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
1332 RAMSEUR Lane Winchester, VA Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exte...	3 beds \| 2 baths \| 2,648 sq.ft.	$459,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 4% Airbnb Rental Income: $3402 Traditional Rental Income: $2609 Airbnb ROI: 4.09% Traditional ROI: 4%
369 CHARLES Street Winchester, VA This two-story home offers classic charm with a covered front porch, fenced backyard, and ...	3 beds \| 2 baths \| 1,526 sq.ft.	$285,000	Airbnb cash on cash: 7.81% Traditional cash on cash: 6.19% Airbnb Rental Income: $3402 Traditional Rental Income: $2212 Airbnb ROI: 7.81% Traditional ROI: 6.19%
275 GREENWOOD Road Winchester, VA Charming split-foyer home situated on a generous 13,000 sq. ft. lot with convenient access...	3 beds \| 3 baths \| 1,732 sq.ft.	$439,900	Airbnb cash on cash: 4.77% Traditional cash on cash: 4.69% Airbnb Rental Income: $3402 Traditional Rental Income: $2611 Airbnb ROI: 4.77% Traditional ROI: 4.69%
2150 HARVEST Drive Winchester, VA END-UNIT ALL-BRICK TOWNHOUSE WITH NO HOA! This meticulously maintained, move-in ready home...	3 beds \| 2 baths \| 1,368 sq.ft.	$315,000	Airbnb cash on cash: 6.83% Traditional cash on cash: 5.14% Airbnb Rental Income: $3402 Traditional Rental Income: $2147 Airbnb ROI: 6.83% Traditional ROI: 5.14%
608 GREEN Street Winchester, VA Welcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 renovated full ba...	3 beds \| 1 baths \| 1,040 sq.ft.	$289,999	Airbnb cash on cash: 7.7% Traditional cash on cash: 4.37% Airbnb Rental Income: $3402 Traditional Rental Income: $1737 Airbnb ROI: 7.7% Traditional ROI: 4.37%
2225 HARRISON Street Winchester, VA 2225 Harrison Street located in Winchester, VA. One level living in a home remodeled in th...	3 beds \| 2 baths \| 1,300 sq.ft.	$334,900	Airbnb cash on cash: 6.46% Traditional cash on cash: 4.02% Airbnb Rental Income: $3402 Traditional Rental Income: $1880 Airbnb ROI: 6.46% Traditional ROI: 4.02%
511 GROUSE Drive Winchester, VA This is a fantastic opportunity to purchase a new construction home and have the ability t...	3 beds \| 2 baths \| 1,333 sq.ft.	$319,000	Airbnb cash on cash: 6.51% Traditional cash on cash: 3.4% Airbnb Rental Income: $3402 Traditional Rental Income: $1713 Airbnb ROI: 6.51% Traditional ROI: 3.4%
939 WOODLAND AVE Winchester, VA Price Reduced!!! Need your Own Space? or you're looking to Downsize or Just Starting Out, ...	1 beds \| 2 baths \| N/A	$287,500	Airbnb cash on cash: 4.19% Traditional cash on cash: 2.85% Airbnb Rental Income: $2220 Traditional Rental Income: $1298 Airbnb ROI: 4.19% Traditional ROI: 2.85%
100 MAURY Way Winchester, VA Welcome to this Former Model Home for the Grand Nassau Cove model by Ryan Homes - once the...	3 beds \| 3 baths \| 1,678 sq.ft.	$392,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 3.99% Airbnb Rental Income: $3402 Traditional Rental Income: $2231 Airbnb ROI: 5.12% Traditional ROI: 3.99%
101 DELAWARE Trail Winchester, VA Huge Price Reduction! Motivated Seller. Fabulous remodel featuring the finest materials fr...	3 beds \| 2 baths \| 2,302 sq.ft.	$489,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.02% Airbnb Rental Income: $3402 Traditional Rental Income: $2053 Airbnb ROI: 4.32% Traditional ROI: 3.02%
339 LANNY Drive Winchester, VA Right off of Amherst St. in sought after Whittier Acres, we are proud to present 339 Lanny...	3 beds \| 3 baths \| 2,444 sq.ft.	$515,900	Airbnb cash on cash: 3.69% Traditional cash on cash: 3.57% Airbnb Rental Income: $3402 Traditional Rental Income: $2584 Airbnb ROI: 3.69% Traditional ROI: 3.57%
129 INDIANA Winchester, VA I am done! Large lot on private street with valley views and private. HW floors entire mai...	3 beds \| 3 baths \| 1,660 sq.ft.	$389,900	Airbnb cash on cash: 5.17% Traditional cash on cash: 4.46% Airbnb Rental Income: $3402 Traditional Rental Income: $2388 Airbnb ROI: 5.17% Traditional ROI: 4.46%
221 CRESTWOOD Lane Winchester, VA Charming well maintained corner lot unit in desirable Woodbrook Village 55 and over commun...	2 beds \| 2 baths \| 1,384 sq.ft.	$389,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.78% Airbnb Rental Income: $2499 Traditional Rental Income: $1856 Airbnb ROI: 2.88% Traditional ROI: 2.78%
