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
316 VIRGINIA AVENUE Winchester, VA Well maintained Colonial offering timeless character and modern potential in the heart of ...	3 beds \| 1 baths \| 1,192 sq.ft.	$349,900	Airbnb cash on cash: 6.47% Traditional cash on cash: 3.97% Airbnb Rental Income: $3402 Traditional Rental Income: $1825 Airbnb ROI: 6.47% Traditional ROI: 3.97%
209 S BRADDOCK ST Winchester, VA Opportunity is knocking! Here's your chance to purchase a unique home in the beautiful Win...	2 beds \| 2 baths \| N/A	$285,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 4.02% Airbnb Rental Income: $2499 Traditional Rental Income: $1692 Airbnb ROI: 4.77% Traditional ROI: 4.02%
104 AZTEC TRL Winchester, VA Spacious & Renovated 3-Bedroom Home with Den, Patio & Basketball Hoop! Welcome to this bea...	3 beds \| 3 baths \| N/A	$359,900	Airbnb cash on cash: 6.08% Traditional cash on cash: 3.08% Airbnb Rental Income: $3402 Traditional Rental Income: $1631 Airbnb ROI: 6.08% Traditional ROI: 3.08%
216 MONTICELLO SQ Winchester, VA Seller is offering $5,000 toward purchasers closing cost with acceptable offer! Step into ...	3 beds \| 3 baths \| N/A	$350,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 5.13% Airbnb Rental Income: $3402 Traditional Rental Income: $2273 Airbnb ROI: 6.26% Traditional ROI: 5.13%
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.	$305,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 5.73% Airbnb Rental Income: $3402 Traditional Rental Income: $2212 Airbnb ROI: 7.24% Traditional ROI: 5.73%
208 OPOSSUM TRAIL Winchester, VA Welcome to this charming two-story home nestled in a peaceful country setting, surrounded ...	3 beds \| 1 baths \| 946 sq.ft.	$249,500	Airbnb cash on cash: 9.11% Traditional cash on cash: 5.65% Airbnb Rental Income: $3402 Traditional Rental Income: $1832 Airbnb ROI: 9.11% Traditional ROI: 5.65%
966 WOODSTOCK LANE Winchester, VA Beautiful 3-bedroom, 2-bath split-foyer home in the heart of Winchester City! The main lev...	3 beds \| 2 baths \| 1,529 sq.ft.	$349,900	Airbnb cash on cash: 6.04% Traditional cash on cash: 4.7% Airbnb Rental Income: $3402 Traditional Rental Income: $2203 Airbnb ROI: 6.04% Traditional ROI: 4.7%
822 PHEASANT DRIVE Winchester, VA PRICE IMPROVEMENT! Welcome to this charming ranch home with spacious backyard and unfinish...	3 beds \| 2 baths \| 1,152 sq.ft.	$274,900	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.62% Airbnb Rental Income: $3402 Traditional Rental Income: $1986 Airbnb ROI: 8.17% Traditional ROI: 5.62%
102 ZEPHYR LANE Winchester, VA Motivated Sellers! Carpet allowance and Professional Cleaning will be provided prior to cl...	3 beds \| 2 baths \| 1,634 sq.ft.	$317,500	Airbnb cash on cash: 6.94% Traditional cash on cash: 5.06% Airbnb Rental Income: $3402 Traditional Rental Income: $2085 Airbnb ROI: 6.94% Traditional ROI: 5.06%
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 \| 1,924 sq.ft.	$439,900	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.73% Airbnb Rental Income: $3402 Traditional Rental Income: $2611 Airbnb ROI: 4.82% Traditional ROI: 4.73%
320 HIGHLAND AVENUE Winchester, VA Welcome to this centrally located home in the heart of Winchester. With easy access to I-8...	3 beds \| 2 baths \| 1,313 sq.ft.	$299,900	Airbnb cash on cash: 7.54% Traditional cash on cash: 5.58% Airbnb Rental Income: $3402 Traditional Rental Income: $2093 Airbnb ROI: 7.54% Traditional ROI: 5.58%
121 N WASHINGTON STREET Winchester, VA A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet k...	3 beds \| 3 baths \| 3,100 sq.ft.	$550,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.77% Airbnb Rental Income: $3402 Traditional Rental Income: $2409 Airbnb ROI: 3.24% Traditional ROI: 2.77%
