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 33 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: 1.06% Traditional cash on cash: 3.74% Airbnb Rental Income: $1032 Traditional Rental Income: $1368 Airbnb ROI: 1.06% 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: -0.72% Traditional cash on cash: 3.67% Airbnb Rental Income: $748 Traditional Rental Income: $2446 Airbnb ROI: -0.72% 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	$369,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.44% Airbnb Rental Income: $748 Traditional Rental Income: $2112 Airbnb ROI: -0.4% Traditional ROI: 4.44%
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.	$399,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 3.33% Airbnb Rental Income: $1032 Traditional Rental Income: $2144 Airbnb ROI: -0.6% Traditional ROI: 3.33%
610 PUMA Trail Winchester, VA Tucked away at the end of the neighborhood and surrounded by serene woods, 610 Puma Trl of...	2 beds \| 1 baths \| 560 sq.ft.	$224,990	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.09% Airbnb Rental Income: $1032 Traditional Rental Income: $1284 Airbnb ROI: 1.21% Traditional ROI: 4.09%
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.	$385,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 4.41% Airbnb Rental Income: $748 Traditional Rental Income: $2263 Airbnb ROI: -0.65% Traditional ROI: 4.41%
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.	$235,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 5.83% Airbnb Rental Income: $748 Traditional Rental Income: $1693 Airbnb ROI: 0.17% Traditional ROI: 5.83%
511 GROUSE Drive Winchester, VA Estimated completion by end of March 2026 This is a fantastic opportunity to purchase ...	3 beds \| 2 baths \| 1,333 sq.ft.	$304,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 3.64% Airbnb Rental Income: $748 Traditional Rental Income: $1713 Airbnb ROI: -0.82% Traditional ROI: 3.64%
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 \| 2,683 sq.ft.	$399,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 3.06% Airbnb Rental Income: $748 Traditional Rental Income: $1757 Airbnb ROI: -0.47% Traditional ROI: 3.06%
1049 LAUREL GROVE RD Winchester, VA This custom-built 3-bedroom, 3-bath home is perfectly positioned on a private, wooded lot ...	3 beds \| 3 baths \| N/A	$767,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 1.85% Airbnb Rental Income: $748 Traditional Rental Income: $2366 Airbnb ROI: -0.85% Traditional ROI: 1.85%
1419 RAMSEUR Lane Winchester, VA This property is NOT in a 55+ community. A rare opportunity for one-level living with over...	4 beds \| 3 baths \| 3,482 sq.ft.	$735,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.26% Airbnb Rental Income: $null Traditional Rental Income: $2984 Airbnb ROI: N/A Traditional ROI: 2.26%
2225 CEDAR GROVE Road Winchester, VA 4-14-26 Getting close. Delivery estimated end April. At front of Keplinger Estates near th...	3 beds \| 4 baths \| 3,100 sq.ft.	$1,049,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 2% Airbnb Rental Income: $748 Traditional Rental Income: $3060 Airbnb ROI: -0.69% Traditional ROI: 2%
603 OPOSSUM TRL Winchester, VA Coming June 2026. Blue Ocean Modulars introduces The Laurel, a new modular home to be lo...	3 beds \| 2 baths \| N/A	$295,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 5.4% Airbnb Rental Income: $748 Traditional Rental Income: $2165 Airbnb ROI: -0.83% 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: 0.01% Traditional cash on cash: 7.18% Airbnb Rental Income: $748 Traditional Rental Income: $2062 Airbnb ROI: 0.01% 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.	$414,999	Airbnb cash on cash: -0.51% Traditional cash on cash: 4.82% Airbnb Rental Income: $748 Traditional Rental Income: $2510 Airbnb ROI: -0.51% Traditional ROI: 4.82%
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: 0.8% Traditional cash on cash: 4.38% Airbnb Rental Income: $1032 Traditional Rental Income: $1631 Airbnb ROI: 0.8% Traditional ROI: 4.38%
KEVAL GYAN Way lot: 1 Winchester, VA Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, u...	4 beds \| 4 baths \| 3,100 sq.ft.	$1,029,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $3566 Airbnb ROI: N/A Traditional ROI: 2.59%
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.	$879,900	Airbnb cash on cash: -0.62% Traditional cash on cash: 2.17% Airbnb Rental Income: $748 Traditional Rental Income: $2717 Airbnb ROI: -0.62% Traditional ROI: 2.17%
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: -0.88% Traditional cash on cash: 0.09% Airbnb Rental Income: $748 Traditional Rental Income: $2348 Airbnb ROI: -0.88% Traditional ROI: 0.09%
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.	$279,900	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.96% Airbnb Rental Income: $1032 Traditional Rental Income: $1478 Airbnb ROI: 0.9% Traditional ROI: 3.96%
KEVAL GYAN Way lot: 13 Winchester, VA Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, u...	3 beds \| 2 baths \| 2,512 sq.ft.	$849,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 1.85% Airbnb Rental Income: $748 Traditional Rental Income: $2373 Airbnb ROI: -0.6% Traditional ROI: 1.85%
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	$324,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 5.23% Airbnb Rental Income: $748 Traditional Rental Income: $2122 Airbnb ROI: -0.29% Traditional ROI: 5.23%
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.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $2670 Airbnb ROI: N/A Traditional ROI: 3.29%
154 NEVERMORE DR Winchester, VA Elevated living at its very best! A very rare blend of modern luxury and serene surroundin...	3 beds \| 2 baths \| 1,839 sq.ft.	$579,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 2.54% Airbnb Rental Income: $748 Traditional Rental Income: $2333 Airbnb ROI: -0.97% Traditional ROI: 2.54%
406 RACCOON DR Winchester, VA Tucked away in the peaceful Wilde Acres neighborhood, this beautiful home offers the perfe...	3 beds \| 2 baths \| 1,850 sq.ft.	$315,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 6.11% Airbnb Rental Income: $748 Traditional Rental Income: $2382 Airbnb ROI: -0.47% Traditional ROI: 6.11%
126 S EUCLID Avenue Winchester, VA This 3-bedroom, 1 full bath home is ready for you to move right in! Entire inside has been...	3 beds \| 1 baths \| 1,086 sq.ft.	$309,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.02% Airbnb Rental Income: $748 Traditional Rental Income: $1722 Airbnb ROI: -0.4% Traditional ROI: 4.02%
128 CHARMWOOD LN Winchester, VA First time on the market, this private wooded retreat offers the perfect blend of seclusio...	3 beds \| 2 baths \| N/A	$524,900	Airbnb cash on cash: -0.67% Traditional cash on cash: 2.77% Airbnb Rental Income: $748 Traditional Rental Income: $2125 Airbnb ROI: -0.67% Traditional ROI: 2.77%
303 FOX Winchester, VA Major Price Reduction! Welcome to this beautifully renovated 2-bedroom, 1-bath ranch-style...	2 beds \| 1 baths \| 960 sq.ft.	$240,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 4.93% Airbnb Rental Income: $1032 Traditional Rental Income: $1506 Airbnb ROI: 1.25% Traditional ROI: 4.93%
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: -0.58% Traditional cash on cash: 2.51% Airbnb Rental Income: $748 Traditional Rental Income: $2737 Airbnb ROI: -0.58% 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: -1.36% Traditional cash on cash: 1.4% Airbnb Rental Income: $748 Traditional Rental Income: $2487 Airbnb ROI: -1.36% Traditional ROI: 1.4%
2956 GRACE Street Winchester, VA Welcome to 2956 Grace Street - a 3-bedroom, 1-bath ranch-style home offering comfortable s...	3 beds \| 1 baths \| 1,699 sq.ft.	$339,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 3.76% Airbnb Rental Income: $748 Traditional Rental Income: $1812 Airbnb ROI: -0.57% Traditional ROI: 3.76%
1057 FOREMAN LN Winchester, VA NEED YOUR OWN SPACE, THEN COME CHECK OUT THIS RAISED RANCHER, IT HAS 1 BEDROOM 1 BATH, FRE...	1 beds \| 1 baths \| N/A	$242,500	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.84% Airbnb Rental Income: $786 Traditional Rental Income: $1283 Airbnb ROI: 0.28% Traditional ROI: 3.84%
126 HARVEST RIDGE DR Winchester, VA This meticulously cared-for home is located in the sought-after 55+ community The Village ...	3 beds \| 2 baths \| N/A	$629,900	Airbnb cash on cash: -0.92% Traditional cash on cash: 1.93% Airbnb Rental Income: $748 Traditional Rental Income: $2106 Airbnb ROI: -0.92% Traditional ROI: 1.93%

