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 18 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
3466 MIDDLE RD Winchester, VA Quiet Elegance with Blue Ridge Views: A Remarkable All-Brick Home Tucked away in a peacefu...	3 beds \| 3 baths \| N/A	$529,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.32% Airbnb Rental Income: $1134 Traditional Rental Income: $2446 Airbnb ROI: -0.09% Traditional ROI: 3.32%
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: 0.27% Traditional cash on cash: 3.55% Airbnb Rental Income: $1134 Traditional Rental Income: $1713 Airbnb ROI: 0.27% Traditional ROI: 3.55%
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%
126 ARMSTRONG Place Winchester, VA SHORT SALE: All brick ranch home with 4 bedrooms close to town and a short walk to the gol...	4 beds \| 3 baths \| 1,617 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.66% Airbnb Rental Income: $null Traditional Rental Income: $2603 Airbnb ROI: N/A Traditional ROI: 5.66%
1049 LAUREL GROVE RD Winchester, VA This CUSTOM 3-bedroom, 3-bath home is sited on a private, wooded lot offering stunning mou...	3 beds \| 3 baths \| N/A	$767,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.85% Airbnb Rental Income: $1134 Traditional Rental Income: $2366 Airbnb ROI: -0.4% Traditional ROI: 1.85%
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: 0.05% Traditional cash on cash: 3.52% Airbnb Rental Income: $1134 Traditional Rental Income: $2192 Airbnb ROI: 0.05% Traditional ROI: 3.52%
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: -0.25% Traditional cash on cash: 2.75% Airbnb Rental Income: $1134 Traditional Rental Income: $2353 Airbnb ROI: -0.25% Traditional ROI: 2.75%
428 WESTSIDE STATION DR Winchester, VA Beautiful, and stately 4-5BR 3.5 BA, (bonus room on upper level could be utilized as a 5t...	4 beds \| 4 baths \| N/A	$564,777	Airbnb cash on cash: N/A Traditional cash on cash: 3.36% Airbnb Rental Income: $null Traditional Rental Income: $2643 Airbnb ROI: N/A Traditional ROI: 3.36%
113 WILLIAMSON Road Winchester, VA Welcome home to this solid all-brick rancher offering timeless charm and endless potential...	3 beds \| 3 baths \| 2,547 sq.ft.	$434,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.77% Airbnb Rental Income: $1134 Traditional Rental Income: $2179 Airbnb ROI: 0.28% Traditional ROI: 3.77%
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: 0.32% Traditional cash on cash: 3.27% Airbnb Rental Income: $1134 Traditional Rental Income: $1917 Airbnb ROI: 0.32% Traditional ROI: 3.27%
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.	$414,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.81% Airbnb Rental Income: $1134 Traditional Rental Income: $2282 Airbnb ROI: -0.11% Traditional ROI: 3.81%
114 WOODYS PL Winchester, VA This exceptional residential property, located in the desirable Carlisle Estates subdivisi...	3 beds \| 2 baths \| N/A	$255,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 6.83% Airbnb Rental Income: $1134 Traditional Rental Income: $2154 Airbnb ROI: 1.02% Traditional ROI: 6.83%
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: 0.57% Traditional cash on cash: 4.38% Airbnb Rental Income: $956 Traditional Rental Income: $1631 Airbnb ROI: 0.57% Traditional ROI: 4.38%
436 WESTSIDE STATION Drive Winchester, VA Exceptional opportunity to enjoy one-level, low maintenance living in this all-brick ranch...	4 beds \| 3 baths \| 2,644 sq.ft.	$569,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.2% Airbnb Rental Income: $null Traditional Rental Income: $3093 Airbnb ROI: N/A Traditional ROI: 4.2%
372 BETHEL GRANGE Road Winchester, VA Spacious doublewide home offering endless potential, situated on 2.47 unrestricted acres i...	3 beds \| 2 baths \| 1,728 sq.ft.	$275,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 6.83% Airbnb Rental Income: $1134 Traditional Rental Income: $2250 Airbnb ROI: 1.07% Traditional ROI: 6.83%
450 CANYON Road Winchester, VA Discover absolutely stunning main-level living in this beautifully updated home! Boasting ...	3 beds \| 3 baths \| 2,290 sq.ft.	$629,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.93% Airbnb Rental Income: $1134 Traditional Rental Income: $2651 Airbnb ROI: -0.29% Traditional ROI: 2.93%
103 KINGSLAND Court Winchester, VA This adorable rambler is tucked away at the end of a quiet cul-de-sac, yet conveniently lo...	3 beds \| 2 baths \| 1,104 sq.ft.	$298,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 5.36% Airbnb Rental Income: $1134 Traditional Rental Income: $1995 Airbnb ROI: 0.94% Traditional ROI: 5.36%
113 KILLBUCK Trail Winchester, VA Nestled in the wooded mountain community of Shawneeland, this delightful ranch-style home ...	3 beds \| 3 baths \| 2,324 sq.ft.	$359,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 6.36% Airbnb Rental Income: $1134 Traditional Rental Income: $2744 Airbnb ROI: 0.47% Traditional ROI: 6.36%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

3466 MIDDLE RD

Winchester, VA

3 beds | 3 baths | N/A

$529,900

Airbnb cash on cash: -0.09%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1134

Traditional Rental Income: $2446

Airbnb ROI: -0.09%

Traditional ROI: 3.32%

511 GROUSE Drive

Winchester, VA

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

$309,900

Airbnb cash on cash: 0.27%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $1134

Traditional Rental Income: $1713

Airbnb ROI: 0.27%

Traditional ROI: 3.55%

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%

126 ARMSTRONG Place

Winchester, VA

4 beds | 3 baths | 1,617 sq.ft.

$375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.66%

Airbnb Rental Income: $null

Traditional Rental Income: $2603

Airbnb ROI: N/A

Traditional ROI: 5.66%

1049 LAUREL GROVE RD

Winchester, VA

3 beds | 3 baths | N/A

$767,900

Airbnb cash on cash: -0.4%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $1134

Traditional Rental Income: $2366

Airbnb ROI: -0.4%

Traditional ROI: 1.85%

421 SUPERIOR AVE

Winchester, VA

3 beds | 2 baths | 1,800 sq.ft.

$441,700

Airbnb cash on cash: 0.05%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $1134

Traditional Rental Income: $2192

Airbnb ROI: 0.05%

Traditional ROI: 3.52%

114 HAROLD Court

Winchester, VA

3 beds | 2 baths | 1,862 sq.ft.

$570,000

Airbnb cash on cash: -0.25%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $1134

Traditional Rental Income: $2353

Airbnb ROI: -0.25%

Traditional ROI: 2.75%

428 WESTSIDE STATION DR

Winchester, VA

4 beds | 4 baths | N/A

$564,777

Airbnb cash on cash: N/A

Traditional cash on cash: 3.36%

Airbnb Rental Income: $null

Traditional Rental Income: $2643

Airbnb ROI: N/A