621 PANTHER DRIVE Winchester, VA Wilde Acres offers peaceful country living just 1520 minutes from Winchester City. The pro...	2 beds \| 1 baths \| 856 sq.ft.	$279,999	Airbnb cash on cash: 5.31% Traditional cash on cash: 3.86% Airbnb Rental Income: $2499 Traditional Rental Income: $1511 Airbnb ROI: 5.31% Traditional ROI: 3.86%
560 FAIR LANE Winchester, VA Welcome home to 560 Fair Lane in Winchester, Virginia. This beautifully maintained Ranch/R...	3 beds \| 3 baths \| 2,491 sq.ft.	$675,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 2.17% Airbnb Rental Income: $3402 Traditional Rental Income: $2318 Airbnb ROI: 2.69% Traditional ROI: 2.17%
101 DELAWARE TRAIL Winchester, VA Price Reduced! Be in before the leaves start to change! You must see this home to believe ...	3 beds \| 2 baths \| 2,302 sq.ft.	$497,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 2.96% Airbnb Rental Income: $3402 Traditional Rental Income: $2053 Airbnb ROI: 4.24% Traditional ROI: 2.96%
129 INDIANA Winchester, VA $10,000 CLOSING COSTS WITH ACCEPTABLE CONTRACT. Done and ready! Large lot on private stree...	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%
230 TRANQUIL WOOD LANE Winchester, VA NO HOA! READY TO BUILD! LOT CLEARED! NEW PRICE-DECK AND FINISHED REC ROOM! Are you in sear...	3 beds \| 3 baths \| 2,046 sq.ft.	$810,127	Airbnb cash on cash: 2.35% Traditional cash on cash: 2.25% Airbnb Rental Income: $3402 Traditional Rental Income: $2570 Airbnb ROI: 2.35% Traditional ROI: 2.25%
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%
84 POMMEL LN Winchester, VA The Cabral, a 1913 square foot open concept two-story home, offers three bedrooms, two and...	3 beds \| 3 baths \| 1,333 sq.ft.	$304,990	Airbnb cash on cash: 7.01% Traditional cash on cash: 6.99% Airbnb Rental Income: $3402 Traditional Rental Income: $2642 Airbnb ROI: 7.01% Traditional ROI: 6.99%
129 JALAPA TRAIL Winchester, VA Brand new everything, Roof, appliances, water treatment , bathrooms, deck, Sunroom, floori...	3 beds \| 2 baths \| 2,400 sq.ft.	$475,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 4% Airbnb Rental Income: $3402 Traditional Rental Income: $2400 Airbnb ROI: 4.55% Traditional ROI: 4%
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 re...	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%
1049 LAUREL GROVE RD Winchester, VA Nestled at the end of a peaceful cul-de-sac, this stunning, property offers the perfect bl...	3 beds \| 3 baths \| N/A	$769,900	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.88% Airbnb Rental Income: $3402 Traditional Rental Income: $2366 Airbnb ROI: 2.27% Traditional ROI: 1.88%
881 ADAMS RD Winchester, VA Price Adjustment on this beautiful property! Welcome to this exquisite 3-bedroom, 2-bath...	3 beds \| 2 baths \| N/A	$699,900	Airbnb cash on cash: 2.6% Traditional cash on cash: 2.05% Airbnb Rental Income: $3402 Traditional Rental Income: $2286 Airbnb ROI: 2.6% Traditional ROI: 2.05%
196 HODGES LANE Winchester, VA Incredible Builder or Private Estate Opportunity on Nearly 80 Acres! This 79.16-acre prope...	2 beds \| 1 baths \| 609 sq.ft.	$910,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 0.28% Airbnb Rental Income: $2499 Traditional Rental Income: $1255 Airbnb ROI: 1.03% Traditional ROI: 0.28%
1420 FISHEL ROAD Winchester, VA Nestled away in the trees, this updated retreat on 2.67 acres offers the perfect blend of ...	3 beds \| 2 baths \| 1,680 sq.ft.	$549,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 3.07% Airbnb Rental Income: $3402 Traditional Rental Income: $2328 Airbnb ROI: 3.69% Traditional ROI: 3.07%
164 BETHEL GRANGE ROAD Winchester, VA Beautiful brick ranch in a lovely rural setting with mountain views and only minutes to sc...	3 beds \| 2 baths \| 1,952 sq.ft.	$450,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.9% Airbnb Rental Income: $3402 Traditional Rental Income: $2287 Airbnb ROI: 4.75% Traditional ROI: 3.9%