112 FAIRWAY Drive Winchester, VA New roof just installed! This beautiful ranch-style home is located in a quiet cul-de-sac ...	3 beds \| 1 baths \| 1,200 sq.ft.	$379,000	Airbnb cash on cash: 5.87% Traditional cash on cash: 3.62% Airbnb Rental Income: $3402 Traditional Rental Income: $1846 Airbnb ROI: 5.87% Traditional ROI: 3.62%
129 JALAPA TRAIL Winchester, VA Brand new everything, Roof, appliances, water treatment , bathrooms, deck, Sunroom, floori...	3 beds \| 2 baths \| 2,400 sq.ft.	$444,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 4.34% Airbnb Rental Income: $3402 Traditional Rental Income: $2400 Airbnb ROI: 4.93% Traditional ROI: 4.34%
22 HORIZON DR Winchester, VA No HOA! 1 LEVEL LIVING home - 3 BR / 2 BA offers spacious kitchen with granite counters, f...	3 beds \| 2 baths \| 2,092 sq.ft.	$700,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.17% Airbnb Rental Income: $3402 Traditional Rental Income: $2485 Airbnb ROI: 2.41% Traditional ROI: 2.17%
112 W GERMAIN Street Winchester, VA 100-Year-Old Downtown Winchester Charmer - Brought Back to Life in 2025! This beautifully ...	3 beds \| 3 baths \| 1,650 sq.ft.	$665,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 2.8% Airbnb Rental Income: $3402 Traditional Rental Income: $2555 Airbnb ROI: 2.95% Traditional ROI: 2.8%
129 E CORK Street Winchester, VA Welcome home to this charming 2-bedroom Craftsman-style home! Take a few steps up to this ...	2 beds \| 2 baths \| 935 sq.ft.	$297,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 4.3% Airbnb Rental Income: $2499 Traditional Rental Income: $1734 Airbnb ROI: 4.88% Traditional ROI: 4.3%
1049 LAUREL GROVE RD Winchester, VA Tucked away on a quiet cul-de-sac, this custom 3-bedroom, 3-bath home is sited on a privat...	3 beds \| 3 baths \| N/A	$767,900	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.85% Airbnb Rental Income: $3402 Traditional Rental Income: $2366 Airbnb ROI: 2.24% Traditional ROI: 1.85%
881 ADAMS RD Winchester, VA Back on the Market and fully Certified! Appraised over asking, All inspections completed (...	3 beds \| 2 baths \| N/A	$689,900	Airbnb cash on cash: 2.66% Traditional cash on cash: 2.1% Airbnb Rental Income: $3402 Traditional Rental Income: $2286 Airbnb ROI: 2.66% Traditional ROI: 2.1%
1420 FISHEL Road Winchester, VA Tucked deep into the trees on 2.67 wooded acres, this home offers a quiet sense of seclusi...	3 beds \| 2 baths \| 1,680 sq.ft.	$499,900	Airbnb cash on cash: 4.15% Traditional cash on cash: 3.47% Airbnb Rental Income: $3402 Traditional Rental Income: $2328 Airbnb ROI: 4.15% Traditional ROI: 3.47%
164 BETHEL GRANGE Road Winchester, VA Beautiful brick ranch in a lovely, country rural setting with mountain views and only minu...	3 beds \| 2 baths \| 1,952 sq.ft.	$435,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 4.07% Airbnb Rental Income: $3402 Traditional Rental Income: $2287 Airbnb ROI: 4.95% Traditional ROI: 4.07%
421 SUPERIOR AVE Winchester, VA Renovated and move in ready! Let's start with the new mailbox, new 16' wide asphalt drivew...	3 beds \| 2 baths \| 1,800 sq.ft.	$462,700	Airbnb cash on cash: 4.36% Traditional cash on cash: 3.32% Airbnb Rental Income: $3402 Traditional Rental Income: $2192 Airbnb ROI: 4.36% Traditional ROI: 3.32%
125 WHISPERING KNOLLS Drive Winchester, VA This property with almost 9 acres of land but just 15 mins from Winchester amenities is th...	3 beds \| 2 baths \| N/A	$245,000	Airbnb cash on cash: 9.61% Traditional cash on cash: 5.8% Airbnb Rental Income: $3402 Traditional Rental Income: $1764 Airbnb ROI: 9.61% Traditional ROI: 5.8%
553 HIGHLAND Avenue Winchester, VA One Way street = quiet Gorgeous Rehab - you have to see it! Secure Parking off the alley E...	3 beds \| 2 baths \| 1,362 sq.ft.	$335,000	Airbnb cash on cash: 6.75% Traditional cash on cash: 5.22% Airbnb Rental Income: $3402 Traditional Rental Income: $2164 Airbnb ROI: 6.75% Traditional ROI: 5.22%
101 DUTTON Place Winchester, VA Welcome to 101 Dutton Place- Location, Location, Location! + One Level living! Nestled jus...	3 beds \| 2 baths \| 2,517 sq.ft.	$535,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 3.43% Airbnb Rental Income: $3402 Traditional Rental Income: $2485 Airbnb ROI: 3.75% Traditional ROI: 3.43%
1399 CHESTNUT GROVE Road Winchester, VA One Level home on a private 5 acre lot. Bring your horses, goats, chickens - this is the p...	3 beds \| 2 baths \| 1,680 sq.ft.	$384,900	Airbnb cash on cash: 5.79% Traditional cash on cash: 4.3% Airbnb Rental Income: $3402 Traditional Rental Income: $2109 Airbnb ROI: 5.79% Traditional ROI: 4.3%
