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 67 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 Ct Winchester, VA Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-s...	4 beds \| 3 baths \| 2,261 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 4.63%
354 Valley Mill Rd Winchester, VA Two level townhome, Hardwood Floors * Huge Eat-In Kitchen * Full size Washer & Dryer * Dec...	2 beds \| 1 baths \| 1,200 sq.ft.	$274,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 2.72% Airbnb Rental Income: $956 Traditional Rental Income: $1232 Airbnb ROI: 0.3% Traditional ROI: 2.72%
139 Biscane Ct Winchester, VA Welcome to 139 Biscane Ct., a beautiful townhome located in desirable Fieldstone community...	3 beds \| 3 baths \| 2,250 sq.ft.	$414,900	Airbnb cash on cash: -0.02% Traditional cash on cash: 3.77% Airbnb Rental Income: $1134 Traditional Rental Income: $2228 Airbnb ROI: -0.02% Traditional ROI: 3.77%
2431 Cedar Creek Grade Winchester, VA This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/...	3 beds \| 1 baths \| 1,036 sq.ft.	$370,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 5.11% Airbnb Rental Income: $1134 Traditional Rental Income: $2331 Airbnb ROI: 0.58% Traditional ROI: 5.11%
TBB Monteith Dr #BEDFORD II Winchester, VA ***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVE...	3 beds \| 3 baths \| 1,784 sq.ft.	$389,990	Airbnb cash on cash: -4.57% Traditional cash on cash: 1.11% Airbnb Rental Income: $1134 Traditional Rental Income: $2835 Airbnb ROI: -4.57% Traditional ROI: 1.11%
206 Monteith Dr Winchester, VA Luxury 3 level/4 bedroom townhome with 1 car garage located in the heart of Winchester! *O...	4 beds \| 3 baths \| 1,784 sq.ft.	$369,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.4% Airbnb Rental Income: $null Traditional Rental Income: $2430 Airbnb ROI: N/A Traditional ROI: 4.4%
210 Monteith Dr Winchester, VA Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Po...	3 beds \| 3 baths \| 1,784 sq.ft.	$371,990	Airbnb cash on cash: -0.42% Traditional cash on cash: 4.37% Airbnb Rental Income: $1134 Traditional Rental Income: $2430 Airbnb ROI: -0.42% Traditional ROI: 4.37%
119 Wagtail Ln Winchester, VA MOVE IN READY HOME AND OFFERING UP TO $20,000 in CLOSING COST ASSISTANCE OR SPECIAL FINANC...	3 beds \| 2 baths \| 2,195 sq.ft.	$474,929	Airbnb cash on cash: -4.04% Traditional cash on cash: 0.53% Airbnb Rental Income: $1134 Traditional Rental Income: $2787 Airbnb ROI: -4.04% Traditional ROI: 0.53%
214 Monteith Dr Winchester, VA END UNIT Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winch...	3 beds \| 3 baths \| 1,784 sq.ft.	$389,990	Airbnb cash on cash: -4.57% Traditional cash on cash: 0.37% Airbnb Rental Income: $1134 Traditional Rental Income: $2564 Airbnb ROI: -4.57% Traditional ROI: 0.37%
122 Hardy Way Winchester, VA This Beautiful 3 bedroom 2 1/2 bath Villa is in Winchester Landing a 55+ community. Only o...	3 beds \| 2 baths \| 1,630 sq.ft.	$375,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.41% Airbnb Rental Income: $1134 Traditional Rental Income: $2298 Airbnb ROI: 0.03% Traditional ROI: 4.41%
45 and 45 1/2 Race St Winchester, VA Investors Dream - $36,000 rental income, low maintenance, long term tenants in place. This...	2 beds \| 1 baths \| 1,249 sq.ft.	$339,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 3.29% Airbnb Rental Income: $956 Traditional Rental Income: $1515 Airbnb ROI: 0.44% Traditional ROI: 3.29%
218 Tudor Dr Winchester, VA Welcome home to this beautifully updated townhome tucked away in a private, peaceful neigh...	2 beds \| 3 baths \| 1,740 sq.ft.	$309,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 5.5% Airbnb Rental Income: $956 Traditional Rental Income: $2218 Airbnb ROI: 0.06% Traditional ROI: 5.5%
