Real Estate Investment Properties for Sale in Winchester, VA

Looking for investment property in Winchester, VA with high ROI ?

Explore a variety of short-term homes & houses in Winchester, VA. Invest wisely with VRBO & Winchester, VA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes 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 26 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
219 MILAM Drive Winchester, VA Welcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet nei...	4 beds \| 3 baths \| 2,654 sq.ft.	$467,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.46% Airbnb Rental Income: $null Traditional Rental Income: $3073 Airbnb ROI: N/A Traditional ROI: 5.46%
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.	$309,900	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.55% Airbnb Rental Income: $1372 Traditional Rental Income: $1713 Airbnb ROI: 0.95% Traditional ROI: 3.55%
939 WOODLAND AVE Winchester, VA Motivated sellers, Price Reduced!!! Don't Miss The Boat...Need your Own Space? or you're l...	2 beds \| 2 baths \| N/A	$274,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.02% Airbnb Rental Income: $1121 Traditional Rental Income: $1298 Airbnb ROI: 0.89% Traditional ROI: 3.02%
513 VAN FOSSEN Street Winchester, VA Welcome to 513 Van Fossen St, a beautifully updated 4-bedroom, 2.5-bathroom brick ranch co...	4 beds \| 3 baths \| 2,804 sq.ft.	$355,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $2218 Airbnb ROI: N/A Traditional ROI: 4.72%
110 CARTER PL Winchester, VA Contract fell through! Interest rates have gone down! Extensive Renovations: The home ha...	5 beds \| 3 baths \| N/A	$489,970	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 4.37%
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: 0.19% Traditional cash on cash: 3.57% Airbnb Rental Income: $1372 Traditional Rental Income: $2584 Airbnb ROI: 0.19% Traditional ROI: 3.57%
121 SWEETBRIAR Lane Winchester, VA "Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors...	4 beds \| 3 baths \| 3,442 sq.ft.	$642,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 3.19%
281 LIGHT Road Winchester, VA NO HOA/NO RESTRICTIONS! Motivated Sellers! Bring your offers! Main Level Living! POOL! 5 G...	3 beds \| 3 baths \| 2,618 sq.ft.	$609,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.56% Airbnb Rental Income: $1372 Traditional Rental Income: $2912 Airbnb ROI: 0.13% Traditional ROI: 3.56%
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: -0.13% Traditional cash on cash: 1.85% Airbnb Rental Income: $1372 Traditional Rental Income: $2366 Airbnb ROI: -0.13% Traditional ROI: 1.85%
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: 0.79% Traditional cash on cash: 4.07% Airbnb Rental Income: $1372 Traditional Rental Income: $2287 Airbnb ROI: 0.79% 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.	$441,700	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.52% Airbnb Rental Income: $1372 Traditional Rental Income: $2192 Airbnb ROI: 0.53% Traditional ROI: 3.52%
128 RAVEN OAKS DR Winchester, VA Back on the market with no fault to the seller. This is your second chance to snatch this ...	4 beds \| 3 baths \| N/A	$684,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.25% Airbnb Rental Income: $null Traditional Rental Income: $2484 Airbnb ROI: N/A Traditional ROI: 2.25%
159 ASHTON Drive Winchester, VA Cash only -Sold "AS IS" Great Location! 2-Bedroom, 2-Bath Ranch with Great Potential! Ranc...	2 beds \| 2 baths \| 2,795 sq.ft.	$250,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 7.75% Airbnb Rental Income: $1121 Traditional Rental Income: $2337 Airbnb ROI: 1.01% Traditional ROI: 7.75%
114 HAROLD Court Winchester, VA BACK ON THE MARKET THROUGH NO FAULT OF THE SELLER!! Welcome to this beautiful brick-front ...	3 beds \| 2 baths \| 1,862 sq.ft.	$570,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 2.75% Airbnb Rental Income: $1372 Traditional Rental Income: $2353 Airbnb ROI: 0.12% Traditional ROI: 2.75%
112 STAR FORT DR Winchester, VA Unlock the Potential! 3BR/2BA Fixer-Upper in Winchester/Frederick County. Nestled in a qu...	3 beds \| 2 baths \| N/A	$300,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 5.58% Airbnb Rental Income: $1372 Traditional Rental Income: $2062 Airbnb ROI: 1.65% Traditional ROI: 5.58%
134 CARDINAL Lane Winchester, VA Back to Active at no fault of the owner. One-level living with commuter convenience! This ...	3 beds \| 3 baths \| 1,280 sq.ft.	$365,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 5.08% Airbnb Rental Income: $1372 Traditional Rental Income: $2317 Airbnb ROI: 1.11% Traditional ROI: 5.08%
525 E CORK ST Winchester, VA Beautiful and affordable Gem in the middle of Winchester City. Private, fully fenced yard ...	2 beds \| 1 baths \| N/A	$299,900	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.31% Airbnb Rental Income: $1121 Traditional Rental Income: $1483 Airbnb ROI: 0.7% Traditional ROI: 3.31%
2294 FRONT ROYAL Winchester, VA 3 Beds \| 1 Bath \| Partially Finished Basement \| .60 Acres \| New Roof WELCOME HOME!!!! Char...	3 beds \| 1 baths \| 1,974 sq.ft.	$320,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 4.36% Airbnb Rental Income: $1372 Traditional Rental Income: $1838 Airbnb ROI: 1.43% Traditional ROI: 4.36%
534 Grouse Drive Winchester, VA Like new construction without the wait! Lovely 2024, ranch home with partially finished ba...	3 beds \| 3 baths \| 1,966 sq.ft.	$325,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 6.15% Airbnb Rental Income: $1372 Traditional Rental Income: $2532 Airbnb ROI: 0.99% Traditional ROI: 6.15%
113 WILLIAMSON RD Winchester, VA Charming All-Brick Ranch just minutes from in Prime Winchester Location. Beautifully main...	3 beds \| 2 baths \| N/A	$450,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.61% Airbnb Rental Income: $1372 Traditional Rental Income: $2179 Airbnb ROI: 0.7% Traditional ROI: 3.61%
1133 TOMAHAWK TRL TRL Winchester, VA Nestled in the serene Shawneeland community, this exquisite chalet-style residence offers ...	3 beds \| 2 baths \| N/A	$419,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 3.27% Airbnb Rental Income: $1372 Traditional Rental Income: $1917 Airbnb ROI: 0.82% Traditional ROI: 3.27%
400 HANDLEY AVE Winchester, VA Welcome to this beautifully preserved American brick Foursquare, an exceptional home that ...	3 beds \| 3 baths \| N/A	$629,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.68% Airbnb Rental Income: $1372 Traditional Rental Income: $2592 Airbnb ROI: -0.11% Traditional ROI: 2.68%
113 GLEN RIDGE Road Winchester, VA Welcome to this stunning new construction ranch style home offering the perfect blend of c...	3 beds \| 2 baths \| 1,620 sq.ft.	$429,900	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.62% Airbnb Rental Income: $1372 Traditional Rental Income: $2282 Airbnb ROI: 0.32% Traditional ROI: 3.62%
163 CABIN LN Winchester, VA Discover the potential in this 3 bedroom, 2 bath home on 6.10 unrestricted acres, the perf...	3 beds \| 2 baths \| N/A	$200,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 7.41% Airbnb Rental Income: $1372 Traditional Rental Income: $1848 Airbnb ROI: 2.7% Traditional ROI: 7.41%
728 GREEN Street Winchester, VA This spacious rancher is ideal for someone looking to add their personal touch on a home! ...	4 beds \| 2 baths \| 1,659 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.8% Airbnb Rental Income: $null Traditional Rental Income: $2393 Airbnb ROI: N/A Traditional ROI: 5.8%
114 WOODYS PL Winchester, VA This exceptional residential property, located in the desirable Carlisle Estates subdivisi...	3 beds \| 2 baths \| N/A	$299,999	Airbnb cash on cash: 1.43% Traditional cash on cash: 5.67% Airbnb Rental Income: $1372 Traditional Rental Income: $2154 Airbnb ROI: 1.43% Traditional ROI: 5.67%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

