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 22 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
2225 HARRISON Street Winchester, VA 2225 Harrison Street located in Winchester, VA. One level living in a home remodeled in th...	3 beds \| 2 baths \| 1,300 sq.ft.	$334,900	Airbnb cash on cash: 6.46% Traditional cash on cash: 4.02% Airbnb Rental Income: $3402 Traditional Rental Income: $1880 Airbnb ROI: 6.46% Traditional ROI: 4.02%
939 WOODLAND AVE Winchester, VA Price Reduced!!! Need your Own Space? or you're looking to Downsize or Just Starting Out, ...	2 beds \| 2 baths \| N/A	$287,500	Airbnb cash on cash: 5.05% Traditional cash on cash: 2.85% Airbnb Rental Income: $2499 Traditional Rental Income: $1298 Airbnb ROI: 5.05% Traditional ROI: 2.85%
513 VAN FOSSEN Street Winchester, VA Welcome to 513 Van Fossen St, a beautifully updated 4-bedroom, 2.5-bathroom brick ranch co...	4 beds \| 3 baths \| 2,804 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $2218 Airbnb ROI: N/A Traditional ROI: 4.64%
110 CARTER PL Winchester, VA Contract fell through! Interest rates have gone down! Extensive Renovations: The home ha...	5 beds \| 3 baths \| N/A	$494,970	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 4.32%
221 CRESTWOOD Lane Winchester, VA Charming well maintained corner lot unit in desirable Woodbrook Village 55 and over commun...	2 beds \| 2 baths \| 1,384 sq.ft.	$389,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.78% Airbnb Rental Income: $2499 Traditional Rental Income: $1856 Airbnb ROI: 2.88% Traditional ROI: 2.78%
22 HORIZON DR Winchester, VA No HOA! 1 LEVEL LIVING home - 3 BR / 2 BA offers spacious kitchen with granite counters, f...	3 beds \| 2 baths \| 2,092 sq.ft.	$700,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.17% Airbnb Rental Income: $3402 Traditional Rental Income: $2485 Airbnb ROI: 2.41% Traditional ROI: 2.17%
1049 LAUREL GROVE RD Winchester, VA Tucked away on a quiet cul-de-sac, this custom 3-bedroom, 3-bath home is sited on a privat...	3 beds \| 3 baths \| N/A	$767,900	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.85% Airbnb Rental Income: $3402 Traditional Rental Income: $2366 Airbnb ROI: 2.24% Traditional ROI: 1.85%
881 ADAMS RD Winchester, VA Back on the Market and fully Certified! Appraised over asking, All inspections completed (...	3 beds \| 2 baths \| N/A	$689,900	Airbnb cash on cash: 2.66% Traditional cash on cash: 2.1% Airbnb Rental Income: $3402 Traditional Rental Income: $2286 Airbnb ROI: 2.66% Traditional ROI: 2.1%
128 RAVEN OAKS DR Winchester, VA Back on the market with no fault to the seller. This is your second chance to snatch this ...	4 beds \| 3 baths \| N/A	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.23% Airbnb Rental Income: $null Traditional Rental Income: $2484 Airbnb ROI: N/A Traditional ROI: 2.23%
2723 WINDWOOD DR Winchester, VA Premier Single-Level Living on a Private Cul-de-Sac! Nestled at the end of a quiet, presti...	3 beds \| 3 baths \| N/A	$549,900	Airbnb cash on cash: 3.23% Traditional cash on cash: 3.04% Airbnb Rental Income: $3402 Traditional Rental Income: $2551 Airbnb ROI: 3.23% Traditional ROI: 3.04%
1818 KERSHAW LN Winchester, VA First time on market. Very desirable location. Sun room with many extra windows, A/c unit ...	2 beds \| 2 baths \| N/A	$382,500	Airbnb cash on cash: 3.25% Traditional cash on cash: 3.82% Airbnb Rental Income: $2499 Traditional Rental Income: $2100 Airbnb ROI: 3.25% Traditional ROI: 3.82%
428 WESTSIDE STATION DR Winchester, VA Beautiful, stately 5 BR 3.5 BA, 4000sq ft, colonial situated on a quiet cul de sac in a co...	5 beds \| 4 baths \| N/A	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $2643 Airbnb ROI: N/A Traditional ROI: 3.29%
112 STAR FORT DR Winchester, VA Unlock the Potential! 3BR/2BA Fixer-Upper in Winchester/Frederick County. Nestled in a qu...	3 beds \| 2 baths \| N/A	$300,000	Airbnb cash on cash: 7.64% Traditional cash on cash: 5.58% Airbnb Rental Income: $3402 Traditional Rental Income: $2062 Airbnb ROI: 7.64% Traditional ROI: 5.58%
2808 SARATOGA Drive Winchester, VA Unbeatable location on quiet street with oversized parcel in city limits within walking di...	3 beds \| 2 baths \| 2,018 sq.ft.	$449,900	Airbnb cash on cash: 4.27% Traditional cash on cash: 3.79% Airbnb Rental Income: $3402 Traditional Rental Income: $2443 Airbnb ROI: 4.27% Traditional ROI: 3.79%
1666 APPLE PIE RIDGE RD. Winchester, VA "A Slice Of Apple Pie" This 2-bedroom, 1 full bath ranch style home is ready for it's next...	2 beds \| 1 baths \| 1,631 sq.ft.	$314,900	Airbnb cash on cash: 4.81% Traditional cash on cash: 3.64% Airbnb Rental Income: $2499 Traditional Rental Income: $1546 Airbnb ROI: 4.81% Traditional ROI: 3.64%
461 IMPERIAL Street Winchester, VA Charming Rancher In Winchester, VA! Beautifully updated 4-bedroom, 2 full bath home offers...	4 beds \| 2 baths \| 2,450 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.27% Airbnb Rental Income: $null Traditional Rental Income: $2685 Airbnb ROI: N/A Traditional ROI: 5.27%
1823 KERSHAW Lane Winchester, VA This beautiful home in Willow Lawn Cottages has been freshly painted, professionally clean...	2 beds \| 2 baths \| 1,591 sq.ft.	$389,900	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.95% Airbnb Rental Income: $2499 Traditional Rental Income: $2197 Airbnb ROI: 3.12% Traditional ROI: 3.95%
525 E CORK ST Winchester, VA More information COMING SOON! Beautiful and affordable Gem in the middle of Winchester Cit...	2 beds \| 1 baths \| N/A	$305,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 3.24% Airbnb Rental Income: $2499 Traditional Rental Income: $1483 Airbnb ROI: 4.67% Traditional ROI: 3.24%
138 COUNTRY CLUB Circle Winchester, VA Charming All-Brick Rancher with Pool Across from Winchester Country Club This beautifully ...	3 beds \| 2 baths \| 2,326 sq.ft.	$424,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 5.64% Airbnb Rental Income: $3402 Traditional Rental Income: $2888 Airbnb ROI: 5.04% Traditional ROI: 5.64%
852 BUTLER AVE Winchester, VA Nestled in a fantastic location near shopping, schools, and historic downtown Winchester, ...	3 beds \| 2 baths \| N/A	$279,900	Airbnb cash on cash: 8.19% Traditional cash on cash: 6.11% Airbnb Rental Income: $3402 Traditional Rental Income: $2095 Airbnb ROI: 8.19% Traditional ROI: 6.11%
534 Grouse Drive Winchester, VA Like new construction without the wait! Lovely 2024, ranch home with partially finished ba...	3 beds \| 3 baths \| 1,966 sq.ft.	$330,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 6.03% Airbnb Rental Income: $3402 Traditional Rental Income: $2532 Airbnb ROI: 6.4% Traditional ROI: 6.03%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, VA

