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 40 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! This 2 bed/1 bath home is move-in ready after a 2025 Refre...	2 beds \| 1 baths \| 720 sq.ft.	$275,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.74% Airbnb Rental Income: $1077 Traditional Rental Income: $1368 Airbnb ROI: 1.2% Traditional ROI: 3.74%
3466 MIDDLE RD Winchester, VA Welcome to a place where comfort meets quiet beauty. This all brick home sits on a hillsid...	3 beds \| 3 baths \| N/A	$489,999	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.67% Airbnb Rental Income: $1015 Traditional Rental Income: $2446 Airbnb ROI: -0.24% Traditional ROI: 3.67%
145 Graywolf Trail Winchester, VA Looking for privacy, modern finishes, and a extra lot? This 2021-built Colonial checks all...	3 beds \| 3 baths \| 1,660 sq.ft.	$375,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 3.73% Airbnb Rental Income: $1015 Traditional Rental Income: $2042 Airbnb ROI: -0.21% Traditional ROI: 3.73%
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: -0.04% Traditional cash on cash: 3.64% Airbnb Rental Income: $1015 Traditional Rental Income: $1713 Airbnb ROI: -0.04% Traditional ROI: 3.64%
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%
209 WOOD Avenue Winchester, VA Welcome to this beautifully-updated brick rancher, a masterclass in blending timeless char...	3 beds \| 3 baths \| 1,528 sq.ft.	$429,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.46% Airbnb Rental Income: $1015 Traditional Rental Income: $2098 Airbnb ROI: -0.13% Traditional ROI: 3.46%
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: -0.54% Traditional cash on cash: 1.85% Airbnb Rental Income: $1015 Traditional Rental Income: $2366 Airbnb ROI: -0.54% Traditional ROI: 1.85%
2225 CEDAR GROVE Road Winchester, VA 3-26-26 Cabinets going in. Painted,, trimmed, and hardwood floors stained and finished. Ge...	3 beds \| 4 baths \| 3,100 sq.ft.	$1,049,900	Airbnb cash on cash: -0.46% Traditional cash on cash: 2% Airbnb Rental Income: $1015 Traditional Rental Income: $3060 Airbnb ROI: -0.46% Traditional ROI: 2%
603 OPOSSUM TRL Winchester, VA Coming April 2026. Blue Ocean Modulars introduces The Laurel, a new modular home to be l...	3 beds \| 2 baths \| N/A	$295,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 5.4% Airbnb Rental Income: $1015 Traditional Rental Income: $2165 Airbnb ROI: -0.03% 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.	$414,999	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.82% Airbnb Rental Income: $1015 Traditional Rental Income: $2510 Airbnb ROI: 0.06% 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: 0.94% Traditional cash on cash: 4.38% Airbnb Rental Income: $1077 Traditional Rental Income: $1631 Airbnb ROI: 0.94% Traditional ROI: 4.38%
KEVAL GYAN Way lot: 12 Winchester, VA Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, u...	3 beds \| 3 baths \| 3,100 sq.ft.	$950,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 2.31% Airbnb Rental Income: $1015 Traditional Rental Income: $3050 Airbnb ROI: -0.39% Traditional ROI: 2.31%
709 DICKS HOLLOW Road Winchester, VA Welcome to this private gem nestled on a corner lot in beautiful Winchester, VA! This stun...	3 beds \| 2 baths \| 1,368 sq.ft.	$422,999	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.93% Airbnb Rental Income: $1015 Traditional Rental Income: $2160 Airbnb ROI: 0.13% Traditional ROI: 3.93%
254 WHISTLEWOOD LANE Winchester, VA Welcome home to a perfect blend of space, serenity, and style. This exceptional property o...	5 beds \| 7 baths \| N/A	$894,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $6090 Airbnb ROI: N/A Traditional ROI: 6.14%
570 WELLTOWN Road Winchester, VA Built to last but updated and move in ready! This charming brick home has a lot to offer. ...	4 beds \| 3 baths \| 1,783 sq.ft.	$429,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.21% Airbnb Rental Income: $null Traditional Rental Income: $3129 Airbnb ROI: N/A Traditional ROI: 6.21%
803 TOMAHAWK Trail Winchester, VA Welcome to this cozy 3-bedroom, 1.5-bath ranch home in Shawneeland. Featuring hardwood flo...	3 beds \| 2 baths \| 960 sq.ft.	$250,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 6.34% Airbnb Rental Income: $1015 Traditional Rental Income: $1914 Airbnb ROI: 1.02% Traditional ROI: 6.34%
116 PINTO Winchester, VA The Perfect Starter Home Awaits! 3-26-26 almost done. Granite and septic going in and fina...	2 beds \| 1 baths \| 1,140 sq.ft.	$349,900	Airbnb cash on cash: 0.06% Traditional cash on cash: 3.53% Airbnb Rental Income: $1077 Traditional Rental Income: $1850 Airbnb ROI: 0.06% Traditional ROI: 3.53%
249 WEST STREET ST Winchester, VA Great opportunity for income producing property in city limits. Property consists of 249 a...	3 beds \| 1 baths \| N/A	$349,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 2.82% Airbnb Rental Income: $1015 Traditional Rental Income: $1462 Airbnb ROI: 0.37% Traditional ROI: 2.82%
188 MARQUIS CT Winchester, VA This spacious 4 bedroom ranch style home situated on 8.72 acres has a GREAT location conve...	4 beds \| 4 baths \| N/A	$659,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $3291 Airbnb ROI: N/A Traditional ROI: 3.82%
424 HIGHLAND AVE Winchester, VA CUTE AS A BUTTON! This updated Cottage Rambler perched on a quiet tree lined street sits i...	2 beds \| 1 baths \| N/A	$279,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.11% Airbnb Rental Income: $1077 Traditional Rental Income: $1286 Airbnb ROI: 0.91% Traditional ROI: 3.11%
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	$332,900	Airbnb cash on cash: 0.4% Traditional cash on cash: 4.83% Airbnb Rental Income: $1015 Traditional Rental Income: $2042 Airbnb ROI: 0.4% Traditional ROI: 4.83%
2967 South Pleasant Valley Road Winchester, VA New, new, new & ready for YOU! 3 beds/2 baths with so much work done you should be able to...	3 beds \| 2 baths \| 915 sq.ft.	$329,900	Airbnb cash on cash: 0.01% Traditional cash on cash: 4.47% Airbnb Rental Income: $1015 Traditional Rental Income: $2042 Airbnb ROI: 0.01% Traditional ROI: 4.47%
199 LAUREL GROVE Road Winchester, VA Nestled in the scenic countryside of Winchester, this impressive custom built home offers ...	4 beds \| 4 baths \| 4,880 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.51% Airbnb Rental Income: $null Traditional Rental Income: $2364 Airbnb ROI: N/A Traditional ROI: 0.51%
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: 0.29% Traditional cash on cash: 4.96% Airbnb Rental Income: $1015 Traditional Rental Income: $2042 Airbnb ROI: 0.29% Traditional ROI: 4.96%
130 MORGAN Street Winchester, VA Location, Location, Location! Built in 1971 is this 2700 + Sq. Ft. Finished Quality Brick ...	3 beds \| 3 baths \| 2,722 sq.ft.	$625,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 1.76% Airbnb Rental Income: $1015 Traditional Rental Income: $2042 Airbnb ROI: -0.62% Traditional ROI: 1.76%
224 DOE Trail Winchester, VA Welcome home to this spacious 4-bedroom, 2.5-bath ranch nestled on two wooded lots in Shaw...	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%
101 MOLDEN Drive Winchester, VA This 1963 brick ranch is conveniently located off Pleasant Valley Road in Eastview Subdivi...	3 beds \| 2 baths \| 1,260 sq.ft.	$360,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.04% Airbnb Rental Income: $1015 Traditional Rental Income: $2042 Airbnb ROI: -0.05% Traditional ROI: 4.04%
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: -0.22% Traditional cash on cash: 2.77% Airbnb Rental Income: $1015 Traditional Rental Income: $2125 Airbnb ROI: -0.22% Traditional ROI: 2.77%
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: -0.28% Traditional cash on cash: 1.58% Airbnb Rental Income: $1015 Traditional Rental Income: $2042 Airbnb ROI: -0.28% Traditional ROI: 1.58%
169 CATHER Lane Winchester, VA Estimated completion August 2026. Photos shown are of a similar home previously constructe...	3 beds \| 2 baths \| 2,139 sq.ft.	$799,900	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.8% Airbnb Rental Income: $1015 Traditional Rental Income: $2042 Airbnb ROI: -1.06% Traditional ROI: 0.8%