154 SOLARA DRIVE Winchester, VA This lovely modern townhome is better than new! Featuring a fully fenced and level backyar...	3 beds \| 3 baths \| 2,281 sq.ft.	$408,900	Airbnb cash on cash: 4.91% Traditional cash on cash: 4.8% Airbnb Rental Income: $3402 Traditional Rental Income: $2603 Airbnb ROI: 4.91% Traditional ROI: 4.8%
311 ASH HOLLOW DRIVE Winchester, VA Opportunity awaits in Ash Hollow Estates! This 3-bedroom, 2-bath townhouse is full of pote...	3 beds \| 2 baths \| 1,070 sq.ft.	$244,900	Airbnb cash on cash: 9.51% Traditional cash on cash: 6.51% Airbnb Rental Income: $3402 Traditional Rental Income: $1952 Airbnb ROI: 9.51% Traditional ROI: 6.51%
2940 GRACE STREET Winchester, VA Welcome to your charming Cape Cod retreat! Built in 1955, this delightful 3-bedroom, 1-bat...	3 beds \| 1 baths \| 936 sq.ft.	$355,000	Airbnb cash on cash: 6.33% Traditional cash on cash: 3.17% Airbnb Rental Income: $3402 Traditional Rental Income: $1591 Airbnb ROI: 6.33% Traditional ROI: 3.17%
230 ALLISON AVENUE Winchester, VA Welcome to 230 Allison Avenue, a recently renovated 3-bedroom, 1-bath home on a spacious 0...	3 beds \| 1 baths \| 1,376 sq.ft.	$339,900	Airbnb cash on cash: 6.54% Traditional cash on cash: 3.94% Airbnb Rental Income: $3402 Traditional Rental Income: $1816 Airbnb ROI: 6.54% Traditional ROI: 3.94%
1826 KERSHAW LN Winchester, VA This charming one-level home is perfectly situated in one of Winchester's desirable 55+ s...	2 beds \| 2 baths \| N/A	$387,900	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.09% Airbnb Rental Income: $2499 Traditional Rental Income: $1873 Airbnb ROI: 3.15% Traditional ROI: 3.09%
327 BRYARLY ROAD Winchester, VA Location! Location! Location! Back on the Market with Beautiful Renovations A Must-See! ...	3 beds \| 2 baths \| 2,165 sq.ft.	$475,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 3.39% Airbnb Rental Income: $3402 Traditional Rental Income: $2175 Airbnb ROI: 4.45% Traditional ROI: 3.39%
527 GROUSE DRIVE Winchester, VA **$5000 seller closing cost concessions with acceptable contract plus $600 towards Starlin...	3 beds \| 3 baths \| 1,909 sq.ft.	$389,900	Airbnb cash on cash: 5.07% Traditional cash on cash: 4.97% Airbnb Rental Income: $3402 Traditional Rental Income: $2607 Airbnb ROI: 5.07% Traditional ROI: 4.97%
133 Woodrow Road Winchester, VA Welcome home to this charming split foyer in Carlisle Heights, ideally located on the east...	3 beds \| 3 baths \| 1,806 sq.ft.	$415,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 4.38% Airbnb Rental Income: $3402 Traditional Rental Income: $2349 Airbnb ROI: 5.15% Traditional ROI: 4.38%
133 COUNTRY PARK DRIVE Winchester, VA Charming Rancher Move-In Ready! Dont miss this great opportunity to own a recently refresh...	3 beds \| 1 baths \| 960 sq.ft.	$279,900	Airbnb cash on cash: 8.35% Traditional cash on cash: 4.37% Airbnb Rental Income: $3402 Traditional Rental Income: $1597 Airbnb ROI: 8.35% Traditional ROI: 4.37%
117 TYE COURT Winchester, VA Modern, Move-In Ready Townhome with Premium Upgrades Ideally located just outside the bus...	3 beds \| 3 baths \| 1,962 sq.ft.	$409,900	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.77% Airbnb Rental Income: $3402 Traditional Rental Income: $2553 Airbnb ROI: 5.01% Traditional ROI: 4.77%
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 Completely remodeled! Come enjoy ALL new everything, new electric, new windows, luxury flo...	3 beds \| 2 baths \| 1,500 sq.ft.	$359,900	Airbnb cash on cash: 6.22% Traditional cash on cash: 4.79% Airbnb Rental Income: $3402 Traditional Rental Income: $2164 Airbnb ROI: 6.22% Traditional ROI: 4.79%
143 DOWELL J CIRCLE Winchester, VA Charming Rancher with Prime Location and Endless Potential! Seller offering $5,000 towar...	3 beds \| 1 baths \| 1,094 sq.ft.	$294,900	Airbnb cash on cash: 7.91% Traditional cash on cash: 4.95% Airbnb Rental Income: $3402 Traditional Rental Income: $1824 Airbnb ROI: 7.91% Traditional ROI: 4.95%

