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 4 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
1332 RAMSEUR Lane Winchester, VA Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exte...	3 beds \| 2 baths \| 2,648 sq.ft.	$459,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 4% Airbnb Rental Income: $3402 Traditional Rental Income: $2609 Airbnb ROI: 4.09% Traditional ROI: 4%
140 MCCORMICK Circle unit: 302 #302 Winchester, VA Welcome home to this gorgeous, like-new condo! This stunning unit was constructed last yea...	2 beds \| 2 baths \| 1,156 sq.ft.	$314,900	Airbnb cash on cash: 4.02% Traditional cash on cash: 5.03% Airbnb Rental Income: $2499 Traditional Rental Income: $2193 Airbnb ROI: 4.02% Traditional ROI: 5.03%
140 MCCORMICK Circle unit: 403 #403 Winchester, VA Motivated Sellers! Bring all offers. Nearly-new 55+ condominium located in Winchester Land...	2 beds \| 2 baths \| 1,156 sq.ft.	$324,900	Airbnb cash on cash: 4.74% Traditional cash on cash: 5.5% Airbnb Rental Income: $2499 Traditional Rental Income: $2125 Airbnb ROI: 4.74% Traditional ROI: 5.5%
151 MCCORMICK CIR unit: 203 #203 Winchester, VA 55+ Condo Community, this charming 2-bedroom, 2-bathroom unit offers a perfect blend of co...	2 beds \| 2 baths \| 1,156 sq.ft.	$312,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 5.39% Airbnb Rental Income: $2499 Traditional Rental Income: $2207 Airbnb ROI: 4.32% Traditional ROI: 5.39%
Other Investment Properties for Sale in Winchester
219 MILAM Drive Winchester , VA Welcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet nei...	4 beds \| 3 baths \| 2,654 sq.ft.	$468,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $3073 Airbnb ROI: N/A Traditional ROI: 5.45%
226 TAGGART Drive Winchester , VA Welcome to 226 Taggart Drive - a sunlit Colonial in the heart of Winchester's sought-after...	4 beds \| 4 baths \| 4,411 sq.ft.	$689,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $3501 Airbnb ROI: N/A Traditional ROI: 3.84%
316 VIRGINIA Avenue Winchester , VA Well maintained Colonial offering timeless character and modern potential in the heart of ...	3 beds \| 2 baths \| 1,192 sq.ft.	$338,000	Airbnb cash on cash: 6.73% Traditional cash on cash: 4.14% Airbnb Rental Income: $3402 Traditional Rental Income: $1825 Airbnb ROI: 6.73% Traditional ROI: 4.14%
2321 STONERIDGE Road Winchester , VA Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The o...	4 beds \| 3 baths \| 3,512 sq.ft.	$625,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $2979 Airbnb ROI: N/A Traditional ROI: 3.14%
109 SHELBY Court Winchester , VA Welcome to this beautiful colonial home in the sought-after Chapel Hill community. Set on ...	3 beds \| 3 baths \| 2,412 sq.ft.	$489,999	Airbnb cash on cash: 4.12% Traditional cash on cash: 4.28% Airbnb Rental Income: $3402 Traditional Rental Income: $2721 Airbnb ROI: 4.12% Traditional ROI: 4.28%
320 LINDEN DR Winchester , VA Experience generational refined living in this stunning luxury home just minutes from Winc...	4 beds \| 3 baths \| N/A	$628,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 2.5%
105 BUCKWOOD Lane Winchester , VA Enjoy the ease of one-level living in this spacious 2-bedroom, 2-bath home located in a we...	2 beds \| 2 baths \| 1,584 sq.ft.	$375,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 3.94% Airbnb Rental Income: $2499 Traditional Rental Income: $2189 Airbnb ROI: 3.1% Traditional ROI: 3.94%
127 KINROSS Drive Winchester , VA Welcome to 127 Kinross Dr in Winchester, VA! This spacious 5-bedroom, 3.5-bath home offers...	5 beds \| 4 baths \| 3,494 sq.ft.	$620,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $3737 Airbnb ROI: N/A Traditional ROI: 4.91%
106 FOXGLOVE Drive Winchester , VA This 3BD/3.5BA Colonial combines modern upgrades with a versatile layout. The upper level ...	3 beds \| 4 baths \| 2,686 sq.ft.	$459,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 5.13% Airbnb Rental Income: $3402 Traditional Rental Income: $2935 Airbnb ROI: 4.46% Traditional ROI: 5.13%
137 STONEBROOK Road Winchester , VA Perched on an elevated lot, this handsome Colonial provides panoramic views from the spaci...	4 beds \| 4 baths \| 3,783 sq.ft.	$789,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.07% Airbnb Rental Income: $null Traditional Rental Income: $3385 Airbnb ROI: N/A Traditional ROI: 3.07%
107 OKEEFE Drive Winchester , VA Carpeting has been replaced with rich hardwood flooring on main level. 2020 New HVAC & Roo...	4 beds \| 5 baths \| 3,076 sq.ft.	$569,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $4129 Airbnb ROI: N/A Traditional ROI: 6.12%
369 CHARLES Street Winchester , VA This two-story home offers classic charm with a covered front porch, fenced backyard, and ...	3 beds \| 2 baths \| 1,526 sq.ft.	$285,000	Airbnb cash on cash: 7.81% Traditional cash on cash: 6.19% Airbnb Rental Income: $3402 Traditional Rental Income: $2212 Airbnb ROI: 7.81% Traditional ROI: 6.19%
1950 MELVOR Lane Winchester , VA <html> <head> <title>1950 Melvor Ln</title> <style> body { font-family: sans-serif; margin...	4 beds \| 3 baths \| 3,108 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $2732 Airbnb ROI: N/A Traditional ROI: 2.47%
3980 MIDDLE Road Winchester , VA Custom, all-brick white rambler with a French Country ambience, enjoys boundaries of a lov...	4 beds \| 4 baths \| 3,504 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3466 Airbnb ROI: N/A Traditional ROI: 3.26%

