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 43 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
719 Smithfield Avenue Winchester, VA Bringing all the bungalow love! . **$8,000 closing cost credit to buyer with acceptable of...	2 beds \| 1 baths \| 720 sq.ft.	$274,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 3.74% Airbnb Rental Income: $897 Traditional Rental Income: $1368 Airbnb ROI: 0.62% Traditional ROI: 3.74%
3466 MIDDLE RD Winchester, VA Welcome to a private retreat where timeless charm meets peaceful mountain beauty. Set on 0...	3 beds \| 3 baths \| N/A	$489,999	Airbnb cash on cash: -0.62% Traditional cash on cash: 3.67% Airbnb Rental Income: $805 Traditional Rental Income: $2446 Airbnb ROI: -0.62% Traditional ROI: 3.67%
109 HURON TRL Winchester, VA Discover this inviting 3-bedroom, 2-bath tri""Ã¢â¬Ëlevel home, offering flexible living ...	3 beds \| 2 baths \| N/A	$359,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 4.59% Airbnb Rental Income: $805 Traditional Rental Income: $2112 Airbnb ROI: -0.24% Traditional ROI: 4.59%
775 PACK HORSE Road Winchester, VA Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in F...	3 beds \| 2 baths \| 1,188 sq.ft.	$420,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.41% Airbnb Rental Income: $805 Traditional Rental Income: $1940 Airbnb ROI: -0.3% Traditional ROI: 3.41%
1851 MELVOR Lane Winchester, VA Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottag...	2 beds \| 2 baths \| 1,405 sq.ft.	$389,900	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.43% Airbnb Rental Income: $897 Traditional Rental Income: $2144 Airbnb ROI: -0.9% Traditional ROI: 3.43%
540 Eagle Place Winchester, VA Great opportunity for a rental investment! This well-maintained one-level rancher is tucke...	3 beds \| 2 baths \| 1,450 sq.ft.	$382,500	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.45% Airbnb Rental Income: $805 Traditional Rental Income: $2263 Airbnb ROI: -0.52% Traditional ROI: 4.45%
1015 REDBUD Winchester, VA Set on over 10 private acres in the quiet Locust Level Estates community, this beautifully...	4 beds \| 5 baths \| 4,188 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $4576 Airbnb ROI: N/A Traditional ROI: 2.61%
104 HILLTOP Terrace Winchester, VA THIS HOME IS A MUST SEE! THIS WELL CARED FOR MOVE IN READY HOME HAS NEW UPDATED STAINLESS ...	3 beds \| 1 baths \| 1,360 sq.ft.	$349,900	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.87% Airbnb Rental Income: $805 Traditional Rental Income: $1811 Airbnb ROI: -0.17% Traditional ROI: 3.87%
357 HUNTING RIDGE Road Winchester, VA Completely remodeled in 2023, this 3-bedroom, 2-bath rancher offers modern updates and a f...	3 beds \| 2 baths \| 3,029 sq.ft.	$525,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.12% Airbnb Rental Income: $805 Traditional Rental Income: $2351 Airbnb ROI: -0.69% Traditional ROI: 3.12%
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.	$235,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 5.83% Airbnb Rental Income: $805 Traditional Rental Income: $1693 Airbnb ROI: 0.38% Traditional ROI: 5.83%
428 APPLE PIE RIDGE RD Winchester, VA Rare Log""Ã¢â¬ËHome Retreat on Nearly 8 Acres - Private, Peaceful, and Close to Everythi...	3 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 1.98% Airbnb Rental Income: $805 Traditional Rental Income: $1913 Airbnb ROI: -0.69% Traditional ROI: 1.98%
307 FOX RUN Lane Winchester, VA Wake up to breathtaking views of the Shenandoah Valley every day in this peaceful, beautif...	3 beds \| 1 baths \| 1,260 sq.ft.	$399,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.06% Airbnb Rental Income: $805 Traditional Rental Income: $1757 Airbnb ROI: -0.35% Traditional ROI: 3.06%
121 SWEETBRIAR Lane Winchester, VA 121 Sweetbriar Ln, Winchester, VA 22603 is a Stunning "Private Haven" ranch-style home sit...	4 beds \| 3 baths \| 3,442 sq.ft.	$619,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 3.35%
1049 LAUREL GROVE RD Winchester, VA Discover the perfect blend of privacy, comfort, and natural beauty in this custom-built 3-...	3 beds \| 3 baths \| N/A	$749,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.91% Airbnb Rental Income: $805 Traditional Rental Income: $2366 Airbnb ROI: -0.78% Traditional ROI: 1.91%
323 RUSSELCROFT Road Winchester, VA Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living ...	4 beds \| 2 baths \| 1,534 sq.ft.	$358,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.31% Airbnb Rental Income: $null Traditional Rental Income: $2461 Airbnb ROI: N/A Traditional ROI: 5.31%
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: -0.66% Traditional cash on cash: 5.4% Airbnb Rental Income: $805 Traditional Rental Income: $2165 Airbnb ROI: -0.66% Traditional ROI: 5.4%
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	$240,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 7.18% Airbnb Rental Income: $805 Traditional Rental Income: $2062 Airbnb ROI: 0.22% Traditional ROI: 7.18%
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: -0.37% Traditional cash on cash: 5.04% Airbnb Rental Income: $805 Traditional Rental Income: $2510 Airbnb ROI: -0.37% Traditional ROI: 5.04%
108 MARTIN Drive Winchester, VA Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-...	2 beds \| 1 baths \| 997 sq.ft.	$285,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 4.38% Airbnb Rental Income: $897 Traditional Rental Income: $1631 Airbnb ROI: 0.38% Traditional ROI: 4.38%