117 Wagtail Ln Winchester, VA Welcome to 117 Wagtail Lane, a brand-new Van Metre townhome located in the sought-after 55...	3 beds \| 2 baths \| 2,195 sq.ft.	$454,990	Airbnb cash on cash: -4.24% Traditional cash on cash: -0.01% Airbnb Rental Income: $1134 Traditional Rental Income: $2620 Airbnb ROI: -4.24% Traditional ROI: -0.01%
114 Webster Ct Winchester, VA Welcome to 114 Webster Ct, a brand-new construction home located in a sought-after 55+ com...	3 beds \| 3 baths \| 3,200 sq.ft.	$509,489	Airbnb cash on cash: -3.88% Traditional cash on cash: 0.47% Airbnb Rental Income: $1134 Traditional Rental Income: $2910 Airbnb ROI: -3.88% Traditional ROI: 0.47%
105 Boone Ct Winchester, VA 105 Boone Ct, Winchester, VA 22602 \| Townhouse	3 beds \| 2 baths \| 1,966 sq.ft.	$384,990	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.3% Airbnb Rental Income: $1134 Traditional Rental Income: $2049 Airbnb ROI: -0.29% Traditional ROI: 3.3%
117 Boone Ct Winchester, VA 117 Boone Ct, Winchester, VA 22602 \| Townhouse	3 beds \| 3 baths \| 1,966 sq.ft.	$389,990	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.23% Airbnb Rental Income: $1134 Traditional Rental Income: $2049 Airbnb ROI: -0.3% Traditional ROI: 3.23%
109 Boone Ct Winchester, VA 109 Boone Ct, Winchester, VA 22602 \| Townhouse	3 beds \| 2 baths \| 1,989 sq.ft.	$374,990	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.23% Airbnb Rental Income: $1134 Traditional Rental Income: $2049 Airbnb ROI: -0.3% Traditional ROI: 3.23%
112 Trellis View Ln Winchester, VA 112 Trellis View Ln, Winchester, VA 22602 \| Townhouse	4 beds \| 3 baths \| 2,168 sq.ft.	$474,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $2335 Airbnb ROI: N/A Traditional ROI: 2.61%
107 Sunflower Way Winchester, VA 107 Sunflower Way, Winchester, VA 22603 \| Townhouse	3 beds \| 3 baths \| 2,050 sq.ft.	$509,990	Airbnb cash on cash: -0.9% Traditional cash on cash: 2.19% Airbnb Rental Income: $1134 Traditional Rental Income: $2257 Airbnb ROI: -0.9% Traditional ROI: 2.19%
110 Trellis View Ln Winchester, VA 110 Trellis View Ln, Winchester, VA 22602 \| Townhouse	4 beds \| 3 baths \| 2,168 sq.ft.	$474,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $2335 Airbnb ROI: N/A Traditional ROI: 2.57%
108 Trellis View Ln Winchester, VA 108 Trellis View Ln, Winchester, VA 22602 \| Townhouse	4 beds \| 3 baths \| 2,168 sq.ft.	$504,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.27% Airbnb Rental Income: $null Traditional Rental Income: $2335 Airbnb ROI: N/A Traditional ROI: 2.27%
119 Castaway Pl Winchester, VA 119 Castaway Pl, Winchester, VA 22603 \| Townhouse	3 beds \| 2 baths \| 1,752 sq.ft.	$394,990	Airbnb cash on cash: -0.62% Traditional cash on cash: 2.6% Airbnb Rental Income: $1134 Traditional Rental Income: $1949 Airbnb ROI: -0.62% Traditional ROI: 2.6%
127 Lakota St Winchester, VA 127 Lakota St, Winchester, VA 22602 \| Townhouse	4 beds \| 3 baths \| 1,889 sq.ft.	$399,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $2234 Airbnb ROI: N/A Traditional ROI: 3.51%
123 Lakota St Winchester, VA 123 Lakota St, Winchester, VA 22602 \| Townhouse	4 beds \| 3 baths \| 1,889 sq.ft.	$424,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $2230 Airbnb ROI: N/A Traditional ROI: 3.13%
1817 Harvest Dr Winchester, VA 1817 Harvest Dr, Winchester, VA 22601 \| Townhouse	4 beds \| 3 baths \| 1,939 sq.ft.	$419,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $2238 Airbnb ROI: N/A Traditional ROI: 2.88%
1805 Harvest Dr Winchester, VA 1805 Harvest Dr, Winchester, VA 22601 \| Townhouse	4 beds \| 3 baths \| 1,920 sq.ft.	$409,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $2234 Airbnb ROI: N/A Traditional ROI: 2.98%