115 BLUE RIDGE Lane Winchester, VA Welcome to 115 Blue Ridge Ln in Winchester, VA. This recently renovated 3-bedroom, 2-bath ...	3 beds \| 2 baths \| 1,404 sq.ft.	$340,000	Airbnb cash on cash: 6.62% Traditional cash on cash: 5% Airbnb Rental Income: $3402 Traditional Rental Income: $2127 Airbnb ROI: 6.62% Traditional ROI: 5%
103 BLUE RIDGE Lane Winchester, VA Welcome to this beautifully renovated brick rancher on a spacious 0.55-acre lot in a quiet...	3 beds \| 1 baths \| 1,925 sq.ft.	$430,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 3.56% Airbnb Rental Income: $3402 Traditional Rental Income: $2087 Airbnb ROI: 4.95% Traditional ROI: 3.56%
611 TUDOR Drive Winchester, VA This charming townhome is a perfect for first time homebuyer or an investor! Priced to sel...	3 beds \| 3 baths \| N/A	$285,000	Airbnb cash on cash: 7.95% Traditional cash on cash: 6.74% Airbnb Rental Income: $3402 Traditional Rental Income: $2321 Airbnb ROI: 7.95% Traditional ROI: 6.74%
163 MARGARET Lane Winchester, VA (Magnificent Margaret) This home has a lot to offer: All bedrooms and bathrooms on the mai...	3 beds \| 2 baths \| 1,176 sq.ft.	$409,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 4.33% Airbnb Rental Income: $3402 Traditional Rental Income: $2227 Airbnb ROI: 5.42% Traditional ROI: 4.33%
2723 WINDWOOD DR Winchester, VA Premier Single-Level Living on a Private Cul-de-Sac! Nestled at the end of a quiet, presti...	3 beds \| 3 baths \| N/A	$549,900	Airbnb cash on cash: 3.23% Traditional cash on cash: 3.04% Airbnb Rental Income: $3402 Traditional Rental Income: $2551 Airbnb ROI: 3.23% Traditional ROI: 3.04%
116 CAMDEN Drive Winchester, VA BRAND NEW HOME. FULLY FINISHED. No HOA. Discover the charm of this stunning new constructi...	3 beds \| 3 baths \| 1,313 sq.ft.	$429,900	Airbnb cash on cash: 5.25% Traditional cash on cash: 4.63% Airbnb Rental Income: $3402 Traditional Rental Income: $2395 Airbnb ROI: 5.25% Traditional ROI: 4.63%
106 W SOUTHWERK Street Winchester, VA Charming 3 bedroom, 1.5 bath colonial just blocks from downtown Winchester! Enjoy a covere...	3 beds \| 2 baths \| 1,144 sq.ft.	$299,500	Airbnb cash on cash: 7.58% Traditional cash on cash: 5.54% Airbnb Rental Income: $3402 Traditional Rental Income: $2069 Airbnb ROI: 7.58% Traditional ROI: 5.54%
3634 WARDENSVILLE Grade Winchester, VA Country charm meets convenience at 3634 Wardensville Grade-just minutes to Rt 50, Rt 37 an...	3 beds \| 1 baths \| 2,050 sq.ft.	$425,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 2.67% Airbnb Rental Income: $3402 Traditional Rental Income: $1703 Airbnb ROI: 5.03% Traditional ROI: 2.67%
513 PHEASANT Drive Winchester, VA Welcome to this newly built colonial in Wilde Acres situated on 1/4 acre lot nestled among...	3 beds \| 2 baths \| 1,368 sq.ft.	$365,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 5.18% Airbnb Rental Income: $3402 Traditional Rental Income: $2320 Airbnb ROI: 6.13% Traditional ROI: 5.18%
133 ERIE Trail Winchester, VA Motivated Seller! Professional photos on the way Discover this charming ranch-style home n...	3 beds \| 2 baths \| 1,456 sq.ft.	$379,000	Airbnb cash on cash: 5.8% Traditional cash on cash: 5.47% Airbnb Rental Income: $3402 Traditional Rental Income: $2527 Airbnb ROI: 5.8% Traditional ROI: 5.47%
205 SHENANDOAH Avenue Winchester, VA LOCATION LOCATION LOCATION!!!!!!! INVESTORS DREAM. HOUSE NEEDS SOME WORK AND IS SOLD AS IS...	3 beds \| 1 baths \| 925 sq.ft.	$235,000	Airbnb cash on cash: 9.77% Traditional cash on cash: 5.59% Airbnb Rental Income: $3402 Traditional Rental Income: $1717 Airbnb ROI: 9.77% Traditional ROI: 5.59%
715 BERRYVILLE Avenue Winchester, VA This renovated jewel on the east side of Winchester is ready for you! Enjoy the new modern...	3 beds \| 2 baths \| 1,426 sq.ft.	$375,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 4.81% Airbnb Rental Income: $3402 Traditional Rental Income: $2323 Airbnb ROI: 5.72% Traditional ROI: 4.81%
105 WORSHAM Terrace Winchester, VA This Is IT! Updated and modern 3 bed/ 4 bath Townhome, ready for You! Ground level entry l...	3 beds \| 4 baths \| 2,444 sq.ft.	$349,990	Airbnb cash on cash: 5.96% Traditional cash on cash: 5.83% Airbnb Rental Income: $3402 Traditional Rental Income: $2603 Airbnb ROI: 5.96% Traditional ROI: 5.83%

