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.

Condos for Sale in Winchester, VA

Search for Condo for Sale in Winchester, Virginia. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 11 Condo 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 Brookland Ct #10 Winchester, VA Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transfor...	2 beds \| 2 baths \| 1,173 sq.ft.	$299,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 4.83% Airbnb Rental Income: $1126 Traditional Rental Income: $2042 Airbnb ROI: 0.26% Traditional ROI: 4.83%
135 S Kent St #202 Winchester, VA Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban ...	1 beds \| 1 baths \| 740 sq.ft.	$259,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.61% Airbnb Rental Income: $762 Traditional Rental Income: $1462 Airbnb ROI: -0.31% Traditional ROI: 3.61%
121-8 Brookland Ct #8 Winchester, VA 2 Bed, 2 bath condominium. New appliances, including water heater and heat pump. Gas firep...	2 beds \| 2 baths \| 1,173 sq.ft.	$229,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 6.8% Airbnb Rental Income: $1126 Traditional Rental Income: $1954 Airbnb ROI: 1.47% Traditional ROI: 6.8%
136-8 Brookland Ct #8 Winchester, VA Fully Renovated 2026 \| Turnkey 2BR/2BA Condo in Park Place Welcome to 136-8 Brookland Ct-w...	2 beds \| 2 baths \| 1,173 sq.ft.	$249,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 6.5% Airbnb Rental Income: $1126 Traditional Rental Income: $1998 Airbnb ROI: 1.32% Traditional ROI: 6.5%
127-8 Brookland Ter #8 Winchester, VA Fantastic location! This spacious second-floor condo offers vaulted ceilings, generously s...	2 beds \| 2 baths \| 1,173 sq.ft.	$240,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 7.2% Airbnb Rental Income: $1126 Traditional Rental Income: $2050 Airbnb ROI: 1.46% Traditional ROI: 7.2%
136-6 Brookland Ct #6 Winchester, VA Discover the charm of Parkplace Condominiums, where comfort meets convenience in a vibrant...	2 beds \| 2 baths \| 1,173 sq.ft.	$254,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 6.01% Airbnb Rental Income: $1126 Traditional Rental Income: $1879 Airbnb ROI: 1.32% Traditional ROI: 6.01%
157-6 Brookland Ter #6 Winchester, VA Fantastic location! This spacious second-floor condo offers more square footage than most ...	2 beds \| 2 baths \| 1,257 sq.ft.	$239,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 6.9% Airbnb Rental Income: $1126 Traditional Rental Income: $2048 Airbnb ROI: 1.38% Traditional ROI: 6.9%

Your search for investment property begins and ends here

Condos for Sale in Winchester, VA

110 Brookland Ct #10

Winchester, VA

2 beds | 2 baths | 1,173 sq.ft.

$299,900

Airbnb cash on cash: 0.26%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $1126

Traditional Rental Income: $2042

Airbnb ROI: 0.26%

Traditional ROI: 4.83%

135 S Kent St #202

Winchester, VA

1 beds | 1 baths | 740 sq.ft.

$259,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $762

Traditional Rental Income: $1462

Airbnb ROI: -0.31%

Traditional ROI: 3.61%

121-8 Brookland Ct #8

Winchester, VA

2 beds | 2 baths | 1,173 sq.ft.

$229,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 6.8%

Airbnb Rental Income: $1126

Traditional Rental Income: $1954

Airbnb ROI: 1.47%

Traditional ROI: 6.8%

136-8 Brookland Ct #8

Winchester, VA

2 beds | 2 baths | 1,173 sq.ft.

$249,900

Airbnb cash on cash: 1.32%

Traditional cash on cash: 6.5%

Airbnb Rental Income: $1126

Traditional Rental Income: $1998

Airbnb ROI: 1.32%

Traditional ROI: 6.5%

127-8 Brookland Ter #8

Winchester, VA

2 beds | 2 baths | 1,173 sq.ft.

$240,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 7.2%

Airbnb Rental Income: $1126

Traditional Rental Income: $2050

Airbnb ROI: 1.46%

Traditional ROI: 7.2%

136-6 Brookland Ct #6

Winchester, VA

2 beds | 2 baths | 1,173 sq.ft.

$254,900

Airbnb cash on cash: 1.32%

Traditional cash on cash: 6.01%

Airbnb Rental Income: $1126

Traditional Rental Income: $1879

Airbnb ROI: 1.32%

Traditional ROI: 6.01%

157-6 Brookland Ter #6

Winchester, VA

2 beds | 2 baths | 1,257 sq.ft.

$239,000

Airbnb cash on cash: 1.38%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $1126

Traditional Rental Income: $2048

Airbnb ROI: 1.38%

Traditional ROI: 6.9%

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