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 44 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
316 VIRGINIA AVENUE Winchester, VA Well maintained Colonial offering timeless character and modern potential in the heart of ...	3 beds \| 2 baths \| 1,192 sq.ft.	$338,000	Airbnb cash on cash: 6.73% Traditional cash on cash: 4.14% Airbnb Rental Income: $3402 Traditional Rental Income: $1825 Airbnb ROI: 6.73% Traditional ROI: 4.14%
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%
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.	$339,900	Airbnb cash on cash: 6.25% Traditional cash on cash: 4.86% Airbnb Rental Income: $3402 Traditional Rental Income: $2203 Airbnb ROI: 6.25% Traditional ROI: 4.86%
116 MALOY DRIVE Winchester, VA Buyers will instantly fall in love with this CUTE AS A BUTTON renovated, expanded and upda...	3 beds \| 2 baths \| 1,598 sq.ft.	$400,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.49% Airbnb Rental Income: $3402 Traditional Rental Income: $2319 Airbnb ROI: 5.36% Traditional ROI: 4.49%
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%
242 FOOTSTONE LANE Winchester, VA Peaceful Country Retreat on 4.7 Acres Minutes from Winchester Discover the perfect blend o...	2 beds \| 1 baths \| 1,348 sq.ft.	$359,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 3.32% Airbnb Rental Income: $2499 Traditional Rental Income: $1669 Airbnb ROI: 3.99% Traditional ROI: 3.32%
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.	$285,000	Airbnb cash on cash: 7.98% Traditional cash on cash: 5.92% Airbnb Rental Income: $3402 Traditional Rental Income: $2093 Airbnb ROI: 7.98% Traditional ROI: 5.92%
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%
206 CUSTER AVENUE Winchester, VA Being Sold As Is but with great potential. Situate in a great location. This brick 3 bed, ...	3 beds \| 1 baths \| 1,006 sq.ft.	$285,000	Airbnb cash on cash: 8.04% Traditional cash on cash: 4.89% Airbnb Rental Income: $3402 Traditional Rental Income: $1799 Airbnb ROI: 8.04% Traditional ROI: 4.89%
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 If you're looking to Downsize or Just Starting Out, Come Checkout this 1-2-bedroom 2 full ...	2 beds \| 2 baths \| N/A	$289,900	Airbnb cash on cash: 5% Traditional cash on cash: 2.82% Airbnb Rental Income: $2499 Traditional Rental Income: $1298 Airbnb ROI: 5% Traditional ROI: 2.82%
2964 GRACE STREET Winchester, VA OPEN Sat 9/20 Wonderful Light filled 2 story Mid-Century Bungalow Updated for Modern Livin...	2 beds \| 1 baths \| 780 sq.ft.	$315,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 3.12% Airbnb Rental Income: $2499 Traditional Rental Income: $1477 Airbnb ROI: 4.53% Traditional ROI: 3.12%
101 DELAWARE TRAIL Winchester, VA Shenandoah Valley Dream Home! Ideally situated between the Blue Ridge Mountains and the Ap...	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%
129 INDIANA Winchester, VA Driveway will be paved before closing. Done and ready! Large lot on private street with va...	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 \| 3,476 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%
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%
129 E CORK STREET Winchester, VA Welcome home to this charming 2-bedroom Craftsman-style home! Inside, youll find a warm an...	2 beds \| 2 baths \| 935 sq.ft.	$339,999	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.64% Airbnb Rental Income: $2499 Traditional Rental Income: $1734 Airbnb ROI: 4.14% Traditional ROI: 3.64%
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 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.	$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 rural setting with mountain views and only minutes to sc...	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.	$469,700	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.25% Airbnb Rental Income: $3402 Traditional Rental Income: $2192 Airbnb ROI: 4.28% Traditional ROI: 3.25%
527 GROUSE DRIVE Winchester, VA **Final pictures are up!! READY TO MOVE IN! $600 towards Starlink service purchase and ins...	3 beds \| 3 baths \| 1,909 sq.ft.	$379,900	Airbnb cash on cash: 5.25% Traditional cash on cash: 5.14% Airbnb Rental Income: $3402 Traditional Rental Income: $2607 Airbnb ROI: 5.25% Traditional ROI: 5.14%
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%
101 DUTTON PLACE Winchester, VA Welcome to 101 Dutton Place Location, Location, Location! + One Level living! Nestled just...	3 beds \| 2 baths \| 2,517 sq.ft.	$549,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 3.32% Airbnb Rental Income: $3402 Traditional Rental Income: $2485 Airbnb ROI: 3.63% Traditional ROI: 3.32%
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.	$389,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 4.25% Airbnb Rental Income: $3402 Traditional Rental Income: $2109 Airbnb ROI: 5.72% Traditional ROI: 4.25%
107 FAY STREET Winchester, VA This beauty will be available mid august or earlier has exceptional renovation and superb ...	3 beds \| 2 baths \| 1,560 sq.ft.	$379,999	Airbnb cash on cash: 5.85% Traditional cash on cash: 5.08% Airbnb Rental Income: $3402 Traditional Rental Income: $2369 Airbnb ROI: 5.85% Traditional ROI: 5.08%
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%
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.	$419,000	Airbnb cash on cash: 5.27% Traditional cash on cash: 4.2% Airbnb Rental Income: $3402 Traditional Rental Income: $2227 Airbnb ROI: 5.27% Traditional ROI: 4.2%
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	$564,900	Airbnb cash on cash: 3.12% Traditional cash on cash: 2.94% Airbnb Rental Income: $3402 Traditional Rental Income: $2551 Airbnb ROI: 3.12% Traditional ROI: 2.94%
226 MUSE DRIVE Winchester, VA Welcome to this almost completely renovated duplex home! Excellent location on the map, cl...	3 beds \| 2 baths \| 1,064 sq.ft.	$289,900	Airbnb cash on cash: 7.96% Traditional cash on cash: 5.68% Airbnb Rental Income: $3402 Traditional Rental Income: $2023 Airbnb ROI: 7.96% Traditional ROI: 5.68%
116 CAMDEN DRIVE Winchester, VA BRAND NEW HOME. ALMOST FULLY FINISHED. No HOA. Discover the charm of this stunning new con...	3 beds \| 3 baths \| 1,313 sq.ft.	$439,900	Airbnb cash on cash: 5.11% Traditional cash on cash: 4.5% Airbnb Rental Income: $3402 Traditional Rental Income: $2395 Airbnb ROI: 5.11% Traditional ROI: 4.5%
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%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winchester, VA

316 VIRGINIA AVENUE

Winchester, VA

3 beds | 2 baths | 1,192 sq.ft.

$338,000

Airbnb cash on cash: 6.73%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $3402

Traditional Rental Income: $1825

Airbnb ROI: 6.73%

Traditional ROI: 4.14%

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%

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.

$339,900

Airbnb cash on cash: 6.25%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $3402

Traditional Rental Income: $2203

Airbnb ROI: 6.25%

Traditional ROI: 4.86%

116 MALOY DRIVE

Winchester, VA

3 beds | 2 baths | 1,598 sq.ft.

$400,000

Airbnb cash on cash: 5.36%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $3402

Traditional Rental Income: $2319

Airbnb ROI: 5.36%

Traditional ROI: 4.49%

275 GREENWOOD ROAD

Winchester, VA

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%

242 FOOTSTONE LANE

Winchester, VA

2 beds | 1 baths | 1,348 sq.ft.

$359,000

Airbnb cash on cash: 3.99%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $2499

Traditional Rental Income: $1669

Airbnb ROI: 3.99%