Vacation Rentals in Winchester

There are 61 vacation rental properties available for sale in the city of Winchester . The median list price of Airbnb properties available for sale in Winchester is $459,450 and the average price per square foot is $187. The cash on cash return on vacation rentals in Winchester is 5.00%. The average monthly short term rental income in Winchester is $3,402.

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

There are 61 Airbnb properties available for sale in Winchester.

In 2025, the best neighborhood to buy short term rental property is Winchester.

In October 2025, the average Airbnb occupancy rate in Winchester is 66%.

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

1332 RAMSEUR Lane

Winchester, VA

3 beds | 2 baths | 2,648 sq.ft.

$459,000

Airbnb cash on cash: 4.09%

Traditional cash on cash: 4%

Airbnb Rental Income: $3402

Traditional Rental Income: $2609

Airbnb ROI: 4.09%

Traditional ROI: 4%

369 CHARLES Street

Winchester, VA

3 beds | 2 baths | 1,526 sq.ft.

$285,000

Airbnb cash on cash: 7.81%

Traditional cash on cash: 6.19%

Airbnb Rental Income: $3402

Traditional Rental Income: $2212

Airbnb ROI: 7.81%

Traditional ROI: 6.19%

275 GREENWOOD Road

Winchester, VA

3 beds | 3 baths | 1,732 sq.ft.

$439,900

Airbnb cash on cash: 4.77%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $3402

Traditional Rental Income: $2611

Airbnb ROI: 4.77%

Traditional ROI: 4.69%

2150 HARVEST Drive

Winchester, VA

3 beds | 2 baths | 1,368 sq.ft.

$315,000

Airbnb cash on cash: 6.83%

Traditional cash on cash: 5.14%

Airbnb Rental Income: $3402

Traditional Rental Income: $2147

Airbnb ROI: 6.83%

Traditional ROI: 5.14%

608 GREEN Street

Winchester, VA

3 beds | 1 baths | 1,040 sq.ft.

$289,999

Airbnb cash on cash: 7.7%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $3402

Traditional Rental Income: $1737

Airbnb ROI: 7.7%

Traditional ROI: 4.37%

2225 HARRISON Street

Winchester, VA

3 beds | 2 baths | 1,300 sq.ft.

$334,900

Airbnb cash on cash: 6.46%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $3402

Traditional Rental Income: $1880

Airbnb ROI: 6.46%

Traditional ROI: 4.02%

511 GROUSE Drive

Winchester, VA

3 beds | 2 baths | 1,333 sq.ft.

$319,000

Airbnb cash on cash: 6.51%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $3402

Traditional Rental Income: $1713

Airbnb ROI: 6.51%

Traditional ROI: 3.4%

939 WOODLAND AVE

Winchester, VA

1 beds | 2 baths | N/A

$287,500

Airbnb cash on cash: 4.19%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $2220

Traditional Rental Income: $1298

Airbnb ROI: 4.19%