219 MILAM Drive

Winchester, VA

4 beds | 3 baths | 2,654 sq.ft.

$467,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.46%

Airbnb Rental Income: $null

Traditional Rental Income: $3073

Airbnb ROI: N/A

Traditional ROI: 5.46%

511 GROUSE Drive

Winchester, VA

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

$309,900

Airbnb cash on cash: 0.95%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $1372

Traditional Rental Income: $1713

Airbnb ROI: 0.95%

Traditional ROI: 3.55%

939 WOODLAND AVE

Winchester, VA

2 beds | 2 baths | N/A

$274,900

Airbnb cash on cash: 0.89%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $1121

Traditional Rental Income: $1298

Airbnb ROI: 0.89%

Traditional ROI: 3.02%

513 VAN FOSSEN Street

Winchester, VA

4 beds | 3 baths | 2,804 sq.ft.

$355,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.72%

Airbnb Rental Income: $null

Traditional Rental Income: $2218

Airbnb ROI: N/A

Traditional ROI: 4.72%

110 CARTER PL

Winchester, VA

5 beds | 3 baths | N/A

$489,970

Airbnb cash on cash: N/A

Traditional cash on cash: 4.37%

Airbnb Rental Income: $null

Traditional Rental Income: $2719

Airbnb ROI: N/A

Traditional ROI: 4.37%

339 LANNY Drive

Winchester, VA

3 beds | 3 baths | 2,444 sq.ft.

$515,900

Airbnb cash on cash: 0.19%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $1372

Traditional Rental Income: $2584

Airbnb ROI: 0.19%

Traditional ROI: 3.57%

121 SWEETBRIAR Lane

Winchester, VA

4 beds | 3 baths | 3,442 sq.ft.

$642,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2788

Airbnb ROI: N/A

Traditional ROI: 3.19%

281 LIGHT Road

Winchester, VA

3 beds | 3 baths | 2,618 sq.ft.

$609,900

Airbnb cash on cash: 0.13%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $1372

Traditional Rental Income: $2912

Airbnb ROI: 0.13%