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: 1.06%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $1032

Traditional Rental Income: $1368

Airbnb ROI: 1.06%

Traditional ROI: 3.74%

3466 MIDDLE RD

Winchester, VA

3 beds | 3 baths | N/A

$489,999

Airbnb cash on cash: -0.72%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $748

Traditional Rental Income: $2446

Airbnb ROI: -0.72%

Traditional ROI: 3.67%

109 HURON TRL

Winchester, VA

3 beds | 2 baths | N/A

$369,900

Airbnb cash on cash: -0.4%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $748

Traditional Rental Income: $2112

Airbnb ROI: -0.4%

Traditional ROI: 4.44%

1851 MELVOR Lane

Winchester, VA

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

$399,900

Airbnb cash on cash: -0.6%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $1032

Traditional Rental Income: $2144

Airbnb ROI: -0.6%

Traditional ROI: 3.33%

610 PUMA Trail

Winchester, VA

2 beds | 1 baths | 560 sq.ft.

$224,990

Airbnb cash on cash: 1.21%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $1032

Traditional Rental Income: $1284

Airbnb ROI: 1.21%

Traditional ROI: 4.09%

540 Eagle Place

Winchester, VA

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

$385,000

Airbnb cash on cash: -0.65%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $748

Traditional Rental Income: $2263

Airbnb ROI: -0.65%

Traditional ROI: 4.41%

127 GERONIMO Trail

Winchester, VA

3 beds | 1 baths | 970 sq.ft.

$235,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 5.83%

Airbnb Rental Income: $748

Traditional Rental Income: $1693

Airbnb ROI: 0.17%

Traditional ROI: 5.83%

511 GROUSE Drive

Winchester, VA

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

$304,900

Airbnb cash on cash: -0.82%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $748

Traditional Rental Income: $1713

Airbnb ROI: -0.82%