%

1125 CONWAY Street

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%

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%