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.

$275,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $1077

Traditional Rental Income: $1368

Airbnb ROI: 1.2%

Traditional ROI: 3.74%

3466 MIDDLE RD

Winchester, VA

3 beds | 3 baths | N/A

$489,999

Airbnb cash on cash: -0.24%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $1015

Traditional Rental Income: $2446

Airbnb ROI: -0.24%

Traditional ROI: 3.67%

145 Graywolf Trail

Winchester, VA

3 beds | 3 baths | 1,660 sq.ft.

$375,000

Airbnb cash on cash: -0.21%

Traditional cash on cash: 3.73%

Airbnb Rental Income: $1015

Traditional Rental Income: $2042

Airbnb ROI: -0.21%

Traditional ROI: 3.73%

511 GROUSE Drive

Winchester, VA

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

$304,900

Airbnb cash on cash: -0.04%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $1015

Traditional Rental Income: $1713

Airbnb ROI: -0.04%

Traditional ROI: 3.64%

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%

209 WOOD Avenue

Winchester, VA

3 beds | 3 baths | 1,528 sq.ft.

$429,000

Airbnb cash on cash: -0.13%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1015

Traditional Rental Income: $2098

Airbnb ROI: -0.13%

Traditional ROI: 3.46%

1049 LAUREL GROVE RD

Winchester, VA

3 beds | 3 baths | N/A

$767,900

Airbnb cash on cash: -0.54%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $1015

Traditional Rental Income: $2366

Airbnb ROI: -0.54%

Traditional ROI: 1.85%

2225 CEDAR GROVE Road

Winchester, VA

3 beds | 4 baths | 3,100 sq.ft.

$1,049,900

Airbnb cash on cash: -0.46%

Traditional cash on cash: 2%

Airbnb Rental Income: $1015

Traditional Rental Income: $3060

Airbnb ROI: -0.46%