188 MARQUIS CT Winchester, VA Great home with a Great location at a Great price! This home is convenient to everything, ...	4 beds \| 4 baths \| N/A	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.9% Airbnb Rental Income: $null Traditional Rental Income: $3291 Airbnb ROI: N/A Traditional ROI: 3.9%
111 GENESEE Trail Winchester, VA Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painte...	2 beds \| 1 baths \| 924 sq.ft.	$259,900	Airbnb cash on cash: 0.59% Traditional cash on cash: 4.33% Airbnb Rental Income: $897 Traditional Rental Income: $1478 Airbnb ROI: 0.59% Traditional ROI: 4.33%
105 BUCKSKIN TRL Winchester, VA Nestled in the charming Shawneeland community, you will enjoy the mountain views in this d...	3 beds \| 2 baths \| N/A	$310,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 5.53% Airbnb Rental Income: $805 Traditional Rental Income: $2122 Airbnb ROI: -0.1% Traditional ROI: 5.53%
1317 CAROLINE Street Winchester, VA Welcome to 1317 Caroline Street, a well-appointed brick rancher in a fantastic Winchester ...	4 beds \| 2 baths \| 2,837 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.37% Airbnb Rental Income: $null Traditional Rental Income: $2670 Airbnb ROI: N/A Traditional ROI: 3.37%
406 RACCOON DR Winchester, VA Back on market, no fault of seller! Tucked away in the peaceful Wilde Acres neighborhood, ...	3 beds \| 2 baths \| 1,850 sq.ft.	$315,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 6.11% Airbnb Rental Income: $805 Traditional Rental Income: $2382 Airbnb ROI: -0.31% Traditional ROI: 6.11%
224 DOE Trail Winchester, VA NEW ROOF TO BE INSTALLED PRIOR TO CLOSING Second chance to own this home!!! Welcome ho...	4 beds \| 3 baths \| 2,058 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.1% Airbnb Rental Income: $null Traditional Rental Income: $2874 Airbnb ROI: N/A Traditional ROI: 7.1%
123 STETSON Street Winchester, VA Don't miss this incredible opportunity to own a brand-new ranch home set on 2.66 beautiful...	3 beds \| 3 baths \| 2,331 sq.ft.	$799,900	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.51% Airbnb Rental Income: $805 Traditional Rental Income: $2737 Airbnb ROI: -0.51% Traditional ROI: 2.51%
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.	$799,900	Airbnb cash on cash: -1.29% Traditional cash on cash: 1.4% Airbnb Rental Income: $805 Traditional Rental Income: $2487 Airbnb ROI: -1.29% Traditional ROI: 1.4%
274 WOODSIDE Lane Winchester, VA Welcome to 274 Woodside - a secluded house on 5.06 acres with tons of storage! This 4,310 ...	5 beds \| 4 baths \| 4,075 sq.ft.	$795,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $3605 Airbnb ROI: N/A Traditional ROI: 3.34%
2956 GRACE Street Winchester, VA Brand new carpet and paint on main level Welcome to 2956 Grace Street, this 3-bedroom ...	3 beds \| 1 baths \| 1,699 sq.ft.	$319,900	Airbnb cash on cash: -0.38% Traditional cash on cash: 4.04% Airbnb Rental Income: $805 Traditional Rental Income: $1812 Airbnb ROI: -0.38% Traditional ROI: 4.04%
1057 FOREMAN LN Winchester, VA NEED YOUR OWN SPACE, THEN COME CHECK OUT THIS RAISED RANCHER, 1-2 BEDROOM 1 BATH, 5 ROOMS ...	2 beds \| 1 baths \| N/A	$234,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 4% Airbnb Rental Income: $897 Traditional Rental Income: $1283 Airbnb ROI: 0.74% Traditional ROI: 4%
231 BENTLEY Avenue Winchester, VA Easy main-level living with bonus space when you need it-this one just works. A beautiful,...	3 beds \| 2 baths \| 1,703 sq.ft.	$479,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.72% Airbnb Rental Income: $805 Traditional Rental Income: $2386 Airbnb ROI: -0.53% Traditional ROI: 3.72%
126 HARVEST RIDGE DR Winchester, VA This meticulously cared-for home is located in the sought-after 55+ community The Village ...	4 beds \| N/A baths \| N/A	$629,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.93% Airbnb Rental Income: $null Traditional Rental Income: $2106 Airbnb ROI: N/A Traditional ROI: 1.93%
466 MERRIMANS Lane Winchester, VA An extraordinary and rarely available offering within the city limits, 466 Merrimans Lane ...	3 beds \| 4 baths \| 3,497 sq.ft.	$1,200,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 1.31% Airbnb Rental Income: $805 Traditional Rental Income: $3199 Airbnb ROI: -1.12% Traditional ROI: 1.31%
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: -0.01% Traditional cash on cash: 3.88% Airbnb Rental Income: $805 Traditional Rental Income: $1618 Airbnb ROI: -0.01% Traditional ROI: 3.88%
110 Red Fox Trl Winchester, VA 3-bedroom cottage in Shawneeland offering great potential to make it your own. Recent upda...	3 beds \| 2 baths \| 1,230 sq.ft.	$275,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 6.05% Airbnb Rental Income: $805 Traditional Rental Income: $2020 Airbnb ROI: 0.11% Traditional ROI: 6.05%
156 GERONIMO Trail Winchester, VA .Welcome home to this charming ranch-style retreat featuring 3 bedrooms and 2 full baths, ...	3 beds \| 2 baths \| 1,584 sq.ft.	$364,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 5.15% Airbnb Rental Income: $805 Traditional Rental Income: $2313 Airbnb ROI: -0.2% Traditional ROI: 5.15%
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	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $2681 Airbnb ROI: N/A Traditional ROI: 4.12%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