103 Castaway Pl Winchester, VA 103 Castaway Pl, Winchester, VA 22603 \| Townhouse	3 beds \| 2 baths \| 1,752 sq.ft.	$359,990	Airbnb cash on cash: -0.55% Traditional cash on cash: 2.84% Airbnb Rental Income: $1134 Traditional Rental Income: $1949 Airbnb ROI: -0.55% Traditional ROI: 2.84%
110 Carnation Way Winchester, VA 110 Carnation Way, Winchester, VA 22603 \| Townhouse	2 beds \| 2 baths \| 1,564 sq.ft.	$474,990	Airbnb cash on cash: -1.18% Traditional cash on cash: 1.48% Airbnb Rental Income: $956 Traditional Rental Income: $1853 Airbnb ROI: -1.18% Traditional ROI: 1.48%
113 Sunflower Way Winchester, VA 113 Sunflower Way, Winchester, VA 22603 \| Townhouse	3 beds \| 3 baths \| 2,050 sq.ft.	$509,990	Airbnb cash on cash: -0.94% Traditional cash on cash: 2.04% Airbnb Rental Income: $1134 Traditional Rental Income: $2257 Airbnb ROI: -0.94% Traditional ROI: 2.04%
106 Heirloom Way Winchester, VA 106 Heirloom Way, Winchester, VA 22603 \| Townhouse	3 beds \| 2 baths \| 1,752 sq.ft.	$389,990	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.49% Airbnb Rental Income: $1134 Traditional Rental Income: $1949 Airbnb ROI: -0.65% Traditional ROI: 2.49%
FREEPORT DUPLEX Plan Winchester, VA FREEPORT DUPLEX Plan, Winchester, VA 22602 \| Townhouse	4 beds \| 3 baths \| 2,168 sq.ft.	$449,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $2228 Airbnb ROI: N/A Traditional ROI: 2.66%
114 Keystone Ln Winchester, VA 114 Keystone Ln, Winchester, VA 22603 \| Townhouse	3 beds \| 2 baths \| 2,187 sq.ft.	$452,669	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.96% Airbnb Rental Income: $1134 Traditional Rental Income: $2115 Airbnb ROI: -0.25% Traditional ROI: 2.96%
CABRAL Plan Winchester, VA CABRAL Plan, Winchester, VA 22602 \| Townhouse	3 beds \| 2 baths \| 1,665 sq.ft.	$454,990	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.16% Airbnb Rental Income: $1134 Traditional Rental Income: $1787 Airbnb ROI: -0.26% Traditional ROI: 2.16%
ELM Plan Winchester, VA ELM Plan, Winchester, VA 22602 \| Townhouse	5 beds \| 3 baths \| 2,415 sq.ft.	$529,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.76% Airbnb Rental Income: $null Traditional Rental Income: $2360 Airbnb ROI: N/A Traditional ROI: 2.76%
119 Heirloom Way Winchester, VA 119 Heirloom Way, Winchester, VA 22603 \| Townhouse	3 beds \| 2 baths \| 1,752 sq.ft.	$409,990	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.39% Airbnb Rental Income: $1134 Traditional Rental Income: $1949 Airbnb ROI: -0.68% Traditional ROI: 2.39%
Deep Creek II Plan Winchester, VA Deep Creek II Plan, Winchester, VA 22601 \| Townhouse	3 beds \| 2 baths \| 2,060 sq.ft.	$409,990	Airbnb cash on cash: -0.09% Traditional cash on cash: 2.98% Airbnb Rental Income: $1134 Traditional Rental Income: $1934 Airbnb ROI: -0.09% Traditional ROI: 2.98%
113 Trellis View Ln Winchester, VA 113 Trellis View Ln, Winchester, VA 22602 \| Townhouse	4 beds \| 3 baths \| 2,168 sq.ft.	$479,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.27% Airbnb Rental Income: $null Traditional Rental Income: $2335 Airbnb ROI: N/A Traditional ROI: 2.27%
Bedford II Plan Winchester, VA Bedford II Plan, Winchester, VA 22601 \| Townhouse	3 beds \| 3 baths \| 1,784 sq.ft.	$389,990	Airbnb cash on cash: 0% Traditional cash on cash: 3.28% Airbnb Rental Income: $1134 Traditional Rental Income: $1955 Airbnb ROI: 0% Traditional ROI: 3.28%
HAYDEN Plan Winchester, VA HAYDEN Plan, Winchester, VA 22602 \| Townhouse	6 beds \| 4 baths \| 3,127 sq.ft.	$579,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.86% Airbnb Rental Income: $null Traditional Rental Income: $2605 Airbnb ROI: N/A Traditional ROI: 2.86%

