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 47 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
110 GRINDSTONE Drive Winchester, VA Private pool, half-acre homesite, main-level living, and a fully finished lower-level livi...	4 beds \| 4 baths \| 4,055 sq.ft.	$529,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.63% Airbnb Rental Income: $null Traditional Rental Income: $4153 Airbnb ROI: N/A Traditional ROI: 6.63%
1004 HETH PL Winchester, VA Stepping onto the Southern style covered front porc.h you enter the large foyer with a Sc...	4 beds \| 5 baths \| N/A	$1,179,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.4% Airbnb Rental Income: $null Traditional Rental Income: $4479 Airbnb ROI: N/A Traditional ROI: 2.4%
122 ARMSTRONG Place Winchester, VA "Welcome to 122 Armstrong Place, a beautifully maintained 4-bedroom, 3-bath retreat locate...	4 beds \| 3 baths \| 2,706 sq.ft.	$549,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $3198 Airbnb ROI: N/A Traditional ROI: 4.72%
121 CHEROKEE Trail Winchester, VA Lake and mountain views, a private in-ground pool, and an adjoining .63-acre lot - this be...	3 beds \| 4 baths \| 2,650 sq.ft.	$474,500	Airbnb cash on cash: 0.94% Traditional cash on cash: 5.89% Airbnb Rental Income: $1572 Traditional Rental Income: $3319 Airbnb ROI: 0.94% Traditional ROI: 5.89%
621 PATTERSON AVE Winchester, VA Enchanting Cape Cod in an ideal in""Ã¢â¬Ëtown location, this home has a welcoming ease t...	4 beds \| 3 baths \| N/A	$364,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $2408 Airbnb ROI: N/A Traditional ROI: 5.02%
2561 APPLE PIE RIDGE Road Winchester, VA Welcome home to this beautifully updated rambler, offering comfort, character, and room to...	3 beds \| 2 baths \| 1,412 sq.ft.	$349,900	Airbnb cash on cash: 1.77% Traditional cash on cash: 4.71% Airbnb Rental Income: $1572 Traditional Rental Income: $2088 Airbnb ROI: 1.77% Traditional ROI: 4.71%
357 HUNTING RIDGE Road Winchester, VA Over 3,000 finished square feet! Completely remodeled in 2023, this 3-bedroom, 2-bath ranc...	3 beds \| 2 baths \| 3,029 sq.ft.	$489,900	Airbnb cash on cash: 0.73% Traditional cash on cash: 3.41% Airbnb Rental Income: $1572 Traditional Rental Income: $2351 Airbnb ROI: 0.73% Traditional ROI: 3.41%
127 GERONIMO Trail Winchester, VA Nestled in the serene Shawneeland community, this charming ranch-style home offers a perfe...	3 beds \| 1 baths \| 970 sq.ft.	$213,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 6.52% Airbnb Rental Income: $1572 Traditional Rental Income: $1693 Airbnb ROI: 3.68% Traditional ROI: 6.52%
1049 LAUREL GROVE RD Winchester, VA This is the one that offers the perfect blend of privacy, comfort, and natural beauty. Thi...	3 beds \| 3 baths \| N/A	$749,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.91% Airbnb Rental Income: $1572 Traditional Rental Income: $2366 Airbnb ROI: 0.13% Traditional ROI: 1.91%
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.	$399,900	Airbnb cash on cash: 1.49% Traditional cash on cash: 4.44% Airbnb Rental Income: $1572 Traditional Rental Income: $2227 Airbnb ROI: 1.49% Traditional ROI: 4.44%
603 OPOSSUM TRL Winchester, VA Coming June 2026. Blue Ocean Modulars introduces The Laurel, a new modular hybrid home i...	3 beds \| 2 baths \| N/A	$295,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 5.4% Airbnb Rental Income: $1572 Traditional Rental Income: $2165 Airbnb ROI: 1.64% Traditional ROI: 5.4%
204 RIDGE Road Winchester, VA Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) o...	3 beds \| 2 baths \| 2,131 sq.ft.	$399,999	Airbnb cash on cash: 1.33% Traditional cash on cash: 5.04% Airbnb Rental Income: $1572 Traditional Rental Income: $2510 Airbnb ROI: 1.33% Traditional ROI: 5.04%
KEVAL GYAN Way lot: 11 Winchester, VA Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, u...	3 beds \| 2 baths \| 2,488 sq.ft.	$899,900	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.1% Airbnb Rental Income: $1572 Traditional Rental Income: $2717 Airbnb ROI: 0.2% Traditional ROI: 2.1%
152.44 Acres Lot 2 LAUREL GROVE Road Winchester, VA This is a rare opportunity to build a fully custom home tailored to your vision, crafted b...	3 beds \| 2 baths \| 1,801 sq.ft.	$2,124,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.09% Airbnb Rental Income: $1572 Traditional Rental Income: $2348 Airbnb ROI: -0.53% Traditional ROI: 0.09%
105 BUCKSKIN TRL Winchester, VA This home is gorgeous. It is move-in ready. Completely renovated. Nestled in the charming ...	3 beds \| 2 baths \| N/A	$299,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 5.76% Airbnb Rental Income: $1572 Traditional Rental Income: $2122 Airbnb ROI: 2.21% Traditional ROI: 5.76%
