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.

Townhouses for Sale in Winchester, VA

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

Showing 19 Townhouse 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
125 CHESHIRE Court Winchester, VA Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-s...	4 beds \| 4 baths \| 2,261 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 4.67%
222 CRESTWOOD Lane Winchester, VA Welcome home to easy, maintenance-free living in the sought-after 55+ community of Woodbro...	2 beds \| 2 baths \| 1,260 sq.ft.	$379,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.56% Airbnb Rental Income: $1121 Traditional Rental Income: $2074 Airbnb ROI: -0.17% Traditional ROI: 3.56%
100 MAURY Way Winchester, VA Welcome to this Former Model Home for the Grand Nassau model by Ryan Homes - once the Winc...	3 beds \| 3 baths \| 1,678 sq.ft.	$385,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.08% Airbnb Rental Income: $1372 Traditional Rental Income: $2231 Airbnb ROI: 0.55% Traditional ROI: 4.08%
154 SOLARA Drive Winchester, VA This lovely modern townhome is better than new! Featuring a fully fenced and level backyar...	3 beds \| 3 baths \| 2,281 sq.ft.	$404,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 4.87% Airbnb Rental Income: $1372 Traditional Rental Income: $2603 Airbnb ROI: 0.52% Traditional ROI: 4.87%
117 TYE Court Winchester, VA Modern Townhome with Premium Upgrades. Great for Investor as it is currently rented. Ideal...	3 beds \| 3 baths \| 1,962 sq.ft.	$409,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 4.77% Airbnb Rental Income: $1372 Traditional Rental Income: $2553 Airbnb ROI: 0.6% Traditional ROI: 4.77%
211 EASTSIDE Lane Winchester, VA Welcome to this spacious 4-bedroom, 2.5-bath townhouse in the heart of Winchester! Ideally...	4 beds \| 3 baths \| 1,840 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.65% Airbnb Rental Income: $null Traditional Rental Income: $2536 Airbnb ROI: N/A Traditional ROI: 6.65%
206 MONTEITH Drive Winchester, VA Luxury 3 level/4 bedroom townhome with 1 car garage located in the heart of Winchester! *O...	4 beds \| 4 baths \| 1,658 sq.ft.	$389,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.58% Airbnb Rental Income: $null Traditional Rental Income: $2430 Airbnb ROI: N/A Traditional ROI: 4.58%
210 MONTEITH Drive Winchester, VA Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Po...	3 beds \| 4 baths \| 1,784 sq.ft.	$389,990	Airbnb cash on cash: 0.54% Traditional cash on cash: 4.58% Airbnb Rental Income: $1372 Traditional Rental Income: $2430 Airbnb ROI: 0.54% Traditional ROI: 4.58%
201 MONTEITH Drive Winchester, VA End Unit luxury 3 level/3 bedroom townhome with a chef's kitchen and 1 car garage located ...	3 beds \| 4 baths \| 1,784 sq.ft.	$422,539	Airbnb cash on cash: 0.36% Traditional cash on cash: 4.09% Airbnb Rental Income: $1372 Traditional Rental Income: $2430 Airbnb ROI: 0.36% Traditional ROI: 4.09%
26-A JACKSON Avenue Winchester, VA Rare Opportunity: Turnkey Duplex in Winchester - Vacant, Updated, and Ready for Your Next ...	4 beds \| 4 baths \| 2,152 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.91% Airbnb Rental Income: $null Traditional Rental Income: $1596 Airbnb ROI: N/A Traditional ROI: 1.91%
2918 SORRELL Court Winchester, VA Welcome to your new home! This beautifully maintained 2 -bedroom, 1.5 bath townhome offers...	2 beds \| 2 baths \| 1,251 sq.ft.	$269,900	Airbnb cash on cash: 0.87% Traditional cash on cash: 5.76% Airbnb Rental Income: $1121 Traditional Rental Income: $1990 Airbnb ROI: 0.87% Traditional ROI: 5.76%
105 TANGLEWOOD Lane Winchester, VA	2 beds \| 2 baths \| 1,372 sq.ft.	$375,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 4.28% Airbnb Rental Income: $1121 Traditional Rental Income: $2099 Airbnb ROI: 0.43% Traditional ROI: 4.28%
205 MONTEITH Drive Winchester, VA 3 level/3 bedroom townhome with a chef's kitchen and 1 car garage located in the heart of ...	3 beds \| 4 baths \| 1,784 sq.ft.	$369,990	Airbnb cash on cash: 0.67% Traditional cash on cash: 4.93% Airbnb Rental Income: $1372 Traditional Rental Income: $2435 Airbnb ROI: 0.67% Traditional ROI: 4.93%
138 WINDSTONE Drive Winchester, VA HAVE IT ALL! BEAUTIFUL 3-LEVEL TOWNHOUSE WITH A GAS LOG FIREPLACE, GARAGE AND A COMMUNITY ...	3 beds \| 3 baths \| 1,488 sq.ft.	$340,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 5.29% Airbnb Rental Income: $1372 Traditional Rental Income: $2242 Airbnb ROI: 1.26% Traditional ROI: 5.29%
2901 SORRELL Court Winchester, VA Investor Opportunity, current tenants have a lease until May of 2027 Welcome to your new...	3 beds \| 2 baths \| 1,332 sq.ft.	$279,900	Airbnb cash on cash: 1.57% Traditional cash on cash: 5.63% Airbnb Rental Income: $1372 Traditional Rental Income: $2026 Airbnb ROI: 1.57% Traditional ROI: 5.63%
627 WATSON Avenue Winchester, VA CLASSIC CHARM MEETS CONTEMPORARY COMFORT IN THIS FANTASTIC DUPLEX UNIT! This charming Winc...	3 beds \| 1 baths \| 1,205 sq.ft.	$299,990	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.9% Airbnb Rental Income: $1372 Traditional Rental Income: $1601 Airbnb ROI: 1.61% Traditional ROI: 3.9%
305 SUTTON Court Winchester, VA Whether you are looking for the perfect Investment Property or Your New Home...This Move-i...	2 beds \| 2 baths \| 1,214 sq.ft.	$305,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 5.03% Airbnb Rental Income: $1121 Traditional Rental Income: $1934 Airbnb ROI: 0.89% Traditional ROI: 5.03%
207 EASTSIDE Winchester, VA Enjoy all this spacious 4 bedroom 3.5 bath town home has to offer. Located with easy acces...	4 beds \| 4 baths \| 1,840 sq.ft.	$314,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.91% Airbnb Rental Income: $null Traditional Rental Income: $2553 Airbnb ROI: N/A Traditional ROI: 6.91%
203 CRESTWOOD Lane Winchester, VA Welcome home to this well-maintained property located in an established Winchester neighbo...	2 beds \| 2 baths \| 1,590 sq.ft.	$379,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 4.42% Airbnb Rental Income: $1121 Traditional Rental Income: $2182 Airbnb ROI: 0.38% Traditional ROI: 4.42%