320 LINDEN DR

Winchester, VA

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%

2225 HARRISON Street

Winchester, VA

3 beds | 2 baths | 1,300 sq.ft.

$334,900

Airbnb cash on cash: 6.46%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $3402

Traditional Rental Income: $1880

Airbnb ROI: 6.46%

Traditional ROI: 4.02%

939 WOODLAND AVE

Winchester, VA

2 beds | 2 baths | N/A

$287,500

Airbnb cash on cash: 5.05%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $2499

Traditional Rental Income: $1298

Airbnb ROI: 5.05%

Traditional ROI: 2.85%

513 VAN FOSSEN Street

Winchester, VA

4 beds | 3 baths | 2,804 sq.ft.

$360,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.64%

Airbnb Rental Income: $null

Traditional Rental Income: $2218

Airbnb ROI: N/A

Traditional ROI: 4.64%

110 CARTER PL

Winchester, VA

5 beds | 3 baths | N/A

$494,970

Airbnb cash on cash: N/A

Traditional cash on cash: 4.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2719

Airbnb ROI: N/A

Traditional ROI: 4.32%

221 CRESTWOOD Lane

Winchester, VA

2 beds | 2 baths | 1,384 sq.ft.

$389,900

Airbnb cash on cash: 2.88%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $2499

Traditional Rental Income: $1856

Airbnb ROI: 2.88%

Traditional ROI: 2.78%

22 HORIZON DR

Winchester, VA

3 beds | 2 baths | 2,092 sq.ft.

$700,000

Airbnb cash on cash: 2.41%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $3402

Traditional Rental Income: $2485

Airbnb ROI: 2.41%

Traditional ROI: 2.17%

1049 LAUREL GROVE RD

Winchester, VA

3 beds | 3 baths | N/A

$767,900

Airbnb cash on cash: 2.24%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $3402

Traditional Rental Income: $2366

Airbnb ROI: 2.24%