169 CATHER Lane Winchester, VA Estimated completion August 2026. Photos shown are of a similar home previously constructe...	3 beds \| 3 baths \| 2,139 sq.ft.	$799,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 1.4% Airbnb Rental Income: $1572 Traditional Rental Income: $2487 Airbnb ROI: -0.43% Traditional ROI: 1.4%
274 WOODSIDE Lane Winchester, VA PRICE JUST REDUCED! Come take a look at this beautiful home located in the coveted neighbo...	5 beds \| 4 baths \| 4,075 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $3605 Airbnb ROI: N/A Traditional ROI: 3.45%
466 MERRIMANS Lane Winchester, VA Your long search is over! Beautifully renovated all-brick ranch home situated on a seclude...	3 beds \| 4 baths \| 3,497 sq.ft.	$899,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 2.08% Airbnb Rental Income: $1572 Traditional Rental Income: $3199 Airbnb ROI: -0.4% Traditional ROI: 2.08%
413 VALLEY MILL RD Winchester, VA Welcome to a home filled with love, memories, and over 55 years of care by the same family...	3 beds \| 1 baths \| N/A	$309,900	Airbnb cash on cash: 2.18% Traditional cash on cash: 3.88% Airbnb Rental Income: $1572 Traditional Rental Income: $1618 Airbnb ROI: 2.18% Traditional ROI: 3.88%
156 GERONIMO Trail Winchester, VA Welcome to your own private retreat in Shawneeland, where wooded surroundings, community a...	3 beds \| 2 baths \| 1,584 sq.ft.	$359,900	Airbnb cash on cash: 1.71% Traditional cash on cash: 5.23% Airbnb Rental Income: $1572 Traditional Rental Income: $2313 Airbnb ROI: 1.71% Traditional ROI: 5.23%
111 HAIDA LN Winchester, VA ""ÃÂ¢""ÃÂ¢Welcome to The Retreat at Winding Creek, your haven in Winchester, VA, where l...	4 beds \| 3 baths \| N/A	$484,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $2681 Airbnb ROI: N/A Traditional ROI: 4.27%
447 PLOW RUN LN Winchester, VA Hello there... I'm going to be patiently waiting for the perfect new owners to call me hom...	3 beds \| 2 baths \| N/A	$569,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.84% Airbnb Rental Income: $1572 Traditional Rental Income: $2353 Airbnb ROI: 0.52% Traditional ROI: 2.84%
700 TOMAHAWK Trail Winchester, VA Welcome to this charming ranch-style home situated on a spacious .44-acre corner lot in th...	3 beds \| 1 baths \| 1,104 sq.ft.	$290,000	Airbnb cash on cash: 2.4% Traditional cash on cash: 4.54% Airbnb Rental Income: $1572 Traditional Rental Income: $1705 Airbnb ROI: 2.4% Traditional ROI: 4.54%
540 BELLVIEW AVE Winchester, VA Charming rambler just minutes from historic Old Town Winchester with convenient access to ...	3 beds \| 1 baths \| 1,280 sq.ft.	$385,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 2.76% Airbnb Rental Income: $1572 Traditional Rental Income: $1694 Airbnb ROI: 1.17% Traditional ROI: 2.76%
217 PEMBRIDGE DR Winchester, VA Welcome to this well-maintained home in the sought-after Pembridge Heights community on th...	3 beds \| 3 baths \| N/A	$399,999	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.36% Airbnb Rental Income: $1572 Traditional Rental Income: $2264 Airbnb ROI: 1.31% Traditional ROI: 4.36%
100 HUNTCREST CIR Winchester, VA Well""Ã¢â¬ËMaintained Ranch Home in a Peaceful, Convenient Winchester Location. This wel...	4 beds \| 3 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.77% Airbnb Rental Income: $null Traditional Rental Income: $2245 Airbnb ROI: N/A Traditional ROI: 3.77%
300 TAVISTOCK Drive Winchester, VA Discover the perfect blend of space, privacy and convenience this expansive 3500 sq ft plu...	4 beds \| 4 baths \| 3,803 sq.ft.	$999,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.29% Airbnb Rental Income: $null Traditional Rental Income: $3572 Airbnb ROI: N/A Traditional ROI: 2.29%
207 Stanley Drive Winchester, VA Well-maintained Colonial offering over 2,800 finished square feet, ideally situated on a l...	3 beds \| 4 baths \| 2,835 sq.ft.	$515,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 3.97% Airbnb Rental Income: $1572 Traditional Rental Income: $2684 Airbnb ROI: 0.73% Traditional ROI: 3.97%
443 FAIRMONT AVE Winchester, VA So much potential !!! Great location, private yard, lots of square feet. Lot is 3/4 acre !...	2 beds \| 2 baths \| N/A	$449,900	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.04% Airbnb Rental Income: $1289 Traditional Rental Income: $2138 Airbnb ROI: 0.07% Traditional ROI: 3.04%
120 GABRIEL Court Winchester, VA Upgraded home in a desirable 55+ community on Winchester's east side! Thoughtfully upgrade...	3 beds \| 3 baths \| 2,072 sq.ft.	$524,900	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.87% Airbnb Rental Income: $1572 Traditional Rental Income: $2677 Airbnb ROI: 0.7% Traditional ROI: 3.87%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