Your search for investment property begins and ends here

Townhouses for Sale in Winchester, VA

125 CHESHIRE Court

Winchester, VA

4 beds | 4 baths | 2,261 sq.ft.

$410,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.67%

Airbnb Rental Income: $null

Traditional Rental Income: $2534

Airbnb ROI: N/A

Traditional ROI: 4.67%

222 CRESTWOOD Lane

Winchester, VA

2 beds | 2 baths | 1,260 sq.ft.

$379,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $1121

Traditional Rental Income: $2074

Airbnb ROI: -0.17%

Traditional ROI: 3.56%

100 MAURY Way

Winchester, VA

3 beds | 3 baths | 1,678 sq.ft.

$385,000

Airbnb cash on cash: 0.55%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $1372

Traditional Rental Income: $2231

Airbnb ROI: 0.55%

Traditional ROI: 4.08%

154 SOLARA Drive

Winchester, VA

3 beds | 3 baths | 2,281 sq.ft.

$404,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 4.87%

Airbnb Rental Income: $1372

Traditional Rental Income: $2603

Airbnb ROI: 0.52%

Traditional ROI: 4.87%

117 TYE Court

Winchester, VA

3 beds | 3 baths | 1,962 sq.ft.

$409,900

Airbnb cash on cash: 0.6%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1372

Traditional Rental Income: $2553

Airbnb ROI: 0.6%

Traditional ROI: 4.77%

211 EASTSIDE Lane

Winchester, VA

4 beds | 3 baths | 1,840 sq.ft.

$309,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.65%

Airbnb Rental Income: $null

Traditional Rental Income: $2536

Airbnb ROI: N/A

Traditional ROI: 6.65%

206 MONTEITH Drive

Winchester, VA

4 beds | 4 baths | 1,658 sq.ft.

$389,990

Airbnb cash on cash: N/A

Traditional cash on cash: 4.58%

Airbnb Rental Income: $null

Traditional Rental Income: $2430

Airbnb ROI: N/A

Traditional ROI: 4.58%

210 MONTEITH Drive

Winchester, VA

3 beds | 4 baths | 1,784 sq.ft.

$389,990

Airbnb cash on cash: 0.54%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $1372

Traditional Rental Income: $2430

Airbnb ROI: 0.54%