Your search for investment property begins and ends here

Townhouses for Sale in Winchester, VA

125 Cheshire Ct

Winchester, VA

4 beds | 3 baths | 2,261 sq.ft.

$410,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.63%

Airbnb Rental Income: $null

Traditional Rental Income: $2534

Airbnb ROI: N/A

Traditional ROI: 4.63%

354 Valley Mill Rd

Winchester, VA

2 beds | 1 baths | 1,200 sq.ft.

$274,000

Airbnb cash on cash: 0.3%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $956

Traditional Rental Income: $1232

Airbnb ROI: 0.3%

Traditional ROI: 2.72%

139 Biscane Ct

Winchester, VA

3 beds | 3 baths | 2,250 sq.ft.

$414,900

Airbnb cash on cash: -0.02%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $1134

Traditional Rental Income: $2228

Airbnb ROI: -0.02%

Traditional ROI: 3.77%

2431 Cedar Creek Grade

Winchester, VA

3 beds | 1 baths | 1,036 sq.ft.

$370,000

Airbnb cash on cash: 0.58%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $1134

Traditional Rental Income: $2331

Airbnb ROI: 0.58%

Traditional ROI: 5.11%

TBB Monteith Dr #BEDFORD II

Winchester, VA

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

$389,990

Airbnb cash on cash: -4.57%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $1134

Traditional Rental Income: $2835

Airbnb ROI: -4.57%

Traditional ROI: 1.11%

206 Monteith Dr

Winchester, VA

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

$369,990

Airbnb cash on cash: N/A

Traditional cash on cash: 4.4%

Airbnb Rental Income: $null

Traditional Rental Income: $2430

Airbnb ROI: N/A

Traditional ROI: 4.4%

210 Monteith Dr

Winchester, VA

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

$371,990

Airbnb cash on cash: -0.42%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1134

Traditional Rental Income: $2430

Airbnb ROI: -0.42%

Traditional ROI: 4.37%

119 Wagtail Ln

Winchester, VA

3 beds | 2 baths | 2,195 sq.ft.

$474,929

Airbnb cash on cash: -4.04%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $1134

Traditional Rental Income: $2787

Airbnb ROI: -4.04%