719 Smithfield Avenue

Winchester, VA

2 beds | 1 baths | 720 sq.ft.

$274,900

Airbnb cash on cash: 0.62%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $897

Traditional Rental Income: $1368

Airbnb ROI: 0.62%

Traditional ROI: 3.74%

3466 MIDDLE RD

Winchester, VA

3 beds | 3 baths | N/A

$489,999

Airbnb cash on cash: -0.62%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $805

Traditional Rental Income: $2446

Airbnb ROI: -0.62%

Traditional ROI: 3.67%

109 HURON TRL

Winchester, VA

3 beds | 2 baths | N/A

$359,900

Airbnb cash on cash: -0.24%

Traditional cash on cash: 4.59%

Airbnb Rental Income: $805

Traditional Rental Income: $2112

Airbnb ROI: -0.24%

Traditional ROI: 4.59%

775 PACK HORSE Road

Winchester, VA

3 beds | 2 baths | 1,188 sq.ft.

$420,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $805

Traditional Rental Income: $1940

Airbnb ROI: -0.3%

Traditional ROI: 3.41%

1851 MELVOR Lane

Winchester, VA

2 beds | 2 baths | 1,405 sq.ft.

$389,900

Airbnb cash on cash: -0.9%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $897

Traditional Rental Income: $2144

Airbnb ROI: -0.9%

Traditional ROI: 3.43%

540 Eagle Place

Winchester, VA

3 beds | 2 baths | 1,450 sq.ft.

$382,500

Airbnb cash on cash: -0.52%

Traditional cash on cash: 4.45%

Airbnb Rental Income: $805

Traditional Rental Income: $2263

Airbnb ROI: -0.52%

Traditional ROI: 4.45%

1015 REDBUD

Winchester, VA

4 beds | 5 baths | 4,188 sq.ft.

$1,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.61%

Airbnb Rental Income: $null

Traditional Rental Income: $4576

Airbnb ROI: N/A

Traditional ROI: 2.61%

104 HILLTOP Terrace

Winchester, VA

3 beds | 1 baths | 1,360 sq.ft.

$349,900

Airbnb cash on cash: -0.17%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $805

Traditional Rental Income: $1811

Airbnb ROI: -0.17%