110 GRINDSTONE Drive

Winchester, VA

4 beds | 4 baths | 4,055 sq.ft.

$529,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.63%

Airbnb Rental Income: $null

Traditional Rental Income: $4153

Airbnb ROI: N/A

Traditional ROI: 6.63%

1004 HETH PL

Winchester, VA

4 beds | 5 baths | N/A

$1,179,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.4%

Airbnb Rental Income: $null

Traditional Rental Income: $4479

Airbnb ROI: N/A

Traditional ROI: 2.4%

122 ARMSTRONG Place

Winchester, VA

4 beds | 3 baths | 2,706 sq.ft.

$549,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.72%

Airbnb Rental Income: $null

Traditional Rental Income: $3198

Airbnb ROI: N/A

Traditional ROI: 4.72%

121 CHEROKEE Trail

Winchester, VA

3 beds | 4 baths | 2,650 sq.ft.

$474,500

Airbnb cash on cash: 0.94%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $1572

Traditional Rental Income: $3319

Airbnb ROI: 0.94%

Traditional ROI: 5.89%

621 PATTERSON AVE

Winchester, VA

4 beds | 3 baths | N/A

$364,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.02%

Airbnb Rental Income: $null

Traditional Rental Income: $2408

Airbnb ROI: N/A

Traditional ROI: 5.02%

2561 APPLE PIE RIDGE Road

Winchester, VA

3 beds | 2 baths | 1,412 sq.ft.

$349,900

Airbnb cash on cash: 1.77%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $1572

Traditional Rental Income: $2088

Airbnb ROI: 1.77%

Traditional ROI: 4.71%

357 HUNTING RIDGE Road

Winchester, VA

3 beds | 2 baths | 3,029 sq.ft.

$489,900

Airbnb cash on cash: 0.73%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $1572

Traditional Rental Income: $2351

Airbnb ROI: 0.73%

Traditional ROI: 3.41%

127 GERONIMO Trail

Winchester, VA

3 beds | 1 baths | 970 sq.ft.

$213,000

Airbnb cash on cash: 3.68%

Traditional cash on cash: 6.52%

Airbnb Rental Income: $1572

Traditional Rental Income: $1693

Airbnb ROI: 3.68%