Vacation Rentals in Winchester

There are 53 vacation rental properties available for sale in the city of Winchester . The median list price of Airbnb properties available for sale in Winchester is $479,900 and the average price per square foot is $194. 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 53 Airbnb properties available for sale in Winchester.

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

In September 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

316 VIRGINIA AVENUE

Winchester, VA

3 beds | 1 baths | 1,192 sq.ft.

$349,900

Airbnb cash on cash: 6.47%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $3402

Traditional Rental Income: $1825

Airbnb ROI: 6.47%

Traditional ROI: 3.97%

209 S BRADDOCK ST

Winchester, VA

2 beds | 2 baths | N/A

$285,000

Airbnb cash on cash: 4.77%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $2499

Traditional Rental Income: $1692

Airbnb ROI: 4.77%

Traditional ROI: 4.02%

104 AZTEC TRL

Winchester, VA

3 beds | 3 baths | N/A

$359,900

Airbnb cash on cash: 6.08%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $3402

Traditional Rental Income: $1631

Airbnb ROI: 6.08%

Traditional ROI: 3.08%

216 MONTICELLO SQ

Winchester, VA

3 beds | 3 baths | N/A

$350,000

Airbnb cash on cash: 6.26%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $3402

Traditional Rental Income: $2273

Airbnb ROI: 6.26%

Traditional ROI: 5.13%

369 CHARLES STREET

Winchester, VA

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

$305,000

Airbnb cash on cash: 7.24%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $3402

Traditional Rental Income: $2212

Airbnb ROI: 7.24%

Traditional ROI: 5.73%

208 OPOSSUM TRAIL

Winchester, VA

3 beds | 1 baths | 946 sq.ft.

$249,500

Airbnb cash on cash: 9.11%

Traditional cash on cash: 5.65%

Airbnb Rental Income: $3402

Traditional Rental Income: $1832

Airbnb ROI: 9.11%

Traditional ROI: 5.65%

966 WOODSTOCK LANE

Winchester, VA

3 beds | 2 baths | 1,529 sq.ft.

$349,900

Airbnb cash on cash: 6.04%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $3402

Traditional Rental Income: $2203

Airbnb ROI: 6.04%

Traditional ROI: 4.7%

822 PHEASANT DRIVE

Winchester, VA

3 beds | 2 baths | 1,152 sq.ft.

$274,900

Airbnb cash on cash: 8.17%

Traditional cash on cash: 5.62%

Airbnb Rental Income: $3402

Traditional Rental Income: $1986

Airbnb ROI: 8.17%