Your search for investment property begins and ends here

Condos for Sale in Winchester, VA

1332 RAMSEUR Lane

Winchester, VA

3 beds | 2 baths | 2,648 sq.ft.

$459,000

Airbnb cash on cash: 4.09%

Traditional cash on cash: 4%

Airbnb Rental Income: $3402

Traditional Rental Income: $2609

Airbnb ROI: 4.09%

Traditional ROI: 4%

140 MCCORMICK Circle unit: 302 #302

Winchester, VA

2 beds | 2 baths | 1,156 sq.ft.

$314,900

Airbnb cash on cash: 4.02%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $2499

Traditional Rental Income: $2193

Airbnb ROI: 4.02%

Traditional ROI: 5.03%

140 MCCORMICK Circle unit: 403 #403

Winchester, VA

2 beds | 2 baths | 1,156 sq.ft.

$324,900

Airbnb cash on cash: 4.74%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $2499

Traditional Rental Income: $2125

Airbnb ROI: 4.74%

Traditional ROI: 5.5%

151 MCCORMICK CIR unit: 203 #203

Winchester, VA

2 beds | 2 baths | 1,156 sq.ft.

$312,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 5.39%

Airbnb Rental Income: $2499

Traditional Rental Income: $2207

Airbnb ROI: 4.32%

Traditional ROI: 5.39%

Other Investment Properties for Sale in Winchester

Winchester , VA

4 beds | 3 baths | 2,654 sq.ft.

$468,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.45%

Airbnb Rental Income: $null

Traditional Rental Income: $3073

Airbnb ROI: N/A

Traditional ROI: 5.45%

Winchester , VA

4 beds | 4 baths | 4,411 sq.ft.

$689,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.84%

Airbnb Rental Income: $null

Traditional Rental Income: $3501

Airbnb ROI: N/A

Traditional ROI: 3.84%

Winchester , VA

3 beds | 2 baths | 1,192 sq.ft.

$338,000

Airbnb cash on cash: 6.73%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $3402

Traditional Rental Income: $1825

Airbnb ROI: 6.73%

Traditional ROI: 4.14%

Winchester , VA

4 beds | 3 baths | 3,512 sq.ft.

$625,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2979

Airbnb ROI: N/A

Traditional ROI: 3.14%

Winchester , VA

3 beds | 3 baths | 2,412 sq.ft.